Locked On Celtics – Boston Celtics Trade Deadline: Possibilities, Waiting to Deal, and Brad Stevens Curveballs
Episode date: January 23, 2026
Host: John Karalis (with guest Tom Westerholm)

Episode Overview

This episode dives into the upcoming NBA trade deadline and its implications for the Boston Celtics. John Karalis and Tom Westerholm analyze what options are available, what Brad Stevens might have up his sleeve, and how any moves will reflect the front office’s confidence in the current roster. They also discuss the impact of new CBA rules, the trade value of key players, and why waiting to deal might make the most sense this season.

Key Discussion Points & Insights

1. The Trade Deadline: What Can vs. What Should Happen

• With two weeks until the trade deadline, the hosts debate possible moves and emphasize that Brad Stevens is the unpredictable "wild card" in the process:

  "Whenever we assume something with Brad Stevens, that’s like, no, that’s not what he’s gonna do." – John Corrales (05:09)

• The commonly-discussed trade chip is Anthony (presumably Anfernee) Simons’ expiring contract, but the hosts stress that Boston’s possible moves aren’t limited to him.

2. Other Trade Chips Beyond Simons

• Sam Hauser stands out as another intriguing asset, particularly for teams needing shooting:

  "If a team traded for Sam Hauser, that’s getting like a big press push... he just shoots you to a win." – Tom Westerholm (07:43, 08:23)

• Hauser’s value peaks in his dominant stretches, but inconsistency raises concerns for playoff reliability.
• Derrick White is also discussed. While it's unlikely Boston moves him, his salary could make deals possible.

3. The Brad Stevens Curveball Factor

• Brad Stevens’ history of unpredictable deals makes reading Boston’s intentions difficult.

  "Brad works in mysterious ways." – Tom Westerholm (12:48) "I don’t know what Brad’s cooking." – John Corrales (12:54)

• The ultimate "pump fake" move would be making no substantial trade at all just to keep everyone guessing.

4. New CBA & Second Apron Challenges

• The new CBA’s financial rules severely complicate trades between contending teams.

  "They don’t want good teams trading with each other anymore... expensive players have to trade with bad teams." – John Corrales (16:25)

• Aggregation of salaries and hard cap implications make bringing in players like Daniel Gafford or Ivica Zubac highly complex—even with third teams and extra draft assets.

5. Asset Management and Timing

• The Celtics are positioned with "one more big move" around the Tatum/Brown core, and timing that move is crucial:

  "With Tatum and Brown as the centerpiece, [the Celtics] have one more move." – John Corrales (20:40) "I think [Derrick White] is a big part of this, but the cupboards are starting to get bare move." – John Corrales (21:58)

• Derrick White is likened to Milwaukee’s Chris Middleton—a vital last-resort asset.

6. To Trade Now or Wait Until the Summer?

• Given the East’s fluid standings and internal uncertainties, waiting may bring clearer answers regarding team needs, Jason Tatum’s return, and the future of Anthony Simons:

  "There’s value... in waiting to see what you need after Tatum comes back." – (Paraphrased, 23:46)

• The possibility that Tatum or Simons’ fit changes is discussed, and the potential for Simons to leave as a free agent must inform the deadline strategy.

7. The Broader NBA Landscape

• The impact of other teams, especially potential changes involving players like Giannis Antetokounmpo or Ja Morant, and advances by teams like OKC or San Antonio, looms large over risk assessment.

  "If you’re going to push all your chips in, it’s got to be to the point you can actually win it all." – Tom Westerholm (31:03)

• There is awareness that future offseason opportunities (or threats) could dictate the best timing for Boston’s "all-in" move.

8. The Unknowns: Monitoring Tatum & Simons

• The health and playoff readiness of Jason Tatum is the single biggest X-factor:

  "Whether to do it now or later is Jason Tatum, because you don’t push in now without it being Jason Tatum coming back." – John Corrales (32:55)

• Boston must also gauge Simons’ willingness to re-sign at a reasonable price after this year, as the restricted CBA market could impact his value and options.

Notable Quotes & Moments

• Brad Stevens unpredictability:
  • "I just don’t know what Brad’s cooking." – John Corrales (12:54)
  • "The ultimate pump fake would be to do nothing." – Tom Westerholm (13:06)
• On Sam Hauser’s value:
  • "There are games where he just shoots you to a win... that's why his 3-point percentage is so high at season’s end." – Tom Westerholm (08:22)
• On asset management:
  • "With Tatum and Brown... you have one more move—one more arrow in the quiver. You gotta make sure to use it the right way." – John Corrales (21:04)
• Trade landscape complexities:
  • "It’s impossible to just play with the trade machine now. You have to have, like, an advanced degree." – John Corrales (15:05)
• Team’s mentality reflection:
  • "What they do will tell us how they feel about this team." – John Corrales (01:46)

Important Timestamps

• 05:09 – Brad Stevens unpredictability and the assumption of Simons as the main trade chip
• 06:53–10:05 – In-depth discussion of Sam Hauser’s trade value
• 12:48 – Stevens’ mysterious approach, setting the tone for deadline speculation
• 15:05–17:00 – CBA rules and how they complicate salary aggregation and trades
• 20:40–22:44 – The "one more move" era, Derrick White’s status, and asset prioritization
• 23:46–24:11 – Importance of seeing Tatum and the current roster together before making major moves
• 27:36–31:03 – Changing Eastern Conference dynamics and whether now is the time to push in
• 32:55–34:52 – Framing the entire deadline decision around Jason Tatum’s health, role, and timing
• 35:38–39:16 – Possibilities with Simons, risk of waiting/not acting, and need for more “answers” before acting aggressively

Summary for New Listeners

This episode provides a smart, nuanced look at the Celtics’ options and challenges as the trade deadline looms. The hosts focus on:

• The unpredictability of Brad Stevens’ approach
• Why Boston could make a move—but also why standing pat and reassessing in the summer might make sense
• How the NBA’s new financial rules make even simple trades a massive headache
• The necessity of building around Tatum and Brown—and the danger of mistiming the team’s "one last big move"
• How the team’s output, injuries, and locker-room dynamics since the start of the season complicate decision-making

Listeners will walk away with a strong sense of what’s possible, what’s realistic, and why patience could be the most strategic play in a volatile market—despite Celtics fans’ hunger for another bold move.

Tone & Language:
The podcast maintains a conversational, analytical style, full of Celtics-specific insight, humor, and a bit of anxious anticipation about what Brad Stevens may or may not do as the deadline approaches.