Ziggler made his WWE television debut on the September 19, 2005 episode of Sunday Night Heat. He was made the enforcer and sidekick for Chavo Guerrero, who was using a golfer in-ring persona and going by the ring name of "Kerwin White". As such, Ziggler became White's caddy. His wrestling debut came on an episode of Sunday Night Heat, teaming up with White in a tag team match against Shelton Benjamin and Matt Striker. After the death of Eddie Guerrero, Chavo Guerrero dropped the "Kerwin White" character, and Ziggler no longer played the role of his caddy and tag partner.
Ziggler then became a part of The Spirit Squad faction, a group of five wrestlers who used the in-ring personas of male cheerleaders, and adopted the name Nicky. On January 23, 2006, they had their WWE television debut as a group, appearing on Raw and helping Jonathan Coachman win a Royal Rumble qualifying match against Jerry "The King" Lawler by performing cheers for Coachman and distracting Lawler. They later became a part of the ongoing scripted feud between WWE chairman Vince McMahon and Shawn Michaels. The heel McMahon brought in the Squad to attack Michaels on numerous occasions, including placing them in multiple handicap matches.
They also wrestled in the tag team division, and on April 3, on Raw, won the World Tag Team Championship when Kenny and Mikey, with outside help from the other three Squad members, defeated Big Show and Kane. After winning the championship, all five members of the Spirit Squad were recognized as the champions, allowing any combination of them to defend the championship under the Freebird Rule.
In May, McMahon signed another Handicap match, with the Spirit Squad facing Michaels. The match never started, however; instead the Spirit Squad attacked Michaels, and, as part of the storyline, shattered his knee with a steel chair. McMahon brought Triple H to the ring to attack Michaels with a sledgehammer; however, after Triple H felt that the Squad had disrespected him, he attacked the group. This led to Triple H and Michaels reforming D-Generation X (DX) and they began a feud with the Spirit Squad. DX played various sophomoric jokes on the Squad and the McMahons, as well as defeating the Spirit Squad in handicap tag team matches at Vengeance and a clean sweep in an elimination handicap match on Saturday Night's Main Event.
At the same time as their feud with DX and their alignment with McMahon, the Squad also wrestled other teams in Raw's tag division over their World Tag Team Championship, successfully defending the championship against the teams of Jim Duggan and Eugene, Charlie Haas and Viscera, and Snitsky and Val Venis. They then entered a lengthy feud with The Highlanders, whom they eventually defeated to retain the championship at the Unforgiven pay-per-view in September. The Squad as a whole later began a losing streak with separate members losing singles matches to Ric Flair on consecutive episodes of Raw, until Kenny managed to defeat him on the October 23 episode. It was then announced that Flair and a WWE legend, selected by interactive voting, would wrestle the team for the World Tag Team Championship at the Cyber Sunday pay-per-view in early November. The fans chose Roddy Piper, and he and Flair defeated Kenny and Mikey to win the championship.
The group disbanded on the November 27 episode of Raw, when they were defeated in a five-on-three handicap match by DX and Flair. In a backstage segment later that night, DX placed all members into a crate.
On September 15, 2008, Nicky re-debuted on Raw (as a heel), introducing himself in a backstage segment under the name "Dolph Ziggler". On October 10, Ziggler was suspended for 30 days for a violation of WWE's Wellness Program policy. He returned to Raw on November 17 in a backstage segment with Rey Mysterio and Shawn Michaels. In his first match on Raw under the Ziggler name, he lost to Batista on the December 1 episode. The following week he got his first victory as Ziggler, by countout, against R-Truth. The next week on Raw, he picked up his first televised pinfall victory, when he defeated Charlie Haas. Ziggler competed in the 2009 Royal Rumble match, in which he was eliminated by Kane after 21 seconds.
On April 15, 2009, Ziggler was drafted to the SmackDown brand as part of the 2009 Supplemental Draft. He made his debut on the April 17 episode of SmackDown, defeating the United States Champion, Montel Vontavious Porter (MVP) in a non-title match, and, as a result, the following week he demanded a match for the championship. On the May 1 episode of SmackDown, however, he failed to win the championship, after he was pinned by MVP. Ziggler then started a rivalry with The Great Khali, losing to him by disqualification after attacking Khali with a steel chair As a result, Khali began coming out to the ring during and after Ziggler's matches, in attempt to gain revenge and to stop Ziggler from cheating. Over the next few weeks, Ziggler would defeat Khali by countout and disqualification after making it look like Khali had struck him with a steel chair. At The Bash pay-per-view, Ziggler defeated Khali in a No Disqualification match by pinfall, after Kane interfered and attacked Khali.
Ziggler then entered an on-screen relationship with WWE Diva Maria and she became his valet. He simultaneously started a scripted rivalry with Intercontinental Champion Rey Mysterio, who defeated Ziggler at the Night of Champions and SummerSlam pay-per-views to retain the championship. In September, Mysterio lost the Intercontinental Championship to John Morrison, and Ziggler entered a feud with Morrison after defeating him by countout in a non-title match, but lost to him at the Hell in a Cell pay-per-view. On the episode of SmackDown following Hell in a Cell, Ziggler ended his on-screen relationship with Maria after she accidentally cost him a match against Morrison for the Intercontinental Championship. He again failed to win the Intercontinental title from Morrison twice, wrestling him to a double countout on the November 13 episode of SmackDown and losing a two-out-of-three falls match the following week to end the feud. On the February 26, 2010 episode of SmackDown, Ziggler defeated John Morrison and R-Truth in a triple threat qualifying match to compete in the Money in the Bank ladder match at WrestleMania XXVI, but was ultimately unsuccessful.
