In 1963, Skaaland was a part of the newly created, New York City-based World Wide Wrestling Federation. On June 1, 1967, he collected his only title as one half of the WWWF United States Tag Team Champions, when Tony Parisi gave his half of the title to Skaaland. Skaaland and his partner, Spiros Arion, soon lost the titles to The Sicilians (Lou Albano and Tony Altimore) on July 10, 1967 in Atlantic City, New Jersey. Arion and Bruno Sammartino regained the belts two weeks later, and retired them.
Skaaland then managed Bruno Sammartino and Bob Backlund, with both men winning the WWF World Heavyweight Championship under his tutelage.
In 1978, Skaaland retired from regular wrestling, though he occasionally appeared as a late substitute for wrestlers that couldn't make a show. Backlund's lengthy reign ended on December 26, 1983 when Skaaland threw in the towel while Backlund was trapped in the camel clutch, the finishing move of challenger The Iron Sheik.
In 1994, he was inducted into the WWF Hall of Fame class of 1994 for managing both Sammartino and Backlund to the (W)WWF World Heavyweight Championship. He appeared on WWF television later that year, with Backlund attacking him in order to consolidate his heel turn.
On March 13, 2007, Skaaland passed away.