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The Bucks Have One Last Offseason to Convince Giannis to Stay

Keeping the two-time MVP past next season may all come down to what Milwaukee does in the next few weeks. The options are limited, but it should start by addressing the major issue in the backcourt.

Getty Images/Ringer illustration

The Milwaukee Bucks, like a great genre movie, have taken a familiar premise to extraordinary circumstances. By now, we all know the log line: As one of the NBA’s true superstars enters his final season under contract, his small-market team will go to great lengths to contend for a title and to prove itself as the place he belongs. A bit trite, but fascinating still. Similar scenarios played out in Cleveland with LeBron James and in Oklahoma City with Kevin Durant. Other teams, like New Orleans and San Antonio, subverted this classic plot by trading their franchise players (Anthony Davis and Kawhi Leonard, respectively) before the final, dramatic season of their deals even began. Now it’s Milwaukee’s turn to manage a similar juncture with Giannis Antetokounmpo—all at one of the most precarious moments in the NBA’s history.

Consider, for a moment, the degree of difficulty involved here. When a talent like Antetokounmpo plays in the NBA’s fourth-smallest market, his upcoming free agency is publicly debated years in advance. Some of that coverage is sensational, perhaps unfair. Some of it is an honest reflection of a league whose stars often leave their teams to play with other stars. In practice, the combination of the two has made Antetokounmpo’s future the dominant Bucks story line following their past two playoff exits. That would be pressure enough—as close to an existential threat as it gets for an NBA team. Only now, the Bucks will have to contend with that mounting stress in an unstable league. NBA teams don’t know where their revenue will come from next season, when that season will start, or where it will be played. They don’t yet know the salary cap that will determine how they build their rosters, or even when, exactly, they will be allowed to make trades.

Under those constraints, the Bucks will have to find ways to improve a team that sputtered out in the second round of the playoffs. Some of their problems are conceptual; Mike Budenholzer will need to compromise in his vision for what the Bucks should run, most of all on defense, where a team with one of the most elastic defenders in the league (Antetokounmpo) managed to pigeonhole itself into predictability. It’s fine to lean on a conservative, dropping defense, but not to a fault. Milwaukee needs to get enough reps in other styles of coverage to actually become fluent in the rotations they require. To be proactive rather than reactive. A contending team can be confident without being staid—as demonstrated clearly by the past two teams to eliminate the Bucks in the postseason.

In terms of personnel, Milwaukee is badly in need of seaworthy rotation players; apart from Giannis and Khris Middleton, precious few Bucks could even keep their heads above water against the Heat. Eric Bledsoe’s performance, in particular, proved damning. For the second consecutive postseason, Bledsoe (who averaged 11.8 points per game against Miami while hitting just a third of his shots) mucked up the offense in a way that deadened any sort of improvisation. Budenholzer’s offense is made simple by design. Clearly that isn’t a problem in the regular season, but when opponents are able to fully leverage Bledsoe’s errant shooting against Milwaukee in the playoffs, that simplicity reveals itself as a tragic flaw.

Something has to give. Odd as it may seem for a top-seeded club that wrecked its opponents in the regular season, Milwaukee doesn’t actually have all that many attractive trade candidates it can afford to lose. Bledsoe is the exception, which is why moving him this offseason feels like a practical necessity—both to liven up the roster and to change Milwaukee’s broader approach at point guard. Antetokounmpo deserves a pick-and-roll partner who can hold the defense’s attention and reel in the coverage with the threat of his jumper. Bledsoe, for all that he offers as a defender and driver, is not that.

If Bledsoe’s performance in the 2020 playoffs were some one-off occurrence, it could be explained away as a product of Miami’s outstanding team defense or a result of Bledsoe reporting late to the bubble after testing positive for COVID-19—though by his own account, he didn’t experience any symptoms. The trouble is that every piece of playoff evidence from Bledsoe’s three years in Milwaukee points to the same conclusion. The grace period is over. The Bucks have exactly one season to show Antetokounmpo that this team can be something beyond what it’s been, and Bledsoe is both the most logical centerpiece for a trade and the team’s most obvious obstruction.

The Chris Paul trade rumors practically started themselves. Milwaukee could use some more order to its half-court operations, and a creator who better understands how to manage them. The flawed Thunder had one of the better half-court offenses last season under his guidance. Paul’s presence alone would be an antidote to the Bucks’ more aimless indulgences of the system: the constant shuffle of half-hearted handoffs and false-started pick-and-rolls that leave a possession to die in its preamble.

