The NBA campaign is full of exciting moments, but there’s no question that the free-agency period is one of the league’s most exhilarating stretches. The transactions that are completed throughout July and August can completely alter the landscape of the NBA and play a crucial role in determining the 2019-20 champion.

In the modern NBA, there’s a lot of player movement, which generates a ton of intriguing storylines. Free agency is obviously a lot of fun for anyone who’s on the outside looking in, but what is it like to be an NBA decision-maker around this time of year? This is their crunch time, as all of their hard work comes down to this span.

Five NBA executives agreed to give HoopsHype an unprecedented glimpse behind the scenes at the free-agency process (much like NBA agents did last year). Most spoke on the condition of anonymity since they aren’t allowed to give on-the-record interviews or reveal this information. The executives discussed the free-agency prep work that begins months in advance, how teams determine who to target, what it’s like to negotiate with agents, how chaotic things get at the start of free agency and more.

FREE AGENCY PREPARATION STARTS EARLY

While free-agency chatter starts to pick up at the NBA Draft Combine in May, front offices spend much of the year getting ready for their summer spending spree. One Western Conference general manager pointed out that it can be difficult to plan things out too precisely because every situation is so fluid and there are so many factors that are out of the front office’s control. For example, big trades and surprising developments on draft night (which is just 10 days before free agency begins) force teams to adjust on the fly. Still, there’s a lot of work that must be done ahead of time to ensure that everything happens smoothly in July.

Former Eastern Conference general manager: “It’s a really tough period because you go right from obsessing over the draft into obsessing about free agency. From about June 10 to July 10, it’s exhausting. It really is so tiring and nerve-wracking. You may think that you have a guy, but then some team will make a trade to create a ton cap space and, suddenly, that team becomes the front-runner to land your top target. You can feel so confident that you’re going to land a guy, but then one thing changes and you’re forced to move on to your Plan B or Plan C. It can be fun when things are going smoothly, but it can also be very stressful.”

Eastern Conference executive: “There’s an excitement, a high, associated with the draft and free agency. But when you’re doing the prep work for those big events, it’s just really tiring. The weeks leading up to the draft and free agency are definitely an important time of year, but it’s not the sexiest time of year. There aren’t too many fireworks. It’s a grind and it’s stressful. It’s probably the toughest time of the year on our families too because we’re rarely around. And if we are home, we’re so drained. It’s a lot of work.”

Teams and agents aren’t supposed to communicate until June 30, but the executives confirmed that there are always conversations happening behind the scenes. The NBA does punish teams if there’s obvious tampering (such as public comments about a player), but the league typically looks the other way when it comes to private talks.

Eastern Conference executive: “We’re technically not supposed to talk until a certain point – June 30 this year – but we’re talking about this stuff all year through intermediaries. That’s part of what makes these weeks leading up to July 1 so exhausting. You don’t just show up with a bag of money. This is a year-round recruitment.”

Former assistant general manager Bobby Marks: “A lot of the free-agency legwork gets done during the week of the NBA Draft Combine in May. There are a lot of meetings between teams and agents to discuss draft prospects, but the free agents will come up throughout the course of the conversation too. There aren’t any agreements being made, but you’re letting the agent know, ‘Hey, we have interest in Player X.’ You’re setting the stage. I think you have to start [free-agency discussions] before June 30. If you wait until June 30, you’re going to be so far behind. As long as you aren’t blatantly [tampering], there are ways you can go about it and the league will look in a different direction. There’s not much the league can do about it. It’s not like the NBA can start tapping phones (laughs).

Former Eastern Conference general manager: “By the time free agency is a few weeks away, you’ve mapped out who you want and now you’re trying to figure out what the market is going to be for each player, who else is competing for your top target, what it’ll take to sign him and what he’s looking for in a new team. You’re setting up a meeting and figuring out logistics like whether the meeting will take place at his agent’s office or in your city. You’re planning out what’s going to happen during the meeting and how you can sell him on your organization and situation. You’re also trying to figure out Plan B and Plan C, and prepare for those possibilities as well (without anyone realizing they aren’t your top priority).