In June 2010, he began a romantic storyline with Vickie Guerrero, who began accompanying him to the ring. On the July 9 episode of SmackDown, Ziggler defeated Chavo Guerrero and Montel Vontavious Porter in a triple threat match to qualify for the SmackDown Money in the Bank ladder match at the Money in the Bank pay-per-view, where he once again failed to win the match. On July 28 at the tapings of the August 6 episode of SmackDown, Ziggler defeated Kofi Kingston to win the WWE Intercontinental Championship for the first time. In his first title defense at SummerSlam, he retained the championship against Kingston when the match ended in a no contest due to interference from The Nexus. Ziggler was able to make a successful title defense against Kingston at the Night of Champions pay-per-view, and against Kaval at Survivor Series.
In November 2010, Ziggler was chosen a Pro for the fourth season of NXT, with Jacob Novak as his rookie. On the January 4, 2011 episode of NXT, Ziggler won a battle royal to earn the right to choose a new rookie, and chose Byron Saxton. His original rookie, Novak, was the first rookie eliminated later that night. On February 8, 2011, Ziggler's second rookie, Byron Saxton, was also voted off of NXT.
Ziggler successfully retained the Intercontinental Championship at TLC: Tables, Ladders and Chairs in a three-way ladder match against Kingston and Jack Swagger, but lost the title to Kingston at SmackDown on January 4, ending a five-month reign at 160 days. That same night, Ziggler won a four-way match against Cody Rhodes, Drew McIntyre and The Big Show to become the number one contender to the World Heavyweight Championship. At the Royal Rumble, Ziggler was unsuccessful in his title match against Edge. On February 4, Ziggler's storyline girlfriend Vickie Guerrero, who was the acting General Manager of SmackDown, banned the spear – Edge's finishing move – and decided that if Edge used it, Ziggler would be awarded the championship. Ziggler was again defeated by Edge in a rematch on the February 11 episode of SmackDown, but because Edge used the spear, Guerrero declared Ziggler the new champion on the February 14 episode of Raw. Prior to Ziggler's official coronation ceremony on SmackDown on February 18, Guerrero also fired Edge, claiming that he had attacked SmackDown General Manager Theodore Long several weeks prior. However, Long interrupted Ziggler's ceremony and accused Guerrero of orchestrating the attack, prompting Guerrero to reveal Ziggler as the attacker and Long to rehire Edge. Long also gave Edge a rematch against Ziggler, who lost the championship back to Edge and was then fired by Long.
On the March 7 episode of Raw, Ziggler was introduced as the newest member of the Raw roster, and defeated John Morrison in a singles match; Ziggler was accompanied by Guerrero, who had also been fired from SmackDown, but she was forced to earn her spot on the Raw roster. Ziggler, along with Guerrero, and LayCool then feuded with Morrison, Trish Stratus, and Jersey Shore guest star Snooki, culminating in a mixed tag team match at WrestleMania XXVII which Ziggler and his team lost. On the April 18 episode of Raw, Vickie introduced the "new and improved" Ziggler, who came out with his hair cut short and brown and went on to defeat Evan Bourne in a singles match. Ziggler had re-bleached his hair by the May 23 episode of Raw.
Ziggler beat United States Champion Kofi Kingston in a non-title match on the May 30 episode of Raw, leading to a championship match at Capitol Punishment which Ziggler won to earn his first United States Championship. The next night on Raw, Kingston invoked his rematch clause in a two out of three falls match and won via disqualification, allowing Ziggler to retain. After Jack Swagger suggested to Guerrero that she should manage him in addition to Ziggler, a jealous Ziggler teased tension with Swagger. This, coupled with Ziggler's concurrent feud with Alex Riley, led Ziggler to defend and retain his United States Championship in a fatal four-way match against Swagger, Riley, and John Morrison at Night of Champions. On the September 19 episode of Raw, Ziggler lost a non-title match to Zack Ryder when guest star Hugh Jackman helped Ryder by punching Ziggler in the face. Although Ziggler later claimed to have a broken jaw due to Jackman's punch, it was reported that the supposed injury was fake. Later that night, Guerrero officially began managing Swagger, and Swagger began interfering in Ziggler's matches to help him win. Ziggler and Swagger unsuccessfully challenged Air Boom for the WWE Tag Team Championship at Hell in a Cell and at Vengeance, where Ziggler also successfully defended the United States Championship against Ryder. He went on to successfully defend the championship against Morrison at Survivor Series. At TLC: Tables, Ladders and Chairs, Ziggler lost the United States Championship to Ryder.
On the December 26 episode of Raw, Ziggler defeated WWE Champion CM Punk in a gauntlet match for a championship opportunity following interference from John Laurinaitis. The following Raw, Ziggler defeated Punk by countout after Laurinaitis interfered again; as a result, Ziggler did not win the championship. At the 2012 Royal Rumble pay-per-view, Ziggler failed to capture the WWE Championship from CM Punk. At the Elimination Chamber, Ziggler failed again to capture the WWE Championship after being eliminated second by Chris Jericho.
