Around this time last year, the Jacksonville Jaguars were looking for a way to reverse their fortunes following yet another disappointing season (they finished with a 3-13 record). The Jags wound up taking two huge swings for the fences in the free agent market, signing defensive end Calais Campbell and cornerback A.J. Bouye.

The Campbell deal, worth $60 million over four years, was knocked by many analysts who felt that, at 30, he was past his prime. Bouye’s five-year, $67.5 million contract was also deemed a risk, because the Jaguars were banking on just one good year out of the Tucker, Georgia native. Despite all the questions surrounding the signings, both players had exceptional years in their first season with the Jags, helping them reach the AFC Championship Game for the first time since 2000.

Every year, NFL teams come into the free agency period hoping to emulate the magic of last year’s Jaguars. Unfortunately, most wind up missing the mark. Because for every Bouye, there will be a Deion Sanders, and for every Campbell, there will be an Albert Haynesworth. Most GMs looking to find that lightning in a bottle to turn their franchise around quickly find out that their role is a mix of skill and luck, and if both don’t match up perfectly, the results can be damaging to the organization.

Money is a terrible thing to waste, but if these organizations want to raise that Lombardi Trophy one day, they have to take some chances—chances that sometimes become regrettable within a year or two, and make both sides wish they had a do-over. So, let’s take a trip down memory lane and remember the last 18 years of disappointing acquisitions. Here are the 20 worst NFL free agency signings in recent memory.