Who Mike Gansey Might Choose Between Kelly Oubre Jr. and Quentin Grimes

The Sixers will enter the offseason focused on revamping their rotation, as they’re likely locked into the trio of Tyrese Maxey, Joel Embiid, and Paul George. Philadelphia, which is projected to be $22.8 million below the first tax apron, has four unrestricted free agents. Among them are Kelly Oubre Jr. and Quentin Grimes, whose futures could dictate the Sixers’ offseason plans.

If the Sixers play their cards right, they could access the $15 million non-taxpayer mid-level exception. That exception could land Philadelphia a starting-caliber player like Rui Hachimura, Dean Wade, Ayo Dosunmu, etc. But the Sixers likely cannot do so without forfeiting one if not both of Oubre or Grimes, since both will seek a payday of their liking.

It’s now Mike Gansey’s, Philadelphia’s new President of Basketball Operations, job to figure out who to prioritize, Oubre or Grimes. Based on the Cleveland Cavaliers’ track record during his four-year tenure as general manager, it’s fair to assume he will choose Grimes.

A West executive believes Quentin Grimes will re-sign with the Sixers:

“I do think he stays there out of pressure. You have to keep at least one of [Grimes or Oubre], if not both… And if they don’t go into the tax, they’re going to get crushed.” 🤔

(h/t @TimBontemps) pic.twitter.com/1NZ00WafD3
— Sleeper76ers (@sleeper76ers) May 28, 2026

The 3-ball matters

Cleveland’s front office has emphasized spacing around its core of Donovan Mitchell, Jarrett Allen, Evan Mobley, and James Harden/Darius Garland. The Cavaliers ranked top eight leaguewide in three-point tries in the last three years, rostering marksmen like Wade, Max Strus, Sam Merrill, and Caris LeVert throughout those seasons.

Although Oubre recorded the best shooting season of his 11-year career (36%), it was just one season, compared to two others in Philadelphia when he shot below 32%. The Boston Celtics often ignored him beyond the arc to surround Tyrese Maxey in the Eastern Conference Quarterfinals due to Oubre shooting 25.6% this playoffs.

Asked Kelly Oubre Jr. about what he is prioritizing as far as situation is concerned. He said he wants to be “somewhere I’m loved,” then spoke at length about how, as a husband and father of two kids, he wants his children to have a place they can call home.
— Adam Aaronson (@SixersAdam) May 10, 2026

Grimes may have turned in a worse shooting season than Oubre, but he is a career 36.6% from downtown. The eye test will also tell you that Grimes is a superior shooter off the dribble, without the ball, and using screens.

Oubre is a marginally better perimeter defender than Grimes but Gansey’s Cavaliers tenure showed that their front office valued both sides of the court. Isaac Okoro, whom Cleveland drafted fifth overall in 2020, was one of its best perimeter defenders in his five-year stint. But, Okoro shot below 31% from distance in two of the three postseason runs he saw, so the Cavaliers traded him in July 2025.

Other factors

It’s also worth pointing out that Grimes’ value is at a low point while Oubre is coming off one of the best years of his career. That means Oubre could command more money than the Sixers are willing to pay, while Grimes may return on a contract lower than the $8.7 million qualifying offer he took this season.

Many fans have also theorized that Philadelphia could target Wade in free agency. After all, Gansey was Cleveland’s guy when it came to finding diamonds in the rough, which Wade turned out to be for it.

So if the Sixers poached Wade using some or all of their MLE, it may not be worthwhile for them to spend a pretty penny on Oubre as well.

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