Ahead of the 2020–2021 NBA season, there were two specific moves I wanted to see Jon Horst make for the Milwaukee Bucks:
- Acquire Jrue Holiday from the New Orleans Pelicans
- Trade for the Houston Rockets’ P.J. Tucker
Both moves happened eventually, and both paid dividends as the Bucks brought home their second championship in franchise history. (I would have also accepted the ill-fated Bogdan Bogdanović trade from the Sacramento Kings as a net-win, although it isn’t as clear whether or not that move would have reapt the same rewards.)
Three years and many more successes later, the franchise finds itself at another inflection point. With one domino down after the firing of head coach Mike Budenholzer, Horst and Co. must still face the tasks of resolving Khris Middleton’s player option and deciding on an extension for Brook Lopez, as Mitchell so diligently outlined.
But we know those aren’t all the dominoes in play.
Saying that Holiday served as a key cog in Milwaukee’s title run would be a vast understatement. But when assessing the shortcomings of a 58-win team after a first-round flameout, it’s easy to highlight a defense-first point guard whose main assignment averaged over 37 points per game and chastised him in front of cameras en route to a 4-1 series win.
There isn’t a clear solution, and there isn’t an easy solution, but there are options. One avenue worth exploring: trading Holiday to the Chicago Bulls in return for DeMar DeRozan.
While this move would not relieve any of the Bucks’ age woes—though they are both members of the 2009 draft class, DeRozan is actually 10 months older than Holiday—it would certainly mark a shift in the Bucks’ approach to the court.
Swapping one head of the Bucks’ perennial-DPOY-contender hydra for a release valve like DeRozan could be a step in the right direction to addressing their playoff woes as they would be more apt to outduel opponents on the offensive side of the ball.
In 2022–2023—like in many previous seasons—DeRozan was an elite isolation scorer, ranking no. 13 overall according to StatMuse. Adding this skill, particularly in the less-defended mid-range of the modern NBA, could bail out the Bucks when the half-court offense stalls or in the playoffs when defenses get stauncher.
Per NBA stats and info, Holiday spent 7.2 possessions per game as a pick-and-roll ball-handler in the 2022–2023 regular season, resulting in 1.00 point per possession and a 56.3 effective field goal percentage while turning the ball over 14.8 percent of the time. DeRozan —given just over two more opportunities per game than Holiday—created 1.06 points per possession at 53.2 eFG% and just a 10.4 percent turnover rate.
During his three seasons with the San Antonio Spurs, DeRozan recorded career highs in assist percentage, peaking when he facilitated 32 percent of the Spurs’ baskets during his time on the floor in the 2020–2021 season.
Since Holiday doesn’t serve as a point guard in the traditional pass-first sense, swapping him for DeRozan wouldn’t create positional waves throughout the roster. As presently constructed, DeRozan could revert back to his more natural shooting guard spot while Khris Middleton and Giannis Antetokounmpo hold down their roles as forwards.
Depending on how the Bucks’ spin on the coaching carousel goes, trading for DeRozan could also mean a reunion between the Compton native and former Raptors coach Nick Nurse. Before succeeding Dwane Casey at the head of Toronto’s bench, Nurse served as an assistant coach for the franchise and ushered in an offensive system that emphasized more ball movement and three-point shooting—something DeRozan was slower to adapt to at the time than he may be now as he enters the autumn of his career.
Stripping a potential deal down to brass tacks, DeRozan only has one year left on his current contract with a cap hit of $28.6 million. Holiday, on the other hand, holds a base salary of $34.9 million in 2023–2024 as well as a player option of $37.3 million for the following season that it seems likely he would opt into before playing his age-34 season.
Clearing the books of Holiday’s player option could be viewed as crucial if you’re a pessimist. According to Spotrac, that $37.3 million would account for just over 27% of the Bucks’ cap room in the last guaranteed year of Antetokounmpo’s contract. While dealing with the constraints of the new CBA guidelines, a good-faith move by the front office to improve the woes of Milwaukee’s current roster would likely be better than appearing stagnant as Giannis weighs his 2025–2026 player option and another extension. That a Holiday-for-DeRozan deal would replace one humble, low-key player with another could ease the transition by offering a semblance of personality continuity in the locker room.
From the Bulls’ perspective, bringing Holiday into the fold would replace the primary points of production that they have lost throughout Lonzo Ball’s knee injury saga, most importantly as a primary defender. Pairing Holiday with Alex Caruso would create a formidable tandem on the perimeter, while the Bulls have enough ball handlers and scorers that Holiday could settle into a rotational initiator role and spot-up more often than he has been afforded with Milwaukee—especially if Nikola Vucevic chooses to re-sign with the Bulls rather than another franchise in free agency. Also, without DeRozan’s need for touches, Ayo Dosunmu could see a deserved bump in usage as he continues to develop.
There is a scenario where each player would be worth more to his new team than to his current team. From an aerial view, the Bulls and Bucks would be pushing their sliders in opposite directions with a Holiday-for-DeRozan trade, as Chicago would further solidify a top-five defense while Milwaukee would hope to become more balanced, sacrificing the team’s point-of-attack brick wall in return for a bolstered offensive approach and perhaps even an improvement on it’s top-four clutch time performance from the 2022–2023 season.
In the effort to win a second NBA championship in four years and, in equal measure, ensure the future of the best basketball player in the world is centered in Milwaukee, it might be worth moving DeRozan 90 miles north.