Are you ready for the NBA’s Silly Season? At 5pm Central this Thursday evening, teams can ostensibly begin negotiating with free agents. As we’ve seen in years past, though, news of contract agreements immediately begins flooding Woj’s and Shams’ Twitter feeds mere seconds after the clock strikes 5 (or 6, or 4, or whatever). So while we can definitely question the efficacy of this process and whether or not it’s good for the league, the fact of the matter is that things will kick off in a big way once the proverbial 5 o’clock whistle blows.
What will we see happen from the Bucks in those early hours (or minutes)? What will follow in the ensuing days and weeks? Typically the dust settles by mid-July: all the top-name free agents are gone and most (though not all) of the big trades are complete. In 2019, one of the busiest offseasons in recent Bucks history, we know well before 5pm that both Khris Middleton and Brook Lopez would return on new deals, while Malcolm Brogdon was off to Indiana in a sign-and-trade. By 5:30pm, we knew the answers to the biggest questions of the offseason. While the NBA cracked down a bit on the preemptive tweets, I don’t doubt that we’ll have a general idea of next year’s roster within minutes of the deadline.
Let’s take a look at what the general manager Jon Horst’s possibilities are both in the trade market and free agency, using the same approach I use each year at the trade deadline.
Who are the Bucks’ pending free agents?
Bobby Portis has until tomorrow to decide on his 2022–23 player option worth $4.56m and it’s widely expected that he’ll decline it, becoming an unrestricted free agent. It’s also widely expected that he’ll remain with the Bucks on a new, long-term contract after signing a pair of 1+1 deals with player options. Though he may be able to earn slightly more on the open market than he can by staying, it’s very obvious how much Bobby Barista loves playing in Milwaukee and it seems almost a given that he’ll be back for years to come.
Now that he’s spent two seasons with the Bucks, the team can exceed the cap to re-sign Portis this offseason by using his early Bird rights exception. That means they can offer him a new contract at a minimum of 2 years and $22.6m and a maximum of $48.9m over 4 years. Either way, he would earn about $10.85m next season. The Bucks will likely want to reward him with that salary for his loyalty to the franchise, which included re-signing last offseason far below his market value.
With Pat Connaughton pulling a Bobby by opting into the final year of his deal at significantly beneath his market value, that’s one role player whose free agency the Bucks needn’t worry about this year. All year long I expected a new contract for Pat would be eight figures, though projections ended up more like $8–10m back in May. We always knew what Portis’ next contract would look like if he remained, but seemed like it would cost at least $20m annually to keep both. Now, however, their combined cost will be much cheaper.
Milwaukee’s other unrestricted free agents are Serge Ibaka, Wesley Matthews, and Jevon Carter. I can’t recall hearing anything about Ibaka staying and when he hardly played against Boston, the writing was very much on the wall. Matthews wants to remain in his home state for a third tour of duty with the franchise and Horst mentioned in his end-of-season press conference that he’d like to re-sign Carter. Both players received the league minimum last year and probably will again wherever they end up; Matthews is a clear vet minimum guy at this point and I have a hard time seeing Carter getting more. The Bucks cannot give them much of a raise on his minimum anyway.
Finally, Jordan Nwora can become a restricted free agent tomorrow if the Bucks extend up a $2.01m qualifying offer. If they do and he declines as is typical, Milwaukee can then match any offer he receives from other franchises. Nwora didn’t take much of a step forward in his sophomore season and I’d be shocked if any team offered him more than a couple million bucks on top of the $1.52m he made last year. I think it’s more likely he takes a minimum deal elsewhere, on a team that could give him a bigger role.
How much can the Bucks offer to free agents?
As a taxpaying team, this is pretty straightforward. Taxpayers do not have access to the bi-annual exception and can only use $6.39m of the mid-level exception, known as the tax-player mid-level (TPMLE). This is the main tool they have to sign players: they can use it all on one guy or split it between multiple guys (as they did last year) and they aren’t obligated to use all of it.
Like all teams, they can also offer minimum-salary deals. For veterans with at least two years of experience, their cap hit to their employer is $1.81m even though their actual salary is higher (the difference is paid by the league). A second-year player has a $1.62m minimum and an undrafted rookie has $1.0m.
These numbers are based on a $122m salary cap and $149m luxury tax line, which was the league’s most recent projection.
What do the Bucks have to trade?
Among the non-stars the Bucks have under contract next year, we can rule out Connaughton at his team-friendly salary, Thanasis Antetokounmpo (who opted into the final year of his deal for $1.88m) to keep Giannis happy, and first-round pick MarJon Beauchamp if all the praise surrounding him from the front office is to be believed. Milwaukee also has both Luca Vildoza and Rayjon Tucker on non-guaranteed salaries next year, which makes them a good way to get out of cap obligations for an acquiring team, but these two are so unproven that their only purpose in a trade would be salary filler.
