Bucks Trade Proposal Bracket: 2-15 Matchup

For an overview of this project, check out the introduction here.

Yesterday’s matchup was met with relative apathy, in no small part because neither trade proposal went far enough to meet the Bucks’ biggest need (point guard) or moved the needle in ways our readers felt were significant. Still, the Houston Rockets package returning Robert Covington and Ben McLemore won out, and will move on to the next round.

We turn our attention now to another matchup, where each deal is fun in theory but difficult to pull off in actuality. Both trades also involve replacing Eric Bledsoe with another starting-caliber point guard, but the paths for the Milwaukee Bucks to get there is complicated and, if we’re being honest, pretty farfetched. That doesn’t mean they’re not worth considering, though, so here we go!

2) Oklahoma City Thunder: Chris Paul

Editor’s note: Thanks to munchtime for pointing out the error with this trade. Cap holds were not active on the tradenba.com trade machine, so the Bucks needed to add an additional $5M in salary to make it legal. We opted to send Robin Lopez to Oklahoma City, where he could be a decent backup to Steven Adams.

Why the Bucks do it:

The name of the game for the Bucks is to keep Giannis Antetokounmpo in Milwaukee. The best (and quickest) way to do that is to get him to sign the supermax extension as soon as possible, and the best way to persuade him to do that is to demonstrate a commitment to building a winning roster around him. Chris Paul is exactly the type of player that raises the ceiling of this Bucks team now, despite his age, size, and enormous salary commitments. He’s not called the Point God for no reason, and his excellence on offense (while remaining competent on defense) could be enough to put the Bucks over the top. Perhaps most importantly, Chris Paul is reported to want to be in Milwaukee. That matters!

Why the Thunder do it:

The present-day Thunder have reached their ceiling, and hanging on to Paul now would prevent them from evolving into whatever their next iteration is. Furthermore, the keys to the backcourt belong to Shai Gilgeous-Alexander, who needs the freedom to develop into the player OKC needs him to be. Of course, you don’t want to give away a player on Chris Paul’s level, and the pair of Pacers picks that Milwaukee can offer, along with the chance to see what Aaron Gordon can do in a non-Orlando environment while on a very team-friendly contract adds up to a decent return.

Why the Magic do it:

Orlando is stuck in the middle and going nowhere fast. Markelle Fultz has a chance to develop nicely, as did Jonathan Isaac before a torn ACL put him on the sideline for the foreseeable future. Nikola Vucevic is not going to be the centerpiece of a Finals-bound team (and moving him makes a lot of sense too), and neither is Gordon. The six-year pro has elite athleticism, but Orlando is not in a position to harness it for a serious playoff run, and Gordon’s development has stagnated since the Magic have allowed their glut of frontcourt players allow Gordon to live out his fantasy of playing as a wing. Both parties need to move on from one another, and getting a free look at D.J. Wilson (who has the length that former Bucks front office executives Jeff Weltman and John Hammond love), a future second rounder, and a team-friendly contract in Eric Bledsoe is a quick way to help develop the team’s defensive identity as they navigate the next few seasons to find out just what the next version of the Magic that matters could be.

Milwaukee receives: Chris Paul

Oklahoma City receives: Aaron Gordon, Ersan Ilyasova, 2020 IND 1st (via MIL), 2022 IND 2nd (via MIL), Robin Lopez

Orlando receives: Eric Bledsoe, D.J. Wilson, 2023 MIL 2nd

We’ve known for a while that we ought to not get our hopes up. It has never been outright stated but generally alluded to that Milwaukee has only lukewarm interest in Chris Paul, in no small part because of how his personality might clash with Giannis. From The Athletic’s Eric Nehm and Sam Amick:

As for the reported prospect of the Bucks pursuing Oklahoma City point guard Chris Paul as a possible solution to the roster deficiencies, sources with knowledge of ownership’s thinking said it is highly unlikely. The cost of bringing him aboard — Paul is owed $41.3 million next season and has a player option worth $44.2 million in the 2021-22 campaign — and the potential difficulty of bringing Paul onto a roster already led by a strong personality in Antetokounmpo seems to limit the chances of the Bucks moving to pair the two All-Stars. All indications are that the Bucks would rather look elsewhere.

However, I would like to present the case that maybe a personality clash is exactly what the Bucks need right now. Everybody gets along and everybody knows their role, both of which are good things. The Bucks have created a system that fosters regular season success and promises advantageous playoff seeding, but the flaws of that system undermine their chances in the playoffs, and sometimes a dissenting voice is required to lead the group towards the right outcome. The Bucks have been challenged by other teams, and failed to meet that challenge. Now that the stakes are at their highest, perhaps they need to invite that challenge onto their roster in order to arrive at the best version they can be this season. Change is never comfortable, and the Bucks have already undergone some significant growing pains. Perhaps picking up Chris Paul is the unlikely discomfort that Milwaukee needs to reach the NBA Finals.

That being said, any three-team trade is inherently unrealistic because there’s now a third party who needs to be satisfied with the outcome, and Orlando is by no means guaranteed to be satisfied to move Aaron Gordon for a relatively weak return. Teams value success, and Gordon could make them slightly more successful in the short-term. Allowing for that success to be traded for the possibility of future success is a hard sell, the type that scuttles multi-team trades before they can come to fruition.

15) Toronto Raptors: Kyle Lowry, 2023 TOR 2nd

Why the Bucks do it:

One of the knocks on the Bucks over the last two postseasons is that they’ve been stymied in similar ways. It’s not so much that they folded under pressure, but that they failed to rise to the occasion, and the performance of their backcourt has been front and center when those criticisms are raised. While it’s a gamble, Kyle Lowry would be a proven playoff performer who has demonstrated the ability to be relied upon when it matters most, and his savvy guard play would fit well with a pair of ball-dominant wings like Giannis Antetokounmpo and Khris Middleton. Lowry expires next season and will turn 35 in the middle of it, but the six-time All Star is tough as nails and controls the game well enough to be worth exploring, no matter the risk. The future second round pick is relatively low-value, but it’s a minor asset that might be nice to have.

Why the Raptors do it:

Trading DeMar DeRozan was tough...but it paid off in the best way when Toronto won their championship. Now, with both Marc Gasol and Serge Ibaka facing free agency in their 30s, trading Kyle Lowry now might be a way to stabilize their roster. Lopez figures to fit well within the Raptors’ other frontcourt players, and Bledsoe is still a dynamic enough defender to fuel Nick Nurse’s mad scientist approach to defensive strategy. Getting a late-first is icing on the cake for trading a franchise cornerstone.

Milwaukee receives: Kyle Lowry, 2023 TOR 2nd

Toronto receives: Brook Lopez, Eric Bledsoe, 2020 IND 1st (via MIL)

It should be said that Toronto may have little interest in this deal specifically because of how their cap sheet would be affected not this summer, but next summer. Lowry is an expiring $30M, while both Bledsoe and Lopez are under contract the following season, which would undermine the NBA’s worst kept secret: Toronto has hopes for wooing Giannis in free agency in 2021. It’s reasonable to build your roster strategy around keeping cap space available for one of the league’s best players – it has worked before – so this trade is likely a non-starter unless Giannis signs the supermax extension this offseason. Were that to take place, the Raptors would benefit by quickly pivoting and keeping themselves relevant in the short-term while seeking their next avenue to NBA Finals contention.

Vote for your preferred trade package!