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The Bucks’ All-In Moves Were Worth It if They Keep Giannis In Milwaukee

It took every asset that isn’t nailed down to land Jrue Holiday and Bogdan Bogdanovic, but the success of the deals will come down to what it means for the long-term future of the two-time MVP

Getty Images/Ringer illustration

It’s tempting to say that the Raptors and Heat pushed the Bucks to the monumental decisions they made late Monday night and early Tuesday morning, but that’s not entirely true. What Kawhi Leonard and Jimmy Butler did to Mike Budenholzer’s team in consecutive postseasons certainly helped, but it took years of misses, misfortunes, and mishaps for Milwaukee to enter this offseason with the Doomsday Clock—the prospect of two-time Most Valuable Player Giannis Antetokounmpo turning down a five-year, $228 million supermax contract extension in favor of hitting the open market next offseason and possibly leaving Milwaukee to seek greener pastures—ticking ever closer to midnight.

After the all-time draft home run of landing Antetokounmpo with 2013’s 15th pick, the Bucks took a healthy Jabari Parker one spot ahead of an injured Joel Embiid, and then watched as Parker tore his left ACL twice and Embiid became an All-NBA cornerstone. They shipped out picks that became Norman Powell and OG Anunoby, legit playoff rotation pieces on excellent Raptors teams, for 23 games of Greivis Vásquez. They chose Thon Maker one spot ahead of Domantas Sabonis. They used a first-round pick on Rashad Vaughn, out of the league before the end of his rookie contract and last seen in Montenegro; they’re still paying Larry Sanders, once their center of the future before things fell apart, and will be for two more seasons.

The Bucks scored with Malcolm Brogdon in the second round in 2016, saw him win Rookie of the Year and develop into a trusted playoff hand—and then, after extending Eric Bledsoe’s contract, flipped Brogdon to the Pacers instead of paying him, because they viewed him as “a luxury” rather than a necessity, and because an ownership group that took a quarter of a billion dollars in public funding to build Fiserv Forum “balked at going into the luxury tax.” By waiving Jon Leuer to re-sign Brook Lopez and George Hill with cap space, they also squandered the eight-figure trade exception the Brogdon deal could have created; this eliminated an avenue to add another piece to the 2019-20 roster, which ran aground when Bledsoe (having again turned into a pumpkin in the postseason) and Wesley Matthews (never a creator, and certainly not one in his twilight post-Achilles tear) couldn’t fight fire with fire against the Heat’s guards in the second round of the playoffs. (Antetokounmpo’s ankle sprain certainly played a role, but Miami was already dominating the series when he went down.)

Every franchise has these missed opportunities and inflection points; some matter more than others. Milwaukee’s have the potential to matter a great deal, because this is how an organization can nail big things—like not only drafting a talent as unique as Giannis, but figuring out how to develop him; like hiring Budenholzer to provide the schematic framework that allowed him to bloom into his crowning MVP glory; like building a team good enough to win three-quarters of its regular-season games in a two-year span—and still wind up staring into the abyss of knowing the best player it has produced in half a century might walk out the door in a year if it can’t alchemize iffy ingredients into a gold trophy.

And so: in comes two-way ace Jrue Holiday from New Orleans, and out go Bledsoe, Hill, and “significant” draft consideration to the Pelicans—three first-round picks and two pick swaps. In comes restricted free agent Bogdan Bogdanovic (and young swingman Justin James) from Sacramento, and out go Donte DiVincenzo, Ersan Ilyasova, and D.J. Wilson. In less than two hours, the Bucks forked over a half-decade’s worth of first-round picks and their most promising young player. Facing an existential crisis has a way of clarifying your priorities. In this case, the only future planning Milwaukee can engage in is attempting to ensure a future in which Antetokounmpo stays in Milwaukee.

It’s possible that they’ve already done that. The Bucks just gave up the 24th pick in Wednesday’s draft (originally Indiana’s, sent to Milwaukee for Brogdon) and, much more importantly, unprotected firsts in 2025 and 2027 plus swap rights in 2024 and 2026, for Holiday, who is 30 years old and holds a player option that will allow him to hit free agency next offseason. It stands to reason that the only way Bucks general manager Jon Horst would have agreed to do that is if Giannis had communicated either that doing so would convince him to sign the supermax contract extension Milwaukee will offer him as soon as free agency opens this Friday, or that he’d already decided to do it and intends to stay put through 2026, ratcheting up the likelihood that nearly all of the picks the Bucks convey to New Orleans will land in the bottom third of the draft. (There is that unprotected 2027 first, though. David Griffin might be good at his job.)

If that rationale is based in fact (and a number of plugged-in insiders seem to think that it is) and if Holiday’s arrival is followed in a few months by a multiyear extension, then the calculus shifts, taking on a shape similar to the Clippers’ megadeal with the Thunder last offseason. Milwaukee’s not trading three good players, five picks, and about $11.5 million in expiring contracts for Holiday and Bogdanovic; it’s trading that package for Holiday, Bogdanovic, and Giannis. And if that’s what it is, then you do it 100 times out of 100.

Yes, the cost—and the associated costs of Holiday’s extension and Bogdanovic’s new deal in the sign-and-trade—is steep. But there’s no price too high if it means keeping Antetokounmpo in town, putting him and the new additions together on a multiyear timeline concurrent with Khris Middleton’s contract, and giving the Bucks (at least) a three-year window of maximum title contention. If Horst’s late-night wheeling and dealing accomplishes that objective, it’ll all be worth it. If it results in a championship at some point in the next few years, then none of the missteps that led Milwaukee to the brink will matter; they’ll just be confetti in the ticker-tape parade, blowing in the breeze and falling to the ground while the banner flies forever.

