THE TIME DEXTER JACKSON ROBBED JAY CUTLER 

Generation Iron Dexter Jackson Jay Cutler

Rising above Jay Cutler and Phil Heath.

When it comes to sports there’s no doubting the fact that everyone loves a good underdog story. A tale of someone who, against all odds, ends up triumphing in the end, turning the impossible into the possible. It’s as compelling as you can get. If you don’t think that’s true then watch movies like Rocky, Gridiron Gang, or any number of sports movies and try to tell me you’re not rooting for the underdog to come out on top. It’s what makes sports so powerful and emotional.

The investment you have in your favorite football team winning the Super Bowl, the joy you feel when your favorite fighter, someone touted to lose by all the experts and pundits, triumphs through adversity and wins the UFC championship. The love of the underdog achieving their dreams and goals is something that most people can relate to. To achieve the one thing you’ve been working all your life to achieve is something that everyone wishes for. The sport of bodybuilding is no different, seeing its own fair share of upsets and turnarounds. Never was that more clear than in 2008 when a skilled bodybuilder who was talented, but thought unlikely to take victory, would shock the world.


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Dexter Jackson is a true legend of the sport. He’s been competing in bodybuilding competition for over two decades and yet can still hang with the best in the world. His crowning achievement in bodybuilding no doubt came on the historic night that he upset then champion Jay Cutler who many pegged to dominate the scene at that time. The Blade would have plans of his own however displaying one of the best physiques ever seen on a posing stage.

Take a look at the epic moment that saw Dexter Jackson beat out the likes of Phil Heath, Flex Wheeler, and Jay Cutler.

What do you think the biggest upset and bodybuilding history was? Let us know in the comments and the forum and be sure to follow Generation Iron on Facebook and Twitter.

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