NBATV analyst Wes Wilcox has worked almost every front office job imaginable since he first entered the NBA, from video coordinator, to advance scout, to assistant coach, to director of player personnel, to general manager. He’s worked with the Miami Heat, New Orleans Pelicans, Cleveland Cavaliers, and Atlanta Hawks.

Now, with one of the NBA’s most unpredictable and important free agency periods right around the corner, it felt like a good time to pick his brain for insight about numerous situations around the league and how free agency actually works for front offices.

This interview, which was conducted the week before free agency began, has been edited for clarity.

Michael Pina: Heading into free agency, what has been the move, bet, or educated decision that might’ve been a risk in the moment, but paid off for you the most in your career.

Wes Wilcox: Back in the summer, I think it was 2013, we had three plans laid out in Atlanta. We had Plan A, which was that we had max room after trading Joe Johnson in 2012 and we thought we had a chance to get involved with Chris Paul or Dwight Howard, or maybe even potentially both. We were one of the only teams, with a little bit of financial engineering, that could get to two spots. So that was Plan A. Probably a bit unrealistic, but that was Plan A.

Plan B was, maybe we could build a really good team through depth, through what we deemed as the middle. And then Plan C, we were seriously considering, you know, do we go in the other direction? Has this team peaked? And we didn’t want to invest in the future. We wanted to exhaust our ability to build a great team or a very good team. Because of that, we were juggling multiple paths at the same time. And really, all of this was led by Danny Ferry, who did a great job structuring all this for us.

But because of that, we were in conversations with Golden State potentially about taking Andris Biedrins and Richard Jefferson. Golden State needed to move those two contracts to sign [Andre] Iguodala. And we were in conversations with Iguodala and [Iguodala’s agent] Rob Pelinka, as well. We were in conversations with Golden State to potentially take those contracts for multiple picks, and we were in conversations with Pelinka, and we were in conversations with Paul Millsap.

And so we were fortunate to pull all this together and juggle multiple paths simultaneously. What we were able to extract out of all of that was Golden State had two homes for those contracts. They had the Atlanta Hawks and the Utah Jazz. And — this wasn’t anything we were told by Golden State, but just by assessing the market — there’s only a finite number of places this could happen. So we knew we weren’t going to be there with Pelinka and Iguodala, because Pelinka was very straightforward in how we handled that negotiation. And so when we were able to confirm, or verify internally, that it was going to be Utah that was gonna do the deal for the Golden State salary dump to create the room to sign Iguodala.

Then, we knew, in order for them to do that, Paul Millsap was going to be renounced. And at that point, we were able to call Paul Millsap’s representative, DeAngelo Simmons, and say ‘DeAngelo, listen, this is gonna happen, and as soon as it happens we just want to let you know that [Millsap] will be renounced, Utah will no longer have the room or capability to re-sign you. When that happens, just know you’ll have a home in Atlanta.’

Sure enough, the next day, boom, it all happens. We were ahead of it. We got the phone call very quickly from Simmons, we did the deal, and Paul was a four-time All-Star in Atlanta. But really, that only came about because we were juggling three paths simultaneously.

I would say that’s the higher level there. That’s the benefit of working parallel paths on multiple plans.

Pina: Just to clarify, when you mentioned before that Rob Pelinka was “straightforward” with you about Iguodala, did that just mean he didn’t view Atlanta as a destination for his client?

Wilcox: Yeah, he did not tell us who he was going to sign with, but the contract offer that we made was very respectable. But he told us, he was very straightforward, ‘Hey, your contract offer is certainly in the game, but just so you know, there’s another location that Andre has prioritized. That team needs to do some work to get to the contract that we would be comfortable with, but we think that team is going to be able to do that.’ And so he was great about saying, ‘Listen, it’s not a no, but it’s unlikely because we think this is going to happen.’

Pelinka did a great job protecting his client, protecting the other organization. We were just able to piece it all together. And it really worked out for everybody.

Pina: I have another question about your time in Atlanta that runs parallel to a situation that’s going on right now.

It was a few years ago when Al Horford left the Hawks to sign with the Boston Celtics, and you then pivoted by signing Dwight Howard. I was wondering if you could go back and just tell me what do you remember about that time. Was it chaotic? Did Horford blindside you? How many contingency plans at that time did you have prepared for his departure? What was that experience like?

