Locked On Celtics — September 16, 2025

Episode: “Celtics Face CRUCIAL Decision on Simons' Playing Time | Will CHEMISTRY Issues ARISE?”

Episode Overview

Host John Karalis, joined by guest Tom Westerholm, delivers a deep-dive analysis of the Anthony Simons situation in Boston. Simons, recently acquired in a trade, unexpectedly remains on the Celtics roster as the new season approaches, igniting debate: Should he start or come off the bench? Karalis and Westerholm break down the basketball, chemistry, and narrative angles, explore lineup implications, and set expectations for Simons’ future and the team’s evolving hierarchy.

Main Theme

The central question: What should the Celtics do with Anthony Simons? With his uncertain role and unique skillset, the hosts debate whether Simons should start, come off the bench, or serve in a hybrid/staggered capacity—and what those decisions mean for the team’s chemistry, performance, and long-term plans.

Key Discussion Points & Insights

1. The Awkwardness of Simons’ Situation ([03:36]–[07:00])

• No introduction, no certainty: Simons hadn’t been introduced via a Celtics press conference, highlighting his “tenuous” status and raising questions about whether he was intended to stay.
  • “They didn’t do an introductory press conference. They waited, because no one knew if he was going to be a part of this team… Right away, it’s awkward.” — John Karalis [03:36]
• New opportunity: Despite the odd context, Simons enters an enviable situation—on a playoff-caliber roster, no longer the focal point of defenses, and with a chance to redefine his NBA role.
  • “He really is in kind of an enviable situation… he’s going to have a lot of opportunities to prove himself.” — Tom Westerholm [04:36]

2. Simons’ Value and Mindset: Offense, Scouting Reports, and Professionalism ([07:00]–[11:30])

• Uniqueness as an offensive fulcrum: Simons is the only Celtic who’s been the lead focus of every opposing defense all season—his Portland experience is unlike those of Brown or Tatum.
  • “Of all the players on this roster, he’s the only one that’s been at the top of the opposing team’s scout for an entire season.” — John Karalis [07:00]
• Adjustment to new reality: Freed from top defender attention in Boston, Simons should enjoy “more space to work with.”
• Will he accept a non-star role? With his contract year looming, there’s risk he’ll “default” to seeking his own shot to boost value. The hosts, however, see this as logical—not selfish.
  • “If Anthony Simons’ default is… ‘I’m just gonna go get a bucket here’, that’s not a bad thing. That’s as good an option as you’ve got.” — Tom Westerholm [09:01]
• Professional maturity: Simons has incentive to prove himself a winning, efficient player—not just a volume scorer—boosting both team performance and his next contract.
  • “If he can show people, ‘Hey, I can produce numbers on a winning team and contribute to winning,’ that money is a heck of a lot different…” — Tom Westerholm [10:00]

3. The Decision: Should Simons Start? ([13:48]–[22:12])

Arguments FOR Simons as a Starter

• Offensive firepower and flexibility: Putting Simons on the floor with Derrick White and Jalen Brown relieves pressure, offers more options if Brown is doubled, and helps “get off to better starts.”
  • “Having more guys on the floor right away that can get buckets can help you get off to better starts. I like that it takes pressure off of Jalen Brown.” — John Karalis [14:00]
• Elite pick-and-roll, deep shooting: Simons brings above-average pick-and-roll play and “off-the-bounce” three-point shooting—skills that synergize with Boston’s system.
  • “He’s really good. Like, he’s good in the pick and roll. He’s a really good three point shooter, like, off the bounce. That really matters.” — Tom Westerholm [15:37]

Defensive Concerns

• Track record of poor defense: Seven years as a below-average defender can be hard to overcome; the staff (Missoula, Brown, White, Pritchard) sets high standards.
  • “Seven years is a long time to build up those bad habits… after a while, that becomes your default setting.” — John Karalis [18:02]
• Potential for improvement: With better role models and motivation, there’s optimism Simons can make strides defensively, but he’ll need to show tangible growth—fast.
  • “You could make the argument that you put Simons in that situation and he’s like, oh damn, I gotta keep up… If they harp on him, then great.” — John Karalis [19:31]

Who Needs to Be Better?

