Milwaukee Bucks: Exploring 4 trade proposals for Jrue Holiday

Let’s explore four potential trade offers the Milwaukee Bucks can send to the New Orleans Pelicans in exchange for Jrue Holiday.

New Orleans Pelicans’ guard Jrue Holiday has always been thought of as someone who would be available via trade this offseason. Well, good news for Milwaukee Bucks‘ fans who were hoping their team would pursue him: According to The Athletic’s Shams Charania, the Pelicans are “open to trading Holiday.”

Although it may not actually be good news for the Bucks that New Orleans is actively shopping him (they don’t necessarily have the resources to bid against other teams), it does open up the world of Jrue Holiday trade scenarios. So, without further ado, let’s explore four potential trade packages the Bucks could offer.

4. Swapping Stars

Bucks receive Jrue Holiday and J.J. Redick. Pelicans receiver Khris Middleton

I floated this idea on Twitter and it received a resounding heck no from fans–and for good reason. For as good as Holiday is and for everything he’d bring to the Bucks, Khris Middleton means so much more to the organization both on and off the court. He’s a better scorer and overall fit with Giannis Antetokounmpo on offense and is above average on defense. Even if you throw in J.J. Redick, it wouldn’t be worth it for Milwaukee.

3. From Twitter:

Bucks receive Jrue Holiday. Pelicans receive Eric Bledsoe, Ersan Ilyasova, D.J. Wilson and Donte DiVincenzo

Cody Bauer hit me with this trade proposal on Twitter, and it makes some sense. Eric Bledsoe wouldn’t be asked to do as much creating in New Orleans with Lonzo Ball holding down the fort at point guard, allowing Bled to potentially come off the bench. Ersan Ilyasova is simply a salary-filler while D.J. Wilson and (more specifically) Donte DiVincenzo are the cream of this trade. DiVincenzo has the potential to develop into an average starter or high-end bench player which would fit well into the Pelicans’ plans.

In a competitive market, it’s unlikely the Pelicans make this move. Do they really want to pay two more years of Bledsoe (the final year of his contract is mostly non-guaranteed) as well as $7 million to Ilyasova to watch the former choke in the playoffs and the latter sit on the bench? There is also a gluttony of better assets out there that would trump DiVincenzo in any potential deal.

2. 3-Teamer from Eric Nehm at the Athletic:

Bucks receive Jrue Holiday. Pistons receive Eric Bledsoe, Donte DiVincenzo, Pacers 2022 2nd rounder (from Bucks). Pelicans receive Derrick Rose, Tony Snell, Luke Kennard, No. 24 pick in 2020 and 2024 first (from Bucks) top 5 protected.

This trade was proposed by The Athletic’s Eric Nehm when he was previewing Milwaukee’s point guard position at the beginning of October. Bucks give up significantly more in this trade (two first-round selections as well as DiVincenzo and Bledsoe), but that’s probably closer to what it’s going to take. Especially since opening up negotiations with multiple teams will drive up the price–at least that’s what the Pelicans are hoping for. Involving a third team who isn’t necessarily trying to go deep into the postseason in the immediate future to take on Bledsoe’s contract is probably the way to go. It’s unlikely New Orleans, with their postseason aspirations, will want two years of a point guard who has proven to be a liability when the games matter most.

1. A sign-and-trade

Bucks receive Jrue Holiday. Pelicans receive Eric Bledsoe, Donte DiVincenzo, sign-and-trade with Sterling Brown and 2024 protected first.

We get a little spicey with this trade, as Milwaukee includes Bledsoe, DiVincenzo, Brown and a 2024 protected first. Brown seemed to regress during his third season with the Bucks, but there’s still some hope he can turn into a serviceable three-and-D wing–one of the most sought after positions across the NBA. Adding Brown into this deal via a sign-and-trade gives the Pelicans some more wing depth they might not be able to find anywhere else. The 2024 first also improves the potential assets they receive, as who knows what position the Bucks will be in four years from now. Also, the Pelicans already have four selections (one first and three seconds) in the upcoming draft so it’s unclear if they’d want to add to that collection.