In April 1992, he arrived in Extreme Championship Wrestling as a crowd favorite. He won his first ECW Championship from Don Muraco on November 16, 1992, but lost it back to Muraco on April 3, 1993. For the rest of 1993, Sandman would team on and off with JT Smith and be featured regularly. He began a feud with his former tag team partner Tommy Cairo after The Sandman was temporarily blinded following a match and inadvertently struck his valet Peaches. When The Sandman regained his sight and saw Cairo assisting Peaches to her feet, he attacked Cairo. The Sandman subsequently became estranged from his wife. After losing a match against Cairo, that led to Peaches hitting him with a strap profusely, Woman attacked Peaches and led her back to the ring where Sandman held her and Woman applied the strap to her skin before Cairo returned to save her. After this event, Sandman adopted Woman as his new manager. In keeping with The Sandman's character, Woman would open his beers and light his cigarettes prior to matches. She began carrying a Singapore cane with which she would strike The Sandman's opponents. Sandman and Woman faced Cairo and Peaches in a mixed Singapore Caning match on May 14, 1994. After Cairo and Lori defeated their opponents, Lori caned Sandman's crotch until Woman threw salt in her eyes, enabling Sandman to regroup and use his cane on both Lori and Cairo.
During a match against Tommy Dreamer, Sandman's valet Woman attempted to attack Dreamer on his behalf when Dreamer planted a long kiss on her. After the match, Sandman was told by Woman that Dreamer was with Cairo and that they were both sleeping with his wife, which enraged Sandman. Woman wanted to make Dreamer suffer and so lured Dreamer into a match with Sandman wherein whoever lost would have to receive ten strikes from the other with a Singapore cane. After losing the match, Tommy began to take the strokes, when it became clear that Woman intention was to humiliate him by making him beg her for mercy, which he did not do, much to her chagrin, and Dreamer was idolized by the fans for his resolve and the level of disdain for the Sandman was increased.
In late 1994, The Sandman was once again blinded after a lit cigarette was pushed into his eye during an "I Quit" match with Tommy Dreamer. Woman blamed Sandman for the injury and abandoned him. The Sandman subsequently claimed that he would have to retire as a result, with Dreamer responding by dedicating the remainder of his career to The Sandman. Cairo began mocking The Sandman, which led to Dreamer heavily beating him during a match at November to Remember. At Sandman's retirement ceremony during the same event, an attempted reconciliation with Peaches was interrupted by Woman, who caned Lori and threatened Sandman. As Dreamer came to the rescue, Sandman revealed that he was not in fact blinded and attacked Dreamer. The Sandman later revealed that his blinding had been an elaborate ruse concocted to trick Dreamer into hurting Cairo on his behalf. Sandman had to wrestle Dreamer again the following month when he and now reconciled partner Tommy Cairo, teamed up against Cactus Jack and Dreamer, but were defeated by the duo.
Sandman challenged Shane Douglas for the ECW Championship in April 1995, but was attacked by his own valet, Woman, who helped Shane Douglas retain the title. In a rematch at Hostile City Showdown on April 15, 1995, Sandman faced Douglas (who had Woman in his corner) in a rematch. During the course of the match, Woman turned on the now-overconfident Douglas, helping Sandman become the ECW Champion. It was revealed that the entire sequence of events was a double-cross planned all along by Woman to aid Sandman while psychologically destroying Douglas in the process. Douglas attempted to regain the championship in the following months, but left the company before he was able. Sandman's first title defenses after winning the ECW Championship were against Cactus Jack (with the latter never getting the upper hand due to interference by Woman), Terry Funk, 'stickler' referee Bill Alfonso, and Douglas, who was bitter over losing his title.
Sandman's feud with Cactus Jack lasted throughout 1995 and culminated in a series of matches involving barbed wire. In a Texas death match in February 1995, Sandman was hit with a heavy metal frying pan, giving Sandman a legitimate concussion. Throughout the remainder of the match, he was visibly disoriented; several times Cactus Jack hit Sandman with his signature double underhook DDT and again and again Sandman instinctively kicked out. This went on for about a minute before Cactus Jack delivered a legit maneuver, hoping it would keep Sandman down.
On October 25, Sandman lost the title to Mikey Whipwreck in a ladder match. Three days later, Sandman teamed up with then-Television Champion 2 Cold Scorpio to win the ECW Tag Team Championship from The Public Enemy. On December 9, Sandman regained his World Heavyweight title by defeating Whipwreck and Steve Austin in a three-way dance. At the end of the month, 2 Cold Scorpio lost both the Television and Tag Team Championships to Whipwreck in a singles match on December 29, while Sandman became embroiled in his feud with Raven.