Not that Milwaukee’s brass should start planning the parade just yet. (Well, nobody should be having parades right now, but that’s a different column.) Even if Giannis signs, adding Holiday and Bogdanovic on their own doesn’t guarantee the Bucks a thing in a conference that still features the Heat team that undressed them on the way to the Finals, a 76ers squad under new management, the always-tough Celtics and Raptors, and a new contender growing in Brooklyn that might wind up including James friggin’ Harden. Even if Milwaukee outlasts those competitors to make its first Finals appearance since 1974, it’ll still have to deal with whatever fresh hell emerges from what promises to be an even-more-brutal-than-usual West, with the reconstituted Clippers, Nuggets, Warriors, Suns (!), and others all chasing the defending champion Lakers. Scaling that mountain’s an awfully tall task for any team—let alone one whose bench at the moment consists solely of the newly acquired James, he of 232 career NBA minutes, and Thanasis Antetokounmpo. (Though giving Coach Bud fewer rotation options might not be such a bad thing.)

With so many roster spots open and so much uncertainty on how Milwaukee will fill them, for all intents and purposes, Giannis-Middleton-Holiday-Bogdanovic-Lopez is the team, now and for the foreseeable future. The good news: It should be a pretty fuckin’ good team.

In Holiday, Milwaukee found a Bledsoe replacement who’s a better 3-point shooter—in career percentage, on catch-and-shoot attempts in each of the last two seasons, and, crucially, in the context of the playoffs—without sacrificing any tip-of-the-spear defensive impact. In fact, the Bucks might have found one of the few lead guards who would represent an upgrade on Bledsoe’s work on that end.

Holiday’s not a true primary initiator on the order of Chris Paul, who you’d want to run 50 pick-and-rolls per game and orchestrate every half-court possession. But he’s a better creator, facilitator, and scorer than Bledsoe—the kind of player opponents can’t just wholesale ignore in a postseason matchup, lying in wait until he bricks a bad jumper or hurtles into traffic with a pell-mell drive with a low chance of producing something positive. On the contrary: While Holiday’s teams in Philly and New Orleans haven’t made the postseason often, when they have, he’s elevated his game, most notably in helping lead the Sixers to Game 7 against the heavily favored Celtics in the 2012 playoffs (you might remember this series from Uncut Gems) and in teaming with Anthony Davis to erase Damian Lillard and CJ McCollum in a 2018 sweep of the Blazers, during which Holiday averaged nearly 28 points and seven assists per game, with a monster 41-point performance to close things out. One imagines he might fare pretty well next to a similarly unbelievable and multifaceted big man like Antetokounmpo on both ends of the floor.

Bogdanovic has yet to make a postseason appearance in the NBA since joining the Kings in 2017, but the 28-year-old has plenty of big game experience, both as a star in the EuroLeague before coming stateside and as one of the best players on the Serbian national team that routinely competes for gold in international competition. Even in a time-share role alongside De’Aaron Fox and Buddy Hield in the Kings’ backcourt, Bogdanovic has been one of the league’s top high-volume marksmen, ranking 30th in the NBA in made 3-pointers since he entered the league. Last season, he was one of just 10 players to attempt nine long balls per 36 minutes and hit at least 37 percent of them; he’s even better on the kind of catch-and-shoot triples he’ll likely feast on playing alongside Giannis, drilling at least 39.4 percent in each of his three NBA seasons.

Like Holiday, Bogdanovic isn’t a prototypical every-possession facilitator. But he’s got the size at 6-foot-6 to see over defenders and enough craft, creativity, and gall to bend a defense and make plays off the dribble. He’d be overtaxed as a true point guard; as a second or third creator who can threaten defenses on or off the ball, he could be dynamite, and gives the Bucks another player capable of—and unafraid of—making a play for himself or others in the guts of a high-pressure game.

Building out the rest of the roster around that core group will be Horst’s next big challenge, and it’ll require plenty of creativity. Under the league’s collective bargaining agreement, teams that pull off sign-and-trade deals submit themselves to a hard cap for the season that limits their spending to $6 million above the luxury tax threshold—a point colloquially known as “the apron.” Bringing in Bogdanovic, then, ensures that the Bucks can’t spend more than $138.9 million in total salary this season. Giannis, Middleton, Holiday, and Lopez on their own combine to make $99.5 million. A new deal for Bogdanovic in the $15 million range (though he can make more than that) would push the total up to about $115 million; Thanasis and James bump it to around $117.7 million, leaving a little over $21 million for seven roster spots.

Maybe Robin Lopez declined his $5 million player option to take a lower, more team-friendly deal. The Bucks might sit near the top of the power rankings when it comes to destinations for ring-chasing vets; if Matthews (who declined his option) decides to head elsewhere, maybe Avery Bradley comes in to take his place as a minimum-salaried, defense-first backcourt option (albeit a smaller one). Beyond that, barring a trade of Brook Lopez—the central figure in the Bucks’ elite regular-season defense, but still someone who could be improved upon in the context of a title chase—Milwaukee might need to make some magic happen on the margins with second-round picks and flyers.

It won’t be easy; even if the Bucks nail those moves around the fringes, it might not be enough to cement them as the favorite to win it all, this year or beyond. But it gives them more options on offense in the playoffs, it maintains the core of what’s been the NBA’s best defense for the last two years, and, if it keeps Antetokounmpo happy enough to sign the supermax, it staves off the nightmare scenario. Under the cover of darkness, the Bucks turned back the hands of the Doomsday Clock; midnight doesn’t look quite so close, now, and a brighter dawn just might.