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Milwaukee’s Makeover Is Complete. Now Comes the $230 Million Question.

The first plan didn’t go so well, but the Bucks still managed to overhaul their roster. Are the changes enough to get Giannis Antetokounmpo to commit to a supermax extension?

Getty Images/Ringer illustration

While the rest of the NBA flew through its offseason business, a critical trade for the Bucks collapsed in slow motion. Arrangements were reportedly made last Monday for Sacramento to send restricted free agent Bogdan Bogdanovic to Milwaukee, but by Wednesday the deal was “in peril.” By Thursday one of the key players involved (Ersan Ilyasova, whose $7 million salary made the murmured trade possible) had been waived, and on Sunday Bogdanovic signed an offer sheet with the Hawks while the Bucks filled out their roster in consolation. Reports now vary on whether there was ever a deal in place at all, but whatever actually happened is obfuscated in the telling now that the whole episode—in which Bogdanovic would have supposedly agreed to a sign-and-trade before teams were even allowed to contact free agents—is under investigation by the league.

This situation was both an object of curiosity around the league and a development of massive import for reasons only somewhat related to Bogdanovic’s fluid, intriguing game. Until December 21, Giannis Antetokounmpo has the opportunity to sign an extension with the Bucks worth up to $230 million over five years, a max contract among max contracts. Everything Milwaukee does in the interim is an overt appeal, in bold and in lights. There’s no subtext in trading Eric Bledsoe, George Hill, two first-round picks, and two pick swaps for Jrue Holiday; the Bucks are attempting to put a roster together that Giannis would want to play with for years to come, which starts with rectifying the flaws of teams past. If Antetokounmpo isn’t satisfied, Milwaukee will be forced to confront Anteteokounmpo’s impending free agency more directly. That possibility is the second-act turn in the front office version of a horror movie, when dread gives way to terror and an organization’s worst fears are realized.

The Bucks haven’t yet reached that point with Giannis, but they know what could be lurking around the corner—making this more Scream than Halloween. Small-market teams are forced to be fluent in the horror genre. To employ one of the NBA’s few genuine superstars is to be extremely aware of the day they might leave. The league as a whole would be worse off—and less interesting—if Antetokounmpo did. There’s a certain romance in the idea that a franchise like the Bucks, which hasn’t won a title since 1971 or been to the Finals since 1974, could sprout a contender from draft-day cunning. That even if they couldn’t sign a generational player, they could find and develop one. It would undercut the sentiment a bit if that generational player then thanked Milwaukee for the memories and took off to play with other stars in a bigger market. It would oversimplify the way great teams are made.

Milwaukee had no choice but to think years in advance where Antetokounmpo’s free agency is concerned because other organizations were already doing the same. Executives in those front offices brainstorm ways to get Giannis’s name from their whiteboard to their team’s roster sheet. They strategize around what Giannis might do in 2021, and they effectively use his free agency as a landmark in their long-term planning. This is a story because those teams make it a story. It was notable when the Warriors were gaming out scenarios internally to make a run at Kevin Durant. There were a conspicuous number of breadcrumbs connecting LeBron James and the Lakers before the summer of 2018. The chatter around Antetokounmpo feels more like the former—driven largely by team interest and circumstance—though even that sort of due diligence creates its own kind of pressure. It turns a botched trade for the NBA’s second-most-popular Bogdanovic into an item of league-wide interest.

Even with the sign-and-trade with the Kings off the table, the Bucks still reworked much of their roster while squeezing in salaries under the hard cap. The finances were always going to be tight for Milwaukee this offseason, Bogdanovic or not; when the best means to add talent to an already-expensive roster is the midlevel exception (which triggers the hard cap), a team might not even have enough spending power to fill all its roster spots. That’s exactly where the Bucks ended up. Gone are Bledsoe, Hill, Ilyasova, Wesley Matthews, Robin Lopez, Marvin Williams, Kyle Korver, and Sterling Brown; in their place are Holiday, D.J. Augustin, Bobby Portis, Bryn Forbes, Torrey Craig, second-rounders Sam Merrill (already signed) and Jordan Nwora (who is likely to sign), and an empty chair. Oddly enough, Milwaukee would have had enough room to fill that final seat if not for their bungled attempt to re-sign Pat Connaughton to a not-quite-legal contract. Maybe any damage done comes out in the wash by adding an overqualified Jaylen Adams on a two-way deal.