• Defensive comparison: Would he need to be at least better than “Darius Garland level” to justify starting? Karalis: “You can make the argument he starts as is right now” [22:00], but defensive improvement could make it a no-brainer.

4. The Alternative: Simons as a Bench Weapon ([22:47]–[34:22])

Arguments FOR Simons Off the Bench

• Honoring incumbents: Peyton Pritchard might have earned the starter role; continuity could matter for chemistry.
• Optimizing usage: As a sixth man, Simons can “cook” as the primary option against bench units—he thrived in this mode in Portland.
  • “If anybody can handle that situation, let’s give it to the guy who’s handled that situation already.” — John Karalis [27:15]
• Shot allocation: Coming off the bench and staggering his minutes grants Simons the highest likelihood to maintain his shot average (16–18 per game).
  • “Would that be the way… hey, this is how you get to 17, 18 shots by middle of the second quarter, middle of the fourth quarter, whatever… you get to just go out there and do your thing.” — John Karalis [31:09]

Counterarguments

• Talent may be too high for a bench role: Westerholm questions whether it’s wise to bench such an offensive weapon, suggesting optimal staggered rotations instead.
  • “I think he’s just a little too good to come off the bench… If it were me, I’d rather kind of stagger things down the line.” — Tom Westerholm [28:00]

Staggering and Rotational Nuance

• It’s not all about ‘starter/bench’ labels: The real key: how rotations are constructed and pairing Simons with (or staggered from) Brown and White for optimal scoring balance.
  • “What it really comes down to is just the respect of starting kind of thing… [but] this is also how you set your rotations.” — John Karalis [32:06]

Notable Quotes & Memorable Moments

• “He knows what’s happening, he understands that the team didn’t get him to keep him… It’s awkward.” — Karalis [04:00]
• “For a guy who is on a team that he wasn’t sure if he was going to be on when he was traded, he really is in kind of an enviable situation… he’s gonna have plenty of opportunities.” — Westerholm [04:36]
• “If Anthony Simons’ default is … ‘I’m just gonna go get a bucket here’, that’s not a bad thing.” — Westerholm [09:01]
• “Your two best, like, most dynamic scorers… subbing them in for one another, there’s sense to that somehow.” — Karalis [32:49]
• [Lighthearted:] “Tom Westerholm? Oh, is he not here?” … “Psych. It’s a bad beat for any of you who bet against me.” — Karalis & Westerholm [25:38]
• “I came on to advocate for the man. I mean, yeah, I’m ready.” — Westerholm [23:03]

Timestamps for Key Segments

• Simons’ Awkward Arrival and Opportunity — [03:36]–[07:00]
• What Simons Adds / Role Debate Begins — [07:00]–[11:30]
• Should Simons Start? (Pros & Cons) — [13:48]–[22:47]
• Argument for the Bench Role — [22:47]–[31:27]
• Rotation, Pairings, and Real-World Impact — [31:27]–[34:22]

Tone & Style

• Engaged, slightly irreverent, knowledgeable, and candid.
• Both hosts mix basketball nerdiness with relatable analogies and a touch of humor, making for accessible but in-depth analysis.
• “Let’s see it” spirit: both insist on Simons proving his fit before making any grand proclamations.

Conclusion

Simons’ role looms as one of the “crucial decisions” for the Celtics as camp opens. With strong arguments for both starting and bench roles, Karalis and Westerholm emphasize that nothing is set—it all comes down to Simons’ willingness to adapt, his defense, and how the coaching staff constructs rotations. Ultimately, whatever the label, playing time and usage are up for grabs, making this preseason one of intrigue in Boston.

Listener Takeaway:
Whether you’re bullish or skeptical on Simons, this episode highlights why the incoming guard sits at the intersection of roster politics, on-court strategy, and locker-room chemistry—making his integration one of the most intriguing Celtics subplots for 2025.