Locked On Celtics - Celtics PUSH Through Growing Pains & The Anfernee Simons Question

Host: John Karalis
Guest: Tom Westerholm
Date: November 26, 2025

Episode Overview

In this episode, John Karalis and guest Tom Westerholm dive deep into the Boston Celtics' early-season struggles and why moving outside their comfort zones may yield positive results down the line. They examine how team roles are evolving, highlight individual challenges—particularly for Jaylen Brown and Derrick White—and debate Anfernee Simons’ emerging value to the Celtics' roster and future flexibility. The conversation blends thoughtful analysis with humor, candor, and a clear understanding of the Celtics’ locker room dynamics.

Celtics Pushing Through Growing Pains: Learning by Discomfort

Timestamps:

• Key discussion begins: [03:22]

Everyone Out of Their Comfort Zone

• Broad Theme: Nearly the entire team, from Jaylen Brown to Brad Stevens, is operating outside familiar roles or responsibilities. This has led to inconsistency, but also potential for long-term benefits.
• John Karalis: "Everyone else, from Jalen to Joe Mazzulla to everybody, you know, Brad Stevens, everybody's out of their comfort zone right now… that's part of why there's no consistency to this team, because no one is doing the thing that they're used to doing." ([03:54])
• Only Sam Hauser has a role unchanged from last year.

Two Possible Outcomes

• Players either acclimate to new demands and grow, or the team seeks changes and possible departures.
  • “Either...you figure it out and great, you figured out this new role...or you can never figure it out and the Celtics say, thanks, but no thanks. Maybe a change of scenery will help you out.” – John Karalis ([05:39])

Examples:

• Jaylen Brown: Taking on a heavier workload and primary scoring responsibilities while missing the simple, flow-based offense of prior seasons. Struggling at times with reads and passing that don’t come as naturally in this new environment.
• Peyton Pritchard: Continues to excel because of his adaptability—“just a pure Hooper.”

Jaylen Brown’s Challenging (But Promising) Evolution

Timestamps:

• Focused Jaylen segment: [07:12] - [11:54]

The Weight of Expectations

• Karalis: Emphasizes that Jaylen’s role—possibly 2nd in the league in usage—is demanding more than he bargained for.
  • "The workload is more than he expected. The scoring is tougher than he thought. ...On a drive, he’s just kind of like, let me lean my head down...and try to score…he’s not in a position to say, I’m just going to give this ball up." ([08:48])
• Brown’s ball distribution and the offensive flow have suffered as players are still learning each other in new roles.

Long-Term Potential

• Karalis: Post-Tatum return could bring a more egalitarian offense.
  • "Next season has the potential to be as equal a partnership...It’s been Jason first and then Jalen, but next season could be a lot more equal." ([10:50])
• Westerholm: "Watching Jaylen Brown this year has been an actual delight. This is a fully realized Jalen Brown...I would like to see more of it.” ([11:54])

Derrick White’s Struggles: Out of Rhythm, But Still Positive

Timestamps:

• Start: [15:05] | Deep Dive: [16:00] - [21:37]

Usage and Shooting Woes

• White’s off-the-dribble jumpers up 20%, rise in contested layups, field goal % at the rim dropped 18 points.
• Taking more low and medium-quality shots per game, but shooting worse from every area and quality compared to last year.
• Karalis: "He’s getting a couple more shots...but the extra shots that he’s getting are not any good." ([15:58])

Defensive Consistency

• Remains a net positive, mainly due to defense: "The defense, they're 10 points better with him on the floor." ([17:05], via Westerholm)
• The offense drops when he's playing, but his defensive impact stabilizes the team.

