It made perfect sense for the Portland Trail Blazers to trade Anfernee Simons this summer.
Although Chauncey Billups benched Shaedon Sharpe for his lack of defense, it was Simons -- not Sharpe -- who was Portland's worst defender. Simons didn't fit Portland's defensive identity, making it hard to justify inking him to his next contract with his current deal set to expire after the 2025-26 season, especially after seeing the limited value that an offensive-minded combo guard archetype has around the league.
Still, one of the cons of that decision was that it would significantly hurt the Blazers' offense, which was already mediocre. Portland ranked 26th in three-point percentage (34.2) and tied for 22nd in both points per game (110.9) and offensive rating (111.0).
While Jrue Holiday is a massive defensive upgrade over Simons, he's an equally offensive downgrade at this stage of his career. That will be an immediate problem for next season, which could cause Portland to miss out on the playoffs for a fifth consecutive year. But the good news is that Portland has offensive reinforcements coming in 2026-27 with the unexpected signing of Damian Lillard to a three-year, $42 million deal.
Damian Lillard is an upgrade over Anfernee Simons
It's unreasonable to expect Lillard to return 100 percent, despite his confidence. But even if the Blazers get an 80-90 percent version of Lillard, that's still a significant upgrade from Simons -- not talent-wise, as Simons has closed the gap due to his progression and Lillard's injury -- but in terms of value. Both have similar combo guard skill sets, but their contract situations make Lillard an upgrade for Portland's roster.
Simons left a considerable void in Portland's offense as a shooter and secondary playmaker. Lillard will seamlessly fill that role, and for significantly cheaper. Simons is owed $27.7 million this upcoming season. Just entering his prime, he could command a similar, if not higher, annual salary once he hits the market.
Going from Simons to Lillard's contract is already a win for Portland. It also doesn't account for: a) the assets they acquired from trading Lillard to Milwaukee, b) turning Simons into Holiday, and c) the best-case scenario where Lillard returns to full strength as Portland's go-to option and missing piece to end their playoff drought.
Of course, the main downside is that Simons fits Portland's rebuilding timeline much better than 35-year-old Lillard. But Portland already has its future point guard in Scoot Henderson. By signing an aging Lillard at a discount, the Blazers continue investing in Henderson, making it clear that the long-term role is his for the taking. The Simons-Lillard upgrade will only further help the Blazers build for the future, while also achieving their win-now goals after his anticipated return from injury.