Since Damian Lillard requested a trade from the Portland Trail Blazers in late June, his teaming up with Jimmy Butler and Bam Adebayo in Miami seemed like a matter of if, not when. Then, the Toronto Raptors reportedly emerged as a stealthy suitor for the All-NBA point guard over recent weeks.
Neither club will enjoy his services this season, though. Instead, the Milwaukee Bucks, months removed from a first-round exit at the hands of the Heat, swooped in and landed Lillard. According to ESPN’s Adrian Wojnarowski, Milwaukee, Portland and the Phoenix Suns maneuvered a three-team, seven-player deal. It’s headlined by Lillard joining the Bucks, with Deandre Ayton and Jrue Holiday en route to the Blazers.
Milwaukee’s now led by a dominant quartet of Lillard, Giannis Antetokounmpo, Khris Middleton and Brook Lopez. The Philadelphia 76ers will get first crack at the new-look Bucks when they kick off their season inside Fiserv Forum on Oct. 26 at 7:30 p.m.
The upgrade from Holiday to Lillard is of obvious appeal. For all of Holiday’s defensive laudits, which helped vault Milwaukee to the 2021 title, his decision-making and scoring efficiency are glaring concerns in the playoffs. In three postseason appearances with the Bucks (40 games), he averaged 17.9 points on 47.6 percent true shooting — a jarring decline from the 18.5 points on 59 percent true shooting he recorded across three regular seasons for Milwaukee.
As one of the NBA’s esteemed pull-ups shooters and drivers, Lillard offers this group a legit half-court engine offensively that it’s lacked over the past five seasons. The Bucks’ championship hopes have rested on an overwhelming defense and grind-it-out offense. Now, that balance skews away from the extremes, with the hopes that generating reliable offense grows significantly easier. Lillard is a far worse defender, but a vastly superior offensive player and is simply much better overall. He addresses their biggest shortcomings, which will outweigh the gaps his arrival and Holiday’s exit presents.
Although currently slated to be a Blazer, Holiday presumably won’t reside in the Pacific Northwest very long. Portland’s youth movement is spearheaded by a trio of perimeter players in Anfernee Simons, Scoot Henderson and Shaedon Sharpe, so its intention is to send the veteran guard elsewhere, according to Wojnarowski.
Among those interested in acquiring the talents of Holiday are the Sixers, per Kyle Neubeck of PHLY Sports. Holiday spent the first four years of his career in Philadelphia before being dealt to the New Orleans Pelicans in 2013.
Once the trade among Portland, Phoenix and Milwaukee is finalized, Holiday can still be moved again, albeit he cannot be aggregated with other players. Holiday on his own is legal. Holiday plus additional players is not.
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The Sixers have a clear path to matching Holiday’s $36.8 million salary, with Tobias Harris owed $39.2 million this upcoming season. Harris could bolster Portland’s frontcourt and a first-round pick may prove enticing enough to facilitate negotiations. As Neubeck noted, Holiday should have plenty of suitors and is well-regarded around the league. But a package of Harris and a first may at least jam Philadelphia’s foot into the door of trade talks.
If the Blazers prefer more draft capital, another possibility is pivoting to a three-team deal involving James Harden and the Los Angeles Clippers. A trade that sends Holiday, Norman Powell, Marcus Morris Sr., and Los Angeles firsts in 2028 and 2030 to Philadelphia, Harden to the Clippers, and Harris, Philadelphia firsts in 2029 and 2030 to Portland works.
That’s a convoluted process, yet it certainly has beneficial aspects for everyone involved and ends in Holiday donning Sixers colors again.
If it materializes, he’d form a dynamic pick-and-roll duo defensively with Embiid. They’d wreak havoc together. Adding him would ultimately salvage a pretty messy Harden situation. The guard trio of Holiday, De’Anthony Melton and Patrick Beverley would constantly insulate Tyrese Maxey as well and protect him from assuming the stiffest point-of-attack tests. Holiday and Maxey are a harmonic pairing on both ends.
Yet for all the justified frustration Harden’s induced the past couple seasons in the playoffs for the Sixers, Holiday’s recent history is even more checkered with head-scratching decisions, ice cold shooting lulls and wretched scoring efficiency (47 percent true shooting since 2020-21). It’s difficult to envision the offense humming deep into the spring if and when he commands such a lofty role. Regardless, given the prospects of a Harden deal at the moment, Holiday and a first would be a tremendous outcome. It’s just unlikely to propel Philadelphia any closer toward a championship than where it’s stood the past few seasons.
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