Question

Bill Belichick was the head coach in Cleveland for five years. Now he’s gone on to win five Super Bowls with the Patriots. What two teams have twice had head coaches in place for more than a season, only to see them later win Super Bowls with other teams?

Answer

It happened twice early with the Baltimore Colts, with Weeb Ewbank and Don Shula. Ewbank’s win came against them. And it happened with two young coaches for the Raiders – Mike Shanahan and Jon Gruden. The Jets technically could also be part of this group. They had Pete Carroll for the 1994 season, and Belichick was twice named the coach of the team. But Belichick never actually coached a game for them.