Martin Brodeur
Brodeur played the first 1259 games of his career with the New Jersey Devils racking up 688 wins and 125 career shutouts. So when he signed with the Blues on December 4th, 2014 many were shocked.
People were even more shocked when he announced on January 29th that he was officially retiring. Brodeur retired as a member of the Blues after playing 7 games. Brodeur not ending his career a Devil is a true shame.
Bobby Orr
When you think of Bobby Orr you think of the Boston Bruins and vice versa. That's why this picture of Orr wearing a Blackhawks' jersey feels so dirty. After 631 games with the Bruins Orr signed with the rival Blackhawks and went on to play two forgettable seasons and only 26 Games with the Hawks, he also provided two very forgettable hockey cards.
Doug Gilmour
Gilmour didn't begin his career with the Leafs, but it's the team he's most commonly associated with when you think of Dougy. Gilmour put up his two most successful seasons with the Maple Leafs and one of those seasons still stands as the Leafs single season points record (127). For many Leafs' fans the sight of Gilmour in a Habs jersey was enough to turn their stomachs.
Gilmour played two seasons in Montreal before being dealt back to the Leafs only to have his return end in heartbreak in his first game back in Blue & White.
Gilmour did provide this amazing clip though so it wasn't all bad.
Brian Leetch
When Leetch was traded from New York to Toronto at the trade deadline it felt wrong. Sure, the jersey was still Blue but it felt like it didn't fit right and seemed like a slap in the face to every Rangers' fan.
What made it worse was Leetch was just 41 points away from becoming the all-time leading scorer in franchise history and he was just 32 games from becoming the all time leader in games played. Leetch was easily the best player in franchise history and he deserved so much better.
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Jaromir Jagr
Jagr definitely didn't play his entire career with one team, but when he signed with the Philadelphia Flyers it definitely felt wrong. After starting his career with the Pittsburgh Penguins it just felt wrong to watch him put on the Orange & Black.
After 3 seasons in the KHL Jagr returned to the NHL and even though he had a rather successful season putting up 54 points in 73 games it just didn't feel right watching him on the Penguins cross state rival.