On the February 27 Raw, Ziggler and Swagger unsuccessfully challenged Primo & Epico for the WWE Tag Team Championship in a Triple Threat tag team match, also involving Kofi Kingston and R-Truth. On the March 19 Raw, Ziggler and Swagger were announced as the newest members of Team Johnny for the 12-man tag team match at WrestleMania XXVIII and on the April 2 Raw, Ziggler and Swagger unsuccessfully challenged Santino Marella for the United States Championship in a triple threat match. After the match, Ziggler began a feud with Brodus Clay, who attacked Ziggler with a headbutt after he and Swagger tried to attack Marella. On the following episode of Raw, Ziggler and Swagger were defeated by Clay and Marella in a tag team match. In the following weeks, Ziggler and Swagger lost to Clay and Hornswoggle in singles and tag matches. At Extreme Rules, Ziggler was again defeated by Clay. In May, Ziggler and Swagger unsuccessfully challenged Kofi Kingston and R-Truth for WWE Tag Team Championship, first at Over the Limit and second on the May 28 episode of Raw, resulting in Ziggler showing signs of wanting to break away from Guerrero and Swagger.
On the June 11 episode of Raw, Ziggler defeated The Great Khali, Swagger and Christian in a fatal four-way elimination match to become the number one contender to the World Heavyweight Championship, but at No Way Out, Ziggler lost the title match to champion Sheamus. On the following Raw, Guerrero, finally tired of the bickering between Ziggler and Swagger, arranged for a match between them; Ziggler won the match and Guerrero's affections. Ziggler received another shot at the World title on the June 29 SmackDown, but was again defeated by Sheamus in a triple threat match, also involving Alberto Del Rio.
On the July 3 SmackDown, Ziggler defeated Alex Riley to qualify for a spot in the World Heavyweight Championship Money in the Bank ladder match. At the Money in the Bank pay-per-view, Ziggler won the Money in the Bank ladder match to guarantee him the opportunity to challenge for the World Heavyweight Championship at a time of his choosing within the next year. Later that night, Ziggler attempted to cash in the briefcase on Sheamus after Alberto Del Rio attacked him after their match, but Del Rio stopped Ziggler from cashing in. On the following episode of SmackDown, Ziggler again attempted to cash in the briefcase on Sheamus following a tag team match with Alberto Del Rio, but was laid out by Rey Mysterio and Sheamus before he could do so. During this time, Ziggler began a feud with Chris Jericho after claiming he had lost his touch, which resulted in Jericho attacking him on two occasions, and defeating him in a singles match at SummerSlam. The night after SummerSlam, Ziggler defeated Jericho in a rematch; as a result Ziggler retained his Money in the Bank contract and Jericho's WWE contract was terminated. Following this, Ziggler began feuding with Randy Orton on SmackDown four days later, after Orton hit him with an RKO when Ziggler tried to cash his Money in the Bank contract on a vulnerable Sheamus. The following week on SmackDown, Ziggler faced Orton in a match that was won by Orton, Ziggler defeated him in a rematch on Raw by pinning him while holding his tights. Ziggler faced Orton again at Night of Champions where he lost again, ending the feud. On November 18 at Survivor Series, Ziggler captained the traditional 5-on-5 elimination tag team match opposite Mick Foley and won the match by last pinning Orton, making him the sole survivor of the match.
Ziggler then began feuding with John Cena after he sided with Vickie Guerrero to help defame Cena and AJ Lee by alleging they had a romantic relationship. On December 16 at TLC: Tables, Ladders and Chairs, Ziggler retained his Money in the Bank briefcase in a ladder match after AJ interfered and turned on Cena. The following night on Raw, while trying to diffuse an argument between Vickie and AJ, AJ unexpectedly kissed Ziggler, leaving him confused. Ziggler then attempted to cash in his Money in the Bank briefcase on Big Show after Show was assaulted by Sheamus, but he was attacked by Cena before the match could start. Later, Ziggler teamed with AJ to face Cena and Vickie Guerrero, however, the match ended in a disqualification after the debuting Big E Langston attacked Cena, also starting an on-screen relationship between Dolph and AJ. Ziggler ended 2012 having wrestled the second most TV/PPV matches that year with 90; however, he had the most TV/PPV losses with 57. Ziggler ended his feud with Cena after losing to him on the January 7, 2013, episode of Raw, in a singles match and in steel cage match the following week, despite outside interference from AJ and Langston in both matches. On the January 21 episode of Raw, Ziggler won a Beat the Clock Challenge to earn the right to choose what number he can enter in the Royal Rumble match, first or second. Six days later at the Royal Rumble, Ziggler entered at number one and lasted nearly fifty minutes before being eliminated by Sheamus. During the match, Ziggler resumed his feud with the returning Chris Jericho whom Ziggler managed to eliminate. The following night on Raw, Ziggler and Jericho were placed in a "Strange Bedfellows" match against WWE Tag Team Champions Team Hell No (Daniel Bryan and Kane), but they lost when Kane hit a chokeslam on Ziggler and pinned him after Jericho framed him for pushing Kane. On the February 18 episode of Raw, Ziggler was defeated by World Heavyweight Champion Alberto Del Rio by submission in a non-title match, and afterwards Langston attacked Del Rio and then Ziggler made a failed attempt to cash in his Money in the Bank briefcase after Del Rio's ring announcer Ricardo Rodriguez ran off with it. After defeating WWE Tag Team Champions Daniel Bryan and Kane in singles matches due to interference from Langston, Ziggler and Langston were given a shot at their titles. The title match took place on April 7 at WrestleMania 29, where Ziggler and Langston unsuccessfully challenged Bryan and Kane for the WWE Tag Team Championship.
