Decisions the Celtics Should Already Regret from This Past Offseason

It's impossible to criticize the Boston Celtics without getting nitpicky.

They've won five of their first six games to open the 2023-24 NBA season, and their lone loss wasn't decided until overtime. They also enter Wednesday night with the Association's best net rating at a whopping plus-14.1 points per 100 possessions, per NBA.com.

Life is objectively great for the Shamrocks, but when they look back on this offseason, they might still have a few regrets.

Letting Grant Williams Walk

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DALLAS, TEXAS - NOVEMBER 05: Grant Williams #3 of the Dallas Mavericks runs up the court during the first half against the Charlotte Hornets at American Airlines Center on November 05, 2023 in Dallas, Texas. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Sam Hodde/Getty Images)

For reasons known only to them, the Celtics effectively decided they were done with Grant Williams last season. That's when they trimmed his rotation to the role to the point he was occasionally a healthy scratch and signaled he'd be on the way out as a restricted free agent this offseason.

So, it wasn't at all surprising when he bounced out of Boston to sign a four-year, $54 million deal with the Dallas Mavericks. Of course, the fact it wasn't surprising doesn't mean it was the right decision to make.

Williams' numbers were never great in Boston, but his impact sometimes was. His defensive versatility was immensely valuable, and his trusty three-ball (39.7 percent accurate over the past three seasons) helped open attack lanes on the offensive end.

The Celtics may have felt the new collective bargaining agreement—which places a host of restrictions on basketball's biggest spenders—forced their hand with Williams, but that hasn't made it any easier to watch his successful start in Dallas, where he's averaging a career-high 15.1 points on 55.6 percent shooting (54.3 percent from range).

Not Addressing Their Wing Depth

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BOSTON, MA - MAY 29: Jaylen Brown #7 and Jayson Tatum #0 of the Boston Celtics look on during round 3 game 7 of the Eastern Conference finals against the Miami Heat on May 29, 2023 at the TD Garden in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2023 NBAE (Photo by Nathaniel S. Butler/NBAE via Getty Images)

Boston might have the Association's top wing tandem in Jayson Tatum and Jaylen Brown. It also has next to nothing behind them in the wing rotation.

That's why the Celtics can't survive any stretches without Tatum. While teams will always feel some type of impact when an MVP candidate needs a breather, this has been—statistically speaking—completely absurd. Boston has outscored opponents by 20.8 points per 100 possessions with Tatum and been outscored by 4.9 points per 100 possessions without him.

That gap is unforgivable, even with the acknowledgment that Tatum is one of the best players on the planet. He should still have at least a competent backup behind him, but Boston never bothered to roster one.

Sam Hauser and Svi Mykhailiuk are shooting specialists. Lamar Stevens and Oshae Brissett are energetic defenders who can't shoot. Even on a limited budget, the Celtics should've been able to nab at least one player who isn't a one-note contributor.

Extending Payton Pritchard

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BOSTON, MA - NOVEMBER 1: Payton Pritchard #11 of the Boston Celtics looks on during the game against the Indiana Pacers on November 1, 2023 at the TD Garden in Boston, Massachusetts. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2023 NBAE (Photo by Brian Babineau/NBAE via Getty Images)

Over the past three seasons, the Celtics were never quite convinced Payton Pritchard could cut it as a regular rotation player.

So, what convinced them he was suddenly worthy of a four-year, $30 million extension this offseason?

That may not be an egregious amount in NBA terms, but it's the kind of coin that should be spent on someone you know can contribute. Pritchard has yet to prove he's that type of player. He has typically enjoyed success from the three-point line, but that's about it. And you don't exactly see this league overflowing with 6'1" shooting specialists.

This contract looks worse for now as he's been trapped in a shooting slump so far (3-of-18 from range), but it might never look great if he can't find other ways to make an impact. His playmaking at least has perked up (3.7 assists against 0.8 turnovers), but it's too early to say that's suddenly a reliable strength.