So You Want To... Building Out the Bucks Roster

There is a lot for the Milwaukee Bucks to work out in the coming months. Without a ticket to the dance, Milwaukee is on the outside looking in at the NBA Playoffs and figuring out their next moves to get back in the thick of it next postseason. It might be easier to just run it back! There are a number of moves that need making, and each major decision affects the one after it; successfully navigating this environment might be the most difficult task general manager Jon Horst has ever attempted.

But that doesn’t mean us amateurs can’t take a crack at it! We may not have years of experience or a treasure trove of data at our fingertips, but that gives us an advantage. Without the limits of “logic” or “common sense” constraining us, we can try our hand at building the next iteration of the Bucks roster. Just like throwing a pot of cooked spaghetti at the wall, you never know what shape you get from the bits that stick.

So that’s what this post will focus on. The Bucks have a handful of seismic decisions to make – and precious little time to make them – so we will do our best to get an overview of the circumstances around those decisions and what outcomes are most likely. Let it be known that this is a hypothetical exercise and is not a verdict on what should be done with each situation; these players are all talented and fit in with the Bucks and could be a part of a renewed run at the title next season. Consider this an example of the adage “leave no stone unturned” when it comes to sorting through what the Bucks could do. With all that in mind, let’s dive in!

So you want to...trade Khris Middleton?

I hope you’re ready for some convoluted prose, because the prospect of trading away Middleton is one of the more complicated challenges Milwaukee could take on this summer. Effectively, the Bucks have between now and June 21 to work out an extension, since that date is the deadline for Middleton to decide on his player option. This effort towards an extension is important for anybody who thinks that sending Middleton out is the right call, because whatever outcome of that process changes the rules for any possible trade.

NBA players can only be traded if they’re under contract. Because Middleton’s final season is an option year, that option must be exercised or declined before a trade can happen. Otherwise, there’s no salary to work with when constructing the deal. That option also needs to be resolved as a part of any extension negotiation; Middleton can either turn the player option into a guaranteed year and use that salary ($40.4M) as the starting point for a new deal, but under the new CBA he could instead decline the player option and still sign an extension with Milwaukee for a number starting at less than the option salary. Of course, Khris Middleton has little incentive to take less money, but the flexibility offered by the changes to league rules means that the Bucks can at least work angles they couldn’t before. For example, perhaps the front office can convince Khris to take a lower salary in Year 1 of a new contract, but they’re willing to provide more years to make it up on the back end.

But this section of the post is about trading Khris, not keeping him, right? Yes indeed! But the terms agreed-upon for Middleton’s contract can drastically change what – and when – trades can even happen. For example, if the team does extend-and-trade Khris, those extra years we mentioned? They go out the window. Per Eric Pincus at Sports Business Classroom:

When a veteran signs an extension, the size and length of the extension determine trade eligibility. Teams are permitted to extend-and-trade players, but such extensions are limited to no more than a five percent raise and two additional seasons.

Anything larger [...] includes a six-month no-trade restriction.

If your diagnosis to cure what ails the Bucks involves trading Khris Middleton, you don’t want to wait until December. You want to get things sorted out as soon as possible, and that means you’re limited to the following circumstances if you want to trade Middleton this summer:

1. You extend Khris Middleton’s contract by the amount allowed for an extend-and-trade, up to 3 years and $127.3 million (Year 1 is the 2023-24 season and turns his $40.4M player option into guaranteed money; Year 2 is $42.4M, Year 3 is $44.5M), and then trade him.
2. Khris stays on his player option (1 year/$40.4M) and you trade him directly off of that figure.
3. Khris exercises his player option to become an unrestricted free agent, then you re-sign him to a longer term deal (at any starting salary, using his full Bird rights), and subsequently move him in a sign-and-trade to a team that can fit his salary underneath the hard cap.

Any outcome other than these three would involve either a six-month no-trade period (meaning the earliest you could trade Khris is mid-season, and in all likelihood you re-signed him to keep him) or Middleton leaving the Bucks for zilch, zip, nada, nothing.

