KEEPING SIMONS: Why the Boston Celtics Could RETAIN Anfernee Simons for a Game-Changing Run

Summary

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

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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.

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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.

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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)

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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

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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.

Transcript

[John Karalis]

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[John Karalis]

Sponsored by Pfizer bonus content here. Because like I had keith on for 35 minutes. I'm like, that's not enough. People want more. Keith and I wrote down you, we were talking about Anthony Simons and put like big circle on that because Simons is obviously a guy that we talk about being traded. But I think there's a potential to keep the guy. You know, like, yep, you have his bird rights. You have the potential to, you can sign him for whatever you want. And it doesn't have to be for more. It could be for less. Like the Celtics have exceptions. They have guys that can move. They're, they could do. I'll throw this at you. They do nothing at the deadline. Tatum comes back. They spend the summer building around this team and filling gaps with the tr, you know, trade exceptions and all that stuff. And then they use the bird rights to bring back Simons at a lesser number because his cap hold is going to be high anyway. So you, you're not, you're not like handcuffed by it. You, you actually end up saving money in the long run. I don't know. I think, I think there's a world where the Celtics don't do anything at the, at the deadline in the summer includes Simons coming back at a mid level deal that's not using the mid level exception because then they could trade him into somebody's exception somewhere down the road. If it's, if it doesn't work, you can take Your flyer on him being here long term. And you can still use other methods to bring back your center of the future. If Kate is not the guy. Like, what do you think about that scenario?

[Keith Smith]

Yeah, it's very funny with Anthony Simons. I checked this the other day because when you do what we do, you will. There's things you think you know and you'll just say or write. And then you're like, probably should have checked that first. Just. And I did it. I said it. And then I went back to check it and I was like, all right. Thankfully it was true. And I was like, you know, if you adjust for minutes and shots and everything, Andre Simons is basically the same player. He's been in Portland just actually hitting threes at a better clip. And all that is true. He's just playing less minutes and taking less shots because on this team he's sharing the ball with Jalen Brown and Derek White and Peyton Pritchard. And it's not in his hands all the time and all those things. When you're a good team. Big part of the Celtics winning the championship a couple years ago, being competitive for a couple years, was that they had good six men. Malcolm Brogdon, Peyton Pritchard, the last two years really step forward into big roles for Boston. So that's where you need to be in a position where you need somebody to come. Especially if you continue to run with. Pritchard's going to be in the starting five. We don't know if he is or isn't, but if I think that's a lot of it depends, right? Because people are already starting to ask when Jason Tatum gets back, who goes to the bench? And it's like, okay, I mean, I guess the gut reaction is Jordan Walsh, but if Jordan Walsh is this new 3 and D stopper like, then maybe it's Pritchard and then do you need Simons if you have Pritchard. But there's still a point for Anthony Simons and free Simons at 27.7 million. Nope, not happening. And free Simons at 15 or maybe you go up to 18 to kind of plus up his trade. Matching in a potential trade down the line. Sure, that's perfectly fine. I have no issue with that. That's about the going rate for really good scoring guard in the NBA. So, yeah, I think there's absolutely a chance he is back on this team next year. Because the other thing you have to look at too, who's chasing them with cap space? None of the cap space teams are Going to be okay and free Simons, you want 30 million and price them right out if anything. What I could see happening is another team says, hey, this guy's been a 20 point per game scorer who can handle the ball. Do a little bit of playmaking. You play on and off ball. We'll give him our full mid level. And if the Celtics are like, that's a little richer than we wanted to go. Or if Simons was like, you know what? Boston will pay me that too. But on this team, I'm going to play a bigger role. Maybe I start. Then I could see him saying, I'm going to go kind of like this year's version of Nikhil Alexander Walker. Different player, but similar type role inside. That could be something that happens. But, but beyond that, I think we're there and I think we're starting to see two. We're not seeing quite as many infrey. Simon's first run lasted two and a half minutes because Joe Missoula lost his mind because he lost this guy on defense and pulled him out to see less of that happen. Both. He's gotten better and I think Missoula is starting to be a little bit more patient with. All right, yeah, he's going to give up some points on the, on the defensive end, but he's generally getting more than he's giving up. So it's still a net positive to have him on the floor, floor. So I could certainly see him back.

[John Karalis]

I think, look, I think the scenario you laid out is certainly feasible. Equal money. Another team says, but you're our, you're our second option as a starter. Third option is a starter. And he says, look, I'm gonna, I want that.

[Keith Smith]

Yeah.

[John Karalis]

But also I think if Boston, especially if it happens this season, I think Simons is going to be the classic guy where trade deadline goes by, he stays on the team and next thing you know his efficiency, efficiency bumps up, you know, a bunch. He starts scoring better, he starts playing more free. Because, look, I can tell you I've said this on the podcast before. I walk into that locker room and you just look around and I see Jason Tatum's locker room locker. It's got like full of stuff. Jalen Brown's locker, full of stuff. Anthony Simon's locker, empty. He takes whatever little stuff he has with him. He takes, he takes because it. And it makes sense. Like 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.