That leaves three players and some future picks, including a first-rounder way down the line which just became tradeable since it’s now within seven years away. Brook Lopez’s expiring contract is worth $13.91m next season and while that’s a good number for salary-matching purposes in any trade, I think it’s unlikely the Bucks will trade him after missing him a good chunk of last season, then seeing him largely return to form once healthy. That leaves the following realistically tradeable assets, in order of how I think trade partners would value them:
- 1. Grayson Allen at $9.35m in the first year of his two-year, $18.7m contract
- 2. 2029 first-round pick
- 3. George Hill at $4m in the final year of his two-year, $8m contract
- 4. 2028 first-round pick swap
- 5. 2023 second-round pick from either Golden State or Cleveland (whichever is less favorable)
- 6. 2024 second-round pick from Portland
- 7. 2025 second-round pick from Indiana
- 8–12. their own second-round picks in 2023, 2024, 2027, 2028, and 2029
By now we’re all well aware that Allen and a perhaps-not-fully-healthy Hill both were rough against Boston in what was a bad matchup for both. As we saw with Portis during 2021’s second-round series against Brooklyn, sometimes role players just aren’t good fits against specific opponents. That doesn’t mean they’re not valuable to the team, though: Allen was one of the Bucks’ standouts in the first round and is a fantastic fit alongside Giannis with his ability to knock down catch-and-shoot threes from kick-out passes. Hill’s offensive numbers were poor last year and he turned 36 last month, but defensively he was quite good in the regular season: the Bucks allowed 11.9 fewer points per 100 possessions when he played versus when he sat. As a bench point guard (though maybe deeper than he was in 2021–22), he’s still a decent option and may have a little left in the tank.
Their contracts are the best salary-matching pieces Milwaukee has. Allen’s extension kicks in on July 1, meaning he’ll no longer be subject to the Poison Pill Provision that complicates his incoming and outgoing salary in a potential trade before his new contract is in effect. For this reason, it’s been seen as very likely Allen would be traded prior to the new league year beginning. If both Allen and Hill are combined in a trade, the Bucks could take back up to $16.79m in salary.
The Bucks also have a $1.51m trade exception generated in last August’s Sam Merrill-Allen trade, but this expires on July 7th and is only big enough to take on an inexperienced minimum player without sending out salary. It can’t be combined with any other salaries and it’s unlikely this gets used.
What type(s) of players should the Bucks target?
Without Middleton in their second-round series, Boston exploited Milwaukee’s lack of size on the wing defensively. Able to switch their star wings/forwards Jayson Tatum and Jaylen Brown onto Bucks defenders who were 2–4 inches shorter, this was an important advantage the Celtics possessed. However, Milwaukee’s main issue was definitely on the other end, because while their defense was actually rather good throughout the series, they could hardly score on Boston’s top-ranked unit. They sorely missed Middleton’s three-level scoring of course, but they perhaps missed his shot creation and ability to initiate the offense even more. Their best remaining offensive options beyond Giannis, Holiday, Lopez, and Portis were pretty one-dimensional three-point shooters.
Obviously, they likely won’t find all these qualities in one player: those are what makes Middleton an All-Star caliber player and the Bucks don’t have the salary or draft assets to acquire another. However, they could cover them between multiple acquisitions. Beyond wing defense and wing scoring, Milwaukee really needed another ball-handler and initiator in the playoffs. Middleton of course does a lot of this but with Hill missing the first round and start of the Boston series, the Bucks lacked another playoff-proven option at the point (apologies to Jevon Carter). While Hill is under contract next year and Carter could return, it would behoove Horst to find an upgrade in the ballhandling department, preferably in the backcourt.
For these reasons, the popular refrain among Bucks fans this offseason is that next year’s squad requires another ball-handler and another big wing that can check opposing forwards, like those two Celtics. Maybe they planned for the 6’6” DeAndre’ Bembry to take on the latter role this past postseason but unfortunately, he tore both his MCL and ACL in March, leading the team to waive him. In any case, wings ranging between 6’6” and 6’9” with good defensive reputations are trendy trade/free agency targets on Bucks Twitter. Rookie MarJon Beauchamp certainly is the right size and earned plaudits for his defense in the G League but banking on him seeing postseason minutes as a rookie is very optimistic.
I also think the Bucks should look for another defensive big man who can play the 5 as Lopez insurance or even as someone who can take over for him when the time comes. This isn’t a high priority since Milwaukee is very set with a three-big rotation of Lopez, Giannis, and Portis. Still, I don’t think anyone would be mad with a defensive big on a veteran’s minimum after last season.
Let’s reiterate and number those player archetypes, in no particular order:
- A big, long wing capable of guarding opposing scorers of a similar size
- A scorer in the backcourt or on the wing who doesn’t strictly launch catch and shoot threes
- A backcourt player capable of being a primary ball-handler and initiator
- A very tall big man with the strength to play good interior defense
Looking back at my post from the trade deadline, these 4 player types are almost exactly the same as what I outlined then. They addressed 4, 1, and 3 with Ibaka, Bembry, and Carter respectively. They didn’t factor into the playoffs much unfortunately due to injury and ineffectiveness, so Horst will try again with some more options this time around.