Outlook & Significance

• Karalis: “If he can figure this out, this changes dramatically...If these guys can come together [by]; the end of the season, then…the Celtics got something.” ([17:23])
• Westerholm: “If Derek and Jalen lineups can go out and handle more minutes, you don’t have to play Jason as much. That just makes things a lot simpler down the stretch.” ([17:23])
• On frustration with sporadic scoring: "We haven’t seen an extended, like, okay, like we saw it with Payton...where’s Derek’s like three, four game stretch? ...That’s the only thing I’m waiting for." ([22:55])

The Team’s Resilience Despite Poor Shooting

Timestamps: [23:11] - [24:26]

• Point: Three best shooters—White, Hauser, (and Simons, by implication)—are all slumping, and yet Boston maintains a winning record.
• With even average shooting, record could easily be 12-5, putting them in the top three of the East.
• Westerholm: “You could easily say with a normal shooting start a few of these games go a different way…and you’d be third seed right now.” ([24:05])

Anfernee Simons: Changing His Narrative & Calculating His Value

Timestamps:

• Segment begins: [27:14]

Simons’ Recent Upswing and Role Evolution

• Recent strong performances: back-to-back 23-point games.
• Learning to impact the game off the bench, as highlighted by both Simons and Joe Mazzulla.
  • “Now I’m learning, like, oh, I know when I come in, I gotta start. I gotta start scoring right away because I don’t have the same number of minutes as I used to have.” (Paraphrased from [29:22])
• Displaying scoring variety—not just reliant on threes.

Future Contract and Fit in Boston

• Contract set to expire; Simons not likely to receive a raise over his current $27M.
  • Karalis: “He’s not going to get $27 million on the open market. He’s not going to get a raise.” ([28:50])
• Potential Scenario: Boston could retain him at a bargain mid-level deal (approximately $15M per year for three years), providing a valuable, movable contract in future trades.

Market Dynamics

• Westerholm compares Simons’ archetype to Jordan Clarkson and similar score-first, defense-light guards, whose market value has declined.
  • "He’s better than [Clarkson], he’s clearly better, but...contractually...I don’t know that he’s going to do a lot better.” ([31:22])
• Karalis: “Anthony Simons at three years, $45 million is not bad. That’s about right I think for him...You put it right at that mid level number, knowing that you can always trade him and teams could use their mid-level exception to accept him in a trade.” ([33:03])
• Offers flexibility for Celtics roster-building under new CBA.

Notable Quote

• Karalis (on mid-tier NBA contracts): “Getting $15 million a year. Yeah, right. I hope I get screwed out of...and get $15 million a year. Please. Somebody really, really put one over on me.” ([36:30])

Notable Quotes & Memorable Moments

On the team’s discomfort:

• “Everyone’s out of their comfort zone right now.” – John Karalis ([03:54])

On Jaylen Brown’s evolution:

• “Watching Jaylen Brown this year has been an actual delight. This is a fully realized Jaylen Brown...that rules.” – Tom Westerholm ([11:54])

On Derrick White’s struggles:

• “We haven’t seen an extended, like...where’s Derek’s three, four-game stretch of 'okay, he’s back, we got it.'”—John Karalis ([22:55])

On Simons’ value:

• “Anthony Simons at three years, $45 million is not bad. That’s about right I think for him...You put it right at that mid level number.” – John Karalis ([33:03])

On NBA contract inflation:

• “Kevin Garnett, people were just like rending their clothes over Kevin Garnett’s contract. And now, now that’s what you…like, those I, I, listen...”—John Karalis ([32:55])

Humor throughout:

• The running philanthropic joke about being “screwed” into $15M/year. ([36:30])

Conclusions & Takeaways

• Short-Term Pain for Long-Term Gain: The Celtics’ current discomfort and growing pains are challenging, but the hosts are optimistic the team will benefit from developing broader skillsets and resilience.
• Spotlight on Individual Growth: Jaylen Brown’s workload, Derrick White’s shooting slump, and Anfernee Simons’ adaptation provide blueprints for how adversity can become advantage—next season, if not by playoffs.
• Roster Flexibility: Simons’ contract situation exemplifies the new CBA realities, giving Boston future options and leverage.
• Optimistic Tone: Despite offensive struggles, hosts see a “delightful” Jaylen Brown season, defensive silver linings, and the foundation for a more dangerous Celtics squad as roles settle.

Segment Timestamps

• Out of Comfort Zone: [03:22]
• Jaylen Brown’s Challenges: [07:12]
• Derrick White’s Struggles: [15:05]
• Team Resilience Despite Shooting: [23:11]
• Anfernee Simons’ Fit and Future: [27:14]
• Simons’ Contract Value: [31:22]

For Celtics fans seeking insight on the team's current ups and downs—and a look ahead to roster maneuvering—this episode delivers sharp, honest analysis and a sense that the best may be yet to come.