Bobby Marks: “The first exercise most front offices do [to determine their targets] is going over all of the free agents and trying to put a price tag on each player. Most teams do this, even if they don’t have cap space. It’s easy to tell who the max-level guys are going to be, but it’s tougher to put a price tag on someone like Marcus Morris or Bojan Bogdanović. The NBA personnel guys and front-office guys all come up with their own price point for each free agent and then everyone compares their numbers. That gives you an idea of who you can afford and you can start putting together a list of targets. Every team’s price range is different. Some teams have to go bargain shopping; some teams get to shop at Nordstrom.”

Western Conference executive: “We do a lot of different exercises to prepare for free agency. We rank all of the available free agents from best to worst by position, and that sometimes leads to big debates about certain guys. Every person in the front office has their own big board that ranks all the free agents. We all try to predict how much money each free agent will get. We try to map out which free agents each team will target. If you have a basic idea of what another team desires, you can potentially use that as leverage and get what your team needs.”

While preparing for free agency, executives aren’t just focused on their team. One GM explained that prior to free agency, his front office does an in-depth examination of every other team from top to bottom – learning their cap situation, positions of need, where they’re at in their development, who they may want to re-sign among their own free agents, who they have to renounce to be a cap player, what might happen with player options and team options, what kind of partially-guaranteed contracts or non-guaranteed contracts are on their books, whether they’re weighing any trade ideas and so on.

Eastern Conference executive: “There are some front offices that set unrealistic expectations for themselves and make strange moves because they’re miscalculating how close they are to competing at a high level. Those teams are the wildcards; you never know what they’re going to do.”

Some rival executives try to take advantage of these wildcard teams by pouncing on their trade chips. For example, if a team believes they’re poised for a deep playoff run, they may be willing to trade some of their young players and/or draft picks to add veterans who can help them win now. Executives are happy to play along with a delusional front office and take their attractive assets. Sometimes, the front office isn’t delusional; they’re just tired of losing and get impatient during their rebuilding effort.

Bobby Marks: “Losing wears on you. If you’re going to rebuild, you better have two feet in and be ready for it. Rebuilding isn’t for everyone. In New Jersey, we were rebuilding from 2007 to 2011 and it got to the point where we said, ‘You know what? Let’s cash in our cap space and cash in our draft picks so we can fast forward this rebuild.’ I think that’s probably when you get in trouble. I think you’re seeing a bit of that with Chicago right now. When they traded for Otto Porter at last year’s deadline, it seemed like they were thinking, ‘We’re tired of going into free agency with cap space [and missing out on players]. Let’s just bring in a proven guy through trade, even if he costs $27 million.’ Losing year after year is tough and it tests your patience.”

GATHERING INTEL IS EXTREMELY IMPORTANT

Whenever an NBA team signs a player to a lucrative contract, they’re taking a big risk and hoping that their investment pays off. One way to mitigate some of that risk is to have a treasure trove of information about the player and what kind of person he is on and off the court.

Eastern Conference executive: “Draft preparation isn’t just about who you’re going to draft; you’re also gathering information for years later in case that player becomes available in trade talks or free agency. Most of us use similar computer systems and most teams have a file on every player. The second a prospect surfaces, you start adding intel to their file. The second you lay eyes on him, whether it’s an international prospect in a junior tournament or a high school prospect at a USA basketball event, you start the file. You just keep building and building that file, putting in information about the player’s character, how he rated analytically, anything you’ve heard about him. Then, when he’s 28 years old, you have this file full of intel that can help the front office during the decision-making process.”

Former Eastern Conference general manager: “Your intel often goes back to the draft. With some of these guys, you may have done psychological testing on them when they were coming out of college. You’re looking at your medical [notes] from when you saw them at the Combine in Chicago. Then, the off-court intel is very important. Are they heavy drinkers? Are they late-night partiers? Do they have a lot of guys around them? Are they married? Are they very religious? You’re trying to gather what type of person they are, you know?”

As the former East GM mentioned, some NBA teams give prospects a psychological test to get a glimpse into how their mind works. But as is the case with any data set, there’s debate over the accuracy and benefits of the info.