The following night on Raw, Ziggler cashed in his Money in the Bank contract on an injured Alberto Del Rio to win his second World Heavyweight Championship. After gaining the World Heavyweight Championship, Ziggler began feuding with Del Rio and Jack Swagger over the title. Ziggler was originally booked to face Del Rio and Swagger in a three-way ladder match at Extreme Rules; however, Ziggler suffered a legitimate concussion at a SmackDown taping, thus removing their match from the pay-per-view and resulting in Ziggler being absent from television for a month. On June 16 at Payback, Ziggler faced Del Rio in his first title defense of the World Heavyweight Championship and during the match, a double turn took place; Ziggler turned face by displaying a never-say-die attitude while Del Rio turned heel by repeatedly and ruthlessly targeting his head to take advantage of his concussion, win the match, and end Ziggler's reign at 69 days. On July 14 at Money in the Bank, AJ cost Ziggler his title rematch against Alberto Del Rio, after she prematurely snuck into the ring and hit Del Rio with her own title, prompting a disqualification. On the following Raw, Ziggler ended his relationship with AJ due to her actions the previous night and AJ exacted revenge by costing Ziggler a non-title match against Del Rio, then she attacked Ziggler and unleashed Langston on him.
On the July 29, 2013 episode of Raw, Ziggler defeated Big E Langston via disqualification after AJ Lee attacked Ziggler. In a rematch on the following week, Ziggler was defeated by Langston after a distraction by AJ and Kaitlyn. This led to a mixed tag team match at SummerSlam, where Ziggler and Kaitlyn defeated Big E and AJ. Ziggler was later unsuccessful in capturing the United States Championship, when he lost to Dean Ambrose, at Night of Champions and on the October 16 episode of Main Event. Ziggler also failed to win the Intercontinental Championship from Curtis Axel on the November 11 episode of Raw. In December, Ziggler lost two number one contender matches for the Intercontinental Championship, first to Damien Sandow and later to Fandango.
At the Royal Rumble on January 26, 2014, Ziggler entered the Royal Rumble match, but was eliminated by Roman Reigns. On April 6 at WrestleMania XXX, Ziggler competed in the 31-man Andre the Giant Memorial Battle Royal, but was eliminated by Alberto Del Rio. On June 29 at Money in the Bank, Ziggler competed in the Money in the Bank ladder match for a WWE World Heavyweight Championship contract, but the match was won by Seth Rollins. Ziggler later competed in a Battle Royal for the vacant Intercontinental Championship on July 20 at Battleground; however, he was abruptly eliminated from behind by The Miz. After Ziggler defeated Miz in a non-title match the following night on Raw, he received a rematch at SummerSlam, where he defeated Miz to win the championship for a second time. The next night on Raw, Ziggler successfully retained his title against Miz, after he was counted out. At Night of Champions, Ziggler dropped the title to Miz, only for Ziggler to win it back the following night on Raw. Ziggler then retained the championship against Cesaro on September 26 episode of SmackDown, in a triple threat match against Cesaro and Miz the next week on Raw and at Hell in a Cell against Cesaro in a 2-out-of-3 falls match.
On the October 28, 2014 episode of Raw, Ziggler and John Cena shook hands together backstage, which The Authority interpreted as a deal to plot against them. As a result, Ziggler was put in a match against Kane, which Ziggler won. Ziggler then joined Team Cena at Survivor Series. On the November 10 episode of Raw, Ziggler was brutally attacked by the returning Luke Harper. The following week, Harper was awarded a title match against Ziggler, which Harper won with assistance from The Authority, ending Ziggler's reign at 56 days. At Survivor Series, Ziggler emerged as the sole survivor for a second time. Ziggler contributed to Rusev being counted out, then after all his teammates were eliminated, he pinned Kane and Luke Harper. Triple H twice prevented Ziggler from pinning final opponent Seth Rollins, but the debuting Sting provided an assist to help Ziggler win the match, thus ousting the Authority from power. At TLC on December 14, Ziggler defeated Harper in a ladder match to win his fourth Intercontinental Championship. On the December 16 episode of SmackDown, Ziggler finally defeated Seth Rollins in a singles match after failing numerous times before. On the first Raw of 2015 (dated January 5), the recently reinstated Authority forced Ziggler to defend his Intercontinental Championship against Bad News Barrett and he initially won. After Barrett then attacked and injured Ziggler's shoulder, Kane declared the match as two-out-of-three falls, Barrett proceeded to defeat Ziggler for the title after Kane distracted him. Later that night, Ziggler alongside Ryback and Erick Rowan were fired by the Authority.
On the January 19 episode of Raw, Sting provided another assist, as John Cena won Ziggler, Ryback and Rowan's jobs back. Ziggler returned to television on the next SmackDown and qualified for the Royal Rumble match by beating Barrett in a non-title match. In the 2015 Royal Rumble match, Ziggler entered as the last entrant, scored two eliminations but was quickly eliminated by Big Show and Kane. At Fastlane, Ziggler competed together with Rowan and Ryback in a six-man tag team match against Rollins, Big Show and Kane, which they lost. On the March 5 episode of SmackDown, Ziggler was announced as a participant in the 7-man ladder match for the Intercontinental Championship at WrestleMania 31, which was won by Daniel Bryan.
