Ottman made his first appearance in the WWF in June 1989 in a dark match under the ring name Big Steel Man with Slick as his manager. He wrestled three more dark matches that summer, defeating Paul Roma and Boris Zukhov, and losing to Mr. Perfect. That September, his name was changed to Tugboat Tyler, then Tugboat Thomas, as he portrayed a fan favorite on house shows, defeating the likes of Barry Horowitz, The Brooklyn Brawler and Boris Zhukov. He debuted on WWF television on the January 27, 1990 episode of "Superstars" under the Tugboat Thomas moniker and defeated Iron Mike Sharpe. His ring name was soon after shortened to Tugboat. His costume consisted of a red striped shirt, white pants, and a sailor's hat. Part of his gimmick included miming pulling the cord of an airhorn and making a "Toot-toot" noise, like a horn of a ship. On the May 20 episode of Wrestling Challenge, Hulk Hogan made a promo explaining that he personally trained Tugboat and brought him to the WWF. Following Tugboat's win on that very same show Hogan came out into the ring and raised his arm, showing his full support. Tugboat railed for fans to send encouraging letters to Hogan after Hogan was brutally attacked by Earthquake. Tugboat aided Hulk Hogan in his feud with Earthquake and "Canada's Strongest Man" Dino Bravo. This coincided with a substantial push that saw Tugboat emerging victorious on television against numerous opponents. He made his pay-per-view debut at that November's "Survivor Series", where he teamed with Hogan, The Big Boss Man and Hacksaw Jim Duggan to face the team of Earthquake, Dino Bravo, Haku and The Barbarian. Tugboat was eliminated when he and Earthquake fought to a double count-out, and Hogan went on to be the sole survivor. Tugboat was the first true test of The Undertaker, who defeated him in numerous matches between December 1990 and March 1991. Tugboat received a shot at Mr. Perfect's Intercontinental Championship on the May 5, 1991 episode of "Wrestling Challenge", but was unsuccessful.