Should the Boston Celtics start Anfernee Simons or Payton Pritchard in the backcourt? There are multiple factors at play. They paint a clear picture.

For starters, Simons might not be in Boston when training camp starts. That seems an unlikely development as the calendar turns to September. However, as recently reinforced by Steve Bulpett of Heavy.com, the Celtics are open to rerouting the former Portland Trail Blazers guard.

Even if that doesn't happen before the upcoming campaign gets underway, it would not come as a surprise if it does before February's trade deadline passes.

The 18-time NBA champions are entering a projected gap year. Priorities include gaining flexibility. Shedding salary and reducing their tax bill will help build future rosters when Jayson Tatum returns from rehabbing a torn Achilles.

Maybe Boston is willing to carry Simons' expiring $27.7 million contract on the books this season. However, if there isn't an appetite to re-sign him because the Celtics don't believe in a team where the top-four salaries belong to Tatum, Jaylen Brown, Derrick White, and Simons, then why start the latter over Pritchard?

Sure, there's a case for propping up his trade value. However, the seven-year veteran has put enough on tape. Teams have a firm grasp of his strengths and weaknesses.

The on-court case for the Celtics to Start Pritchard

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Simons is a gifted scorer. Last season, he ranked 13th among players who attempted at least 3.5 pull-up threes per game, per NBA.com. The six-foot-three guard hoisted 4.2 shots of that nature and converted them at a 34.7 percent clip. He also drilled 37.7 percent of the 4.3 catch-and-shoot 3s he took.

The Florida native has averaged 20 points over the last four seasons. He produced 19.3 points per contest in the 2024-25 campaign. However, there is no question which one of these two players is more well-rounded.

Pritchard, the NBA's reigning Sixth Man of the Year, is a much better defender. An effective on-ball defender, his growth on that end of the floor earned him more opportunities to challenge himself against the opposition's top perimeter players. Those assignments ranged from Shai Gilgeous-Alexander and Cade Cunningham to Luka Doncic. The six-foot-one guard consistently held his own.

In an exclusive interview with Forbes, Pritchard shared what he attributes his best defensive season in his five-year career to.

"I feel like a lot of it has to do with working in the weight room, getting stronger, faster, quicker, and being in better shape," said Pritchard. "But just being fearless and never backing down from a moment."

Given that the former Oregon Duck is a better two-way player and also a dynamic threat from beyond the arc, one that can effectively orchestrate the offense, even from an on-court standpoint, there's more incentive to start Pritchard.

Between that and knowing the latter is a part of the team's future, whereas the Celtics are open to moving Simons at any point between now and the trade deadline, and no matter how you slice it, the one starting alongside Derrick White should be Pritchard.