5. Bernie Kosar
Kosar played in the NFL 411 seasons as a quarterback and even gained a Super Bowl Championship ring. He was definitely the best quarterback to ever play for Cleveland until he retired in 1996. He went on to open a restaurant, but sadly ended up filing for bankruptcy in 2009.
6. Charlie Batch
Charlie played in the NFL as a quarterback, mostly with the Pittsburgh Steelers. Before he retired, he obtained two Super Bowl championship rings. Afterwards, he went into real estate but it backfired when he was left with $8 million debt.