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1.
To force something like Jay Cutler forces the football into double and triple coverage and to epically fail.
1. When I couldn't answer my girlfriend's question and she was looking at me weird, I Jay Cutler'd it and said the first thing that came into my head, and she dumped me. Fail.

2. I was trailing by 14 points in the 4th quarter in Madden '10, I Jay Cutler'd it and threw a pick six. Fail.

3. I had an exam and didn't study, I had to write an essay about something I had no clue about. I then Jay Cutler'd it and wrote a bunch of bullshit, I got an F. Fail.
by brightz[tyop] December 16, 2009
 
2.
When you use a minor injury to sit on the sidelines during an important event.
Tom pulled a Jay Cutler with his boss when he got a paper cut.

Tom: "I can't finish the presentation. I'm hurt."
Boss: "WTF. This is. really important. Millions of dollars are at stake. The whole company is counting on you."
Tom: "I'm injured. Sam the intern can finish. We aren't going to win the contract anyway."

Boss: "Sam you finish. Tom just Jay Cutler'd us."
by presqueisle January 25, 2011