Bucks Trade Proposal Bracket: 5-12 Matchup

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

Our 6-11 matchup was a contentious one, and the lower-seeded package for Buddy Hield and Cory Joseph beat out the Mike Conley proposal, bringing the Milwaukee Bucks a sharpshooter instead of a floor general.

Without further ado, let’s get to today’s proposals. They’re both a tall order to pull off, but the talent coming back could make the challenge worthwhile.

5) New Orleans Pelicans & New York Knicks: Jrue Holiday, Dennis Smith Jr.

Why the Bucks do it:

You get Jrue Holiday. That by itself should be enough to pique your interest, since he’s one of the few guards in the NBA on Eric Bledsoe’s level as a defender, except he also is bigger, more versatile, and a better all-around offensive player. Holiday has somehow only made one All Star team despite producing at an All Star-level for years, in no small part because of the level of competition in the Western Conference and his own injury history. He’s comfortable playing off ball, which is helpful when sharing the court with Giannis Antetokounmpo and Khris Middleton, but is capable of running the offense as well. His playoff resume is short (again, due to the competition he’s faced in the West), but in the few opportunities he’s had, Holiday has shined. This move would already be a major needle-mover, and it has the added benefit of gaining a “second draft” prospect in Dennis Smith Jr. A top-10 pick who’s struggled on some bad teams (most notably the Knicks), Smith Jr. is in a position where he needs to turn himself around and may not be in an environment to do so. Milwaukee could be that place, where he revitalizes his career as a member of the Bucks’ reserves.

Why the Pelicans do it:

The future for New Orleans is with Zion Williamson, who is an incredible offensive talent but a startlingly clueless defender. Bringing in Brook Lopez would help clean up innumerable messes and provide incoming coach Stan Van Gundy an opportunity to mentor Williamson on that side of the ball. It also allows the Pelicans to develop their young backcourt players alongside Williamson and Brandon Ingram (should they retain him), and the incoming Bucks picks help support the roster as the Pelicans turn from potential into actual contention when everybody is ready.

Why the Knicks do it:

The Knicks have a number of disappointing point guards, and Smith Jr. is tops among them. They also have Elfrid Payton and Frank Ntilikina, where the former has shown NBA-level quality and the latter being younger and with more years under team control. Upgrading this position is important for New York to climb back towards respectability, as well as foster the development of young prospects like Mitchell Robinson, RJ Barrett, and Kevin Knox. You can only tank for so long before you need to start trying again, and Bledsoe is the kind of guard that could help the Knicks do just that.

Milwaukee receives: Jrue Holiday, Dennis Smith Jr.

New Orleans receives: Brook Lopez, Ersan Ilyasova, 2020 IND 1st (via MIL), 2024 MIL 1st, 2021 CHA 2nd (via NYK)

New York receives: Eric Bledsoe, 2020 MIL 2nd (via NOP)

As with many trades but especially three-team deals, the circumstances allowing for such a transaction to be agreed on by all parties are difficult to predict. The Knicks are likely to appreciate a free upgrade, but the Pelicans’ interest in this deal hinges on whether or not they can envision a world where Zion is not a full-time center and (somewhat lesser) if Ingram is not a full-time power forward. Lopez’s ability to stretch the floor and create space for both of New Orleans’ young stars is what makes him one of the few true centers that make sense for the Pelicans, and while giving up Jrue Holiday is pricey the picks coming in help soften the blow.

12) Indiana Pacers & New York Knicks:

Why the Bucks do it:

Victor Oladipo is a two-time All Star who was a late bloomer in the league but became a dynamite scorer in Indiana. They’re already (reportedly) making calls about him. He has good size and athleticism for the position and boasts scoring ability at all three levels. He’s not a lockdown defender but at his best he’s a ball hawk and decent team defender, and he’s been a high-level playmaker as well. Players of his caliber rarely come available via trade, but that’s for good reason. Oladipo has a recent major injury and has apparently kept his eyes on Miami when he becomes a free agent next season. Is one year of a possibly-distracted Oladipo worth it? Maybe, and his talent and resume are what would make anybody consider it.

Why the Pacers do it:

Victor Oladipo is a two-time All Star, but continues to rehab a ruptured quad tendon and is entering the final year of his contract. He hasn’t played at a high level in two years and may not be worth the type of money he’s seeking next offseason, making now the time to try and recoup some value for him. In Taj Gibson, they can add a veteran big to put behind Myles Turner and Domantas Sabonis and take a free flier on Kevin Knox, a talented scorer but unimpressive NBA player (in the context of the equally unimpressive Knicks), all while recouping their first round pick. Not bad for a guy who might bolt in free agency regardless.

Why the Knicks do it:

Everything written in the above section where the Knicks end up with Eric Bledsoe still applies, except in this scenario they keep Smith Jr. and have a third young point guard to evaluate behind Bledsoe, or potentially move in another deal to shore up other parts of their roster.

Milwaukee receives: Victor Oladipo

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

New York receives: Eric Bledsoe, 2022 MIL 2nd

The success of this deal, much like the one before it, will be determined by how much Indiana values low-cost contributors, and how real the “Oladipo to the Heat” rumors are. Knox is only 20 and on his rookie scale deal, as will the #24 overall pick they get back from Milwaukee. Oladipo might have the talent to fetch more in a trade, but with an uncertain future (both in terms of his health and free agency) and Malcolm Brogdon ready to lead the way for the Pacers, they may benefit from taking a year to retool and develop before mounting another challenge to the rest of the Eastern Conference.

Vote for your preferred trade package!