his final year of college eligibility, Oates signed a four-year, $1.1 million contract with the Detroit Red Wings that made him the highest paid rookie in the NHL in 1985–86. He made his NHL debut on October 10, 1985, against the Minnesota North Stars, scoring his first goal that night on goaltender Don Beaupre and added an assist. After this, Oates struggled offensively and was pointless in his following 16 games; the team subsequently demoted him to the Adirondack Red Wings of the American Hockey League (AHL). Oates split the remainder of the season between Detroit and Adirondack, finishing his first NHL season with 38 games played, 9 goals and 11 assists. In the AHL, he scored 18 goals and 28 assists in 34 games. Having finished the NHL season in Detroit, he was returned to Adirondack for the AHL playoffs which the team won to take the Calder Cup championship. Oates established himself as a full-time NHLer in 1986–87, scoring 47 points in 76 games. He improved to 54 points in 63 games the following year despite missing a month due to a groin injury, and finished third in team scoring with 78 points in 1988–89. However, Detroit made changes following a first round loss in the playoffs; Oates, along with Paul MacLean, was traded to the St. Louis Blues on June 15, 1989, in exchange for veterans Bernie Federko and Tony McKegney. The deal, which is now considered one of the worst in Red Wings' history, left Oates "heartbroken" to leave his first NHL club. The Blues made Oates their first-line centre and played him alongside Brett Hull. The pair, dubbed "Hull and Oates" as a play on the band Hall and Oates, put up prolific offensive numbers. In 1989–90, Oates topped the 100-point mark for the first time in his career with 102 points. He improved to 115 in 1990–91. He helped Hull score 72 and 86 goals those seasons, the latter the third highest in single-season total in NHL history. Oates was named to the second all-star team following the season and played in the 1991 All-Star Game. Oates signed a four-year, $3 million contract extension with the Blues prior to the 1991–92 season, but after the team signed Brendan Shanahan, Garth Butcher and Ron Sutter to significant deals, felt he was underpaid. After playing in his second career All-Star Game, he threatened to walk off