After losing an Intercontinental Championship match against Daniel Bryan on the Raw following WrestleMania 31, Ziggler was attacked and Brogue kicked by the returning Sheamus. Claiming that "the era of underdogs (like Ziggler) is over", Sheamus and Ziggler started a feud, with Sheamus challenging Ziggler in a Kiss Me Arse match at Extreme Rules, which Ziggler won. However, Sheamus refused to follow the stipulation, and instead made Ziggler kiss his arse. Ziggler lost the rematch against Sheamus at Payback. Ziggler participated in the Elimination Chamber match for the vacated Intercontinental Championship; other participants were winner Ryback, King Barrett, R-Truth, Sheamus who eliminated Ziggler, and Mark Henry at Elimination Chamber. At Money in the Bank, Ziggler competed in the Money in the Bank ladder match, which was won by Sheamus. On July 4 at The Beast in the East live event in Japan, Ziggler and John Cena defeated King Barrett and Kane in the main event.
Ziggler became involved in an on-screen love affair with Lana, the former manager of Rusev, when she kissed him at Raw on May 25, with Lana serving as Ziggler's valet during his matches. During this time, Ziggler started incorporating elements of 80's glam rock fashion into his entrance and ring attire; typical of 80's bands like Mötley Crüe and Poison. In June, after Ziggler and Lana confirmed their storyline relationship, Summer Rae allied with Rusev to even the odds. After an attack by Rusev, Ziggler suffered a bruised trachea in storyline, which was to give him some time off to film a new WWE Studios movie, titled 6:42. Ziggler returned on the August 17 episode of Raw, aiding Lana during a confrontation against Rusev and Summer Rae. This altercation prompted a match between Ziggler and Rusev at SummerSlam, which ended in a double countout due to interference from Lana and Rae. In a rematch on September 20 at Night of Champions, Ziggler emerged victorious. On October 11, the feud ended. The following night on Raw, Ziggler unsuccessfully challenged John Cena for the United States Championship.
On the October 22 episode of SmackDown, Ziggler started a feud with the debuting Tyler Breeze, who aligned with Summer Rae and attacked Ziggler. Ziggler entered a tournament for the vacant WWE World Heavyweight Championship, defeating The Miz in the first round match before being eliminated by Dean Ambrose. Ziggler and Breeze continued their feud, which culminated in a match between the two at Survivor Series, which Ziggler lost. Ziggler would then enter a feud with Kevin Owens with the pair trading victories throughout the rest of December and beginning of 2016. Ziggler entered the 2016 Royal Rumble as the 28th entrant, lasting 7 minutes, but was eliminated by the eventual winner, Triple H. The next night on Raw, Ziggler faced Kevin Owens in a losing effort, but defeated him the following two weeks in a row. On the February 15 Raw, Ziggler was involved in a fatal five-way match for the Intercontinental Championship, where Owens regained the title after pinning Tyler Breeze. At Fastlane, Ziggler challenged Owens to a match for the Intercontinental Championship, which he lost. In the following weeks, Ziggler began to re-ignite his feud with The Authority, and on the March 14 episode of Raw, he confronted Triple H and Stephanie McMahon. This resulted in Ziggler being granted a match against Triple H where if he won, he could pick his match at WrestleMania (excluding the WWE World Heavyweight Championship match); however, Ziggler lost. At WrestleMania 32, Ziggler competed against Kevin Owens, Sami Zayn, The Miz, Stardust, Sin Cara and Zack Ryder in a ladder match for the Intercontinental Championship, which was won by Ryder.
After WrestleMania 32, Ziggler went to a double countout with Baron Corbin on the April 4 episode of Raw, leading to Corbin hitting an End of Days outside of the ring to Ziggler, igniting a feud in the process. On the Payback pre-show, Ziggler faced Baron Corbin in a winning effort. The two then had a no disqualification match at Extreme Rules where Corbin won after hitting a low blow on Ziggler. Following Extreme Rules, on the May 23 episode of Raw, Ziggler had a confrontation backstage with Corbin and challenged him to a technical wrestling match the next week. In that match, Ziggler intentionally got himself disqualified when he kicked Corbin in the groin immediately after the match began. This led to a rubber match at Money in the Bank, which Corbin won to end their feud.
On July 19 at the 2016 WWE draft, Ziggler was drafted to SmackDown. On the July 26 episode of SmackDown, Ziggler won a six-pack challenge against AJ Styles, Apollo Crews, Baron Corbin, Bray Wyatt, and John Cena to become the number one contender for the WWE World Championship. On the August 2 edition of SmackDown, Ziggler defended his contendership against Bray Wyatt, to prove to his critics that he was worthy of being in the main event. Ziggler won the match, but was attacked afterwards by Wyatt and Erick Rowan, who also laid out Dean Ambrose when he attempted to save Ziggler. On August 21 at SummerSlam, Ziggler was defeated by Ambrose. On the following edition of SmackDown, AJ Styles began taunting Ziggler about his defeat, setting up a match with the stipulation that if Ziggler won, the main event at Backlash would have been a triple threat. He would go on to lose the match. At Backlash, Ziggler failed to win The Miz's Intercontinental Championship after Maryse sprayed something at Ziggler whilst Miz distracted the referee. After failing to win the Intercontinental title in the following weeks, Ziggler challenged him for the title one more time at No Mercy with his career on the line. On the October 4 SmackDown, in a MizTV segment, Miz aired a parody "documentary" showing Ziggler's lowest career moments. Afterwards, he introduced Ziggler's former teammates, Kenny and Mikey of The Spirit Squad, who would end up attacking Ziggler on orders from Miz. At No Mercy, Ziggler defeated The Miz, winning the Intercontinental Championship for the fifth time and saving his career.
