To trade or not to trade, that is the question

Evaluating the Milwaukee Bucks short- and long-term trade outlook ahead of the 2023 NBA Trade Deadline

Trade season is picking up all around the NBA with the NBA Trade Deadline exactly one month away, but especially around fans of the Milwaukee Bucks as they watch their team suffer ugly blowout losses and appear in need of more help than simply Khris Middleton returning for real this time.

Bucks general manager Jon Horst has proven to be an active executive around the deadline, and it’s safe to assume something will change about Milwaukee’s roster by mid-afternoon on February 9. The big question, then, is how expansive Horst’s latest roster reformation will go, and what he’s willing to spend to enact it.

The Bucks have spent a ton of draft capital in recent years, most notably in the trade for Jrue Holiday with New Orleans that ultimately netted Milwaukee a championship, but there are still some picks lying around in their cupboard. The best one is the Bucks 2029 first rounder, which is the only first that Horst can trade until 2024 (more on 2024 later).

Thankfully for trade machine addicts, the Bucks do have plenty of second-rounders available, and we’ve seen Horst swing meaningful deals with only later-round picks in the past. (It worked out very poorly, but I maintain to this day it was good process to get Nikola Mirotic for four second-rounders.)

The Bucks have their own seconds in 2023 (which is somehow this year already), 2024, 2027, 2028, and 2029; plus a stinky less favorable of Cleveland and Golden State’s 2023 second rounder, a 2024 second from Portland, and a 2025 second from Indiana. These aren’t premier assets, but 8 second rounders isn’t nothing either.

There would also be players going out in any trade, and instead of going through the whole roster let’s just, for now, assume that any deal would mostly contain neutral-ish value contracts: Grayson Allen, Joe Ingles, George Hill, Jordan Nwora, etc. As useful as any of those players may be to the Bucks, there aren’t any NBA teams scrambling to give up a first round pick for them, so it’s easiest to assume they are more or less salary blocks to make a trade work.

The exception to that is MarJon Beauchamp, who has shown flashes of tantalizing talent and is on the first year of a team-friendly rookie contract. Pinning down exactly what a team would give up for MarJon (or any unproven young player) is difficult, but let’s just say he’s looked at as relatively similar to a current first-round pick given his clear upside. That may seem like I’m selling low, and to be quite clear I wouldn’t give up MarJon Beauchamp for a mid-tier first rounder, but in a value sense I don’t want to inflate what he’s doing for Milwaukee in trade talks.

All of that said, the Bucks have two distinct paths forward at the trade deadline. They can maneuver with their salary block contracts and plethora of second-round picks to make meaningful but not drastic upgrades to this core, or they can swing for the fences and offer up some combo of the 2029 first and MarJon. (Technically they could also do nothing, but given the season so far and Horst’s proclivity to making deals I’m just going to rule that out entirely.)

The argue for going all in (either with or without keeping MarJon, depending on your view of him) is easy to make: Giannis Antetokounmpo is the best player in the world RIGHT NOW, so you’ve got to do whatever you can to win a championship as soon as possible. That’s an entirely fair argument and mostly lines up with how the Bucks have operated.

The case for waiting to deal premier assets relies on a belief that the Bucks aren’t as far away from winning another championship as they’ve looked for the last month, and on looking ahead to a bigger opportunity. I have a specific one of those in mind, actually: the 2024 NBA Draft.

If Horst sends the 2029 first rounder in the next 30 days, the Bucks will not be able to trade another future first round pick until the 2024-25 season, when the 2031 picks become usable. (Convincing rival GMs the heat death of the Earth won’t have occurred by then and that those picks are still valuable is its own hurdle, but we’ll worry about that later.) If he waits and the Bucks are able to get by for not one but two more playoff runs with the Giannis, Khris, and Jrue core, suddenly their opportunities will open up on Draft night in 2024.

In addition to the 2029 and 2031 first rounders (plus a couple of swaps and any second-rounders left over), the Bucks will also be able to trade the rights to whoever they select in 2024 with the worst of their and New Orleans’ first. Suddenly, the Bucks go from a depleted cupboard to what is essentially three first-round picks, plus still-on-his-rookie-deal Beauchamp (if he’s not an All-NBA, untouchable player by then – fingers crossed!).

This is a very fine line to walk, and I’m not here to proclaim the Bucks would be foolish to spend their 2029 first before the middle of 2024 – a season and a half is an eternity in NBA years, and so many things could change by then. I am comfortable proclaiming, though, that 2024 would make sense as a pivot time from the Khris/Jrue/Brook core to a new one closer to Giannis’ age (or even slightly younger), and that sending the ’29 pick before then would lead me to believe the Bucks view whoever they’re acquiring as a crucial piece to a championship this season.

Maybe the importance of winning another ring in 2023 outweighs a grand plan of a second contending core build around Giannis – after all, if the Bucks stay too patient and allow their roster to deteriorate they may not have the chance to do so anyway. Giannis wants to win, and him feeling like he’s not able to win in Milwaukee is a disaster scenario for the Bucks.

But if Milwaukee can straddle that fine line perfectly, and continue to provide Giannis a team worthy of his talents while keeping some of the powder dry for a dramatic retooling, 2024 presents an enticing opportunity to set up a second window of contention with the world’s best player.