He participated in amateur wrestling, becoming a sectional champion in the 215 lb class in 1976, and placing 4th at the New York State Championships.
They won the WWF World Tag Team Championship twice, first from Dick Murdoch and Adrian Adonis in January 1985.
Rotunda began bickering with fellow Varsity Club member Rick Steiner, a graduate of the University of Michigan, over which of the two had a superior alma mater.
Rotunda won the NWA World Television Championship from Nikita Koloff in January 1988, and subsequently gave his Florida Heavyweight title to Steiner.
Referee Theodore Long turned heel during the match and administered a fast three count, enabling Rotunda and Williams to overcome the champions.
In January 1992, he competed in the Royal Rumble match entering at number 18 and lasted 28 minutes, giving him the third longest run behind Roddy Piper and winner Ric Flair.
Ted DiBiase retired from wrestling to become a commentator in the summer of 1993, resulting in Schyster going back to singles competition after a final attempt to reclaim the tag-titles in a cage match in the lead-up to Summerslam '93 in a losing effort against the Steiners.
After Money Inc. disbanded, IRS feuded with Razor Ramon, challenging him for the Intercontinental Championship at the Royal Rumble.
Schyster then feuded with Tatanka, whom he accused of failing to pay a gift tax on a "sacred headdress" he received from Chief Jay Strongbow.
In mid-1994 he joined his former partner DiBiase's Million Dollar Corporation, originally the plan was to have his brother in law Barry Windham return reunite with Schyster and form a new tag team under the name "The New Money Inc." and they would have a big feud with Lex Luger and Tatanka but Windham wasn't up to it and Schyster was paired with Bam Bam Bigelow and after an unsuccessful effort to regain tag team gold.
When the two eventually squared off at the 1995 Royal Rumble, the Undertaker was victorious following a chokeslam, but Schyster stole his urn after the match.
His final appearance came on July 30, 1995, at a house show in Jean, Nevada, where he unsuccessfully challenged Shawn Michaels for the Intercontinental Championship.
an allusion to Vincent Kennedy McMahon) with announcer Eric Bischoff asking Bobby Heenan on-air why his name had suddenly changed.
The highlight of this run came at the 1996 Battlebowl, where he teamed with Jim Duggan and made it to the semifinals before losing to Dick Slater and Earl Robert Eaton.
He returned (as Mike Rotunda) to WCW at Starrcade 1999, reforming the Varsity Club with Rick Steiner and Kevin Sullivan to team with Jim Duggan against The Revolution (Shane Douglas, Dean Malenko, Perry Saturn, and Asya).
In early 2000, he took part in a "Lethal Lottery" tournament for the vacated WCW World Tag Team Championship, paired with Buzzkill.
He returned on October 28, 2001, for a one-night teaming with Masahiro Chono defeating Hiroyoshi Tenzan and Satoshi Kojima.
[20] In autumn, Rotunda and Williams entered the 2002 World's Strongest Tag Determination League, finishing in 4th place with 9 points.
In 2005, Rotunda teamed up with his brother-in-law Barry Windham at WrestleReunion losing to Larry Zbyszko and Ron Bass.
One such appearance was on the August 6, 2007, edition of WWE Raw; Mr. McMahon was discussing his IRS troubles with Jonathan Coachman, and when the conversation ended, I.R.S lowered the paper covering his face (Financial Times) and revealed himself.
[22] On the March 10, 2008, episode of Raw, The U.S. Express were falsely advertised for a rematch from WrestleMania I against Nikolai Volkoff and The Iron Sheik.
Before it could start, Jillian Hall offered to sing "Born in the U.S.A." for them, Rotunda gave her an airplane spin and the show went to commercial, effectively ending the feud.
After Ted DiBiase Jr. and Virgil were confronted by A-Team stars Quinton "Rampage" Jackson and Sharlto Copley, in character as B.A.
Baracus and H.M. "Howling Mad" Murdoch, respectively, Ted called in his "Uncle Irwin" (an allusion to the long-standing association of DiBiase Jr.'s father the Million Dollar Man Ted DiBiase with I.R.S dating back to Money Inc.) into the room wherein Schyster announced he had repossessed Jerry Lawler's crown, because Lawler had not paid long overdue taxes on the crown's gems.
Later in the show, I.R.S, DiBiase Jr., Virgil and Rowdy Roddy Piper were confronted by the A-Team and Dusty Rhodes, who attacked them and reclaimed the crown.
On the June 28 Raw, Rotunda was one of the four people who entered the ring to celebrate Ricky Steamboat's career, but were attacked by the Nexus.
He, along with numerous other WWE officials and superstars, attempted to break up a brawl between Brock Lesnar and John Cena.
Immediately prior, Langston walked past fellow Million Dollar Corporation members, Nikolai Volkoff and Ted DiBiase.
[25][26] In January 2021, on Raw Legends Night, Rotunda, as I.R.S., made his first appearance since being released by the WWE in a segment backstage with Ric Flair.
[30] They have 3 children together, their sons Windham and Taylor were professional wrestlers who worked in WWE, best known as Bray Wyatt and Bo Dallas respectively.