On the November 1 episode of SmackDown, Ziggler's first successful title defense was against Curt Hawkins, who he defeated with in seven seconds, he also made a Survivor Series challenge to anybody on the Raw roster. On the following episode of Raw, Sami Zayn defeated Rusev to challenge for the title; however, Ziggler defended his championship against Miz on the 900th episode of SmackDown, and was defeated after a distraction by Maryse, ending his reign at 37 days. On the November 22nd edition of SmackDown, it was announced that Ziggler would face Miz in a Ladder match at the TLC: Tables, Ladders, & Chairs event for the Intercontinental Championship in what was advertised as their final match, where Ziggler was defeated. On the December 13 edition of SmackDown, Ziggler pinned Dean Ambrose in a fatal four-way elimination match also involving The Miz and Luke Harper, to become the number one contender to AJ Styles' WWE Championship. The following week, Baron Corbin confronted Ziggler, and the two had a match with Ziggler's number one contender's spot on the line. The match ended in a double count-out and Daniel Bryan made the December 27 episode's WWE Championship match a triple-threat between Styles, Ziggler, and Corbin. In that match, Styles retained the WWE Championship after pinning Ziggler.
On the January 3, 2017 episode of SmackDown, after he lost to Baron Corbin, Kalisto came to the save of Ziggler during a post match assault by Corbin, he superkicked Kalisto, turning heel in the process. He would then assault Apollo Crews backstage after being questioned for his actions. On the January 17 episode of SmackDown, he was invited onto a special King's Court segment with Jerry Lawler. He proudly took responsibility for the heart attack suffered by Lawler in September 2012, he then superkicked Lawler in the chest before leaving the ring, thus cementing his heel turn. On January 29, Ziggler entered the Royal Rumble match at #24 but was eliminated by Brock Lesnar. On the following episode of SmackDown, Ziggler defeated Kalisto in a singles match. After the match, Ziggler attempted to remove Kalisto's mask, but was stopped by Apollo Crews. At Elimination Chamber, Ziggler lost to Apollo Crews and Kalisto in two-on-one handicap match. Following the match, Ziggler attacked the victors, stomping on Crews' ankle after placing it in a chair. This led to a chairs match on the February 28 SmackDown, where Ziggler was victorious. On April 2 on the WrestleMania 33 kickoff show, Ziggler was part of the André the Giant Memorial Battle Royal, managing to eliminate R-Truth, Rhyno and Tian Bing, from which he was eliminated by the eventual winner Mojo Rawley. On the April 18 episode of SmackDown, Ziggler failed to become the #1 contender for the WWE Championship after losing a six-pack challenge match. The next week on SmackDown Live, he had a confrontation with Shinsuke Nakamura. Ziggler and Nakamura faced each other at Backlash, where Nakamura emerged victorious. On the May 23 episode of SmackDown Live, it was announced Ziggler would be a participant in the 2017 Money in the Bank ladder match for a WWE Championship match contract. A week later, he defeated fellow participant AJ Styles via pinfall in the main event. Ziggler would fail to win the Money in the Bank ladder match, which was instead won by Baron Corbin. On the July 4 episode of SmackDown Live, Ziggler participated in the Independence Day Battle Royal for the WWE United States Championship in a losing effort, being the first to be eliminated.
After some time away from TV, Ziggler returned on the August 22 edition of SmackDown Live to declare that he would undergo a gimmick change on the following week's edition. He later started mocking, week after week, the entrances of current and former wrestlers such as John Cena, Naomi, Shawn Michaels and Randy Savage. Ziggler believed that fans only cared about elaborated entrances, and not about the in-ring performances, where he claimed he was the best. However, after mocking The Undertaker's entrance, Ziggler was interrupted by Bobby Roode, who challenged Ziggler to a match at Hell in a Cell, which Ziggler accepted. At the event, Ziggler seemed to enter with his usual music and titantron graphics, but the music was scratched off and the graphics turned off, and he simply entered with no music or Titantron (like a wrestler in the 1980s or prior). He was then defeated by Roode, who pinned him while holding his tights. Right after that, Ziggler attacked Roode from behind with a Zig Zag. On the October 17 edition of SmackDown Live, Ziggler defeated Roode in a rematch by pinfall while holding his tights, similar to how Roode defeated him. On the October 31 edition of SmackDown, Ziggler failed to earn a spot on Team SmackDown for the Survivor Series five-on-five elimination match against Raw after being defeated by Roode in a two-out-of-three falls match. Ziggler was involved in a verbal backstage confrontation with both Roode and United States Champion Baron Corbin on the December 5 episode of SmackDown, where Roode defeated Corbin via disqualification after being attacked by Ziggler. The following week, Roode interfered in a match between Ziggler and Corbin in similar fashion, resulting in a disqualification victory for Ziggler. At Clash of Champions, Ziggler defeated Corbin and Roode in a triple threat match to win his second United States Championship. On the following episode of SmackDown on December 19, Ziggler held a celebration that was a retrospective of his WWE career; he said that the fans did not deserve him and placed the title belt in the ring before leaving. A week later, general manager Daniel Bryan said that Ziggler was nowhere to be found and had indeed vacated his title, so that a tournament to crown a new champion would be held (which was won by Bobby Roode).
