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

For a recap of the first round of voting, check out the summary here.

Welcome back to the Milwaukee Bucks Hypothetical Trade Proposal Bracket! This tournament is designed to take (mostly) realistic trade proposals for the Bucks and have you, the fans, vote on which ones you prefer. There were some bumps in the first round but nothing that knocked the whole effort off track, so now that we’ve cut our field in half it’s time to do so again. Today’s focus will be on both matchups on the left side of the bracket, which is illustrated below.

1-4 Matchup

Milwaukee receives: Derrick Rose, Luke Kennard

Detroit receives: Eric Bledsoe, 2022 MIL 2nd, 2025 MIL 2nd

vs.

Milwaukee receives: Dennis Schroder, Reggie Bullock

Oklahoma City receives: Eric Bledsoe, Julius Randle, 2020 LAC 1st (via NYK)

New York receives: Chris Paul, 2022 IND 2nd (via MIL)

Both of these trades originally made it through because the Bucks were able to move Eric Bledsoe (which many fans are treating as a required element of the upcoming offseason) along with relatively light draft assets in return for a pair of contributors. With Detroit, Milwaukee would get back an able pick-and-roll operator in Rose, as well as a heretofore injury-prone backcourt prospect in Kennard. Kennard’s value may be at a low point and, if this news from The Athletic’s James Edwards III is any indication, his stock might be rising.

It’s questionable to know whether or not the Pistons, who are under new management, will be willing to part with Rose, given his status as one of the few bright spots (relatively speaking) on the roster. Here’s Pistons general manager Troy Weaver on Rose:

We’re excited to get them [Derrick Rose and Blake Griffin] healthy and help them move forward,” Weaver said of the two veteran All-Stars. “We feel like we have a good mixture of young guys with those two staples to be able to start there, but obviously we’ve got a lot of work to do with the draft and free agency.

On the OKC side, the Thunder are clearly willing to field Chris Paul offers, and the New York Knicks might end up being the only team willing to make space for his contract. For their trouble in facilitating the deal and sending Eric Bledsoe to the Thunder, Milwaukee could get back Dennis Schroder as an offensive point guard upgrade. Schroder is clearly in limbo, as are the Thunder overall. From Sports Illustrated on Schroder’s future in Oklahoma City:

Schroder’s status with Oklahoma City will depend on if he wants to continue coming off the bench and if Presti is ok with having Shai Gilgeous-Alexander continue to play small forward. [...]

If you’re Schroder, now is the time to ask for your team to run. There’s an excellent chance, Chris Paul and Danilo Gallinari won’t be here next season. If the Thunder is going full rebuild, then logic says Gilgeous-Alexander will be the starting point guard.

Presti has shown if you are willing to be transparent, he will work with you to get a deal that benefits the player as well as the Thunder. Losing Schroder’s energy and scoring will be devastating to the Thunder’s postseason chances; however, if Presti wants to win a championship, then at some point, you have to tear things down.

The Bucks could also bolster their wing depth with Reggie Bullock, who is both a high character player (especially given some of the tragedies he’s endured) and a low-cost 3&D swingman, although he doesn’t control his own destiny next season, per the NY Post and the decision the Knicks need to make on Bullock’s contract:

Bullock, coming off spinal-fusion surgery that delayed his Knicks debut until January, is a free agent. The Knicks have to decide whether to enforce the final guaranteed year for the 29-year-old swingman — at a team-friendly $4.2 million. Originally, the Knicks had to make that decision by June 28 but when the season/free agency was delayed, so was that deadline.

Each trade in this matchup is essentially the same: dump Bledsoe onto a team that isn’t really contending and get a decent point guard and another player in return. You also gain financial flexibility; each of the players involved (Rose, Kennard, Schroder, and Bullock) coming in to the Bucks in these deals are on the final year of their contracts.

Vote for your preferred trade package!

7-12 Matchup

Milwaukee receives: Spencer Dinwiddie

Brooklyn receives: Donte DiVincenzo, Ersan Ilyasova

vs.

Milwaukee receives: Victor Oladipo

Indiana receives: Taj Gibson, Kevin Knox, 2020 IND 1st (via MIL)

New York receives: Eric Bledsoe, 2022 MIL 2nd

These two deals are very different, since one brings back a legitimate star who’s probably a one-year rental, and the other brings back a player who considers himself a star but could be useful if secured long-term. I mean, look at this quote from Dinwiddie:

More seriously, the Brooklyn Nets are a fascinating experiment, given that they seem to be working to apply the Seven Seconds or Less Suns brain trust (Steve Nash, Amare Stoudemire, and Mike D’Antoni) with the recovering Kevin Durant and the prickly Kyrie Irving. There’s still only one ball to go around, though, so the Nets may benefit by swapping a high-usage guy like Dinwiddie with a pair of complementary players like Donte and Ersan.

On the Oladipo side, his value is not as high as most players of his caliber for a number of reasons. The Bucks don’t seem dissuaded from having a conversation, though, given this detail from The Ringer’s Kevin O’Connor, in a piece focusing on new Philadelphia POBO Daryl Morey:

Would the Jazz consider flipping Mike Conley? Could the Raptors trade Kyle Lowry back home to Philly with only one year to go on his contract? What if the Pelicans make Jrue Holiday available? How about Victor Oladipo? League sources say the Pacers have talked with the Bucks about a trade involving Oladipo, though at this point it seems unlikely. Oladipo could be acquired for the right price if the Sixers wanted to bet on a return to his pre-injury form.

Consider these two trades the least realistic of the whole tournament. Oladipo, because the match doesn’t seem to be there even if the Bucks are kicking the tires, and Dinwiddie because the price seems too low for a 20+ ppg scorer. But we’re here now, so you may as well choose!

Vote for your preferred trade package!