Insider Projects Fit of Former Blazers Teammates Reunited on East Title Contender

It's Portland East on this championship hopeful.

Mar 16, 2021; Portland, Oregon, USA; Portland Trail Blazers (from left to right) Robert Covington (23), Damian Lillard (0), Gary Trent Jr. (2), CJ McCollum (3), and Carmelo Anthony (00) walk back to the court after a timeout during the second half against the New Orleans Pelicans at Moda Center. Mandatory Credit: Soobum Im-Imagn Images / Soobum Im-Imagn Images

After helping lead the 2018-19 Portland Trail Blazers to the Western Conference Finals, can reunited backcourt teammates Damian Lillard and Gary Trent Jr. finally win a title together with the Milwaukee Bucks in 2024-25? In fairness, Trent was not a big part of that team, as he was merely a rookie second round draft pick at the time, appearing in just 15 regular season contests.

That's the question on the minds of Bucks fans everywhere. The Trail Blazers flipped eight-time All-Star Lillard to the Bucks late into the 2023 offseason, "improving" a perennial Eastern Conference contender to a mediocre 49-33 record and a second consecutive first round exit. But Milwaukee retooled with some savvy offseason signings, headlined by the club's ability to ink Trent, a free agent after three listless years with the Toronto Raptors, to a shocking below-market veteran's minimum deal this summer.

In a fresh reader mailbag, Eric Nehm of The Athletic unpacks how the team's move to acquire Trent, its new projected starting shooting guard on a veteran-laden first five. The 6-foot-5 swingman now joins Lillard, former three-time All-Star small forward Khris Middleton, eight-time All-Star and two-time MVP power forward Giannis Antetokounmpo, and one-time All-Star Brook Lopez.

With Patrick Beverley, Jae Crowder and Malik Beasley all now elsewhere, the Bucks reconfigured their depth by adding Trent, defense-first guard Delon Wright, and 3-and-D small forward Taurean Prince. Trent will be replacing Beasley in Milwaukee's starting lineup, and he will be looked on to supply supplemental ball handling in addition to off-ball shooting for the club — but he'll also be a massive upgrade over Beasley in another key department: defense.

"Since Antetokounmpo blossomed into a superstar, the player whom the Bucks have invested in the most at shooting guard has tended to be able to put up strong numbers," Nehm writes. "Malcolm Brogdon, Donte DiVincenzo, Wesley Matthews, Grayson Allen and Beasley all put up great seasons in that spot, so Trent will have a great opportunity to do the same. The biggest chance for improvement in that spot, however, will come on the other end. Starting next to Lillard, Trent will be expected to guard the best backcourt scoring threat like Beasley did last season. Trent’s previous stops suggest he may have the defensive proclivity to do better in that role than Beasley."

That said, Beasley still had a solid season prior to his second straight lackluster playoff performance (he was also a dud on the Los Angeles Lakers in 2023). The 6-foot-4 swingman averaged 11.3 points while slashing .443/.413/.714 shooting splits (that 41.3 percent 3-point rate arrived on a high-volume 6.9 triple tries a night), 3.7 rebounds, 1.4 assists and 0.7 steals a night.

Last year on the Raptors, Trent averaged 13.7 points on a .426/.393/.771 slash line, 2.6 rebounds, 1.7 assists and 1.1 steals across 71 games (41 starts). The 25-year-old is suiting up for his third pro team. He was drafted by Portland in 2018 out of Duke, and just as he was starting to blossom in 2020-21, he was flipped midseason to the Raptors.

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