Ziggler returned at the Royal Rumble on January 28, 2018, as the surprise number thirty entrant in the men's Royal Rumble match. After eliminating Goldust, however, Ziggler was eliminated by Finn Bálor. After the February 6 episode of SmackDown, Commissioner Shane McMahon announced on Twitter that the winner of a match between Ziggler and Baron Corbin the following week would be added to the WWE championship match to make it a fatal four-way at Fastlane. Before that match started, Kevin Owens and Sami Zayn attacked Corbin in the backstage area and later went after Ziggler to prevent either from being added. In response, Shane scheduled Owens to face Corbin and Zayn to face Ziggler with both Corbin and Ziggler being added if they won their respective matches, while also threatening that if Owens or Zayn interfered in the other's match, that person would be removed from the title match. Corbin and Ziggler won their respective matches, thus making it a fatal five-way for the WWE Championship at Fastlane. Over the following weeks, Ziggler was attacked by Owens during a match against Zayn and interfered in several of his opponent's matches, including the newly added John Cena for what would later be a six-pack challenge. On the pay-per-view, Styles would retain his title by pinning Kevin Owens. Ziggler took part in the André the Giant Memorial Battle Royal at WrestleMania 34, but did not win the trophy.
On April 16, Ziggler was moved to Raw as part of the Superstar Shake-up. On that night, Ziggler allied himself with the returning Drew McIntyre to attack Titus Worldwide (Titus O'Neil and Apollo Crews). The following week, Ziggler and McIntyre defeated Titus Worldwide. On the June 18 episode of Raw, Ziggler answered Seth Rollins' open challenge for the Intercontinental Championship and defeated Rollins to capture the title for a sixth time. After weeks of McIntyre assisting Ziggler in all situations, including Extreme Rules, where Ziggler defeated Rollins 5-4 in sudden death overtime of a 30-Minute Iron Man match, Dean Ambrose returned on the August 13 episode of Raw to even the odds for Rollins. At SummerSlam, Rollins (with Ambrose in his corner) defeated Ziggler to win back the championship.
On the September 3 episode of Raw, Ziggler and McIntyre temporarily formed a stable with Braun Strowman known as "The Dogs of War" to combat the newly-reunited The Shield (Roman Reigns, Seth Rollins and Dean Ambrose). Later that night, they won the Raw Tag Team Championship by defeating The B-Team (Bo Dallas and Curtis Axel). They then successfully defended their titles at Hell in a Cell against Rollins and Ambrose. At the Super Show-Down event, Ziggler teamed with McIntyre and Strowman in a losing effort to The Shield in a six-man tag team match. Over the next two weeks, the respective groups faced each other again on Raw, with The Dogs of War winning the first match, but losing the latter after Ziggler got pinned by Ambrose. During both matches, tensions arose between Ziggler, McIntyre and Strowman, who felt he was carrying the group. After losing the last match, Strowman turned on Ziggler and attacked him, before being attacked by McIntyre.
A week later, Ziggler and McIntyre lost the Raw Tag Team Championship to Rollins and Ambrose on the October 22 episode of Raw. On the December 3 episode of Raw, the alliance between Ziggler and McIntyre ended when McIntyre claimed that Ziggler was "a means to an end to get him into a prominent position" and ended their association. The two later faced each other in a match, which Ziggler won after interference from Finn Bálor. After the three men had traded wins among each other and interfered in each others matches over the next few weeks, McIntyre defeated Ziggler in a cage match on the December 31 episode of Raw.
After this, Ziggler was off television until his appearance at the Royal Rumble match at the titular event as participant number 28, eliminating McIntyre and lasting until the final three, before being eliminated by Braun Strowman. He would then disappear again from WWE television without notice.
After a four-month hiatus, Ziggler returned on the May 21 episode of SmackDown Live and attacked WWE Champion Kofi Kingston. Ziggler then challenged Kingston to a championship match at Super Showdown, which Kingston accepted. Kingston defeated Ziggler following interference from fellow New Day member Xavier Woods. Backstage after the match, Ziggler challenged Kingston to a rematch at Stomping Grounds in a steel cage match. Kingston defeated Ziggler via escaping the cage.
On the July 2 episode of SmackDown Live, Ziggler interrupted The Kevin Owens Show which featured Shane McMahon and Drew McIntyre. After he and Owens got into an argument, McMahon announced that night's main event: Ziggler and Owens would team together to face Heavy Machinery, where the winning team would be inserted into the SmackDown Tag Team Championship match at Extreme Rules. Ziggler and Owens lost the match. Afterwards, Owens delivered a Stunner to Ziggler. The two had a match at Extreme Rules, where Owens won in 17 seconds. At WWE Smackville, Ziggler unsuccessfully challenged Kingston for the WWE Championship in a triple threat match (also including Samoa Joe).
