As a team, the overall goal of the Milwaukee Bucks is to silence their many doubters and get back on the right track with an NBA Championship next season.
Individually, as several players aim to help the team reach that goal, earning a raise in the offseason will also likely be somewhere in their minds. A handful of Milwaukee Bucks players will be eligible for new deals, and a strong showing in 2024-25, especially one capped off with an NBA title, could be just what they need to ink lucrative new contracts.
That said, let's analyze five Milwaukee Bucks who fit the profile.
Bobby Portis
Bobby Portis will make $12.6 million in 2024-25. After that, he has a player option worth $13.4 million for 2025-26. Though he has shown a willingness to sacrifice his own potential earnings to take more team-friendly deals in the past, there's at least a chance he'd want to be rewarded for his generosity with a handsome new deal, which could lead to him declining that option.
The big man is already one of the best reserves in the business, but if he wants to guarantee that he'll earn a raise next offseason, finally breaking through and taking home Sixth Man of the Year honors in 2024-25 would help. That honor would boost his individual stock tremendously, and teams would be lining up to pursue his services in a year.
Even without the award, plenty of teams would love to have Portis. He's a great second-unit spark on offense and a tenacious rebounder, two things that have made him a fan favorite in the 414. While he has his defensive shortcomings, there's no denying that he can help this team, and if he does so this coming season, the Milwaukee Bucks would likely aim to extend their partnership with him.
Delon Wright
Looking to showcase his talent on a contending team, Delon Wright inked a one-year deal worth just over $2 million with the Milwaukee Bucks earlier this offseason. That's a steal of a deal for the Bucks, who acquired a player who can help them in many different ways on a deal that won't break the bank, given their ever-present financial limitations.
This is the definition of a "prove it" deal. Wright took a cheap contract to join a premier contender to show what he could do on the big stage. If he impresses throughout the 2024-25 season, especially in the NBA Playoffs, there will be no shortage of teams lining up to get him when free agency opens next year, and he'd likely end up getting a nice raise.
For Wright to earn said raise, he'll need to be a second-unit defensive ace for the Bucks, who need as many perimeter defenders as possible. Due to the defense he brings, Wright will likely spend plenty of his minutes alongside Damian Lillard to take some of the workload off of him on that side of the court, putting even more spotlight on him.
At 32 years old, Wright still has some good basketball left in him, and he could possibly earn a quality long-term contract if he lives up to expectations in Milwaukee.
Taurean Prince
Taurean Prince finds himself in the same boat as Delon Wright. After a nice 2023-24 NBA season with the Los Angeles Lakers, he seemingly wasn't getting any sizeable offers in free agency, leading him to sign with the Bucks on a one-year contract worth a tick above $2 million. He'll be looking to raise his stock ahead of 2025 free agency while attempting to help the Milwaukee Bucks win it all.
Prince, 30, can certainly still earn a long-term deal from someone if he impresses. He's a role player in every sense of the word, doing all of the little things to help his team win while typically not being the player under the spotlight. Plenty of teams would love to have him on their side, including the Bucks, who will get plenty of use out of him this coming season.
The big thing that stands out with Prince is his versatility. At 6-foot-6, he slots seamlessly into either forward position and can defend players all over the court, switching seamlessly. The Bucks haven't had a player capable of doing that since P.J. Tucker in 2021, and it's hurt them greatly over the past several seasons, especially in the playoffs. The hope is that Prince can play the Tucker role.
In short, Prince is an excellent 3-and-D wing with incredible versatility, and the Milwaukee Bucks are hoping to see all of that this coming season.
Gary Trent Jr.
It's still shocking that Gary Trent Jr. signed the deal that he did with the Bucks. With his market falling short of what he likely expected, the guard inked a one-year, $2.6 million deal with Milwaukee, thanks to some recruiting efforts from Doc Rivers and, more than likely, Damian Lillard, his former teammate with the Portland Trail Blazers. The Bucks are thrilled to have him on such a team-friendly deal.
Trent can almost already be penciled in as Milwaukee's starting shooting guard, so among all of the players on "prove it" deals, he will have the biggest role. Playing alongside Giannis Antetokounmpo, Damian Lillard and the other key Bucks should only elevate Trent's play, particularly as a shooter, which has always been his bread and butter.
Trent's 3-point shooting will be his greatest strength, but to really earn that lucrative raise, he must show growth on the defensive end. If he can bring solid defense, something he has shown glimpses of throughout his career but not consistently, to the backcourt alongside Lillard while also lighting it up from downtown, opposing teams, especially those with spending money next year, will notice.
Even before the season begins, it feels like Trent is destined to earn a raise next off-season. However, he can guarantee it if he performs well with the Milwaukee Bucks. The 25-year-old will be motivated to earn that raise while also playing a pivotal role for the Bucks. There's a good chance he will end up being one of the most highly-coveted free agents on the market next offseason.
Khris Middleton
When he was a free agent last offseason, Khris Middleton took one for the team and re-signed with the Bucks on a team-friendly deal worth $93 million over three years. He could have asked for more but decided to sign a shorter deal to not only help Milwaukee financially but for him to also keep his options open down the line.
After this season, Middleton has a player option worth $34 million for 2025-26. Having just turned 33, there's a good chance he declines that to seek a multi-year deal to earn more financial security, even if it's another deal on the team-friendly side. If he plays his part this coming season, the Bucks would likely be more than happy to hand him a raise next free agency.
For Middleton to earn himself a lucrative new contract, he'll first have to stay healthy. It's been a huge roadblock for him over the past few seasons, keeping him off the floor quite a bit since he helped the Bucks hoist the Larry O'Brien over three years ago. After undergoing offseason surgery on both of his ankles, the hope is that Khris Middleton can stay healthy for another championship run.
Middleton showed in the playoffs that he still has plenty of juice. In six games against the Pacers, he averaged 24.7 points, 9.2 rebounds and 4.7 assists. With Giannis Antetokounmpo on the sidelines, Damian Lillard banged up and even Middleton himself dealing with an injury, the forward tried to put the team on his back, and it was a marvelous individual showing.
If Khris Middleton can stay healthy and be that player, a raise could inevitably be in his future.
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