It is generally agreed that letting Khris walk for nothing is the worst outcome for the Bucks, considering their current salary cap situation and the fact that they would not create space to sign another player with that money this summer. Both sides know that, and both sides will work from there to find an arrangement that works. Of course, both sides also want to “win” the negotiation, and part of that is understanding their leverage.

The Bucks have very little leverage in this case, mostly because a) Khris Middleton is good, and b) the aforementioned inability to sign anyone else with the money that would go to re-signing him. If Milwaukee doesn’t pay him a rate that satisfies him, Middleton can seek employment elsewhere, either right away or one season from now (depending on what is done with his player option). So what does Middleton’s potential market in free agency look like?

Per Spotrac.com, there are seven NBA teams projected to have $36 million or more in cap space this summer; the Houston Rockets and Orlando Magic have the most by far with $64 million and $60 million (respectively) in spending money, while the Spurs and Jazz will have upwards of $40 million and the Thunder and Pistons are at around $37 million. (For reference, the Bucks are projected to have –$27 million in space, meaning they’re over the cap by about $27M.) Any of these teams could become enamored enough with Middleton to toss a lucrative offer his way, and other teams could make other moves to create enough space to do the same. All it takes is one to force Milwaukee’s hand. Are any of them the sort of team that Middleton would be willing to play for over the Bucks? And if so, are any of them desparate enough to give up assets to acquire Khris in a sign-and-trade?

There has been no reporting one way or the other yet, but it doesn’t seem likely that Khris would use his player option to play out next season on an expiring deal. NBA players who still have gas in the tank (as Middleton does) prefer the security that multiple years offers, and Khris is a three-level scoring wing who can both run efficient offense and hit tough shots. Somebody is going to pay Middleton a lot of money over multiple years. The Bucks will get first dibs on being that somebody, but where things actually go is anyone’s guess. Milwaukee has options, but only a few of them are realistic.

So you want to...trade Jrue Holiday?

Unlike the situation with Khris above, trading Jrue would be much more straightforward. With one full year ($36.2M) and one player option year ($38.6M) remaining on his deal, the Bucks could find a decent return if they chose to ship out the All-Star & All-Defensive Team guard. Of course, the challenge would be twofold: finding a trading partner who wants Jrue Holiday, and fielding a return worth giving up Jrue Holiday.

To acquire Jrue back in late 2020, Milwaukee gave up three unprotected first-round picks and two first-round pick swaps, all of which went to New Orleans. There is absolutely no way that, three years later, the Bucks can recoup those draft assets by flipping Jrue again. No, the goal of any potential Holiday trade would be to change the makeup of the team significantly enough to keep their window for contention propped open...and persuade Giannis Antetokounmpo to stick around for another contract after his current one.

To understand the situation better, let’s look at what the Bucks need compared to what Milwaukee would have to replace. Holiday is the league’s preeminent perimeter defender, according to nearly 30% of active NBA players (second place was Lu Dort, at 11%). No player the Bucks could acquire will be better at doing Jrue-things on defense than Jrue Holiday himself. Holiday is also a talented (if misguided) offensive player, capable of producing 20+ points, shooting 40+% from three, and tallying 5+ assists per game. The trouble has been that these strengths have evaporated in the postseason; Holiday’s shooting accuracy craters, his turnover rate climbs, and the Bucks’ offense stalls out as a result.

While we have an idea of the pros and cons of the individual, what about the team? Coaching woes aside, the Bucks have been exposed as old, slow, and unathletic relative to their NBA counterparts. Basically, the roster in the aggregate is the fundamental opposite of their superstar, Giannis Antetokounmpo, which is why the fallback plan always seems like “spread out and let the big Greek fella do something.” This is one of the underlying causes for the debacles (plural!) against the Miami Heat; their dudes were in better shape and better prepared to fight, scrap, and jostle than our dudes. Khris, Jrue, Brook, Joe Ingles, Jae Crowder, Pat Connaughton, Grayson Allen, and Bobby Portis are all strong, tough players...but they’re not the type of athletes that can hit another gear in terms of speed, quickness, and elevation.

