Locked On Celtics Podcast Summary

Episode Title: KEEPING SIMONS: Why the Boston Celtics Could RETAIN Anfernee Simons for a Game-Changing Run
Host: John Karalis
Guest: Keith Smith
Release Date: December 26, 2025

Main Theme

This bonus episode dives deep into the key question facing the Boston Celtics' roster: Can—and should—the Celtics retain Anfernee Simons for the long term rather than trading him? Host John Karalis and salary cap expert Keith Smith discuss Simons’ current fit, future value as a potential elite sixth man, and the financial and strategic considerations influencing the Celtics’ decision-making process.

Key Discussion Points & Insights

Celtics’ Options with Simons’ Contract (01:07–03:00)

• Bird Rights and Flexibility:
  John Karalis outlines how the Celtics’ possession of Simons’ Bird Rights could allow creative retention options, not necessarily at his current high cap number, but possibly on a mid-level deal.

  • “They do nothing at the deadline… use the bird rights to bring back Simons at a lesser number because his cap hold is going to be high anyway. You actually end up saving money in the long run.” (01:28)

• Roster Construction Possibilities:
  The team could focus on roster tweaks with trade exceptions and fill other gaps, keeping Simons on as a versatile asset—either long-term or as future trade fodder.

Simons’ Production and Role Adjustment (02:57–06:00)

• Statistical Continuity with Portland:
  Keith Smith notes that, per-minute and per-shot, Simons is posting similar stats to his Portland days—he’s simply taking fewer shots due to sharing the ball with other Celtics guards.
  • “Andre Simons is basically the same player. He's been in Portland just actually hitting threes at a better clip…he's sharing the ball with Jalen Brown and Derek White." (02:57)
• Value as a Sixth Man:
  Celtics' success in recent years is tied to strong bench production (e.g., Malcolm Brogdon), and Simons could thrive in a similar role, especially if the lineup shuffles with Tatum’s return.
• Defensive Development and Trust:
  Smith observes that Joe Mazzulla is showing more patience with Simons’ defensive lapses as the player makes marginal improvements. His offensive output outweighs the downsides:
  • “He’s gotten better and I think Missoula is starting to be a little bit more patient…It's still a net positive to have him on the floor.” (05:40)

Financial Market and Tension Between Opportunity & Salary (06:07–09:00)

• Who Would Outbid Boston?
  Smith says few teams with cap space would aggressively chase Simons at a $30M+ price tag; the main risk is another team promising him a bigger or starting role, not necessarily more money.

• Simons’ Mindset and Celtics’ Approach:
  Karalis provides locker-room insight:

  • “You just look around and I see Jason Tatum's locker…full of stuff. Anthony Simons’ locker, empty…he probably is like, I can go at any time. He is very well aware. He's in tuned with everything that's being said.” (06:51)
  • The Celtics have been upfront with Simons about trade possibilities, fostering a transparent environment.

• Potential for Simons' Increased Role/Production:
  If not dealt at the deadline, Simons might become unlocked, playing “more free”—possibly creating a win-win for him and the team as a scoring weapon off the bench.

The New CBA and Changed Valuation (09:00–10:30)

• “Second Apron” Impact:
  Karalis and Smith agree that the new CBA’s spending limitations make it unlikely any team will throw huge money at Simons sight-unseen. Smart mid-level deals, not cap-crushing offers, could define his market.
  • “Now you can't miss on a guy making 30 plus million. If you're paying a guy that much money, you have to be sure. And Simons is not a sure thing.” (10:03)

Simons’ Perspective and Potential Career Path (12:54–18:30)

• Personal and Professional Motivation:
  Smith suggests Simons, having already secured a $100M+ contract, might prioritize winning and professional fulfillment over a purely financial move.

  • “I made over 100 million on my last deal…I can make [mid-level money] playing in Boston, playing with Tatum and Brown on a team that's a contender. I've never won anything.” (13:40)

• Learning from Sixth-Man Icons:
  Both hosts affirm the value and longevity players like Jamal Crawford and Lou Williams found in embracing a bench scoring role:

  • "Lou Williams and Jamal Crawford had 20-year careers as high usage scoring six men…because those guys set the standard for more than a decade…” (18:13)

• Legacy and Veteran Value:
  Karalis paints a scenario in which Simons matures into a player teams crave for both their track record and championship experience:

  • “You go, you win a championship, you prove that you can handle a different role…now you have that championship glow. Teams want that, teams want that veteran...” (16:23)

Strategic Team Building and Trade Value (18:56–21:11)

• Flexible Asset:
  Smith analogizes Simons’ contract to past moves (e.g., how Josh Richardson became Derrick White): signing Simons could serve as a stepping stone for future deals, enabling Boston to adapt as needed.

  • “Maybe that’s what happens with Simons where it’s hey, we’re going to resign him…then what they'll come back around is like…this actually did kind of work out pretty good.” (19:41)

• Final Thoughts: Both believe there’s a realistic path for Simons to remain a Celtic—unless a better “situation” emerges elsewhere for him, but Boston should face little risk of being outbid in pure dollars.

Notable Quotes & Memorable Moments

• John Karalis on Simons’ awareness:
  “He takes whatever little stuff he has with him…he probably is like, I can go at any time. He is very well aware. He's in tuned with everything that's being said.” (06:51)
• Keith Smith on Simons’ Sixth Man Value:
  “There’s absolutely a chance he is back on this team next year…that’s about the going rate for really good scoring guard in the NBA.” (04:24)
• Keith Smith on veteran value:
  “Lou Williams and Jamal Crawford had 20-year careers as high usage scoring six men…that should be what it is because those guys set the standard.” (18:13)
• John Karalis on Simons’ future:
  “He's young enough where a couple of seasons of playing a certain role, winning a championship…now is here to lead you. What better leader than that?” (16:19)
• Keith Smith on prioritizing winning:
  “What I'm going to prioritize is let's try to win. And if I'm the Celtics…this could be the start of what is next…” (19:02)

Important Timestamps

• 01:07 – Bird rights and contract strategy
• 02:57 – Simons’ production & role compared to Portland
• 05:40 – Joe Mazzulla’s patience and Simons’ defensive improvement
• 06:51 – Karalis’ locker room anecdote about Simons’ mindset
• 10:03 – New CBA spending rules and effect on Simons’ value
• 13:40 – Simons’ career earnings and priorities going forward
• 16:19 – Simons’ potential legacy and leadership value
• 18:13 – Longevity of high-usage sixth men (Williams/Crawford comparison)
• 19:41 – Simons as a versatile trade asset

Conclusion

John Karalis and Keith Smith provide a highly nuanced, inside look at the Anfernee Simons conundrum facing the Celtics. Simons may not command top-dollar contracts, but his value as an elite sixth man, flexible asset, and culture-setter could be key for Boston’s roster construction and future championship hopes. The episode is a must-listen for Celtics fans interested in cap management, team building, and the evolving definition of NBA value.