[Keith Smith]

He.

[John Karalis]

And I'm Sure. Knowing Brad, knowing the, the. The team, they're being upfront too. Like, we like you, but also, this is also part, part of the possibility here. And we're not, we're not going to lie to you. We're not going to, you know, mess with you. And I, I'm sure guys appreciate being, you know, teams being up front, but he's, I think in his head, he's like, I'm just. Whatever's happening this season, I don't know, I'm just going to roll with it. If the Celtics get through the trade deadline and he's still here and they say, listen, man, we kind of like what you got. We like your microwave type of, you know, you can get hot in a hurry. We want to keep that around, but we're not going to pay you $27 million for it. He might be like, listen, I got Jalen, I got Jason. I kind of know what's expected of me. I don't know what his opinion is of Joe Missoula, but guys tend to have a decent opinion of him. I, I like the idea of the Celtics tinkering around the edges, you know, shoring up the positions that need to shore up and having Simons as, look, you are our six slash, seventh man. You're the guy. You're the. When we sub out Jason at the six minute mark, you're the one that's coming in, and we expect you to be a scorer. I think there's a real strong possibility that he could be here for a while. And also I think what helps is, I think the system helps them in this regard because without the second apron, somebody would have given. I think you tell me if I'm wrong, somebody would have just paid Anthony Simons. Someone would just been like, here's. Yeah, here's $25. No problem. Well, like, come on, we'll pay you. We like you. We're going to show you how much we like you because we're going to pay you. We don't care about the text, whatever. Now you can't. You can't miss on a guy making 30 plus million. Like, you have to. If you're paying a guy that much money, you have to be sure. And Simons is not a sure thing. So I don't think there's a risk of being outbid. I think the risk is being like, out situation, like you lined up, like you laid out. So I think the Celtics can line up their, their roster in a way where you can bring Simons back, like all of the trade stuff is there, but I think there's a real possibility that he can come back. Today's show is brought to you by Wayfair. The holidays show up faster than we expect. Christmas is 10 days away. If you're still putting together gifts, last minute decor. I mean I'm just shocked by how quickly it came. If you're getting your home ready for guests, Wayfair has you covered. Whether you need a quick room refresh, new bedding, or those final seasonal touches, Wayfair makes it easy to get what you need fast. It's your one stop shop for everything home. There's decor, furniture, kitchen essentials, gifts for every style budget. It's all delivered quickly and easily. 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[Keith Smith]

Yeah, let me give you the counter to this situation too. This is a guy who remember he entered the, he was one of the like out of high school guys because he did the post grad year. He didn't actually go to college. So he did like a little bit of a more or less out of high school, out of IMG Academy. But when he came in, super duper young walked into a Portland team that was, they were a playoff team, they were a good team. And spent his early NBA years playing with Damian Lillard and CJ McCollum and fully realizes you're playing with pretty good players. Boy, they make life easy on you. Yeah. Like and now this guy is 26, I think so 27 next year probably looking at and saying all right, I made a lot of money on my last deal. I made over 100 million on my last deal. I'm pretty well set. I know I'm gonna get money is going to be there for me to some extent. It's not going to be 25, 30 million but I think minimum. No, it's not the minimum. It's somewhere mid level. I like to call those mid level plus where it's like a mid level maybe a little bit more.

[John Karalis]

Yeah.

[Keith Smith]

If you're Simons, I think what you're looking at is say hey, I can make that playing in Boston, playing with Tatum and Brown on a team that's a contender. I've never won anything because those Portland teams never went very far. Let me, let me do this for a little bit. And then if things get weird when we think of players who want a different situation we think of Giannis Ad back in the day, the superstar players, because. Right, because that's what drives the needle. That's what I get it, right? That removes the needle. That's where it goes. But sometimes you do get the guys who are like the, they're like, hey, if like Pete Pritchard, right, at one point was like, I'd like to go somewhere and play. Like, you know, I like being here, but this sucks. I never, I never see the floor unless it's garbage time, I want to play. And I could see Simons kind of going in the world where it's like, hey, all right, yeah, I did this. I resigned for three years. We're two years in. I'm never playing. I'd like to go somewhere and play. And then I think the Celtics were like, all right, let's try to take care of it. But yeah, there's 100% of war where he comes back. And I think too, he's been, he's been everything I expected him to be for the team. Just come in, fill it up off. I honestly, I thought he would start. I, I thought they might say, you know what, let's start this guy and leave Pritchard in that six man role where he's excelled and been comfortable. It's been the right move to start Pritchard. I have no issue, but Simons is just playing a little less. Shots are down a little. But if you adjust all that back to norms, he's right where he had always been in Portland, which is, you know, pretty good offensive player who. I think he's improving defensively, which is. It was going to happen with better defensive players around him.