Wilcox: So that was 2016, where the salary cap jumped from approximately $70 million to $94 million or so. And going into it, I believe Al was on a five-year contract at $12 million per year that was signed prior to the lockout in 2011, which was a deal that Rick Sund signed in partnership with Arn Tellem. Al really took financial security, and that deal ended up being an under-market deal for the level of player that Al Horford was.

There were different beliefs going into the summer of 2016 about what it would take to re-sign Al. Some thought there might be an opportunity to get Al at less than the max and others thought it was going to be very difficult to sign Al to less than the max. It’s also critical to remember that in 2016, Al Horford was a top-five free agent, and there was 26-28 teams with max room.

And so when you look at the landscape, a franchise-level player who’s been on a below-market contract prior to a free agency period where he was going to have multiple max four-year offers, the fifth-year offer for a player like Al, who’s certainly a max player, was more difficult for the incumbent team, because we were gonna have to pay more money on more years. And if we didn’t offer that contract, that was going to be used against us in the negotiation.

It was a very difficult line to walk, and it ended up that Al left the organization. Those are always difficult times. We respected Al’s decision to leave. I can’t say I was ultimately surprised that he left, given the landscape and the financial conditions.

Pina: This leads us to the Celtics finding themselves somewhat ironically in a very similar situation. Horford is rumored now to have a desire to leave Boston. Based on your experience, in the roles that you’ve had, when a max level free agent leaves an organization, on some level there has to be soul searching. But often there’s no time for that, and instead of taking a step back to assess yourself, teams just have to dive back into the market and find someone to replace that production. How difficult of an experience is that for a front office to go through?

Wilcox: Well I don’t think this is going to be an immediate pivot by the Boston Celtics. Danny Ainge, Austin Ainge, Mike Zarren, Brad Stevens have all been thinking, ‘OK, what does this summer look like for us?’ And without question, they’ve been modeling this exact scenario. This will not catch them off guard.

It’s also really important that the situation the Celtics find themselves in is different than the situation the Warriors find themselves in. The Warriors have no ability, from a tools or technical standpoint, to replace Kevin Durant. They’re above the cap and dealing with the taxpayer mid-level exception. In Boston, where Kyrie [Irving] and Al may leave, they’re able to sit there with approximately $33 million room, depending on what you want to do with [Terry] Rozier. Boston has a great deal of flexibility.

Additionally, when the Celtics signed Al Horford, it made more sense for the Celtics than it did the Hawks because of this fact. One of the challenges in the NBA is finding value on the max, or near max. And the closer you get to par or neutral value on a max contract, the harder it is to be good, unless you have a great deal of value on rookie-scale contracts or value contracts. And so let’s say you pay $30 million for LeBron James. To simplify it, he’s gonna be worth $120 or $150 million. I don’t know what the number is, but it’s a lot! When you pay the next tier free agent down $30 million and they’re worth, I don’t know, $60 million or $45 million, it just makes things harder unless you have a ton of value on rookie-scale contracts or value contracts.

Specific to 2016, [the Hawks] didn’t have a ton of value on rookie-scale contracts, and so when you start tacking up very good players at max or near max contracts, it gets very difficult to have the depth to be good when your team was largely built on depth. The Celtics signed Al in that summer and they had a ton of value around him. So paying Al Horford $30 million then made a lot of sense for the Celtics.

Now when we look at them, their timeline has likely changed based on Kyrie leaving and where they’ve established themselves in the East. You look at their timeline and the Celtics could look forward and say ‘Our run is two, three, four years from now as much as it is right now.’

Pina: If you were Boston, how would prioritize the different ways it can use that cap space. Would you max out someone like Kemba Walker or Nikola Vucevic, knowing you do have some depth on rookie-scale and value contracts, or use the cap space to absorb another team’s unwanted salary, take on more future assets for the trouble, and build out for the future.

Editor’s Note: This question was asked before Boston zeroed in on giving Walker a max contract.

Wilcox: Yeah, this is the great question, right? [laughs]. This is one of the great questions for any executive. You have to have the pulse of your team, and know when is the right time to make the type of move you’re making.

And when is that move? It’s hard to speculate, but if you’re the Celtics, you have a lot of flexibility. You have Rozier on the [cap] hold, if he gets an offer sheet, you have until July 8 at the earliest to make that decision. You have to figure out if you have a chance at these free agents. What the probability is. You can get a sense.

And then you can also assess the trade market, most likely simultaneously. We know the [teams in the luxury tax]. We know Oklahoma City. We know Miami. We know teams seeking out potential financial trades. I think [Boston] does all that simultaneously, and if they do none of it and instead split up their cap space among two or three guys and try to create depth on their roster, that makes sense too. And you never put it against the Celtics to be in the trade market as well. So they can trade player for player.

