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1.
Whenever you do a great job and just throw something away at the end, invalidating all work you did earlier, then you pulled a cutler.

The phrase originates due to the performance of the 2009 quarterback of the Chicago Bears: Jay Cutler. He knows

how to ruin games in an epic fashion.

No QB failures were more epic than Cutler's opening game with the Bears against longest-NFL rivalry Green Bay, where he managed to have 6 turnovers in a single game.

Others can argue how on November 12, 2009 when Cutler threw an interception in the end zone with 2 seconds left of play after marching the bears up the field for 70 yards, was a most epic quarterback failure. (He managed to throw 5 total interceptions this game).
Ever shoot pool clearing out every ball only to scratch on the 8 ball? You pulled a Cutler.

Ever been in Vegas, up 2000 dollars, only to bet it all on red and lose it all? You pulled a Cutler.
by New York Transplant November 13, 2009