Western Conference executive: “The psychological tests can reveal certain risks, and I think it’s good for ruling certain things out. But the test isn’t going to reveal, ‘This player has the same make-up as Michael Jordan or Kobe Bryant.’ They don’t rule in like that. It’s used more to spot possible red flags and rule out. I think they’re a resource, but you also have to take everything into context. What kind of environment did the player grow up in? How old are they? Is what you’re seeing an actual character trait or is this just where they’re currently at in their development? Remember, a lot of these players are teenagers when we’re first meeting with them. Psychological tests allow you to look for certain patterns and things that may be problematic, but you’ll never bat .1000 with those things. I’ve seen players have a perfect test and then become problematic, and vice versa.”

Eastern Conference executive: “When gathering intel, you’re trying to learn anything you possibly can about the player. I’ve talked to middle-school coaches, AAU coaches, Uncle Bubba from their neighborhood, you name it. If there’s someone who can provide even the slightest insight on the player, you contact them. When teams gather intel, it goes way beyond basketball.”

Bobby Marks: “We tend to spend so much money on the draft and it’s ultimately for one player (laughs). We bring in 60-to-65 prospects and interview the heck out of them and hire private investigators and do physicals and spend a lot of money in Chicago [at the Combine]. But then when it comes to free agency, where you’re sometimes investing $100 million in a player, you don’t do those things. Now, I think teams are getting a lot smarter and investing more in that by hiring more personnel guys and doing more background on players and things like that.”

While teams start gathering intel on players when they’re going through the pre-draft process, front offices don’t stop adding to the file until the player is out of the league. A great time to gather intel on a player is typically after the individual gets traded, one GM said. Not only are people within the organization more willing to talk since the player is no longer on their team, the information is still fresh on their mind.

Western Conference executive: “Every team is different when it comes to the intel they gather and value. Sometimes it depends on where your team is at in your process. If you’re a young team, maybe bringing in a guy with red flags isn’t going to work. If you have a lot of strong veterans and coaches who may be able to keep the player in check and hold him accountable, maybe it does make sense to go after the high-risk, high-reward player. The general manager’s job security also factors into these decisions. Some GMs can’t afford to attempt a risky move, whereas some GMs know that even if the experiment fails miserably, they won’t be on the hot seat.”

Eastern Conference executive: “Some teams really rely on analytics – their own in-house analytics – and that’s become valuable intel too. If you have certain numbers and projections that other teams don’t have, that’s intel that will go in a player’s file. A lot of intel has to do with who the player is as a person and what’s going on with him off the court, but there’s also on-court intel that some teams really value. It becomes a tricky little recipe and you’re considering a lot of different things, which is why finding the right players can be very difficult. It’s certainly more difficult than fans realize because there’s so much info that will never become public for fan consumption. It’s an inexact science.”

It’s worth noting that not all intel is about a player’s red flags or background. Teams also keep notes on a player’s interests and aspirations. When a team is pursuing a player in free agency, going back through their file can help the front office create a personalized pitch that may really resonate with them.

Former Eastern Conference general manager: “A lot of times, intel can also be really helpful if you’re trying to recruit the guy. In your city, there may be something in particular that would interest them or attract them based on your intel. They may have a son or daughter who has a certain medical condition and your city may have a hospital that could be specifically helpful to them. Their wife may be in a certain occupation and your city may be a perfect fit for her. You want as much intel as possible to help determine if a move should be made, but also because having the right intel can give your franchise an advantage when it comes time for a free agent to make his decision.”

Eastern Conference executive: “When you’re recruiting certain guys, it’s not just the agent that you’re dealing with – it may be their old AAU coach, their manager, all of these people who are in their life. That can be a challenge, but you have to identify those people [because they’re in the player’s ear]. If you can identify whom the player trusts most, you have a big advantage. That’s important intel too.”

MANY EXECUTIVES ARE INVOLVED BEHIND THE SCENES

An NBA front office consists of many different employees – all of whom are working together to build the best team possible. The general manager is the figurehead of the front office, but there are many people involved in every transaction.

Former Eastern Conference general manager: “When you’re preparing to make a big move, you’re talking to everyone – from the assistant general manager to the other personnel people to the analytics staff to the medical staff (your trainers and doctors). You’re going back over their psychological testing and all of your intel. Everyone plays a part and a whole lot goes into it. You talk to your head coach about it and you talk to your owner about it. If the owner signs off on it, the GM ultimately makes the decision, but it’s after gathering all of that information from everybody else who’s involved.”

