Milwaukee Bucks: Retaining Wesley Matthews is pivotal this offseason

The Milwaukee Bucks will have to fill a significant hole at shooting guard in free agency this offseason if they lose Wesley Matthews.

After a devastating close to the 2019-20 season, the Milwaukee Bucks have some roster issues to address this offseason before preparing for a title run in 2021. One, in particular, flying under the radar has been the abundance of Bucks’ shooting guards that will hit free agency and how they plan to approach the situation, particularly with Wesley Matthews.

Aside from second-year guard Donte DiVincenzo, the rest of Milwaukee’s shooting guards can hit the free-agent market this offseason. This list includes Wesley Matthews, Pat Connaughton, Cam Reynolds, Kyle Korver, and Sterling Brown, a hefty portion of the team’s wing depth. That many players could lead the Bucks to make some tough calls, particularly with the potential impending financial implications due to the ongoing coronavirus pandemic and Milwaukee’s already limited flexibility.

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Wesley Matthews remains the most coveted among the bunch, and Milwaukee should see him as a priority. His $2.6 million player option for the 2020-21 season would see him play on an absolute bargain of a contract, which could lead to him seeking a raise after a stellar first year with the Bucks instead.

What the 34-year-old plans to do with that option has been in question all season, but it would be an unquestioned positive if he opted-into playing out that final year with Milwaukee.

Although his role with the Bucks was smaller this season than it had been in previous seasons on other teams, Matthews still played a significant part in Milwaukee’s success this year. Offensively, the guard averaged a career-low 7.4 points per game this season, but his 36.4 percent 3-point shooting provided a much-needed spark from deep. Matthews served as an excellent floor-spacer, streaky on occasion, but embracing Milwaukee’s “let it fly” mentality with open arms nevertheless.

Where Matthews made the most impact with Milwaukee was unquestionably the defensive end. The guard was arguably the team’s best wing defender, tackling top-tier assignments such as Jimmy Butler, James Harden, or LeBron James periodically this past season. That type of presence alleviated pressure off of the Bucks’ other stars and helped make this defense a formidable matchup against any foe. Defenders capable of tasks such as those do not come around often and would be a significant blow for the Bucks if he walked in free agency.

That defensive prowess, along with his sharp 3-point shooting, makes Wes Matthews a desirable target for many teams, one that Milwaukee might not be able to afford to lose. The 34-year-old fits the team’s win-now timeline and proved this season that he could provide a significant contribution to a franchise with championship aspirations.

If there is one strict advantage the Milwaukee Bucks have over the rest of the league when it comes to re-signing Matthews, it is the state they play in. Throughout this hectic 2019-20 season, Matthews has repeatedly remarked on how much of a pleasure it is to play in his home state of Wisconsin. Speaking at media day last offseason:

"“Coming back home is a sentimental feeling, and one that you can’t quite describe. And to see the success, the growth of the city, the growth of the state, what this Bucks organization and what this team has done, I come back and I don’t even recognize some of the stuff around here. It’s cool, and I’m excited to be a part of it. Winning is huge, and I just feel that what I bring as a player fits perfectly with what this team is about.”"

Several months later, Matthews appeared on the Posted up podcast hosted by Yahoo! Sports’ Chris Haynes. When Haynes asked the guard what it was like playing for his hometown team:

"“It’s amazing. It really has, it’s been amazing. I wouldn’t have appreciated it in my younger years. When we first met in Portland, I wouldn’t have appreciated being home. I wouldn’t have appreciated it like that. My family, friends, the supports of the fans, it’s unbelievable.”"

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So, yes, Wesley Matthews appears thrilled to be playing back home for the Milwaukee Bucks, but that does not guarantee a return next season. Only time will tell what comes of Matthews’ looming $2.6 million player option, but Bucks’ fans should have their fingers crossed he opts-in, or he and the organization can come to terms on a deal.

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