Revisiting Some of The Worst Trades in Blackhawks History..

I think the worst one had to be Phil Esposito to the Bruins in 1967. The Blackhawks could have formed a dynasty as they had Bobby Hull, Stan Mikita, Pierre Pilote, Glenn Hall and a young Phil Esposito. Despite that stacked talent, Esposito still managed to be the fourth-highest scorer on the team in his first three seasons. However he had too much to drink at a team party and basically told head coach Billy Reay and general manager Tommy Ivan, that they would screw up the Hawks success.

Well it turns out Esposito was right. He was shipped to Boston along with Ken Hodge and Fred Stanfield for Gilles Marotte, Pit Martin and Jack Norris. Esposito would record 1,590 career points and had one of the most decorated NHL careers of all-time. The Blackhawks meanwhile would underachieve and screw things up, as Espo predicted.

The Blackhawks began the 1990s with two future hall of famers (Ed Belfour and Dominik Hasek) between the pipes, but Chicago would trade perhaps the best goaltender of the 90s in Hasek. Prior to the 1992-93 season, the Hawks capped off a series of bad moves by trading Hasek to Buffalo for Stephane Beauregard and a fourth rounder. Three days later, Beauregard was traded to Winnipeg for Christian Ruuttuu.

Ruuttu would do next-to-nothing as a Blackhawk — 90 points in 158 games. Meanwhile, Hasek had a hall of fame career while playing for the Sabres. He won league MVP honors twice and the Vezina, the top goaltending honor six times, setting an NHL record.

Trading a franchise player because you don't want to pay him, isn't a good look. In 1996, Jeremy Roenick had cemented himself as an elite NHL center with 596 points in 570 games. Unfortunately, the organization did not want to pay him like one. Roenick was a restricted free agent and wanted a five-year contract worth $4 million per year.

Instead, they decided to send him to the Phoenix Coyotes for Alexei Zhamnov, Craig Mills and a first-round pick. Zhamnov was thought to be the next Sergei Federov. He was a solid enough player, averaging 53 points a season with Chicago, but they missed Roenick's leadership and emotion. J.R. meanwhile, got the money he was looking for and averaged 70 points per season.

The state of the franchise could have changed with any of these moves not happening, but three Cups in six years makes you forget about these bad deals.