After winning an NBA Championship in 2021, the Milwaukee Bucks have not made it back to the Eastern Conference Finals.
In 2022, it was a relatively acceptable defeat. They lost in the second round to the Boston Celtics, and considering Khris Middleton was injured, they put up a valiant effort against the eventual East champs.
This past season was a different story. Giannis Antetokounmpo got injured, but even when he returned, the Bucks seemed to be outmatched by a Miami Heat squad led by an incensed Jimmy Butler.
Milwaukee has already fired head coach Mike Budenholzer and more changes could potentially be on the horizon. But how big will those changes be?
5 Jrue Holiday trades to shake up the Milwaukee Bucks this offseason
Well, if the Bucks hope to make significant alterations and ones that would help Antetokounmpo continue competing for championships, they would almost certainly have to trade one of their two stars.
At this point, it could be either one of the two, but in today’s NBA, Jrue Holiday would likely have more value in the trade market. He’s arguably the best perimeter defender in the NBA and is coming off an All-Star season.
So, even if the Bucks would prefer trading Khris Middleton over him, which seems likely, dealing Holiday could be the smarter move, as he would get back a better return.
Plus, it might even be easier to replace him at the starting point guard position than it would be to replace Middleton’s role as the team’s secondary scorer.
With all that in mind, here are five potential Holiday trades that the Bucks should consider this offseason.
5 Jrue Holiday trades to shake up the Milwaukee Bucks: Portland Trail Blazers
This trade package is nothing short of insane. The Milwaukee Bucks might not want to do it because Anfernee Simons is so young and a minus on the defensive end. And the Portland Trail Blazers might not do it because of how much youth they’d be giving up in the deal.
But at the same time, both teams have plenty of reasons to consider this trade.
For the Bucks, this would be a huge change to the roster. They would be doubling back to the days when Giannis Antetokounmpo and Khris Middleton ran things, but this time around, they’d have an elite offensive star next to them.
Milwaukee’s defense was phenomenal this season, but their offense left much to be desired. While adding Simons into the mix would definitely be a defensive downgrade, their offense would improve.
Meanwhile, the addition of Scoot Henderson or Brandon Miller would give the Bucks some help as well. Both are talented enough to help the team win, but it could also help extend Antetokounmpo’s title window in the long run.
As for Portland, this could be their best way to ensure Damian Lillard has a championship-caliber team around him.
Adding Jrue Holiday and Brook Lopez to the mix would not only give Lillard two solid scoring options next to him, but it would also completely transform the Trail Blazers’ defense, which has been terrible for years.
This deal may not be the most likely of the bunch, but it’s certainly one of the most intriguing.
Potential starting lineups:
Bucks: Anfernee Simons, Scoot Henderson/Brandon Miller, Khris Middleton, Giannis Antetokounmpo, Bobby Portis
Trail Blazers: Damian Lillard, Jrue Holiday, Shaedon Sharpe, Jerami Grant, Brook Lopez
5 Jrue Holiday trades to shake up the Milwaukee Bucks: Minnesota Timberwolves
Last summer, the Minnesota Timberwolves made a massive trade for Rudy Gobert, and it already looks like it didn’t work out. They were eliminated in the first round this season.
In turn, they could look to change up the roster, and since Gobert has no value, trading Karl-Anthony Towns may be the best way for them to do that.
Milwaukee would be making a significant change in this deal. Towns obviously isn’t a great defensive presence, meaning Giannis Antetokounmpo would have to take on more responsibilities on that end, but his offensive game would open things up a ton for the Bucks.
They could sign and trade Brook Lopez and run a frontcourt of Antetokounmpo and Towns. That’s a duo that could play together for years to come.
As for the Timberwolves, they would reset things a bit and put another All-Star alongside Anthony Edwards that fits the team a bit better. Jrue Holiday’s game fits beautifully in Minnesota.
His offensive game, mainly his playmaking and 3-point shooting, would complement both Edwards and Gobert. Meanwhile, his defense, combined with Gobert’s interior presence, could help propel the Timberwolves forward and potentially make them a top-10 defense in the league.
Some may not think Holiday’s value lives up to Towns’, but he fits the Timberwolves’ roster so much better.
Potential starting lineups:
Bucks: Jevon Carter (or sign/trade for another point guard), Grayson Allen, Khris Middleton, Giannis Antetokounmpo, Karl-Anthony Towns
Timberwolves: Jrue Holiday, Anthony Edwards, Kyle Anderson, Jaden McDaniels, Rudy Gobert
5 Jrue Holiday trades to shake up the Milwaukee Bucks: Chicago Bulls
At first glance, the first thing most Milwaukee Bucks fans would notice in this deal is the drop-off in defense. And while that’s true, this would definitely help improve the Bucks’ offensive game.
