Back in late 2020, when the prospect of Giannis Antetokounmpo passing on a five-year, $228 million supermax extension was still a concern in Milwaukee, the Bucks felt compelled to convince their superstar there was no need to eventually test the free-agent market.
With the club still in search of a title despite coming off back-to-back seasons in which it had the NBA’s best record and consecutive years in which Antetokounmpo had won the league’s MVP award, general manager Jon Horst took an aggressive approach. He dealt for stud defender Jrue Holiday—a clear upgrade from guard Eric Bledsoe, who’d repeatedly struggled in the playoffs with his jumper, shooting 23.6% and 25% from deep, in 2019 and ’20, respectively.
Shortly after the trade for Holiday, among other transactions, Antetokounmpo agreed to sign the supermax he’d once been noncommittal about. And, as we now know, the Bucks won a title that season, ending a 50-year drought. It was as close to a happily-ever-after ending as there is.
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Fast-forward to now, following Antetokounmpo’s choice to agree to a three-year, $186 million extension Monday after repeatedly saying this summer that it might not make sense to commit long-term, and the vibes seem largely similar to what they were in late 2020. The Bucks, of course, recently traded Holiday for Damian Lillard—a move that followed Antetokounmpo voicing that he’d stay put with the Bucks for the long haul only if he was convinced they were as serious about winning championships as he was. The deal for Lillard seemed to indicate that no one was merely content with results like last season’s, when, much like in ’19 and ’20, Milwaukee earned the NBA’s best mark but didn’t win the championship.
Early returns certainly portend incredible offensive success for Milwaukee, as Antetokounmpo has already said he’s never enjoyed so little defensive attention due to the half-court traps being thrown at Lillard, even during the preseason. “I’ll be very honest: I’ve never been this open,” he said.
Time will tell how the Lillard acquisition grades out on the court—especially with him due to earn a whopping $63 million in 2026–27, his age-36 season. But in terms of getting bang for your buck, you have to view that trade much like the Holiday one back in 2020. Even if you’d be inclined to call the cost of landing Lillard (or Holiday) as steep, bringing him into the fold helped Antetokounmpo feel comfortable in signing on to stay longer. And with Giannis 28 years old and in his prime, never having suffered an injury that kept him out long-term, that reality is priceless.
In that way, the Lillard trade already grades out as a massive victory for the Bucks before the duo has played a single regular-season contest together. They’re hoping now that the 2023–24 season plays out the same way that ’20-21 campaign did, after trading for Holiday.