Sandman spent the time period from December 1995 through May 1997 engaged in a feud with Raven. On January 27, 1996, Sandman lost the World Heavyweight Championship to Raven and the two would subsequently trade the title back and forth. Sandman joined forces with Raven's nemesis Tommy Dreamer and on October 5, 1996, regained the title by pinning Stevie Richards in an Ultimate Jeopardy tag team match pitting Sandman and Dreamer against Brian Lee and Richards, who replaced Raven when he no-showed the event.
During the feud, Raven allied himself to the returned Peaches, and brainwashed her and Sandman's real-life son into joining his cult-like following, turning him against his father. Raven psychologically attacked Sandman by having his son deny his relationship with his father, telling Tyler that his parents' divorce was Sandman's fault, and making him perform Raven's trademark taunt "The Raven's Crucifix" and other mannerisms. On October 26, 1996, during one match, Tyler interfered to help his father. Afterward, the two embraced, but Raven came from behind with a Singapore Cane and smacked his enemy by piledriving Sandman through the table. Stevie Richards and The Blue Meanie came out with a giant wooden cross and crucified him. On December 7 at Holiday Hell, Sandman again lost the title to Raven in a barbed wire match.
In 1996, the team of Sandman and Tommy Dreamer became more permanent as the duo feuded with anti-ECW team of Sabu and Rob Van Dam, as well as the Dudley Boyz.
At the World Wrestling Federation (WWF)'s In Your House: Mind Games pay-per-view, Sandman, Tommy Dreamer, Paul Heyman and a number of other ECW stars caused a storyline disturbance at ringside during a Caribbean Strap match between Savio Vega and Justin "Hawk" Bradshaw. The disturbance resulted in Sandman whacking Vega over the head with his signature Singapore cane and spitting beer in his face. This event marked the start of the on-air working relationship between Vince McMahon's WWF and Paul Heyman's ECW, and eventually led to ECW appearing on the February 24, 1997 WWF program Raw.
At the ECW premier pay-per-view event Barely Legal, Sandman wrestled a three-way dance with Terry Funk and Stevie Richards, for a shot at the ECW Title later that night, but fell short of the title. In the summer of 1997, the Sandman began a long feud with Sabu. Although he was too injured to compete at Hardcore Heaven 1997, Sandman got involved in a skirmish with Rob Van Damn and Sabu, who then brutalized him to the point of hospitalization, however,he would return later that evening to interference in the main event by assaulting Sabu, leading to Sabu's elimination, costing Sabu the ECW Title. In September of that year, Sabu badly burned the Sandman in a scheduled contest between the two. The damage to Sandman from the burn was considered so bad that the match was discontinued. As a result, Sandman would be out of action until he once again attacked Van Dam and Sabu in the ring that November, earning a measure of revenge on Sabu. This led to their match at the November to Remember pay per view, which was promoted as a major cornerstone and culmination of all the events that year. In the match, Sandman dodged an attempt by Sabu to burn him, however Sabu would go on to win the match. Over the next few months, they competed in high profile specialty matches such as ladder matches, tables matches, and a dueling cane match. In one of the most notable examples, the Sandman fought Sabu in the first ever "Stairway to Hell" match, involving tables, ladders, chairs, and barbwire. After suffering heavy damage, Sandman earned the victory by finally pinning Sabu after hitting him with a cane. However, it wasn't until almost two months later that their feud effectively came to an end at Living Dangerously 1998. This match was heavily promoted and designated the penultimate which featured a dueling canes gimmick. During the match, the combination of Rob Van Dam and Sabu turned out to be too much for the Sandman, which led to him losing the contest.
Over the spring and summer of 1998, Sandman teamed up with Dreamer and Spike Dudley to feud with the Dudley Boyz, finally securing a victory in a six-man match at Heat Wave.
In September 1998, The Sandman joined World Championship Wrestling (WCW). He first appeared in vignettes promoting Raven as a spoiled rich kid and Sandman as his preppy neighbor. The original plan to debut under this gimmick were scrapped. He later debuted under his longtime nickname, Hak when he called out Bam Bam Bigelow and challenged him to a hardcore match on Monday Nitro. During the match, he was defeated by Bigelow and was not named on screen during the entire segment. In his short time there, Hak was mostly involved in angles featuring fellow ECW alumni Raven, Bigelow and Raven's storyline sister Chastity, with whom he developed an on-screen relationship after she turned on Raven. His presence also helped to bolster WCW's fledgling hardcore division. At Uncensored 1999, Hak defeated Bam Bam Bigelow and Raven in a falls count anywhere triple threat match. At Spring Stampede 1999, Hak lost to Bam Bam Bigelow in a hardcore match. At The Great American Bash 1999, Hak defeated Brian Knobbs in another hardcore match. A month later at Bash at the Beach 1999, Hak competed in the Junkyard Invitational, which was won by Fit Finlay. Hak was released from his WCW contract in September 1999.
