The men's U.S. Olympic bobsled team will be announced tomorrow morning, and as far as I can tell, Sam McGuffie is a strong contender to make the team.
Shockingly, there's not much of a bobsled media in the U.S., so there isn't much out there to analyze this, but it appears McGuffie has been doing well on the World Cup circuit this winter. He took first place at a World Cup race in November, and that can't hurt his chances.
So, the question is: Would McGuffie be the first former Michigan football player to compete in a Winter or Summer Olympics? I can't think of another one.
Willis Ward would have surely made the 1936 Olympic Team as a track athlete if he hadn't given up on sports in the wake of the Georgia Tech incident, but I can't think of another football player who competed in the Olympics.
[EDIT: As Alton points out below, there was a Michigan football player named John McLean who won a silver medal in the hurdles in the 1900 Paris Olympics. So McGuffie would apparently be the first Michigan football Olympian in 118 years.]
Wishing you good luck tomorrow, Sam.