The Los Angeles Chargers have typically been one of the NFL's better teams over the past 20 years, but have never quite been able to get over the hump into the elite category. A reason for this may be some of the franchise's misses in free agency; here are the five most egregious examples.

5. Derek Cox, 2013

Cox was a very good corner for the Jacksonville Jaguars in 2011, and although his play fell off in 2012, it was still solid. The Chargers gave him $20 million over four years to bolster their secondary, but Cox had the worst season of his career in 2013, being benched multiple times and earning a career-low coverage rating of 43.1 per Pro Football Focus.

Cox was released early the following offseason and spent a little time with the Baltimore Ravens, New England Patriots and Minnesota Vikings, but would never play another down in the NFL.

4. Marcellus Wiley, 2001

In 2000, Wiley totaled 10.5 sacks for the Buffalo Bills at the age of 26, and San Diego thought they were getting an ascending player on his way to becoming a top pass-rusher. Wiley signed for six years and $40 million, at the time the largest contract in Chargers history. This deal equates to paying an EDGE about $19.6 million today, which would rank third behind Khalil Mack, Demarcus Lawrence and Frank Clark.

For the first year, San Diego felt great about its investment. Wiley collected 13 sacks, eight tackles for loss and five forced fumbles on his way to his first Pro Bowl selection in his inaugural season with the Chargers. But Wiley managed only nine combined sacks over the next two seasons, and was cut halfway through his mega-deal. Wiley played one season for the Dallas Cowboys before retiring after two years as a reserve with the Jaguars.

3. Robert Meachum, 2012

The Chargers needed a wide receiver to replace the departed Vincent Jackson, so they looked to New Orleans Saints free agent Robert Meachem as Jackson's replacement. In a part-time role for the Saints, Meachem had totaled 141 catches for 2,269 yards and 23 touchdowns over his first four seasons. San Diego gave him nearly $26 million over four years, including $14 million in guarantees.

Meachem was an absolute flop for the Chargers. Despite playing in 15 games, he caught just 14 of 32 targets for 207 yards and two scores. San Diego decided to rip the band-aid off and cut him after just one year, even though he still had guaranteed money remaining on his deal. Meachem went back to New Orleans for two more seasons before retiring after the 2014 campaign.

2. Jared Gaither, 2012

2012 was not a good free agency year for San Diego. Gaither had a history of work ethic and attitude issues (his nickname was “Big Lazy”). But when the excellent Marcus McNeill landed on Injured Reserve nine games into the 2011 campaign due to a neck injury that would unfortunately end his career, Gaither was the best option available on the waiver wire. He started the Chargers' final five games at left tackle, and played fairly well.

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However, it was a bait-and-switch. With McNeill's retirement, San Diego was desperate for a solution at left tackle and Gaither held a ton of leverage because of how he finished the season. The Chargers eventually caved, giving him a $24.5 million, four-year deal, with $13.5 million of that guaranteed. It was not a massive sum for a left tackle, but far too much for what he gave the team after that.

Gaither played in four games in 2012, and struggled mightily in pass protection. He also dealt with injuries that eventually landed him on Injured Reserve in mid-November, and he was so toxic in the locker room that he was reportedly told to stay away from the team while rehabbing. A player not living up to expectations on the field is one thing. A player not working hard as soon as he got paid? That's another entirely. And yet, Gaither still isn't the biggest free agency disaster in Chargers history.

1. David Boston, 2003

Boston was the wide receiver version of Gaither, except much more expensive and disappointing. Over 56 games for the Miami Dolphins, Boston caught 241 passes for 3,739 yards and 18 touchdowns. He looked like he was on the cusp of breaking out and becoming one of the NFL's very best offensive weapons. The Chargers paid him as such, giving him a massive deal worth $47.4 million over seven years.

He lasted only one solid season in San Diego before being traded back to Miami for a sixth-round pick. Boston was obsessed with body-building, was suspended a game for yelling at the Chargers' strength coach and gave poor effort in practice. Boston could have been an all-time great, but instead he was out of the NFL by age 28.