Let’s start out by hypothesizing some ways the Bucks can address the needs mentioned above through the trade market. As usual, it’s likely that many (all?) of these possible moves would also send out some draft assets, though they could come in too just as they did in the DiVincenzo-Ibaka trade. Note that the outgoing package from Milwaukee is only for salary and value matching purposes; I’m not arguing that the other team would take any or all those assets because any trade could be expanded to a three- or even four-team deal. I highlighted my personal favorites.
Of all the ideas I highlighted, I think all of them would require sending at least one second-round pick. I don’t think, however, that any are worth including a first-round pick in 2029.
Free Agent Possibilities
The free-agent market isn’t quite as fruitful with the type of players the Bucks could use, but there are some very good targets who could claim all part of the TPMLE. There are a handful of minimum guys who could be useful as insurance too.
Recent reporting suggests that old friend P.J. Tucker will command the non-taxpayer mid-level, which makes sense given that he turned down his $7.35 player option. I also think that Tyus Jones will also be priced out of what Milwaukee can offer and maybe Bruce Brown could be as well. However, names like Otto Porter Jr., Thaddeus Young, Kyle Anderson, Taurean Prince, and Nic Batum seem likely enough to be available in the Bucks’ price range. Each would fit in well on the wing alongside lineups with Holiday, Middleton, and Giannis at the 5. T.J. Warren is the most intriguing name, given how the last time we saw him nearly two years ago, he was lighting it up in the bubble. If he can recapture the scoring ability he flashed during his Indiana tenure, Milwaukee will have a microwave scorer off their bench.
You could do worse than Dennis Schröder or graying Goran Dragic, Lou Williams, and Rajon Rondo if adding backcourt depth is necessary. Other old friends like Tony Snell and Robin Lopez would be alright on minimums if the TPMLE is used up. Isaiah Hartenstein is coming off a sneaky breakout year where he established himself as one of the NBA’s better rim protectors: giving him some or all of the TPMLE and grooming him as Brook’s replacement in 2023’s starting lineup isn’t a bad idea, though I’d rather they use their best free agency tool on any of the players I mentioned in the previous paragraph.
Will the Bucks extend any of their players under contract?
Both Khris Middleton and Brook Lopez are extension-eligible this offseason, so they could add more guaranteed years after their current contract. Middleton has a $40.4m player option next offseason and Lopez will be a free agent. I don’t think extending either player is particularly likely; Middleton has a better chance of doing so this summer, but I can also see him waiting to opt into that last year rather than testing the open market—where he’d face a pay cut—or opting out next summer to sign a cheaper new deal with Milwaukee like Chris Paul did for Phoenix last summer.
Pat Connaughton is also now eligible and some reading the tea leaves think that exercising his player option is a signal that an extension is forthcoming, perhaps one more lucrative than what this summer’s open market could offer. I’d wager it’s much more likely we see Connaughton this summer extend rather than Middleton and Lopez.
What about the luxury tax?
If Bobby Portis indeed extends with a $10.85m starting salary, that new money plus Marjon Beauchamp’s soon-to-be signed rookie scale contract pushes the Bucks’ guarantees to $162.27m for 10 players (Vildoza’s and Tucker’s salaries for 2022–23 are non-guaranteed). That’s actually almost $3m more than last year’s payroll of 15 players and Milwaukee would need to fill 4 more roster spots by opening night, but this is a cheaper projection than we expected due to Connaughton’s opt-in.
Thankfully for the Bucks ownership group, the tax threshold shot up by over $12m from last season’s figure, so those 10 players currently rostered would result in a tax penalty of $24.43m. Last year, the Bucks paid $56.8m in penalties on a $159.8m payroll, so they project to have a lot of room under that figure for their additions. If the Bucks use the entire MLE on one player and fill the remaining three roster spots with veteran minimums (each worth $1.8m) to get to the 14-man roster minimum, that would add about $11.83m to their payroll.
While that’s the maximum they can spend on free agents this offseason, they may not use their full value of the MLE and could sign lesser-experienced, cheaper players for smaller salaries than the vet minimum. Using that $11.83m on free agents would result in a $174.1m team salary and increase their tax payment by $39.74m. Still, $64.18m in penalties wouldn’t be that much higher than last season’s and nearly $12m less than forecasted (thanks again Pat). Trading salaries like George Hill’s or Grayson Allen’s could increase or decrease the tax payment by multiples more than team salary does, although since the salaries coming back would be similar to those outgoing, the adjustment might only be a few million dollars.
Oh, the dead money from stretching Jon Leuer’s and Larry Sanders’ contracts are finally coming off the books too, freeing up cash to spend on rostered rather than retired players.
If you made it all the way through that, treat yourself to a beer or something nice, because NBA cap machinations are a doozy. Until the tweets start flying, what do you foresee happening? Do any trade possibilities stick out to you or are there any I hadn’t considered? Which free agent(s) would you like them to sign? Any I didn’t include on my list? Please chime in below with a comment and buckle up for a whirlwind of NBA news on Thursday evening.
Contract and pick info from RealGM, Basketball-Reference, Spotrac, and Larry Coon’s CBA FAQ. Stats from Basketball-Reference. Salary-matching courtesy of Fanspo’s Trade Machine & Cap Manager.