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3.
v.
similar to a tobagon

the act of four black guys gangbanging a chick on top of a staircase and then riding her down.
The hooker asked, "Would you negros care for a jamaican bobsled team?"
by yea bro August 08, 2007
 
1.
A term used to describe a situation that is possible, but unlikely to happen. Popularized by the tv show Glee.

Based on the 1988 Winter Olympics team who fell short of winning any medals but did surprisingly well.
"What do you think the chances are that Jennifer will say yes if I ask her to go out with me?"

"Jamaican Bobsled Team, dude..."
by P Banger February 14, 2010
 
2.
While hooking up with a chick, drop a huge log on her chest and then titty fuck her with it
Oh man so I was watching Cool Runnings with my girl and I asked her if she's ever been introduced to the Jamaican Bobsled Team, she replied no, so I went ahead and fulfilled her wildest dreams.
by blimRU February 09, 2011