Of course, the fate of the Bucks’ 15th roster spot would only be relevant to their championship pursuits if their season takes a bizarre turn. The clarity of contention makes it easier to evaluate Milwaukee’s roster, and by extension, its renovation. There are only a few criteria that really matter when it comes to the new additions: (1) Can this player liven up the Bucks’ half-court offense? and (2) Can this player give Mike Budenholzer more flexibility with his defense? A team that won almost 80 percent of its games last season doesn’t need much—just a bit more direction when the game slows down and the option to change coverage as a playoff series demands. This new rangale is a bit mixed. Holiday is both a more dynamic halfcourt player than Bledsoe and a more varied defender. Augustin, who was a pretty effective pick-and-roll player for an Orlando team with consistently suspect spacing, trades off Hill’s length and defense for cleaner initiation of the offense. Otherwise, the Bucks are largely taking a few more spins in role-player roulette in the hopes of finding the right mix.


Portis is the most interesting of those bets, as a talented player who has rarely had the opportunity to play for serious teams. Some of that is his own doing; serious teams, it turns out, can lose interest when a player breaks his teammate’s jaw in practice by punching him in the face. Portis has toiled on crummy teams ever since, including most recently as one of the Knicks’ surplus power forwards. This is a chance for Portis to channel his intensity toward more productive ends. From what we’ve seen in other stops, his game can be messy and ambitious. That’s in part because his skill set has given him more options than his teams had structure to curtail. A more defined role on an established team where Portis can show some of what he can do might be best for everyone. A little floor spacing here, some hard rolling there, a few duck-ins, and Milwaukee could be well on its way to a viable rotation big.

The combination of Holiday, Augustin, and Portis (relative to Bledsoe, Hill, and Lopez, whom they’ve seemingly replaced) does seem to unfurl the offense a bit more around Giannis. So many of Milwaukee’s postseason problems stem from the staleness of its offense. The lineups around Antetokounmpo couldn’t find enough shooting to give him an open lane or enough shot creation to free him up off the ball. The reigning MVP had to work as a battering ram to get anywhere near the hoop, which is no way to win against a defense ready and eager to turn his aggressive drives against him. In lieu of adding a single, experienced playmaker to direct the offense, the Bucks will try to win by diversifying the angles of attack.

It could well work. As similar as Bledsoe and Holiday might seem by the numbers, swapping the two guards allows Milwaukee to work around problems in the midrange instead of addressing all its issues in straight lines. Given his smaller stature and troublesome shooting, Bledsoe doesn’t have many options to beat a defender beyond backing the ball out, revving up, and attempting to twitch through to the basket. Holiday is long enough and strong enough to take his time. So many of his drives are about leverage—getting one foot into a defender’s space and sealing him off to the side while Holiday explores pockets of open space, making his moves and shots that much more difficult to predict. By pairing Holiday with Khris Middleton, Milwaukee should be better suited to a patient, cerebral sort of mismatch hunting.


There’s still the ghost of what could have been where Bogdanovic is concerned, but completing that deal as reported would have mired the Bucks in bench anxiety, forcing them to stake their contention on a bench full of minimum-salary talent. It’s a moot point, but an interesting counterfactual in what is now a matter of preference for Milwaukee between the roster as it was, the roster as it is, and the roster as it appeared to be.

Giannis may be weighing those same options. Milwaukee’s willingness to trade as much as it did for Holiday (who could also be a free agent in 2021) conveyed both the knowledge that Antetokounmpo might like to play with him and a confidence in the Bucks’ ability to retain both. Other organizations have not taken that optimism as gospel. The Raptors—anchored by Pascal Siakam, OG Anunoby, and the newly re-signed Fred VanVleet—will be eager to make their pitch if given the chance. The Heat re-signed Goran Dragic and Meyers Leonard while adding Avery Bradley and Moe Harkless, all pointedly without committing to any guaranteed money beyond this upcoming season. (That philosophy may have cost the Heat Jae Crowder and Derrick Jones Jr., who signed multiyear deals elsewhere.) The Mavericks have preserved their cap space by doing most of their offseason work via trade while adding another player on an expiring deal in James Johnson to flip if necessary, a continuation of their soft-salaried approach to landing a third star. Teams like the Warriors still loom as well, their cap numbers irrelevant. If Giannis wants to leave for a team like Golden State, a little salary won’t stand in the way.

The culmination of Milwaukee’s moves—including the failed Bogdanovic trade—can be read as acknowledgment from a franchise that recognizes what it’s up against. In the last few seasons, the Bucks have too often defaulted to inertia. The same style. The same lineups. The same results. This suite of transactions leans on the integrity of what the franchise has built but keeps going, developing the ideas behind the Bucks more fully. The season will tell us if that’s enough to take Milwaukee to the Finals. Giannis will tell us if it’s enough for the Bucks to preserve the core of who they are.