There is no doubt that the Los Angeles Clippers came out as the biggest winners out of last summer's free agent frenzy. That was easily one of the most talent-packed free agent classes of recent memory, and by signing reigning Finals MVP in Kawhi Leonard, L.A. hit the jackpot.

Lady Luck hasn't always been this kind to the Clippers. As a matter of fact, this franchise has been the victim of their own erroneous decisions on more than a few occasions. Some of which came via free agency, and we've rounded up five of the worst free agent transactions the Clippers front office has ever gotten themselves involved in.

5. Grant Hill

Former Duke standout Grant Hill was one of the biggest prospects in the league early in his career. Aside from winning Rookie of the Year honors, he was also named as an All-Star in his debut campaign. He was once even dubbed as the next Michael Jordan. Unfortunately, a string of major injuries got in the way of Hill truly reaching the heights many expected him to achieve.

Nonetheless, this did not prevent the Clippers from signing a 40-year-old Hill to a two-year deal worth $4 million in 2012. Sure, that can be considered as a rather insignificant sum, but there's no denying that that was a bad deal. Hill ended up playing in just 29 games for L.A., averaging 3.2 points and 1.7 rebounds in 15.1 minutes per contest.

Grant Hill is a Hall of Famer, but it certainly wasn't because of his stint with the Clippers.

4. Josh Smith

In the summer of 2015, the Clippers were looking for some wing reinforcements, and they decided to turn their attention to Josh Smith. It was clear that the 6-foot-9 swingman was falling off, as his production consistently dipped year after year prior to signing with L.A. Needless to say, he was no longer the versatile and athletic player that once averaged close to a double-double with a healthy dose of defensive stats.

The Clippers played it safe with Smith, signing him on a one-year deal that cost them just $1.5 million. In turn, Smith averaged 5.7 points, 3.9 rebounds, 1.1 assists, and 1.1 blocks in just 32 games played for the squad. The Clippers quickly pulled the plug on the Josh Smith experiment, sending him off to the Houston Rockets after just six months in L.A.

3. Paul Pierce

Much like Grant Hill, Paul Pierce was one of the top players in the league during his prime. A 10-time All-Star, a four-time All-NBA team member, and a former Finals MVP, the 6-foot-7 swingman won the title with the Boston Celtics in 2008. It wasn't until seven years later, though, when the Clippers decided to sign the veteran to a three-year deal worth $10.6 million. At that time, Pierce was already 38, and to say that he was a shadow of his former self would be an understatement.

Pierce ended up playing just two out of the three years he signed for with L.A, averaging 5.4 points, 2.5 rebounds, and 1.0 threes per game. In 2017, after two seasons, the Clippers waived Pierce.

2. Spencer Hawes

Prior to the 2014-15 campaign, the Clippers were in need of a stretch big that could potentially help their current lineup. They turned their attention to free agent Spencer Hawes, who was coming off a tremendous year between the Philadelphia 76ers and the Cleveland Cavaliers. L.A. signed him to a four-year deal worth $22.7 million, and as it turned out, it was not the best decision they ever made.

Hawes just did not fit in with their system, as the 7-foot-1 big man's production dropped significantly in his first season with the Clippers. He put up just 5.8 points, 3.5 rebounds, and 0.8 triples on an inefficient 31.3 percent clip. L.A. cut their losses soon after, trading Hawes to the Charlotte Hornets the following summer.

1. Baron Davis

If you thought the other four deals above were bad, then you're in for a treat with this one. In July of 2008, the Clippers signed Baron Davis to a humongous $65 million deal for five years. It didn't look bad at all at that time, given how the high-scoring point guard averaged 21.8 points, 4.7 rebounds, 7.6 assists, 2.3 steals, 0.5 blocks, and 2.1 triples the previous season with the We Believe Golden State Warriors.

As soon as he joined the Clippers, Davis' production plummeted. He was still a top-notch point guard, but not one that deserved an average of $13 million per season. In tow and a half seasons with L.A., the former third overall pick averaged 14.6 points, 3.4 rebounds, 7.6 assists, 1.6 steals, 0.5 blocks, and 1.2 3-pointers. Again, those numbers were not terrible by any means, but they sure weren't the elite level of production the Clippers were hoping for.