Here's a quick one:
Kentucky beats Duke in the 1992 NCAA East Regional final (men's basketball). Four possibilities:
1. UK beats one of its archrivals, Indiana, in the Final Four and plays Michigan in the championship game (sorry Cincinnati fans; I don't see the butterflies favoring you in the other semi). UK then beats Michigan to win the national championship, coming off a two-year postseason ban. The Unforgettables are forever immortalized in college hoops history, although only one player (Jamal Mashburn) will go on to the NBA
1b. Michigan beats UK, and the Fab Five (five freshmen -- Chris Webber, Juwan Howard, Jalen Rose, Jimmy King, Ray Jackson) are forever immortalized in the history of college basketball
2. IU beats Kentucky, while Michigan beats Cincinnati in the other semi, setting up an all-Big Ten final. The Hoosiers then beat the Wolverines to win their first national title since 1987
2b. The Fab Five prevail, with the same result, and historical legacy, as in 1b
Also: Shaquille O'Neal of LSU is chosen for the Olympic Dream Team over Duke's Christian Laettner.
Also, what if Pitino's teams win in 1992 and 93 or 95? Does he leave UK for the pros sooner?