If the Portland Trail Blazers ultimately end up trading Anfernee Simons to the Orlando Magic, Jonathan Isaac is the one realistic player they should target in a potential return. This comes after Yahoo Sports' Kevin O'Connor reported that Orlando is "open to trading Cole Anthony and Jonathan Isaac with their first for an upgrade."
That was specifically about the Magic trading for Lauri Markkanen, who likely requires more assets to acquire. We could do without Cole Anthony, but the fact that Orlando is rumored to be making Isaac available is a good sign for Portland.
Why the Blazers should trade for Jonathan Isaac
Consider the identity Portland is headed toward, with Deni Avdija, Toumani Camara, and Donovan Clingan as their true building blocks. They prioritize length, defense, and versatility. Issac, a 6-foot-10 forward, would be a perfect complementary piece to help bolster that identity.
He's in his prime at 27 years old and would be a great addition to help Portland achieve both its short and long-term goals. He's polished enough to help make a playoff push next season but also young enough to fit alongside the timeline of Avdija and Camara.
While Isaac's career-low 25.8 three-point percentage this season was concerning, he hovered around 40 percent the previous two years. If he has a bounce-back shooting season, Portland will have a valuable 3-and-D piece on its hands.
Isaac's contract is also unique in that Orlando extended him last summer using a renegotiate-and-extend method. He's owed $25 million for 2024-25, but that number decreases to roughly $15 million annually over the next four seasons.
Even better for Portland, Orlando put injury protection into Isaac's contract -- he needs to reach the 52-game milestone from the previous season to fully guarantee his salary the following year.
But what about Anthony Black?
Anthony Black would be Portland's dream trade target in any Simons deal with Orlando, as the 21-year-old guard fits their rebuilding timeline better and continues to trend in the right direction as a two-way force. But it could be challenging to get the Magic to sign off on shipping Black on top of one of their first-round picks.
The Magic desperately need an offensive-minded guard like Simons, but it would be a fleece to get Black and a first-rounder back, given that Simons will likely demand a hefty contract extension after the 2025-26 season. We also haven't heard anything signaling Black is available, while KOC's latest rumor makes Isaac a more realistic option.
Joe Cronin tends to overvalue Portland's players, and their clock is now ticking after missing the ideal window to trade Simons last season. A package of Isaac and Orlando's first-round pick may not be sexy, but it's realistic. And most importantly, it helps them restructure their roster and have a clearer sense of direction in their rebuild, improving their long-term outlook.