Normally, it’s not big investment news when a Super Bowl-winning quarterback retires or unretires. But then, not every Super Bowl-winning quarterback is Tom Brady. Brady is widely considered to be the greatest quarterback of all time (as a Michigan State alum, I found that sentence painful to write). His 10 Super Bowl appearances and seven Super Bowl victories are unmatched in NFL history. No NFL franchise has won as many Super Bowls as Brady has.