The Top 5 Worst Boston Sports Betrayals Of All Time

A.B. Now that Ray Allen leaving for the Miami Heat has sunk in, I got to thinking… Which Boston fan favorite leaving for a rival team hurt the worst?

So without futher ado, I give you the top 5 worst Boston sports betrayals of all time. This hurts…

#5 – Ray Allen to Miami Heat

I made my thoughts known on Ray leaving town. This really just isn’t that painful for me. I loved the time Ray spent in Boston and I will always picture him as a Celtic as well. Taking a lot less money to go to a new team tells you something was wrong. Better to always picture him in a shining light than to see him unhappy, elderly & riding the pine.

#4 – Adam Vintieri to Colts

This one didn’t sting as much as it should have. I think it had a lot to do with the Patriots not willing to pay him. Vinatieri wanted to stay but wanted to get paid. The Patriots didn’t want to pay big bucks for a kicker. You can’t really blame either side in this one… just sucks it had to be Indy.

#3 – Wade Boggs to Yankees

I don’t really remember much about Wade Boggs except as a kid I liked him. I think I was mesmorized by his ginger mustache – plus I think my father respected him. I’ve heard he was the dirt dog/Pedroia type of the 80/90’s. That’s until he signed with the Yankees after hitting .259 in 1992. A few years later he would help lead the Yankees to a World Series Championship and ride one of the NYC police horses around Yankee Stadium. The Sox would remain ring-less for another 8 years…

#2 – Roger Clemens to Blue Jays… then Yankees

Boston gets the last laugh now – but at the time this wasn’t pretty. It was obvious Clemens was an a$$hole – but he was OUR a$$hole. Leaving for the Blue Jays was understandable. Dan Duquette made it pretty clear that he thought Clemens was past his prime. But to be part of the ’86 Buckner team and experience first hand the pain of Bostonians AND THEN eventually sign with the Yankees was pure treachery.

#1 – Johnny Damon to Yankees

The worst.

“There’s no way I can go play for the Yankees, but I know they are going to come after me hard,” Damon said. “It’s definitely not the most important thing to go out there for the top dollar, which the Yankees are going to offer me. It’s not what I need.”

The beard and mustache were shaved. The hair was cut. The hearts of Red Sox fans worldwide were cut out & stepped on.


Honorable Mention:

Tom Brady to Giselle.

  • Dan

    I feel like Brady to Giselle is the clear winner

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