If the Milwaukee Bucks want to make some very seismic changes to their roster this off-season, one route they could explore is trading Jrue Holiday.
It’s not the likeliest scenario for Milwaukee, but he could undoubtedly bring back a haul, given that he was an All-Star this past season and has a lot left in the tank. Furthermore, no Bucks player on the roster is untouchable, excluding Giannis Antetokounmpo. With that in mind, FanSided’s own Jack Simone put together five Holiday trade packages for the Bucks to consider, and here is a grade for each of them.
Grading a trade proposal between the Milwaukee Bucks and Portland Trail Blazers
At first glance, this trade might puzzle Bucks fans. Why would they trade Holiday, who was named an All-Star for the second time in his career this past season, and Brook Lopez, who just had what many would consider his best season in years, for two young players, a passable center, and a pick that is high, but it not a guaranteed star player? Well, there are a few reasons.
First and foremost, this trade would help the Bucks’ need for youth. It was apparent this last year that Milwaukee’s roster, which was the oldest in the league, could not keep up with young teams, such as the Miami Heat, which the playoffs showcased. Simons (23) and Walker (20) would be a pair of players who would bring some youth to town.
These are not throw-ins either, as Simons has shown legitimate potential as a lethal scorer in this league. He’d be the perfect third fiddle alongside Giannis Antetokounmpo and Khris Middleton on offense. As the past few years have shown, the Bucks’ offense tends to be stagnant at times due to a lack of reliable scorers around those two. Simons would instantly help with that issue. Walker is still incredibly raw, but at 6-foot-9, he would provide some size on the wing and a player with a good amount of upside, something this team does not have much of right now.
Nurkic does not exactly fit with the Bucks as well as Lopez or Bobby Portis, but he could be a fine backup to the latter, who would presumably take on a full-time role as a starter in this situation.
The true prize of this trade would be that third overall pick, given Milwaukee’s desire for youth and just how strong the top three possible picks in this draft class are. Victor Wembanyama will be the first name off the board, but after that, Brandon Miller and Scoot Henderson are the next names. With The Ringer’s Kevin O’Connor reporting that the Charlotte Hornets, who hold the second pick, are likely to take Miller, the Milwaukee Bucks could select Henderson in this scenario.
Henderson, who is 19, would not only add some youth to the roster, but he would be among the best pure athletes this roster has had since Antetokounmpo was drafted. He’s a ball of energy at all times, and he’d be a perfect pairing with Antetokounmpo out in transition, as these two on the break would be must-see. Henderson and Simons would form Milwaukee’s exciting backcourt of the future here and put two tremendous pieces alongside Antetokounmpo and Middleton.
Essentially, the Bucks do this to keep their title-contending window open for as long as possible. Holiday is 32 years old and has said that he will seriously consider retiring when his contract with the Bucks runs out in two years. Lopez is 35, and while he showed that he could still play at a high level this past season, it remains to see how much longer he could keep it up. The young pieces in this trade would give the Bucks a core that still has room to grow rather than one that feels like it is ticking toward the end. Yet, it’s still not a perfect deal, as there could be some growing pains with those young pieces, which could lower the Milwaukee Bucks’ ceiling in the short term.
If the Blazers were to do this, it would be to put this team in a position to contend immediately. Damian Lillard has made it clear that he wants this team to get win-now pieces rather than just focus on building for the future. Adding an All-Star guard and 2023 Defensive Player of the Year runner-up would undeniably fit the billing there.
BTBP Grade: B+
Grading a trade proposal between the Milwaukee Bucks and Minnesota Timberwolves
While most of the trades on this list revolve around the Bucks looking for players on the wing or in the backcourt, this one involves the center position.
Excluding Brook Lopez, it would be hard to find a center who fits better alongside Antetokounmpo in the league not named Karl-Anthony Towns. He’s among the best shooting centers to ever play the game, having hit 39.5 percent of his triples on 4.2 attempts per game in his career. Averaging 23 points per game in that same timeframe, he’d be a great complement on offense to take the pressure off of Milwaukee’s stars. At 27 years old, he’s also young and still has yet to play out his prime years. He and Antetokounmpo could be an exciting one-two punch for years to come.
There are layers to this, as if the Bucks were to do this trade, they would also likely lose Lopez in the process, as having him, Antetokounmpo, Towns, and Portis in the frontcourt would make for some problems. Still, some would say it would be worth it to get a younger player who can score the ball at over 20 points per game nightly with ease.
Towns is not a perfect fit for the Bucks, as he would be a significant step down from Lopez on the defensive side of things. Portis is not known for his play on that end either, so Antetokounmpo’s importance would increase mightily, forcing him to exert even more energy on that end. The Milwaukee Bucks would also have to scour the market for a new point guard to lead the backcourt.
The Timberwolves could consider this because of the ability to add a defensive-minded guard in the backcourt alongside Anthony Edwards. The guard is starting to develop into a legitimate star, and adding an All-Star in Holiday to play with him could help accelerate that development. There are also questions regarding Towns’ fit alongside Rudy Gobert, which has forced the former to play power forward more often. That’s not his strength at all, and no one will be taking on that Gobert contract, so perhaps they would consider moving Towns if they could get impact pieces. A guard who was an All-Star and a first round pick might be a nice starting point.
BTBP Grade: B
Grading a trade proposal between the Milwaukee Bucks and Chicago Bulls
A Central Division shake-up would be in the works with this trade. This particular trade would be beneficial for both teams, to an extent.
