Celtics Beat – Episode 659: Should Celtics Keep Simons Long-Term?

Date: January 18, 2026
Host: Adam Kaufman
Guest: Justin Turpin (WEEI)
Also Featuring: Evan Valenti

Episode Overview

This episode of Celtics Beat centers on the Boston Celtics’ midseason outlook, the rise (and recent struggles) of Jaylen Brown, the performance and long-term value of Anthony Simons, and the looming NBA trade deadline. The crew weighs whether the Celtics should keep Simons, use him as a trade asset, or move another role player (such as Sam Hauser). The conversation also reflects on Boston's sports culture, the shifting hierarchy of athletic stars in the city, and provides a granular look at recent team performance.

Key Discussion Points & Insights

1. Boston Sports Hierarchy: Are the Jays Still Kings?

[03:58-19:49]

• Football vs. Basketball vs. Baseball in Boston
  • Debate over whether Roman Anthony (Red Sox), Drake May (Patriots), or the "Jays" (Jayson Tatum and Jaylen Brown) are the "kings" of Boston sports.
  • Kaufman asserts Boston is still, at its core, a baseball town—but the Patriots’ recent playoff relevancy is "so much freaking fun."
  • Valenti and Turpin: A Super Bowl run by Drake May is likely the minimum required to knock the Jays off the throne. But that could happen quickly because of the quarterback’s importance in football.
  • Race and representation: Turpin floats, “Does race have anything to do with that in this city?” [14:27] – Both he and Kaufman agree position/popularity of football matter most, though Valenti notes there are always people for whom race is a factor.

"I still feel like at our core...it's still a baseball town more than it is anything else." — Justin Turpin [07:28]

"I do think the Jays are still the kings of Boston...they’re the only guys that have titles." — Evan Valenti [11:27]

2. Jaylen Brown’s Recent Slump: Worry or Typical Mid-Season Lull?

[27:24-31:42]

• Slippage in Brown’s Play
  • Kaufman and others note Brown’s recent stretch hasn’t matched the hot start to his season; he’s letting officiating/frustration seep into his game.
  • Brown’s turnovers are up (“He’s averaging currently 4.4 [turnovers] a game this month, which is the worst of any month so far this year”—Valenti [28:49]), and “he forces it...tries too hard...and ends up with these kind of aimless drives and turnovers” — Turpin [27:24].
  • Both Turpin and Valenti believe this is a January lull and that Brown will recover.

3. Role Player Contributions & Guard Play

[31:42-36:04]

• Supporting Cast Stepping Up

  • Even with Jaylen’s dip, the Celtics remain competitive thanks to guards Derrick White, Peyton Pritchard, and Anthony Simons.
  • Special praise for Pritchard's unselfish, steady point guard play and Gata’s (presumably Neemias Queta) impact rebounding and defending.
  • “The guards have been terrific. Pritchard has played the role of the point guard just perfectly.” — Adam Kaufman [33:20]

• Clutch Struggles

  • The Celtics continue to lose close games (three losses by a combined 11 points recently), mostly due to clutch-time offense and rebounding issues.

4. Anthony Simons: Trade Asset or Core Piece?

[42:11-52:41]

• Trade Deadline Dilemma
  • With the NBA trade deadline looming (Feb 5), the big question: Should the Celtics keep or deal Simons?
  • Simons is an expiring ~$30M contract, making him “the only path to acquiring a big man who is actually a good basketball player.” — Turpin [44:29]
  • Debate includes Bobby Manning’s take that Simons should be kept if possible, but Turpin stresses Simons is more valuable as a large matching salary in a deal for a quality big.

"The conversation around Simons is: he is an asset—a tradable asset—... your only path to acquiring a big man." — Justin Turpin [44:29]

• Tax Ramifications

  • Adam notes Boston is ~$12M over the tax, which means a $40M+ penalty looming if they keep the current roster. Ownership’s willingness to continue paying is a storyline.

• Is Hauser More Movable?

  • Turpin offers: "Maybe a guy like Hauser might be more movable than he was before,” citing an abundance of wings and Hauser's shooting and contract value [46:34].
  • But Kaufman counters Hauser’s salary is too low to bring back a major piece by himself.

5. Jason Tatum’s Impending Return—and Realistic Expectations

[52:41-55:43]

• Both agree fans shouldn’t expect Tatum to instantly return to peak form after missing so much time; minutes restriction and rust are realistic.

"To expect [Tatum] to come back and just be Jason Tatum right away is so unfair to him and so unrealistic... that's just not going to happen." — Adam Kaufman [53:38]

Notable Quotes & Memorable Moments

Jaylen Brown’s Mindset:

"He forces it. He tries too hard to go downhill and get a call and he ends up with these kind of aimless drives and these turnovers, and it ended up hurting the team." — Adam Kaufman [27:24]

On Simons’ Role and Potential:

"Personally, I'd love to see him [Simons] next to Tatum. I think the skill set that he provides could fit really well... especially coming off the Achilles, like being that guy that can create for others..." — Adam Kaufman [51:17]

On Boston’s Culture of Overvaluing Role Players:

"The ongoing joke... is that we have a tendency to fall in love with the role players and our own guys and overvalue them... I would also drive Sam [Hauser] to the airport personally if it meant you were getting a good return." — Justin Turpin [50:20]

Simons’ Impact on Team-Building:

“You have this tradable asset...you can bring in a piece that can be under contract...a Claxton, a Zubac...someone who can be under contract...for multiple years and can be a big man that can help you.” — Justin Turpin [44:29]

Timestamps for Key Segments

• Boston’s “King” Athlete/Football v. Baseball/Basketball: [03:58-19:49]
• Jaylen Brown’s Struggles: [27:24-31:42]
• Supporting Cast & Clutch Problems: [31:42-36:04]
• Anthony Simons Trade/Keep Debate: [42:11-52:41]
• Expectations for Tatum’s Return: [52:41-55:43]
• Looking Ahead—Upcoming Games, Who Steps Up Next: [58:53-64:58]

Looking Ahead: What’s Next for the Celtics?

[58:53-64:58]

• Soft schedule ahead; Celtics favored in nearly every upcoming game.
• Clarity is expected on Simons' future by the deadline.
• Watch for which young rotation player (Walsh, Ugo, Shireman, Minott) emerges in the next “hot streak.”
• Main goals: survive trade distractions, pile up wins, keep momentum until Tatum returns.

Summary

This episode robustly analyzes the Celtics’ current crossroads: maximizing Jaylen Brown while he’s hot, maintaining or upgrading the supporting cast with Simons or a potential new big, and gearing up for Jason Tatum’s eventual return. Listeners receive both granular and macro-level perspectives—from offense and clutch time woes, to the business (tax) implications of personnel decisions, and the ever-present daydreaming about city-wide sports royalty. Context, history, and practicality drive the lively, humorous, and insightful discussion among hosts and guest.