Similar to the Karl-Anthony Towns deal, that would have to be a sacrifice the Bucks are willing to make. LaVine’s offensive game could help transform the way Milwaukee plays on that end.
He’s not the playmaker Jrue Holiday is, so the Bucks would have to sign or trade for a new point guard, but LaVine has historically been one of the more efficient players in the NBA.
His 3-point shooting dipped a bit last year, but alongside a player as great as Giannis Antetokounmpo, LaVine would be getting more open shots than he ever has.
For the Chicago Bulls, this deal would be about finally landing a star point guard to pair with their team. Unfortunately, they would have to give up LaVine in the process.
That could be a good thing, though. DeMar DeRozan could transition into the role of the primary scorer, with Holiday backing him up while acting as a primary playmaker.
Plus, adding Grayson Allen to the mix would be great for Chicago, as they desperately need some extra shooting at the wing position.
Chicago would also create the best defensive backcourt in the league with Holiday and Alex Caruso, the two guards from this year’s All-Defensive First Team.
Potential starting lineups:
Bucks: Jevon Carter (or sign/trade for another point guard), Zach LaVine, Khris Middleton, Giannis Antetokounmpo, Brook Lopez
Bulls: Jrue Holiday, Grayson Allen, DeMar DeRozan, Patrick Williams, Nikola Vucevic
5 Jrue Holiday trades to shake up the Milwaukee Bucks: Atlanta Hawks
This would be an intriguing deal for the Milwaukee Bucks, who would be rounding out their roster a bit, adding depth, and getting younger in this deal.
Dejounte Murray just wrapped up a relatively underwhelming season with the Atlanta Hawks, but it wasn’t completely his fault. His fit next to Trae Young was a bit clunky, and it seems like both need to have the ball in their hands too much to work together.
In Milwaukee, Murray could get back to being the full-time point guard like he was with the San Antonio Spurs. Plus, he’d have more weapons to pass to than he ever has before. It would be the perfect recipe for a 10-assist-per-game season.
Plus, the Bucks have had an interest in Bogdan Bogdanovic in the past, so the fit there would absolutely make sense, as he could help space the floor for them.
On the flip side, would the Hawks really trade Murray just one year after they acquired him in the first place? Well, if they want to compete for a title, then they should consider it.
As noted, it’s become clear that Young and Murray both need the ball in their hands, but Jrue Holiday’s comfort playing off the ball could make him a great fit next to Young.
Plus, while Murray is a great defender, Holiday would even be an upgrade on that end. He would also be able to mentor Young, which could be huge for his development.
Potential starting lineups:
Bucks: Dejounte Murray, Bogdan Bogdanovic, Khris Middleton, Giannis Antetokounmpo, Brook Lopez
Hawks: Trae Young, Jrue Holiday, De’Andre Hunter, John Collins, Clint Capela
5 Jrue Holiday trades to shake up the Milwaukee Bucks: Golden State Warriors
After his brutal playoff run, some people are completely out on Jordan Poole. But in reality, he’s still a 23-year-old budding star who has shown an absurd amount of potential throughout his young career.
In a lineup with Giannis Antetokounmpo and Brook Lopez, Poole’s defensive deficiencies would still be mitigated, and he would likely have the ball in his hands a lot more on offense. He could grow as a player in Milwaukee.
The Bucks would also add Gary Payton II to help make up for the defensive loss of Jrue Holiday, Jonathan Kuminga as a high-upside project, and two firsts to replenish their draft cabinet.
Meanwhile, this would be the Golden State Warriors’ effort to put a championship-caliber roster around Stephen Curry again. Their current team can do it, but adding Holiday would be a massive boost.
His defensive presence alongside Curry, Thompson, and Draymond Green would help Golden State be one of the league’s best defenses. And Holiday’s no slouch on offense, either.
Plus, bringing Grayson Allen into the fold would give the Warriors yet another shooter on the wing. His 3-point scoring would be valuable off the bench for them.
In all likelihood, Holiday stays with the Bucks next year, and Poole stays with the Warriors, but this deal could be interesting for both sides.
Potential starting lineups:
Bucks: Jordan Poole, Gary Payton II, Khris Middleton, Giannis Antetokounmpo, Brook Lopez
Warriors: Stephen Curry, Jrue Holiday, Klay Thompson, Andrew Wiggins, Draymond Green (or Kevon Looney)