You’ve surely heard the rumors by now. Giannis Antetokounmpo, eligible for a contract extension as of Sep. 22, will not be re-upping with the Milwaukee Bucks this offseason. He wants to continue competing for championships and needs to be certain the Bucks will do what it takes to make that happen. If you’ve been out of the loop these past few months, don’t worry. The news cycle is more or less the same as it was in 2020.
Antetokounmpo was one championship ring poorer back then, but the sentiment was similar. Antetokounmpo was set to become one of the most anticipated free agents in NBA history in 2021, but his preference was to remain with the Bucks so long as they furnished him with proper supporting talent. Milwaukee ultimately did so, trading three first-round picks and two first-round swaps for Jrue Holiday in a move that satisfied Antetokounmpo… for a time.
That time appears to be over, and Antetokounmpo has justifiable misgivings about committing the remainder of his prime to a rapidly aging Bucks team. Holiday is 33, on an expiring contract and hinting at retirement. Starting center Brook Lopez is even older at 35 and had back surgery during the 2021-22 season. Khris Middleton is the youngest of the supporting Bucks, but is still 32 and coming off of a season in which he played only 33 games.
That group of teammates has given Antetokounmpo a championship. It is perfectly capable of giving him another one. But it is very clearly nearing its expiration date. Those picks they traded for Holiday, on the other hand, largely haven’t conveyed yet. Milwaukee still owes two first-round picks and two swaps as a result of the Holiday trade. It therefore stands to reason that they don’t have the chips to make another Holiday-like trade. Yet without doing so, the Bucks almost certainly won’t be able to maintain a contender around Antetokounmpo for the rest of his prime.
This is the paradox of modern roster-construction. Teams need to do everything in their power to keep their stars happy… and yet doing so eventually prevents them from making their stars happy down the line. It’s the NBA’s all-in era, and as teams around the NBA are finding, you only get to go all-in once.
The Philadelphia 76ers are begging for significant roster changes as Joel Embiid rumors swirl. Too bad. They spent their picks landing James Harden and dumping Al Horford. The Dallas Mavericks made their all-in move on Kristaps Porzingis and were left so asset-depleted that the only way they could afford another credible star-caliber player was to take on an enormously risky one like Kyrie Irving. Even on the off chance that Philadelphia or Dallas wins a championship with their current roster, as Milwaukee did, they’d have to deal with the age conundrum the Bucks are currently struggling with. Irving is seven years older than Luka Doncic. Harden is five years older than Embiid. These partnerships aren’t built to last.
You could of course choose not to make an all-in move at all, but ask Portland how that’s going. Damian Lillard spent the bulk of his prime watching his superstar peers partner up and box him out of the latest stages of the playoffs. Sure, traditionally-built rosters can compete with extraordinary luck. Pick a two-time MVP at No. 41 overall and you’re golden. But for the most part, the super teams are going to win. The commonly accepted logic of the all-in era is that you can either build one or watch your best player leave for one.
But now that this era has played out, its logical endpoint has revealed itself as a combination of both. You build a super team… and then you watch your best player leave for another one when the first has run its course. It’s happening to some combination of Antetokounmpo, Embiid and Doncic now. It won’t be long until it starts happening to the next crop of stars behind them. How is Minnesota supposed to build around Anthony Edwards now that Utah owns all of its picks?
There are exceptions on either end of the age spectrum, but neither appear especially replicable. Stephen Curry is the last of a dying breed, this generation’s answer to Tim Duncan, Kobe Bryant and Dirk Nowitzki. It took for him to join that group was the simultaneous drafting and development of two other Hall of Famers. The Warriors never needed to go all-in for a Klay Thompson or Draymond Green because they already had them. As the Kevin Durant Thunder showed us, though, drafting three superstars does not a dynasty guarantee. Keeping them is another matter. Without deft roster management and the decision to replace Mark Jackson with Steve Kerr, Curry may not have been a one-team superstar.
As they say often do, the San Antonio Spurs have seemingly predicted this problem and taken countermeasures to prepare for it. In addition to accumulating a mountain of draft picks by trading away veterans like Dejounte Murray and Derrick White, they’ve made a point of acquiring pick swaps from a diverse group of teams in different years. Those swaps typically carry fewer protections than picks owed outright. San Antonio currently owns swaps from the Hawks (2026), Celtics (2028) and Mavericks (2030). Only Boston’s pick is protected, and that protection only denies a swap if the pick lands at No. 1 overall.
It’s possible that San Antonio utilizes none of those swaps. But all three have disaster potential, and that is the idea for the Spurs. They’re cherry-picking low-percentage, high-upside assets that will mature right as Victor Wembanyama hits his prime. They don’t want to have to go all-in for an older player. They want to be able to stream high-end younger talent into their organization organically so Wembanyama never aggressively pursues a single, famous teammate. San Antonio executed this approach perfectly during the Duncan era, as Tony Parker, Manu Ginobili and eventually Kawhi Leonard kept Duncan in contention for his entire career.
Teams like Oklahoma City, New Orleans and Utah are in similar positions. What do those teams have in common? Each of their rebuilds started by trading multiple All-Stars. Not only did that give them significant head starts on organic rebuilds, but it allowed all three of them to amass enough draft capital to go all-in as many times as necessary. A typical NBA team has four tradable first-round picks at any given time. Right now, the Thunder have 12.
Going all-out before jumping back all-in might be the next stage of the superstar arms race, but that theory does little to combat the problems facing the Bucks right now. Even if they could turn two or three of their key veterans into hauls for eventual flipping, they’d never be able to keep Antetokounmpo happy long enough to see that plan through to its conclusion. If anything, it might eventually be their plan for salvaging their post-Antetokounmpo future, not the present Giannis already represents.
That present might end soon. It might last another three years. But the Bucks are living on borrowed time. So are the Sixers and Mavericks. So is almost every other team with a prime superstar, and that clock no longer stops with a mega trade or even a championship. Keeping a player of the Curry or Duncan ilk at this point in NBA history means winning as consistently as they did, and winning as consistently as they did means replenishing talent as quickly as it deteriorates. The cost of doing so nowadays is simply too high for that to be a sustainable strategy. It might happen in a year. It might happen in three. It might happen in five. But all of this means that most of this generation’s superstars are eventually going to change teams. The league just isn’t designed for Kobes or Dirks anymore.
