The Red Wings That Could Have Been: How Detroit Let Adam Oates Get Away

In one of the most regrettable trades in Red Wings history, Detroit dealt Adam Oates and Paul MacLean to St. Louis in exchange for future Hall of Famer Bernie Federko and Tony McKegney.

Washington Capitals head coach Adam Oates Credit: Geoff Burke-USA TODAY Sports / IMAGN IMAGES via Reuters Connect

Adam Oates retired as one of the greatest playmakers the NHL has ever seen. He accumulated more than 1,079 assists, which is good for ninth all-time.

Thanks to Oates centering them, fellow Hall of Famers Brett Hull and Cam Neely both scored 50 goals in 50 games. Then the Red Wings traded Oates for 73 games of Bernie Federko and 14 games of Tony McKegney.

On June 15, 1989, then-Red Wings general manager Jim Devellano sent the 26-year-old Oates and winger Paul MacLean to the Blues in exchange for 73 games and 57 points of 33-year-old Bernie Federko, who would eventually get enshrined into the Hall of Fame, and 14 games and three points of 31-year-old Tony McKegney, who was shipped off to the Quebec Nordiques a little less than one-fourth into the 1989-90 season.

According to an Associated Press report published in the Los Angeles Times, MacLean was dealt because he had fallen out of favor with Red Wings coach Jacques Demers.

As great as Oates was on the ice, it's hard to believe he wasn't drafted. He was signed as a free agent by the Red Wings out of Rensselaer Polytechnic Institute in June of 1985.

It would take Oates a few seasons to establish himself before the glimpses of what he would eventually become came out.

In 1988-89, his fourth season with the Red Wings, Oates finally showed why he was a star at RPI when he tallied 16 goals and 62 assists for 78 points in 69 games. He was ready to break out for the Wings until Devellano determined the team needed more leadership to help captain Steve Yzerman.

The Heist

Brett Hull and his former teammate Adam Oates Credit:Scott Rovak-USA TODAY Sports Copyright © Scott Rovak / IMAGN IMAGES via Reuters Connect

The late St. Louis Blues general manager Ron Caron was known for making blockbuster deals. He had just acquired budding superstar Brett Hull from the Calgary Flames in February of 1988. Hull was coming off a career 41-goal season with the late Peter Zezel as his primary centerman.

Federko was still producing, but not at the 100-point level like had been in seasons past. He was still putting up points, as he scored 22 goals and 67 points in 66 games in 1988-89.

McKegney, who had been acquired by the Blues in May of 1987, saw a decline in his production as he fell from 40 points and 78 games in 1987-88, to 25 goals and 42 points in 1988-89.

Demers had coached Federko in St. Louis for three seasons in the mid-80s so he was aware of what Federko could bring to the table. Devellano and Caron agreed to the deal and Devellano immediately regretted it.

"It was the worst trade I ever made," Devellano told Bob Duff of NHL.com. Devellano went on to add that Federko was on the downside of his career. "We thought he would add a leadership element, but we were wrong. Bernie didn't have too much left in the tank."

Federko might not have had much left in the tank, but Oates' gas gauge needle was past F. As soon as he got to St. Louis, Oates became the architect and Hull was the wrecking ball.

In their first season together, Hull broke the all-time record for goals by a right winger when he scored 72 goals, surpassing Jari Kurri's record of 71. Meanwhile, Oates set a career high for goals with 23, assists with 79, and points with 102 in 102.

The scary part is he wasn't close to being finished showing what he could do.

Hull and Oates: An Encore

In 1990-91, Hull and Oates were a two-headed monster NHL teams hadn't had to contend with since the days of Wayne Gretzky and Kurri with the Edmonton Oilers.

Hull went out and shattered his record for goals by a right winger when he scored 86 goals and finished with 131 points, while taking the Hart Trophy as league MVP. He also scored 50 goals in 50 games, becoming only the 5th player in NHL history to accomplish the feat.

Oates surpassed his totals from the year before with 25 goals, 90 assists and 115 points. He did it while playing in only 61 games.

A year later in February of 1992, Oates was dealt to Boston and he picked up with Neely where he left off with Hull. In his first full season with the Bruins, he scored 42 goals and had 142 points in 84 games.

In March of 1994, he helped Neely score an unofficial 50 goals in 44 games. Because it was in the Bruins' 66th game of the season, it does not stand in the official record books.

Oates would then go to Washington, where he made a Stanley Cup Final appearance in a four-game sweep by the Red Wings in 1998, Philadelphia, and Anaheim before calling it a career with the Oilers in 2003-04. He finished his career with 341 goals and 1,420 points, which is good for 20th all-time on the NHL scoring list.

What If?

Yzerman was already there. Sergei Fedorov had just been drafted and would arrive a couple of seasons later. Nicklas Lidstrom was also on the way.

The Red Wings eventually became a powerhouse without Oates, but imagine adding one of the greatest passers in NHL history to that talent pool. The Red Wings ultimately didn't need Oates to become a dynasty.

Oates wasn't drafted. The Red Wings identified him, signed him, developed him and nurtured him. Unfortunately, Oates didn't blossom with them.

Their mistake wasn't failing to recognize Oates in the first place. It was failing to recognize just how good the player they had discovered was going to become.