Western Conference executive: “When you’re just working in a front office, you don’t feel the public pressure that the general manager and president of basketball operations feel. We’ll be going back and forth, debating about two free agents we could target and I’m thinking, ‘There’s no pressure on me at all. I’m just weighing in on these guys. I don’t have to make the final decision.’ (laughs) When you’re the one making the choice and receiving all of the blame if it goes wrong, it’s much harder and much more stressful.”

Eastern Conference executive: “The level of collaboration varies from team to team and how influential your voice is varies from team to team as well. I saw this a lot because I worked full-time in some front offices, but I also worked part-time as a consultant in other front offices. Sometimes, a consultant will have the GM’s ear and more pull than the director of pro personnel or the full-time scouts. There was one organization that I worked in where the person with the most influence didn’t even have an official title! Sometimes, it’s just about having the GM’s ear or the owner’s ear. From what I’ve seen and heard, the well-run organizations like the San Antonio Spurs and Oklahoma City Thunder have a very democratic process where everyone’s input is actually considered. Even if you’re new, they want to hear what you have to say because you may have a different perspective that they hadn’t considered.”

Former Eastern Conference general manager: “Also, while the GM may be ‘in charge,’ he’s not the one making every decision. That’s a big misconception among fans. Just because a team makes a move, it doesn’t always mean the GM wanted to do it. Even if the GM doesn’t agree with the decision and it isn’t ultimately their call, the GM is the one who will get the blame for said decision. That’s just part of the job.”

When a front office is meeting with a high-profile free agent, most of the organization is involved in some fashion. One GM said it’s not uncommon to see a team show up for a free-agent presentation with the GM, assistant GM, several players, the team president, the senior marketing advisor and so on. Sometimes, the owner will be present as well. And that’s not even everyone who’s involved in the pitch, as there are plenty of people who don’t attend the meeting but still play an important role in the process (such as the capologist, analytics experts and medical staff among others).

Eastern Conference executive: “One huge misconception is that there are these ‘stupid teams’ around the league. You hear that from a lot of fans. ‘Oh, that team is so stupid.’ There really aren’t any stupid teams. There are really smart people who work for every single team. Sometimes, a player or their camp just has all of the leverage or the owner will involve themselves more than the front office would like or there is so much pressure on an executive that they basically have to make a certain move.”

Former Eastern Conference general manager: “Sometimes, there are outside forces at play. There are moves that ownership will push on you and you have to agree to it. When you see a team that’s going into a new arena, usually there are deals that are made and it’s obviously about selling a lot of tickets. Look at the Brooklyn Nets’ deal with the Boston Celtics before they moved into Barclays Center. Look at the Orlando Magic giving Rashard Lewis over $100 million just before they moved into Amway Center. Almost every time a new building is opening, there’s going to be splashy deals that happen in order to sell more suites. You want fans to be really excited. I mean, if you can sell all of your suites and lock people in for five years, it’s worth it. Just know the GM isn’t always behind those moves.”

Some owners make the job harder for executives, especially the ones who want to be very involved in every step of the process rather than observe from afar.

Eastern Conference executive: “Sometimes, you’ll advise your owner, ‘Hey I don’t want to do this.’ But the owner can decide whatever he wants. I’m really fortunate that I don’t have to deal with an owner like that where I’m at now. But a lot of times, you aren’t just convincing a free agent or their camp to sign with you, you’re convincing your owner why it makes sense to sign them too. There are very few owners who just rubber-stamp transactions these days. Twenty years ago, there were owners who would just approve of everything, but not anymore.”

Former Eastern Conference general manager: “Usually, the owners who really meddle are the modern-day owners who are new money, as I call it. They’re billionaires, so they often feel like they know everything and it’s easy. They’ll watch games and say, ‘Let’s just trade for that guy.’ And because there’s so much information out there these days, they’re asking, ‘Why aren’t we going after so-and-so?’ Whereas some of the old-school owners would more or less let the GM run things. They were in tune with things and would say if they liked or disliked the move, but that’s it.”