I don’t think I can sit here and say ‘This is what I’d do if I was the Celtics’, but they certainly have the benefit of being able to play in every potential scenario. And they have the benefit of being a good team currently, with the chance to be really good down the road as they continue to develop and work with their young players.

Pina: Switching gears a little bit, how do you forecast how a player like, say, Vucevic or Walker, max guys who seem to get better every year but, in Kemba’s case or even someone like Jimmy Butler’s case, is hitting a certain age where they’re likely to experience physical decline. There are player comps and statistical evaluation, but what specific moves are made to essentially peek into the future with hundreds of millions of dollars on the line?

Wilcox: Analytics are very helpful here. It’s just a raw tool to track a number of different ways, how a player is performing, what level they performed. Not that the analytics are the sole driver in this analysis in any stretch, but they certainly do help because it’s a number and it’s easy to get a sense around that.

It’s also important to know just the normal career trajectory of a player. Pre-prime is what age? Prime is what age? And post-prime is what age? We all know that skill ages gracefully, and a player that lives in condition ages better, and a player who has had fewer injuries typically ages better.

And then also you have to make the decision about where are you in the money on these contracts. Sometimes, it’s worth a great run in the front end of a contract knowing the back end will be painful. But if you do have a great run or set yourself up for the first couple years, you’re gonna be in the money and therefore the back end is just something you’re gonna have to figure out. You go into it with eyes wide open.

Pina: This is the Houston Rockets and Chris Paul.

Wilcox: Yeah, I mean there’s an argument that they’re in the money, and they would probably say they’re in the money because of the run they had two seasons ago. And it’s hard to argue that they’re not.

Pina: Speaking of the Rockets, I’ve been thinking about the five percent theory, that any team that has at least a five percent chance to win the title should do everything they can to win the title. This is something Daryl Morey talked about a few years ago. When was the last time so many teams could talk themselves into going for it, and how much will the uncertainty at the top influence free agency?

Wilcox: I can’t remember a time when you’ve had this many teams going into an offseason thinking that they could be a contender the following year. I don’t have a recollection.

And part of that is the fact that a lot of these free agents have won championships already. Kyrie, Klay [Thompson], Kevin [Durant], Kawhi [Leonard], it’s hard to say how they’re gonna handle free agency. That gives teams like Brooklyn and the Clippers, who have done just a fantastic job of drafting, signing players, developing players, and building their organizational infrastructure to be a home, to think that if they could land one or two of these guys, which they both have the ability to do, they could also be contenders.

So it’s just a fascinating market. It’s gonna be fun to watch. And it certainly seems like it will be an unprecedented time in the NBA, from that perspective.

Pina: What other ripple effects do you foresee over the next few weeks for teams that know there’s nothing close to a unanimous favorite to win it all in 2020? We just saw the Utah Jazz move two first-round picks and a couple valuable role players to get Mike Conley. Do you anticipate more aggressive moves like that one?

Wilcox: The Conley trade, that move makes a ton of sense for Utah. Let’s just say the average payroll is $125 million for a non-tax team. That gives you $50 million for the backcourt. Conley makes a lot, but Donovan [Mitchell] doesn’t make a lot, so you net those two guys out and the Utah Jazz are getting value in the backcourt.

And so it’s a great trade, great timing for Utah. My gut is Utah isn’t making that move because there’s this window. It just so happens to be that there might be a window now and this deal made sense for both teams. You have to spend in order to be a contender. In almost every case, to be a true contender. And if there’s a window that will honestly lead you to believe you can be that contender, then of course it justifies spending.

Now the reality is you get to next year and teams start to struggle midway through the year and it’s going to change everything. There’s going to be a lot of financial trades at the deadline for teams that aren’t actually justifying their payroll. So you’ll see spending, for sure. But you’re also going to see some teams not spend, or try and move some money.

That’s what’s fascinating, at what level can you sustain the spending. We saw Houston do that last trade deadline, get out of the [luxury] tax. Now we see Oklahoma City trying to make financial moves that might take away from their team. So you’re gonna see a lot of teams spend, and you’re gonna see some teams limited because they spent.

My gut is you’ll see Milwaukee in the tax, and certainly if Kawhi returns, Toronto in the tax. Philly can avoid it for a year, but then if they retain all their guys, they’re going to be an incredibly high payroll team. That’s just the cost of doing business if you want to contend or compete at the highest level in the NBA.

