Orlando Magic Receive: Anfernee Simons

Portland Trail Blazers Receive: Cole Anthony, Caleb Houstan, Jett Howard, 2025 first-round pick (least favorable from Denver or Orlando), 2027 first-round pick (lottery protection)

Cobbling together a package is trickier now that Orlando has burned through its spending power. But it has the breathing room beneath the tax to still offer Portland some additional flexibility of its own. This package shaves around $5.7 million from the Blazers’ current payroll, outfitting them with plenty of more runway under the tax themselves.

Roster spots will need to be cleared for Portland in the long run following this trade. That shouldn’t be a deal-breaker. General manager Joe Cronin isn’t done wheeling and dealing himself, and the Blazers can simplify the math, if need be, by roping in a third team to take on Houstan.

The crux of this package, though, should be enough to get Portland thinking.

Howard didn’t play much during his rookie season but provided glimpses into his motion shooting during G League stints with the Osceola Magic. Anthony is just 24, a solid scoring and offensive caretaker option off the bench and about to start a team-friendly three-year, $39.1 million extension. If landing two firsts, on top of Howard, isn’t a home run, then it’s certainly a triple.

Truth be told, the Magic could be the more reticent party.

Simons is an ideal fit in Orlando. He just downed nearly 43 percent of his catch-and-fire triples and continues to nail his off-the-dribble treys at a satisfactory clip, and the 8.8 three-pointers he jacked per game this season would have led the Magic by a colossal margin. But while he brings some secondary playmaking, he doesn’t check the floor-general box.

Here’s the thing: Cole Anthony doesn’t, either. And Orlando retains Anthony Black as part of this proposal. Even so, the Magic are playing some of their best remaining trade chips. They have to really believe their offense will level up with Simons, Paolo Banchero, Jalen Suggs and Franz Wagner running the show. That’s a gamble.

Then again, it’s a wager Orlando is already making. It has so far opted to go after Kentavious Caldwell-Pope and reinvest in non-point guards rather than target a game manager. Simons jibes with the committee approach to offensive initiation, and the live-dribble threat he poses, when attached to everything else this team has in place, is enough for all of us, collectively, to start saying some pretty inflammatory things about the 2024-25 Magic.