[John Karalis]

He's young enough where a couple of seasons of playing a certain role, winning a championship, let's. I'm not saying anything's a guarantee, but you got the Celtics with Tatum next season. Brown, I like where Brown's head's at. I think next season will just be a special kind of season.

[Keith Smith]

They're still in the Eastern Conference.

[John Karalis]

Still in the Eastern Conference. I, I like Brad's, you know, and Brad in the front office. I like where they are and what they can do with everything else. So I trust them to fill in the gaps. You get Simons in there to be a scorer off the bench, I think he can be an elite scorer off the bench. And you tell him, look, give him a two plus one or something short deal, you go, you win a championship, you prove that you can handle a different role. You've proven that you can score as A starter. If you can come off the bench now you have, if you have a championship, if they can get there now, you can, I don't want to say write your own ticket, but you that championship glow. Teams want that, teams want that veteran and like especially, okay, young team, whomever, pick a, pick whatever you want. We're bringing in Anthony Simons. He's at that point 28, 29. Listen to this dude who came in as an elite scorer, had to humble up, played a certain role, won a championship and now is here to lead you. What better leader than that to have on your team? As a guy who's like, yeah, I came in young, brash, I struggled with the transition, but I stuck with the team. I played a different role. I helped them win a championship. And now look at this, I'm still getting paid. Now look at how much people want, like young guys need somebody like that around. I think there's value to that and I think you can get paid off of that and I think you can.

[Keith Smith]

Have a long career.

[John Karalis]

Like when Anthony Simon's career should be over, he might still get two years out of that career as an end of bench vet guy. So I think there's real value to this potential scenario for him.

[Keith Smith]

John, I say this all the time. I usually use right now my, my proxy for this, my example for this is Cam Thomas with the Nets where I think Cam Thomas is best role in the NBA. BA is a high, high usage sixth man scoring guard. And people are like, yeah man, I just want more for him. Lou Williams and Jamal Crawford had 20 year careers as high usage scoring six men to the point where I think the six man of the year award should be named the Crawford Williams Award. And just, you know, that should just be what it is because those guys set the standard for more than a decade of years where how much do they love Lou?

[John Karalis]

How much do people love him?

[Keith Smith]

Yep. Yeah, everybody loves Jamal Crawford too, right? Like, yeah, like he's, you know, right up there with, with, with guys. And that's where, yeah, if you're Anthony Simons and you're like, yeah, what I'm gonna be throughout my late 20s, into my early 30s, then if I'm still playing when I am where Crawford and Williams were in my mid to late 30s, like, because I can still give you 15, 20 off the bench and be a good vet and be, be a, you know, guy who just fits. Yeah, let's go with that. And that's where, yeah, I mean this could be, could be the start of what is Next. And a lot of guys when they hit that late 20s period of life in the NBA, realize, yeah, it's cool scoring 25 points per game, but on a team that stinks, why there needs to be more to it. Especially when again, he's made 100 million now, right? That contract's already in the rear view. He already made his, made, made more money than hopefully if, if he's doing things right, more money than he'll ever need the rest of his life. And I think he's just in a position where, yeah, what I'm going to prioritize is let's try to win. And if I'm the Celtics, I think about when they went out and got Josh Richardson. The idea was, all right, well, we have Josh Richardson. We're going to keep Josh Richardson. Then we, they, they were like, we could turn that into Derrick White. Maybe that's what happens with Simons where it's hey, we're going to resign him. So to a contract. And a lot of people might initially be like, man, why? Who are we competing with? Why do we give them so much money? Whatever. But then I think in the end what they'll come back around is like, all right, you know what? This actually did kind of work out pretty good. And maybe it is Simon's two years from now has turned into whoever did the Derrick White replacement or whatever it may be at that point. Whereas he starts stage out. I, I, I, I, I definitely think there's a war where he's back with the Celtics. And, and I, I love what you called out too. We often see that with players after the trade deadline. It, sometimes it's, everything is like, all right, I didn't get traded and my team is terrible and I could just go out there and gun away because it doesn't matter anymore. Celtics are going to be in a spot where they've got stuff to play for and I think he will play a lot more free and easy where it's all right. At least I know I'm here, you know, for the next, whatever, next few months, at least I can play. And then I'm trying to prove myself for my next deal.

[John Karalis]

Awesome stuff. Bonus content here on the Lockdown Celtics podcast.

[Keith Smith]

Keith.

[John Karalis]

Follow Keith at spotrack Spot Track's the place to go for all of your salary cap stuff. Keith, always love having you on, man. Thanks.

[Keith Smith]

I appreciate it. Thanks so much for having me. Happy holidays.

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