In 2020, the Milwaukee Bucks made history by signing two-time MVP Giannis Antetokounmpo to the largest NBA contract ever. The Bucks front office was more than willing to break the bank to retain the services of their cornerstone superstar — and rightfully so.

With NBA free agency opening Friday, the Bucks will be looking to surround Giannis with more talent to make another run at an NBA title. In the past, however, the team has been on the wrong side of history when it comes to signing players. Today, we take a look back at the worst Bucks free-agent signings in the history of their franchise.

5. Michael Redd

Make no mistake about it — Michael Redd was a tremendous player for the Bucks in the early 2000s. He was an All-Star and an All-NBA Team member during the 2003-04 season, which made him an absolute steal for Milwaukee when they drafted him 43rd overall in 2000.

Come 2005, Redd was due for an extension. The Bucks knew that they had struck gold with the 6-foot-6 swingman, which is why they did not hesitate to sign him on a huge $91 million deal for the next six years. Redd would instantly pay dividends for the team, averaging 25.9 points (on 45.6 percent shooting), 4.0 rebounds, 2.7 assists, 1.2 steals, and 2.1 triples per game over the next two seasons.

Unfortunately, injuries would show its ugly head in what was an otherwise stellar career for Redd in Milwaukee. In the final two years of his deal — during which he earned a total of $35 million, the Ohio State alum would play in no more than 28 games for the Bucks, averaging 9.3 points and 2.2 rebounds.

4. Dan Gadzuric

The Bucks selected 6-foot-11 big man Dan Gadzuric 34th overall in the 2002 draft, and he would prove to be a serviceable backup center during his first three seasons with the team. When he was up for an extension, Milwaukee decided to offer him a deal worth $36 million that would see him with the team for the next six years. Gadzuric obviously did not hesitate in signing the deal, which at that time seemed just too good to be true.

True enough, the Dutch national would average just 4.2 points, 3.5 rebounds, and 0.6 blocks per game over the next five seasons, which is well below his perceived valuation. The Bucks decided to trade Gadzuric and his expiring deal in 2011 to the Golden State Warriors in exchange for a 31-year-old Corey Maggette.

3. Miles Plumlee

The 6-foot-11 center arrived in Milwaukee in 2015 as part of a three-team deal with the Phoenix Suns and the Philadelphia 76ers. The following season, in his first full campaign with the Bucks, Miles Plumlee averaged 5.1 points, 3.8 rebounds, and 0.8 blocks, playing 14.3 minutes per game off the bench.

Who would have thought that this level of production would bring about a four-year, $50 million deal for Plumlee the moment he hit free agency in the summer of 2016. Well, someone in Milwaukee's front office thought obviously so.

After putting pen to paper on that big-money deal, Plumlee put up 2.6 points and 1.7 rebounds per game the following season, prior to being traded to the Charlotte Hornets. The Bucks got Spencer Hawes and Roy Hibbert in exchange but even had to include cash considerations in the deal just to make it work — further adding to their total expenditure on Plumlee.

2. Bobby Simmons

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6-foot-7 forward Bobby Simmons is one of those guys that absolutely balled out during a contract year. The former DePaul standout had a tremendous year with the Los Angeles Clippers in the 2004-05 season, earning him the honor of that season's Most Improved Player award.

Simmons was understandably a highly sought-after name in the summer of 2005, and the Bucks lured him to Milwaukee to the tune of $47 million for four years. He was okay in his debut season with the Bucks, averaging 13.4 points, 4.4 rebounds, 2.3 assists, 1.1 steals, and 1.4 triples, but unfortunately, that was as good as it got.

Simmons sat out the entirety of the 2006-07 season due to an ugly ankle injury, and while he was able to return the following season, he just wasn't the same. In 2008, the Bucks called time on Simmons' stint with the team, trading him away to the New Jersey Nets along with Yi Jinlian. Milwaukee did get Richard Jefferson in return, though, which probably ended up as Simmons' best contribution to the Bucks.

1. Tim Thomas

Tim Thomas arrived in Milwaukee in 1999 following a trade deal with the Sixers. He proved to be a serviceable player for the team's second unit for the next couple of seasons, but it was during the 2000 playoffs that Thomas earned his keep. While the Bucks exited in the first round against the Indiana Pacers, Thomas was a big winner after proving how important he was for the team during that thrilling five-game series.

The Bucks rewarded him with a $67 million deal that same summer, banking on the promise Thomas showed during the previous postseason. Over the next three years, he averaged 12.6 points, 4.4 rebounds, 1.5 assists, 0.9 steals, 0.5 blocks, and 1.3 threes per game. That's obviously not terrible, but certainly not worth the $29 million he earned during that span.