Eastern Conference executive: “One thing that is becoming increasingly common is the agent getting to the owner during negotiations and then the owner wants to pay the player because of their relationship. If I had a nickel for every time I heard that story from an executive, I’d be a millionaire (laughs). Agents are getting smarter and smarter, so they know if they can get to the owner, they can get what they want. It really varies from organization to organization how involved the owner is. There’s so much work that’s done to get on the same page – and stay on the same page – as your owner.”

NEGOTIATING WITH THE AGENTS

During contract negotiations, agents come up with their asking price by presenting a list of comps, which are players who are similar to their client in terms of production and potential. Negotiations typically begin with the agent asking for a deal in the same price range as the comps.

Bobby Marks: “I think when you go into the negotiations, you’re hoping that it’ll be a win-win for both parties. I think if an agent’s intent is trying to one-up the team, that’s not going to be a good relationship for a long time. If you dig your heels in the sand and are really difficult [to negotiate with], people won’t want to do business with you down the road.”

Former Eastern Conference general manager: “At the end of the day, I always want to walk away from a negotiation with both sides feeling good about the deal. If the player and agent are satisfied, they’ll come in happy and that spreads throughout your organization and that can help your culture. If you want to win [the negotiation] and they feel like you screwed them over, they’re going to show up, but they aren’t going to be very happy about how things played out and that player may not completely buy into your culture. I always tried to make sure that everybody felt good about where the talks ended up.”

Eastern Conference executive: “I get the idea that you don’t want to win the negotiation and lose the relationship with the player or the agent. But, at same time, this is a business and you have to get the best deal for your franchise. The player may be upset – because players always compare salaries – but if your culture is really strong, they should be fine and get over with it. And if they’re the type of player who gets upset because you made him $12 million instead of $14 million, that may not be a player you want anyway.”

Western Conference executive: “These negotiations are tough because all it takes is one team to blow your contract out of the water and make your offer look disrespectful.”

Each player considers different factors when making their free-agency decision. If a team’s front office can figure out a player’s priorities, it could help them land the player.

Eastern Conference executive: “The most important thing is the money, without a doubt. The next most important thing is the situation. Players want to play and contribute on some level. If it’s a high-level, big-name player, they want to win. They’re competitive, they have a lot of pride. And most players want to be in an organization that treats them right and does the right thing. I don’t think the market is as big of a focus anymore. Players travel so much during the year and they can live wherever they want in the summer. A lot of players love Los Angeles, but they don’t want to live there because it’s just too much. Some players want to live there, but some don’t want that. And these days, you can’t just sell the market. You usually need success too. This is particularly true now that you can have your own shoe deal in Milwaukee (Giannis Antetokounmpo) or Portland (Damian Lillard) or Oklahoma City (Paul George before the trade) or Cleveland (Kyrie Irving before the trade) or anywhere else. You don’t need to be in Los Angeles or New York to become a superstar.”

WHAT HAPPENS WHEN FREE AGENCY BEGINS?

In the past, the free-agency period officially started at midnight ET on July 1. However, the NBA moved up the start of free agency this year to 6 p.m. ET on June 30. That’s when teams are officially allowed to talk to free agents and the two sides can agree upon a deal.

Bobby Marks: “Usually, your own free agents are your top priority. You’re calling them right at 6 p.m. ET on June 30. It’s not just the stars either; I’m sure the Clippers called Patrick Beverley right away, for example. You want those guys to feel valued and realize that you’re very interested in bringing them back.”

Former Eastern Conference general manager: “Sometimes, you’re meeting with a certain free agent that night. If not, you’re going down your list of targets and calling everyone. It was always weird to be calling guys at 12:00 a.m. ET and 1:00 a.m. ET. You’re trying to call them and get a hold of them, but a lot of other teams are trying to call them too. By, like, 2:15 a.m. ET, you finally finish up all of your calls.”

One GM explained that the player has a lot of control over his free-agency process. Some free agents want to meet with teams and see a big presentation, whereas others just want to do a phone call.