The Bucks also struggle to run offense in the half-court, partially because Giannis is empowered to do whatever he wants (with mixed results...) and partially because they don’t have a “true” point guard. Jrue Holiday is very much not a “true” point guard; he’s an excellent player, but when he’s handed the keys to the offense in the playoffs, things have gone poorly. Acquiring someone that can put pressure on the defense with ball-handling, set up shots for others, and hit shots themselves would be quite a player to have on this Bucks team...to the point that it might be a pipe dream to think that another team would give that floor general up for the Bucks’ benefit.

Just like with Middleton...Jrue Holiday is really good! Giving him up seems like a daunting task, and not just because of the familiarity and leftover affinity from winning the title two years ago. But Holiday is also flawed, and it makes sense that fans would want to move on from him. The fact is, the list of players who are simultaneously a) available, b) similarly talented, and c) acquirable in a potential trade for Holiday might be a blank sheet of paper.

So you want to...keep the Core Four together?

I get it. Giannis Antetokounmpo, Khris Middleton, Jrue Holiday, and Brook Lopez are the backbone of the team that won the 2021 NBA Finals. They would have won in 2022 if it wasn’t for Khris’ injury; they would have won in 2023 if it wasn’t for...well, a lot of things. So the answer isn’t to clean house, it’s to run it back! Within reason, of course.

It is a common-enough opinion that replacing the coach but keeping the main players is a legitimate path forward for Milwaukee. However, changes to the new CBA make that plan more tenuous than ever.

We know the Bucks are over the salary cap. We know that the Bucks are deep in the luxury tax, and therefore unable to use certain roster-building mechanisms because they’re over a line called the “tax apron.” But it turns out that Milwaukee has a new concept in the updated collective bargaining agreement to get acquainted with: the yet-unnamed “second apron.” From CBS Sports:

In the new collective bargaining agreement, there will be a second “apron.” This figure will come in at around $17.5 million above the tax line, and it will trigger a host of restrictions that we will cover in the subsequent sections. The basic idea of those restrictions will be to make it harder for teams like the Los Angeles Clippers and Golden State Warriors to spend significantly more money on talent than their competitors, but we should note that these restrictions will only make it harder for teams to acquire new, expensive players. None of these changes will make it harder to retain players that a team has drafted and developed, and only in a few, rare cases will it become more difficult for teams to retain free agents they’ve signed from other teams. The NBA wants teams to be able to keep their players. It just doesn’t want the rich to get richer.

The luxury tax line for 2023-24 is expected to fall at around $162 million; this means that the mysterious “second apron” will be around $179.5 million. Milwaukee’s current salary obligations, if they bring everybody back at around the same number they were at this season (including a new contract for Brook Lopez, excluding Jae Crowder because ), Milwaukee will boast a salary close to $175 million. Completely disregarding the tax penalties themselves for a moment, going over this new “apron” line imposes two new restrictions on teams: no more taxpayer mid-level exception, and no more “buyout” market additions.

This means that keeping the band together is restrictive to the point of having no real flexibility to add anyone different, outside of trades. You can keep Giannis, and Jrue, and Khris, and Brook, and Bobby and Pat and Grayson and Jevon and MarJon and Wes, and you can even bring back Joe Ingles and Jae Crowder and Goran Dragic and Meyers Leonard and Thanasis Antetokounmpo. You might have to, because otherwise there is no method to bring in anybody else that doesn’t involve a trade or a veteran minimum deal. How do you shore up the team’s weaknesses if your choices are so limited?

This is just where the Milwaukee Bucks are right now. Until they get movement on their head coaching decision and what they’ll do with the contract situations with Khris Middleton and Brook Lopez, there aren’t any ironclad methods to guess where they’ll go from here. Options are limited, tools are scarce, and the clock is ticking. No pressure!