Pina: When do you know your owner’s feeling about going into the luxury tax? If they’re generally against it, do you have to pitch them on why it’s worthwhile or are those conversations that don’t even take place?

Wilcox: I think every owner, with the opportunity to contend for a championship, I believe they’ll spend into the tax. The question is how far into the tax is a given owner willing to spend.

Separate from contending, the question becomes, who’s willing to pay into the tax to buy assets to give themselves better chances to win, and then who’s willing to pay the tax to build a good, but not great team. Those are the tax-related questions.

But I truly believe any owner who has an opportunity to truly contend will spend into the tax.

Pina: You were a finalist for Milwaukee’s GM job a couple years ago. When you look at that team, how would you prioritize their objectives heading into the offseason? Should they be aggressively trying to clear space to make sure they can bring back Brook Lopez, match whatever offer sheet Malcolm Brogdon signs, and max out Khris Middleton? Just, what is the most important thing for them to take care of going forward?

Wilcox: First of all the Bucks are in great hands with [Mike] Budenholzer as the head coach, and Jon Horst has done a terrific job of building this roster.

It’s always challenging when you need to trade draft picks in order to move contracts to create financial flexibility. And it’s not just avoidance of the tax necessarily, but it’s just truly the flexibility of being able to re-sign your most important players. We saw that in two transactions: The [John] Henson-[Matthew] Dellavedova transaction with Cleveland and the more recent transaction with Tony Snell and Jon Leuer. It’s very difficult to lose the value of those rookie-scale contracts, of course.

So from a technical perspective, I don’t think those moves were necessarily about avoiding tax as much as they were about retaining the most important players. In some ways that’s not the Bucks’ fault, because Brook Lopez signs at just over $3 million last summer and that was one of the best signings of the summer, but because he’s a one-year guy you don’t have Bird Rights and so it’s very difficult to re-sign him. You need [cap] room or a [salary-cap] exception. So the financial engineering is complicated for the Bucks.

Partly though, it’s complicated because they did a really good job and built a really good team. When you take a step back and say ‘What does this look like in the short term and the long term’, that’s where the balance gets tricky, because one can argue that even more important than winning in the short-term is retaining Giannis [Antetokounmpo] in the long term. Certainly, the logic is if you win in the short-term, that’s going to help in retaining Giannis in the long term, which makes perfect sense.

So this is a tricky thing for the Bucks to pull off. Certainly with their recent history, you’d believe they’ll be able to do it, but it’s hard when you’re losing those valuable rookie-scale contracts because you’ve got to hit on the draft, to add young players and youth to the team. Otherwise you get really expensive, really fast, and you lack flexibility. That’s what they’ve got to try and figure out.

Pina: Looking at the Nets for a second, there was a recent article in the New York Post about Brooklyn and Kyrie Irving, and how wary they might be to bring him in as a solo act without Kevin Durant or another max star. How valuable is it to “get the guy that you want” in free agency when you’re an organization that hasn’t been viewed as a destination in quite some time. What message does that send to the rest of the league and its players, and how much does any of it impact into a general manager’s calculus, if at all?

Wilcox: You certainly hear this sort of thing talked about, but with respect to the Brooklyn Nets, I don’t believe that will play into their calculus. They’ve done a great job keeping their head down, adding high character players, and developing those players. Kenny Atkinson’s done a fantastic job. Sean has done a great job. Just knowing those people and the job that they’ve done, and their history, I don’t think they’re gonna make some sort of media-driven move. Ultimately what matters most is you make good decisions and you win, and they’ve done that.

So I don’t think this is going to be a scenario by any stretch where they’d do something to justify their position within the NBA. They’re a great market. They’ve done a great job. They have just under $70 million in cap room, and they’ve got a really nice core of young players. They have optionality on D’Angelo [Russell’s] contract. In no way do I think Brooklyn would do something like that.

I’d also say this: I don’t believe that this rumor from Brooklyn is that they’re concerned about Kyrie alone. That’s just not the way Brooklyn does business. Brooklyn is not a team that shares that kind of concern externally.

Therefore, this time of year, you start to wonder where these concerns and where these off-the-record quotes come from. If Brooklyn is concerned, I don’t think they’d share that with anyone. Knowing the people there, I know that’s not how they function. So it just leads me to believe this concern is being shared by someone else outside of their organization, as part of the game of misinformation.

You can see Wes Wilcox on NBA TV, breaking down offseason developments on Free Agent Fever, a live studio show using a deep roster of commentators, through July 4.