Eastern Conference executive: “June 30 was always one of my least favorite days of the year; I’m so happy that the NBA moved the time up. Like I said, we talk to the agents year-round and chat a lot in the days leading up to July 1 anyway, even though we aren’t supposed to talk. We are just waiting and waiting and waiting until we can finally do our deals. If you want to jump in early, you have the deal ready to be completed on July 1. It just depends on whether you want to strike early or not. You have to know when to be aggressive and when to be patient.”

Bobby Marks: “Those first few days, you’re just trying to keep up with everything. You aren’t really sleeping. You’re drinking a lot of coffee. You’re waiting to see what the top players will do. Back in 2010, we were in a holding pattern until about July 7 because nobody was going to make a move until LeBron James made up his mind. You’re just waiting. There’s usually a wave of mid-tier guys who will reach an agreement right away, but most things are on hold until the top-of-the-food-chain guys make a decision. It’s sort of like a storm is coming. It’s off the coast and you’re just sort of waiting on it to hit land; you just don’t know when it’s going to happen.”

While teams are weighing their free-agency options and negotiating with agents, they’re also keeping an eye on the trade market to see who might become available. Some of the biggest offseason acquisitions end up being trades rather than signings (and sometimes they come out of left field, like Paul George being dealt from the Oklahoma City Thunder to the Los Angeles Clippers).

Former Eastern Conference general manager: “In addition to the free-agency chaos, you’re constantly having trade conversations as well. As you’re weighing free-agency moves, there are trade possibilities being thrown your way too. Sometimes, you’re having to decide, ‘Okay, if we do this trade, where does that leave us in free agency?’ Or you may be considering, ‘Should we just make this trade and use our cap space that way?’ It’s a lot of juggling and thinking on your feet. You can spend a lot of time preparing, but things change very quickly.”

Western Conference executive: “Every team tries to come up with a great, well-thought-out plan for free agency, but the plan may get thrown out the window. There’s a lot of freestyling and last-minute changes. You must be able to think on your feet in order to thrive in this job.”

SOME THINGS ARE OUT OF YOUR CONTROL

At the end of the day, no executive is ever sure that a move will work out. Any contract can become ugly if the player struggles or gets seriously injured. Several executives admitted that there is a lot of luck that goes into these moves. Also, how a transaction is perceived can change very quickly.

One general manager recalled an offseason in which he signed a highly-coveted player to a lucrative contract, which was seen as a major win for his franchise. At the time, six other teams were trying to sign this player to a similar max-level deal. At the time, the GM was feeling a lot of pressure from within his organization to sign this player. The front office worked with the franchise’s marketing department on their pitch meeting and everyone was hoping that the player would come away impressed. “I remember thinking, ‘If I come back from this meeting and I don’t have a commitment from this player, I might be in trouble.’ That’s how badly everyone in the organization wanted this to get done,” the GM said.

He ultimately signed the player and the front office celebrated the seemingly terrific move. But the player didn’t continue on the trajectory that the front office had hoped and suddenly, the executive was being criticized for the deal. The same fans and media who initially praised the signing (and considered it a no-brainer) were labeling it a horrible mistake.

“You’re damned if you do, you’re damned if you don’t,” the GM said. “There’s a lot of luck that goes into this. We’re all trying to project how things will play out, but none of us can see the future.”

Former Eastern Conference general manager: “When you first make a move that initially seems good, everyone wants to say, ‘He’s a genius!’ Then, as the season starts and things play out, the same people are saying, ‘I can’t believe he did that deal!’ It happens when you make a big trade. It happens when teams sign players to big contracts. At first, it’s always, ‘This is such a great signing!’ Then, once the guy starts playing, it’s, ‘I can’t believe they paid him this contract!’ It’s the nature of the beast. You have to make decisions on what you feel is right. What you end up realizing is that you’ll be criticized when you don’t sign certain players too. Fans and media will never understand everything at play, but you’re criticized if you ‘let a player walk.’ An owner once told me, ‘If you listen to fans or the media, soon you’ll become one of them.’ That’s so true.”

Western Conference executive: “You may sign a contract that seems amazing and, in just a few years, it’s viewed as a horrible deal that’s holding your franchise back. You never know. You can prepare a ton and try to be smart with your money, but there are a lot of factors that are out of your control after the deal is signed. You just never know with these things. You just try to make the most informed decision and then you just sort of hope for the best.”