
Gary Trent Jr will be reunited with former All-Star teammate Damian Lillard this coming season, after agreeing terms on a one-year deal to join the championship-contending Milwaukee Bucks following weeks of speculation about the now-former Toronto Raptors guard’s future. His new head coach Doc Rivers, who knows Gary’s dad Senior, flew to Miami to help recruit his services.
Bucks’ biggest offseason move? A shrewd one

MUCH was said about Gary Trent Jr, a lot of it derogatory or dismissive, in the days after free agency opened late last month. How could a crafty sharpshooter coming off an underwhelming year expected to be paid as heavily as he was?
Brandon Ingram has a similar, albeit far more expensive situation on his hands in New Orleans while there are plenty of unsigned players around Trent Jr’s age hoping a ball club signs them to a guaranteed deal to help rebuild their future value.
That’s what ESPN’s Jamal Collier has framed this deal as, in a healthy environment for the guard among familar faces. Damian Lillard took the now 25-year-old under his wing during two-and-a-half years together in Portland, and was the big piece in a surprise trade package sending him East last term.
Doc Rivers, who knows Jr’s father Senior intimately, is also a factor. Collier reported the 61-year-old flew to Miami as part of a recruiting pitch for his services, knowing full well they weren’t the first to enquire about getting a deal done this offseason.
Toronto were unprepared to keep him at, or near, the rumoured $25m-a-year figure and didn’t offer an extension after the season while interest from Los Angeles, where the newlook Lakers are still finding their feet under fresh management, died down.
This move represents Milwaukee’s biggest in a period where they weren’t expected to make noise given their existing financial constraints and the long-term guarantees both franchise cornerstone Giannis Antetokoumpo and Lillard are under.
As we’ve seen countless times, adding three-point specialists doesn’t hurt and that’s especially true when trying to share the scoring workload more in the business months of an arduous season with increased defensive attention on star players.

Although they kept the bulk of their existing roster intact Milwaukee lost eight-year SG Malik Beasley, who agreed terms with Detroit on a one-year, $6m deal last week.
Only three other players leaguewide can boast 500 made threes and 300 steals over the past three seasons like Trent Jr has quietly recorded: Houston’s Fred VanVleet plus the All-Star Olympic duo of Anthony Edwards and Tyrese Haliburton.
Possessing heightened defensive awareness as a guard is always a welcome asset showing itself doubly valuable come playoff time – OKC’s summer acquisition Alex Caruso and newly-minted NBA champion Derrick White just two examples.
Per Second Spectrum, Trent Jr has shot 41% on catch-and-shoot triples over the last two seasons and 2023-24 served as his best from distance (39%) since 2019/20.
Having just committed $400m over the next five seasons to Scottie Barnes and Immanuel Quickley this summer, Toronto weren’t best placed in offering a hefty multi-year extension, but he’ll be determined to make them rue their decision soon.
Picture source: Getty Images, stats via ESPN