WithNBA free agency fast approaching on June 30th, a few of us here are taking a stab at an offseason plan if we were heading up the Bucks’ front office. We begin things with Jackson Gross...
We stand on the precipice of a monumental off-season for the Milwaukee Bucks. By some indications, the Bucks got their biggest domino to fall with Giannis Antetokounmpo likely staying with them amid an avalanche of rumors. While that was by far the most important piece to the offseason for GM Jon Horst, there is still much to be done to get this team back into a true contender. It will be an uphill battle, with Damian Lillard out most of the year due to that torn Achilles and minimal trade and financial resources at their disposal. While Horst is still reviewing his cap sheets and trade options, let me give him my road map to creating a contender in Milwaukee.
Step 1: Take advantage of the Celtics' financial woes
It’s been no secret that it will be a difficult season for the Boston Celtics next year. With Jayson Tatum likely out for the entire season after tearing his Achilles, and the reports that the Celtics will be looking to shed payroll, it’s the perfect time for the Bucks to swoop in and nab their long-term center. While there have been rumblings about the Celtics wanting to ship out Jrue Holiday for a first-round pick, I doubt they find a team looking to take on the aging Holiday with two years left on his deal, plus a potential for a third with a player option in 2027 for $37.2m. The only other player I could see them getting rid of that fits the bill for Milwaukee would be Kristaps Porzingis.
The Trade
Bucks receive: Kristaps Porzingis and Lonzo Ball
Celtics receive: Nikola Vucevic, Julian Phillips, and the Bucks’ 2031 first-round pick (lottery protected)
Bulls receive: Kyle Kuzma, Sam Hauser, Pat Connaughton, the Wizards’ 2025 second-round pick (no. 32 overall) from the Celtics, the Pistons’ 2025 second-round pick (no. 47 overall) from the Bucks, and one of four teams’ 2026 second-round pick from the Celtics.
On the Bucks’ side of things, this trade would hard cap them at the first apron since they are receiving more money than they’re sending out. While Porzingis has had numerous health issues, including a nasty post-viral syndrome stemming from an illness he had earlier in the season. It affected his performance in the postseason, as he only averaged 7.7 PPG and shot a rough 15.4% from beyond the arc. Yet when he is fully healthy, he is one of the best big men in the league and a career 36.6% three-point shooter, and averages 1.8 blocks per game. The question is: when is he healthy? He’s only played in 164 of 246 possible games (33% of games missed) in the last three years. He is a perfect fit next to Giannis, acting as a younger, quicker Brook Lopez. There’s a reason the Celtics needed to trade for him, and he was a key cog in the Celtics' 2024 Championship run.
You could say the same thing about the other piece coming into Milwaukee, point guard Lonzo Ball. The former number two overall pick by the Los Angeles Lakers has had an up-and-down NBA career up to this point. Much maligned in his first couple of years with LA for not living up to sky-high expectations, he was shipped off to New Orleans in the Anthony Davis trade. Finally, he seemed to reach some of his true potential when he went to the Bulls in 2021. Then the injuries piled on, and he missed two and a half seasons before returning this past season. He would provide a lot of what the Bucks would need as a floor general and table setter, and is an incredible three-point shooter who’s effective without the ball. He’s also a strong on-ball defender, and if he can get back to 75–80% of where he was in 2021, he’ll be the best point of attack defender Milwaukee has had since they traded Jrue Holiday.
This is a tough pill for the Celtics to swallow, giving up one of the core members of banner number 18 in Porzingis and a solid contributor in Hauser, but they have to start cutting costs. They’d clear up $40m in future money, and next year or sooner, they could look to offload more if they decide to trade Derrick White or Jrue Holiday. For 2025, they get a solid stop-gap option in the middle with the reliable Vucevic, who has been a double-double machine for basically his entire career. While nowhere near the level of Hauser, Phillips has had some flashes this year with the Bulls, playing in 79 contests at an average of 14.2 MPG. With Tatum likely out all season long, Phillips will have an increased role, and with the Celtics’ coaching, could develop into a more consistent shooter in Beantown.
As for the Bulls, the dumping ground of this trade: with the rumors of them wanting to trade up if Rutgers star Ace Bailey slips in the draft, the Bulls could look to ship Kuzma, their first-round pick at 12, and their three newly acquired second-round picks to make a jump into the top six or seven picks. I polled a few Bulls fans I know, and while they said they were getting fleeced, it’s hard to get fleeced when you don’t have a direction. Finally getting rid of Vuc and giving way to the youth movement is what Chicago needs to do. They have all their draft picks through 2031; they just need to let Matas Buzelis, Coby White, and Josh Giddey grow together.
There is also a financial edge to this deal for the Bulls. If they can find a way to get off of Kuzma heading into 2026 free agency, plus give Giddey and White extensions worth about $25m each, the Bulls could have an estimated $65.9m in cap space. Players like Luka Doncic, Kevin Durant, and Trae Young are currently set to hit the open market next summer.