Of course, landing Paul would take more than just Bledsoe. Ersan Ilyasova and George Hill would almost certainly have to be involved as a matter of logistics. Donte DiVincenzo, Milwaukee’s best young player, could be the Thunder’s price. Draft picks could also be involved, though the Bucks already sent out their own 2020 first-round pick to acquire Bledsoe and their 2022 first-round pick to land Hill. They do, however, have a replacement first-rounder in this year’s draft, courtesy of the Pacers, some small consolation for trading away Malcolm Brogdon. It’s at times like these that Milwaukee misses Brogdon, or more specifically, the opportunities that could have been created by re-signing him. After the Bucks chose not to retain the combo guard at a premium last summer, team governor Marc Lasry explained the decision through an organizational preference for cash on hand.

“We’re definitely going to be in [the luxury tax] in a couple years soon,” Lasry said. “That’s not the question. The question is: Was re-signing Malcolm an imperative? I think re-signing Malcolm was a luxury and our view was Malcolm is a phenomenal player. He’s great, but for that amount of money, we thought we could have those dollars better spent elsewhere.”

Of course, for a team operating over the cap as the Bucks are now, that spending is restricted to whatever can fit within a few modest exceptions. Keeping Brogdon wasn’t just a way to keep a growing team intact, but to allow the organization more creative freedom in this critical moment. Bledsoe, by the nature of his game, has a hyperspecific trade market; even a team that needs a point guard might not be interested in a defense-first option with limited range, and even a team that is interested might not be in a position to take on his contract (three years, $54.4 million, though the final year is only partially guaranteed) in these strange financial circumstances. Brogdon would have given the Bucks access to a different group of potential trade partners, and his larger contract would have made it easier to match salaries for some of the more veteran superstars. Simply having him around would open up the possibility of trading Bledsoe for a player at another position, of making a deal that wouldn’t cost the Bucks a valuable backup like Hill, or even of packaging both guards together into a megadeal if the front office was ready for more radical change.

Instead, Milwaukee is stuck cycling three or four of its own players through the trade machine, grinding its gears into the dust of pick swaps. Given the unusual state of team finances around the league and the limits of what the Bucks can package together in a trade, this could turn out to be quite a year for the midlevel exception—an extension of Milwaukee’s “dollars spent elsewhere.” If the cap comes in low (a possibility considering that it’s tied to league revenue, though the NBA and NBPA could agree to artificially inflate it), free agents who would otherwise angle for bigger, longer-term deals could end up giving the Bucks a look. Players in that range might not transform the roster for the long term, but the right MLE candidate could nudge other contributors into slightly more comfortable roles for a title run in 2021.

To run an NBA team is to juggle all sorts of competing incentives, and the Bucks prioritized financial savings and some immediate flexibility over what would have made them the most competitive team possible. Because of that, Milwaukee may now have to gamble on making the most of next season at the expense of what comes after—an attempt to sell Giannis a car while praying he doesn’t look under the hood. If the Bucks keep their roster as is, there might be only one player (DiVincenzo, Delaware’s finest) on the roster who can be expected to improve over the life of Antetokounmpo’s next contract. If Milwaukee manages to trade Bledsoe for Paul, it would improve its immediate title chances while replacing a small 30-year-old guard with a small 35-year-old guard. (Brogdon, it’s worth remembering, is just 27.) It’s easy to sell Giannis on the idea that the Bucks are a very good team today. After all, they were only a possession away from taking a 3-0 lead over the Raptors in the 2019 Eastern Conference finals, and might have made it further in 2020 if not for a Heat team that proved to be a perfect foil. It’s more difficult to sell him on the idea of Milwaukee as an establishment for the next half-decade.

Of course, who even knows what it means to appeal to a superstar in this particular climate? Maybe the demands of the pandemic have made Giannis even more appreciative of the familiarity of a single franchise, and the people he has played and worked with for years. Perhaps he took something from the way the Clippers flamed out of the playoffs after Kawhi Leonard left a championship team for a paper contender. Even those closest to Giannis can’t know for sure, considering that the state of the world has thrown most every aspect of the NBA’s operations up in the air. It feels like the clock is ticking, even though the offseason hasn’t officially started and may not for months.

This is what Milwaukee will have to navigate. Most teams in this position deal with the circus—the questions, the rumors, the mixed messages. The Bucks are dealing with a shake-up of the entire NBA apparatus, down to the mechanisms they rely on to make their team better, and, in this case, to make their pitch to their own franchise player.