For the Bucks, adding LaVine would immediately help with their need for more shot-creators and reliable scorers. The guard is a lethal scorer and long-range shooter, having averaged 24.5 points while shooting 38.4 percent from deep on 5.8 attempts per game. A player like that could surely help the Milwaukee Bucks offensively, especially in the playoffs, where they’ve struggled for years.
LaVine, who is prominently known for his high-flying dunks, would also give the Bucks a boost of much-needed athleticism. At 27 years old, he would also provide youth, which, once again, is a big attribute this team needs more of. This trade would also give the Bucks some long-term security, as LaVine is under contract and has a player option in 2026-27, which is much different than the uncertainty surrounding Holiday and his potential retirement in two years.
The main concerns with this trade would be the drop-off in defense and LaVine’s injury history in his career. LaVine isn’t a complete liability defensively, but his play on that side of the ball is among his strong suits, which could be somewhat troublesome for the Bucks. As for the injuries, LaVine has played more than 70 games just three times in his eight-year career. Still, despite both of the concerns, LaVine is undeniably a captivating target, especially if they’d be able to get him without giving up a pick, as proposed in this hypothetical.
One reason the Bulls may consider this would be their need for a point guard. With Lonzo Ball’s playing career moving forward uncertain, the Bulls very clearly need a new lead guard. There’s a big question as to whether or not it would make sense to trade LaVine for that guard, but if they are willing, this particular deal would give them an All-Star. While Bulls fans would certainly take some warming up to the idea, adding Allen would give them another guard who is a good shooter.
BTBP Grade: B
Grading a trade proposal between the Milwaukee Bucks and Atlanta Hawks
Like the aforementioned trade with the Blazers, this trade between the Bucks and Atlanta Hawks would instantly reform Milwaukee’s backcourt. Also like that trade, this deal would help the Bucks get younger, as Dejounte Murray (26) and Bogdan Bogdanovic (30) would minimize the roster’s age while still keeping them in contention for the next several years with a pair of solid players.
Murray would be a nice addition for the Bucks at the point guard position, as he’s a former All-Star and All-Defensive honoree. Offensively, he could orchestrate the offense to take the pressure off of the Big 2 in Antetokounmpo and Middleton from constantly having to do it. Over the last two years, he’s averaged 20.8 points and 7.6 assists per game. On defense, he’s not on the level of Holiday, but the 6-foot-4 Murray is capable of guarding a handful of different positions and pestering opponents, having claimed the 2021-22 Steals Champion title.
Meanwhile, Bogdanovic makes sense for the Bucks for more reasons than just his on-court play, which is certainly desirable as well. Fans will remember that the Bucks nearly landed Bogdanovic during the 2020 off-season before the sign-and-trade fell through. Jake Fischer, who was a writer for Bleacher Report at the time, said that Antetokounmpo clearly expressed his desire to play with Bogdanovic, as he admired “his fellow European’s toughness and swagger.” The Bucks could now make that dream reality and bring the two together after a failed attempt in 2020. It would never hurt to try and keep Giannis happy while also getting an impact player.
On the court, Bogdanovic would be a seamless fit with the Bucks due to what he provides on the offensive side of the ball. For his career, he’s averaged 14.2 points while shooting 38.7 percent on his 3-pointers on 6.2 attempts per game. Marksmanship and scoring like that would instantly be a perfect fit alongside Antetokounmpo. Over the years, the Bucks have surrounded Antetokounmpo with 3-point shooters such as Grayson Allen, Bryn Forbes, and Kyle Korver, but Bogdanovic would certainly be the best two-guard the Milwaukee Bucks have had in a long time.
If the Hawks were to consider this, it would be to get a guard who fits better alongside their star in Trae Young. Unlike Murray, who has been a point guard throughout his career, Holiday has played a good amount of shooting guard in his career. He could easily play the two next to Young, which would help mightily on the defensive end, as Holiday could take the tougher assignments nightly.
BTBP Grade: A
Grading a trade proposal between the Milwaukee Bucks and Golden State Warriors
Between youth, familiar faces, draft picks, and a wing, this deal has just about everything for the Milwaukee Bucks to desire in a Holiday trade.
Poole, a Milwaukee native, would be an interesting addition to this roster. Despite having the best regular season of his NBA career, he spent a good chunk of the postseason sidelined. His season was full of drama before it started after being punched by teammate Draymond Green. After this season, many said that Poole would benefit from a fresh start, which makes sense. In Milwaukee, he’d be a great third fiddle to Antetokounmpo and Middleton offensively, giving them a player who can score the ball at will. At 23 years old, he’d also give them some youth.
Sticking with youth, Kuminga would be a tremendous piece to this trade. In a league that is quickly becoming so reliant on wings, the 6-foot-8 Kuminga would be a great addition to a roster without a lot of bodies at the position. On top of that, he’s just 20 years old and has not even scratched the surface of his potential. Payton, who began his NBA career with the Bucks, would be a fine piece to add to the backcourt, especially if Jevon Carter leaves in free agency. He’s a scrappy guard who can make things tough on opponents, which the Milwaukee Bucks love.
On top of that, this trade would see the Bucks acquire two first round picks, which they could use to either draft more young players or trade them to get more talent. Either way, that would be an incredible boost to the Milwaukee Bucks’ lacking draft capital stash.
The Warriors may consider this to add an All-Star guard in Holiday and another quality rotational sharpshooter in Allen. With Poole not playing much in the postseason, the team may try to move him to get off of the hefty contract they gave him previously. This deal would allow them to keep contending at the highest level with two quality players in the backcourt.
BTBP Grade: A+
Stay tuned for more Milwaukee Bucks analysis and trade breakdowns.