Step 2: Bring a bunch of the band back together
SG/SF Gary Trent Jr.: Three years, $22.7m
The most obvious player they have to bring back is Gary Trent Jr. If you haven’t read my free agent forecast for him yet, I highly suggest you do. My in-depth reasons on why I want him back are there, so I’m gonna keep this part short to focus on the other players. Trent was a phenomenal addition in late free agency and was part of the best Bucks basketball last season, especially when Dame was out.
But Trent isn’t the only Bucks pending free agent I want to see back. Here are the other players I want to see return to Milwaukee next season...
C/PF Bobby Portis: Three years, $53.5m
By all indications these days, Bobby Portis is looking to get paid. In an appearance on the Run It Back Podcast, Portis gave his view of what could be his final big pay day in the NBA at 31 years old:
“Obviously, I would love to be back in Milwaukee. I’m not saying I don’t want to come back to the Bucks—I would love to—but I just want to be compensated fairly, man. I’ve taken a lot of team-friendly deals to be here. We’re at a point now where I feel like it’s time I get compensated—fairly—to my peers. That’s all I ask for.”
To fulfill that wish, I gave Portis a happy medium between a big raise and something the Bucks can work with. In this universe, Milwaukee gives Bobby a three-year deal worth 53.5m, with the first year starting at $16.5m and ending at $19.2m in year three.
SF Taurean Prince: One year, veteran’s minimum
While he was misused after the Bucks traded for Kuzma, being forced to play shooting guard at times, I still want to see Prince return. He remains a capable defender, and he shot a career-best 43.9% from the three-point line on 4.2 attempts per game.
PG Ryan Rollins: Two years, $9.1m
With Ball now in the point guard rotation, the Bucks are left with a decision of who to pick for their final point guard spot: KPJ or Rollins. My choice between the two is undoubtedly Rollins. While I respect what Porter brings in terms of his passing and driving to the hoop, I would just prefer Rollins to be the backup point guard. First of all, he would be much easier to retain as a restricted free agent than Porter, who opted out and is unrestricted. The Bucks can also re-sign Rollins without dipping into their MLE. He would also be an excellent fit next to Ball in certain lineups and could run the bench unit. Rollins is a good enough three-point shooter (40.8% on 2.1 attempts per game) and can drive through the lane at times.
C Jericho Sims: Two years, veteran’s minimum
Sims showed some flashes with the Bucks a season ago; his athleticism was the driving force behind that. While not the tallest center at 6’10”, his ability to jump out of the gym makes him a great lob threat on offense, and he can switch out to the perimeter on defense. The counting stats won’t show his true value, with 2.4 PPG and 4.9 RPG in his time with Milwaukee. Sims could be a valuable rotation player again, running in some lineups with Bobby Portis at the four and himself at the five in spurts.
Step 3: Fill out the roster
After all the trades, extensions, and re-signings, the Bucks are only left with $5.6m to work with for their final two roster spots. Here are the final two players I have joining the Bucks to complete their 15-man roster:
SF/SG Lindy Waters: One year, veteran’s minimum
This is just a quick veteran minimum for the 27-year-old Waters. He’s played 156 games in his NBA career, but has been sparingly used. He only played 18 games for the Pistons last season after being traded there from Golden State in the Jimmy Butler trade. He has three-point chops, shooting 36.6% in his career. Can’t ever have too many shooters on a team.
SG/SF Damion Lee: One year, veteran’s minimum
After that, the Bucks will have around $3.3m beneath the first apron to work with for their final roster spot, and they’ll use $2.2m of that on a vet minimum on Damion Lee. It’s been a hard road to recovery for Lee, who suffered a brutal knee injury before the 2023–24 season and only returned for 25 games of the 2024–25 season. Before that, he was one of the league’s best shooters, knocking down threes at a 39.8% clip during his last three seasons. I could see a world where Lee becomes that “Gary Trent Jr.” style free agent that Marques Johnson was talking about. A guy who would sign later in the offseason on a minimum contract and pay dividends. While I don’t know his true value as a defender, his size could be usable, and he’s another good shooting option for the Bucks to have.
Final Bucks rotation for 2025/26:
Final 2025–26 payroll: $194.7 (approximately $1.2m in room below the 1st apron)
My Final Thoughts
While this is unrealistic at the end of the day, I believe this would put the Bucks back in discussion for the top tier in the Eastern Conference next season. A new starting center, a three-and-D point guard, plus a tweaked wing core, this team has the chance to win 50 games. They’re faster, have more shooters, would fit the point-Giannis mold, and mesh with Lillard if and when he returns. Let’s just hope this reaches Jon Horst's desk so he can see the path.
How good (or bad) are my trades, free agent signings, and re-signings? What would you do differently? Let me know your thoughts in the comments below!