On the July 23 episode of SmackDown Live, Ziggler interrupted MizTV featuring Shawn Michaels. After Ziggler laid out The Miz, he delivered a superkick to Michaels. On the August 5 episode of Raw, a contract signing for a match between Ziggler and Miz at SummerSlam took place. After Ziggler signed the contract, Miz announced that the two would have a match on the following week's Raw, not SummerSlam. After Michaels denied he was Ziggler's SummerSlam opponent, Goldberg emerged and signed the contract. Goldberg defeated Ziggler at the event.
On the August 26 episode of Raw, Ziggler teamed with Robert Roode to win a tag-team turmoil match to earn a Raw Tag Team Championship match against Seth Rollins and Braun Strowman at Clash of Champions. At the event, Ziggler and Roode would successfully win the titles. On the October 14 episode of Raw, Ziggler and Roode lost the titles to The Viking Raiders (Erik and Ivar) and they were drafted to SmackDown as part of the 2019 WWE Draft.
On December 27, 2019, Ziggler lost to Roman Reigns during a match recorded for Fox's New Year's Eve special after that night's episode of SmackDown. Ziggler was also eliminated by Reigns from the Royal Rumble match at the namesake pay-per-view. At Super ShowDown in Saudi Arabia, Ziggler faced hometown hero Mansoor in a losing effort. A week later at Elimination Chamber, Ziggler and Roode competed in the namesake match for the SmackDown Tag Team Championships, where the champions The Miz and John Morrison retained. Due to the pandemic, Roode was forced to stay in his native Canada, effiectively putting their tag team on hiatus. At the same time, Ziggler entered a feud with Otis over the affections of Mandy Rose, where Ziggler used underhanded tactics to secure a Valentine's Day date and short-term relationship. However, he was exposed and faced Otis in a match at WrestleMania 36, where he lost. After a few more assaults and promos, the feud ended when Otis defeated Ziggler in a Money in the Bank qualifier.
On the June 22, 2020 episode of Raw, Ziggler made his return to the brand (along with tag partner Robert Roode) and challenged Drew McIntyre for the WWE Championship at Extreme Rules, which McIntyre accepted. At the event on July 19, Ziggler failed to win the title. As part of the 2020 draft in October, both Ziggler and Roode were drafted back to the SmackDown brand. On the January 8, 2021 episode of SmackDown, Ziggler and Roode defeated The Street Profits (Angelo Dawkins and Montez Ford) to win the SmackDown Tag Team Championship. At the Royal Rumble, Ziggler entered the Royal Rumble match at number six, but was eliminated by Kane.
At WrestleMania SmackDown on April 8, Roode and Ziggler defeated Alpha Academy, The Mysterios and The Street Profits in a fatal four-way match to retain the titles. On the April 16 episode of SmackDown, Ziggler and Roode would have another successful title defense as they defeated The Street Profits. At WrestleMania Backlash, Ziggler and Roode lost the titles to The Mysterios, ending their reign at 128 days. As part of the 2021 Draft, both Ziggler and Roode were drafted to the Raw brand. On the October 25 episode of Raw, Ziggler and Roode defeated The Street Profits and Alpha Academy (Chad Gable and Otis) in a number one contender’s match for the Raw Tag Team Championship. Later that night, they faced the champions, RK-Bro (Randy Orton and Riddle), for the titles, but lost. At Survivor Series on November 21, Ziggler participated in a 25-man dual-branded battle royal, eliminating Mansoor before he was eliminated by AJ Styles. Ziggler competed in the 2022 Royal Rumble, entering at number sixteen and lasting over twenty minutes before being eliminated by Bad Bunny and Rey Mysterio.
On the March 8, 2022 special edition of NXT Roadblock, Ziggler defeated Tommaso Ciampa and Bron Breakker in a triple threat match to win the NXT Championship, his first world championship in nearly nine years. With that victory, Ziggler became the first wrestler to hold both the World Heavyweight and NXT Championships. The following week, he successfully defended his title after defeating LA Knight. At NXT Stand and Deliver, he retained the title against Breakker due to inteference from Roode. On the April 4 episode of Raw, Ziggler lost the title to Breakker, ending his reign at 27 days.
On the July 11 episode of Raw, Ziggler returned to help Bobby Lashley and Riddle against Seth Rollins and Theory's underhanded tactics during a tag team match, and after the match, Ziggler would superkick Theory, turning face for the first time since 2017. After weeks of Ziggler interrupting Theory's matches, on the August 15 episode of Raw, Theory defeated Ziggler, ending their feud. In early 2023, Ziggler would enter a rivalry with Mustafa Ali, with the two attempting to out-do the other in singles matches. Ali would later develop a positivity gimmick with Ali going on to defeat Ziggler on the February 14 episode of Raw. Ziggler would later go on to compete unsucessfully in the Andre the Giant Memorial Battle Royal on the WrestleMania edition of SmackDown on March 31. On the April 10 taping of WWE Main Event, Ziggler defeated Tyler Bate.
As part of the 2023 WWE Draft, it was announced that Ziggler was one of the selected superstars whom had signed a free agent contract which in turn allowed him to appear on both Raw and SmackDown as an active roster member whenever he desired. After engaging in a mini-feud with the debuting JD McDonagh, Ziggler was released from his WWE contract on September 21.