After leaving WCW in late 1999, Hak, as The Sandman, returned to ECW and remained with the company until its demise in January 2001. He began a feud with Rhino in 2000, losing to him at Hardcore Heaven, Heat Wave, and other shows. On January 7, 2001, at ECW's last pay-per-view, Guilty as Charged, the Sandman won his fifth World Heavyweight Championship in a tables, ladders, chairs, and canes three-way dance with the champion Steve Corino and Justin Credible. After The Sandman won, however, the World Television Champion Rhino came out to the ring and challenged him to an impromptu title match. The Sandman accepted the challenge and after a 60-second match, Rhino defeated The Sandman to become the new World Heavyweight Champion, unifying ECW's two singles titles.
In 2005, he appeared at the World Wrestling Entertainment (WWE) produced ECW One Night Stand pay-per-view event, teaming with Tommy Dreamer to face The Dudley Boyz. The match would see Sandman and Dreamer lose to the Dudleys after Dreamer was powerbombed through a flaming table. In 2006, prior to the June 11 One Night Stand, The Sandman made a number of promotional appearances on WWE programming, first appearing, along with a number of other ECW stars, on Raw attacking John Cena then, two nights later, on the WWE vs. ECW Head to Head special taking part in a battle royal, in which it can be argued that he was the last ECW original eliminated. At One Night Stand, when Eugene made his way to the ring to read a poem expressing his love of ECW, The Sandman came out with his Singapore Cane and caned Eugene to the back.
On June 13, 2006, WWE officially relaunched ECW as a brand equal to Raw and SmackDown! with its own show. In the new ECW, The Sandman was used for the first few weeks as a character who would emerge from the crowd when a non-ECW style character was annoying the audience. Once the character had a few minutes to talk, Sandman appeared and destroyed the character with his cane, often ending the "match" with his signature White Russian Legsweep. This gimmick escalated when Sandman confronted regular ECW fixture Mike Knox while he was attempting to stop his exhibitionist girlfriend, Kelly Kelly, in the middle of her weekly "exposé" strip show. The Sandman began a feud with Knox over this and eventually began teaming up with fellow ECW original Tommy Dreamer to take on Knox and Test in a feud. At the same time Sandman was feuding with Test and Knox, a debuting Matt Striker began to rub him the wrong way and he started a secondary feud with him.
Subsequently, the Sandman has made several short appearances, mostly coming out through the crowd and caning someone whenever some injustice was done. After being briefly included in a feud with Elijah Burke, he became part of the ECW Originals stable and joined their feud with the New Breed. On April 1, 2007, at WrestleMania 23, he teamed with RVD, Sabu, and Dreamer to defeat Marcus Cor Von, Burke, Striker, and Kevin Thorn. On May 16, Sabu was released by WWE and soon after Rob Van Dam left to take a sabbatical from wrestling, leaving Sandman and Dreamer alone to feud with the New Breed. Sandman and Dreamer would team up with CM Punk on multiple occasions, who was also feuding with the New Breed. On the June 4 episode of ECW, Sandman, Dreamer, and Balls Mahoney lost to Bobby Lashley in a hardcore three-on-one handicap match.
On June 17, 2007, Sandman was drafted to the Raw brand via the WWE Supplemental Draft. On the June 18 edition of Raw, Sandman debuted, going after Carlito with his Singapore cane. On the July 2 edition of Raw, Sandman had his first match on Raw, facing Carlito. Carlito won the match due to a disqualification when Sandman struck him with his cane after Carlito tried to use it on him. This started a feud between the two. Sandman did a similar thing next week when he lost to William Regal by disqualification, after hitting Regal and Carlito with his cane. The next week, Sandman faced Carlito again, this time winning when Regal attacked him. The Sandman was saved when Jim Duggan (who had a confrontation with Regal earlier that night) came down to the ring. At The Great American Bash, he lost to Carlito in a Singapore Cane on a Pole match. The Sandman lost in a battle royal to determine the new General Manager of Raw, where he was the last one eliminated by Regal, who had faked an injury and was not in the match until Sandman was the only superstar in the ring; Regal then won after he snuck up on The Sandman and hit him in the back of the head with his boot. His last match was on the September 10 edition of Raw against Santino Marella, which he won by disqualification. Sandman appeared to injure his ankle in this match and was released from his WWE contract on September 12, 2007.