Huge trade completed between the Chicago Blackhawks and Detroit Red Wings that's haunting fans till this day

Not many people in Chicago who were fans of the Blackhawks would have ever believed that captain Chris Chelios would ever play for the divisional foe Detroit Red Wings before the infamous 1999 trade.

In fact, Chelios was on record as saying that he would never play for the Red Wings earlier in his career.

But at the 1999 Trade Deadline, Chicago stunned their fans by trading Chelios to the Red Wings, who has won 2 straight Stanley Cups and were gunning for a 3rd. The acquisition of Chelios by Detroit was part of a haul at the 1999 Deadline by GM Ken Holland that also included Ulf Samuelsson, Wendel Clark, and Bill Ranford.

In return for Chelios, the Blackhawks received Swedish defenseman Anders Eriksson, whose tenure with the team was largely uneventful.

Not even 2 years later, he would be traded to the Florida Panthers, and he would also later play for the Toronto Maple Leafs, Calgary Flames, Phoenix Coyotes, New York Rangers, and Columbus Blue Jackets.

Meanwhile, Chelios would win another 2 Stanley Cups with the Red Wings in 2002 and 2008. It's a trade that continues to haunt Blackhawks fans to this day, especially after Chelios' infamous words that he'd never play for the Red Wings only to turn and become one of their best defensemen for nearly a decade.

Chelios, who later worked for the Red Wings after his retirement from the NHL, would join the Blackhawks as a team ambassador and then later become an analyst for the NHL on ESPN and later, TNT.

He also became the 9th player in Blackhawks history to have their sweater number retired by the team, and fittingly, it was before the Blackhawks faced the Red Wings and ex-Blackhawks icon Patrick Kane in a February 2024 game in Chicago.