#1 – Theo Fleury (1999)
Theoren Fleury was a player whose size didn’t hamper his ability. Although only 5’6″ and 182 pounds, Fleury was a star for the Calgary Flames. He played 11 seasons in Calgary, averaging 33 goals and 75 points per season. He won a Stanley Cup in his rookie season in 1989. and was a second team All Star in 1995, On the verge of unrestricted free agency, he was traded to Colorado where he starred in the 1999 Stanley Cup Playoffs.
Fleury was the top free agent available in the summer of 1999 coming off a 40 goal season. In a full court press, Rangers President Neil Smith and MSG President Dave Checketts got him to sign a four-year $28 million contract although Fleury was leery of leaving small market hockey for the bright lights of Broadway.
That fear would prove to be prophetic. While playing in New York, Fleury constantly battled substance abuse and twice entered the league’s substance abuse program.
He struggled to adapt to New York in his first season, scoring only 15 goals and 64 points. In his second year he was one of the league leaders in goals and points when he ended that season by entering the substance abuse program for the second time in less than a year.
He managed to play all 82 games in his third season in New York, but exhibited increasingly erratic behavior. He had an altercation with the San Jose Sharks mascot in December after he was ejected from the game. The altercation reportedly left Sharkie with a broken rib.
A month later, instead of going to the penalty box after taking a penalty he left the arena, an action that required him to apologize publicly to his teammates. Two week after that he was fined for making an obscene gesture towards Islander fans. He also engaged in a verbal fistfight with the NHL as he claimed that they were treating him unfairly.
He finished the season with 24 goals and 39 assists, but the Rangers, weary of his shenanigans, chose to trade him to San Jose.
It was later revealed that Fleury had been sexually abused by his coach in junior hockey and had been dealing with that torment for his entire career. It’s difficult to relegate Theo Fleury’s time in New York to a list of disastrous free agent signings considering all of the demons he was dealing with, but the fact remains that his tenure in New York was a failure. In an interview with the New York Times, Fleury himself called his time in New York a “nightmare.