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.
