Without googling:

[TheMightyFavog]

How many super bowl rings does Jim McMahon have?

[jobycom]

1. Two.

I can only think of the one with the Bears, but I'm guessing that's the wrong answer, so, two. I can't remember without Google where he went, but I seem to remember him being a backup in the twilight of his career, and I'm guessing they won something.

Now I can google. :)

[TheMightyFavog]

2. You are correct.

And the second team he won on, is one of history's deliciously ironic moments

[jobycom]

3. Yeah, just looked it up. Ironies and coincidences abound.

Beat the same team, in the same place, for the Bears' greatest rival. Though I'm guessing he didn't actually play.

First Bowl in New Orleans, a local broadcaster claimed McMahon had said that all women in New Orleans were sluts. The broadcaster was unable to back that up, and was suspended for it. That was Buddy Diliberto, who became famous nationally last year, even though he died in 2005, because he had once sworn that if the Saints ever played in a Super Bowl he would wear a dress and parade down Bourbon Street. There were several celebrations where men wore dances and paraded down Bourbon Street in his memory, and the local paper ran a doctored photo of Buddy in a dress. His family approved of it. Sounds silly, but it was a sweet moment for the city, tying the past to the moment.

Barely related to the OP, but oh well. :)