NFL handicapping can be difficult for the same reasons that handicapping is difficult in any sport. Experienced gamblers who knew what they were talking about when it comes to NFL handicapping even before the forming of the league itself were just sure that Don Shula and the Baltimore Colts would be able to dominate "Broadway" Joe Namath and the New York Jets in Super Bowl III. Broadway Joe's bold prediction was not enough to change the minds of many during the NFL handicapping of this game, causing a lot of people to lose money on this historic game. Of course Johnny Unitas not playing in the game causing the Colts to lose in the minds of many should have showed people how difficult NFL handicapping was going to be in the future. Super Bowl III is a game that people have been talking about for decades and will continue to talk about for a very long time.

Other legendary upsets or collapses that have made the art of NFL handicapping tougher include the fact that the Buffalo Bills actually lost four straight Super Bowls despite having Hall of Fame players like Jim Kelly, Bruce Smith and Thurman Thomas on their roster. You would have thought just based on the sheer odds of those circumstances that the Bills would have won at least one of those four Super Bowl. It was not to be and simply playing the odds and not looking at the possibility of a snake bitten sports franchise can make NFL handicapping that much tougher. The losing of four straight Super Bowls is a feat that has been talked about for a very long time and is an infamous statistic that may never be matched again.

When Dan Marino played in his first and what turned out to be only Super Bowl in 1985 you had many in the NFL handicapping business saying that he would surely get back to another Super Bowl. In this case despite the Hall of Fame numbers and consistently good seasons that the Miami Dolphins had those who made NFL handicapping predictions that Marino would make it to another Super Bowl were indeed wrong.