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What is it really like to talk trades with Danny Ainge?

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Current and former opposing front office executives spoke about their experiences of talking trades with Boston

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Danny Ainge was named General Manager of the Boston Celtics on May 9th, 2003. During the 18-year period he’s led the Celtics (2020-21 is season 18), Ainge has made 63 trades. That’s more than any other front office executive during the same timeframe. His willingness to deal earned Ainge the “Trader Danny” moniker.

As one Eastern Conference Executive put it: “Danny has been doing this longer in one place than almost anyone else. You only get to do that by being really, really good at what you do.”

Ainge has made at least one trade every season. These range from being part of the largest trade in NBA history in 2005 (five teams, 11 players, two players’ draft rights and two draft picks) to small deals like buying a pick for cash (Henry Walker in 2008) or dumping salary for a protected pick (Jabari Bird in 2019).

During the 2013-14 and 2014-15 seasons, the Celtics GM made a whopping 17 trades. In 2014-15, from mid-December to mid-January, Ainge swung five separate deals, including four in less than one week.

A Western Conference Assistant GM laughed about that spree: “I’ve never seen anything like that. Our office joke became ‘Boston make a trade today yet?’. It was crazy. And I think they did really well in every one of those trades too!”

As Ainge, and ever-present Assistant GM Mike Zarren, made trade after trade and piled up assets in terms of future draft picks, Boston was invariably mentioned whenever a player came on the market. When stars like Jimmy Butler, Paul George, Anthony Davis and James Harden came on the market, the Celtics were linked to all of them. Sometimes, Ainge would do himself no favors, when those players landed elsewhere, by intimating that Boston was “close” to making a move. This type of comment has become a bit of a go-to joke for the media over the years.

Over the years, because of Ainge’s propensity to do well in deals, a narrative has emerged that he feels he must “win” every trade. In an attempt to decipher the truth, CelticsBlog interviewed 16 current and former front office executives from around the NBA about what it’s really like to talk trades with Ainge and the Celtics. All 16 individuals (ranging from final decision-makers to front office assistants) were asked the same set of questions:

· What’s it like to talk trades with Danny Ainge and the Celtics?

· Does Danny Ainge drive as hard of a bargain as is often portrayed in the media?

· How often do you think Boston has really been “close” to trading for a star player?

· Do you think Danny Ainge has actually “won” most of his trades?

· Do you enjoy talking trades with Boston?

In exchange for anonymity, almost all were candid with their answers. Here is what we gleaned from those who have actually gone head-to-head with Boston in trade talks.

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What’s it like to talk trade with Danny Ainge and the Celtics?

· An Eastern Conference General Manager: “In my experience, there are layers. For us, we go through Mike Zarren (Celtics Assistant General Manager) first, before we ever talk to Danny Ainge. Getting through Mike is hard enough, because you have to be buttoned up. Your idea better be cap-legal, or Zarren is going to call you on it. And I’m pretty sure he does it off the top of his head!

Once you get past Zarren, Ainge isn’t so bad. He might try to tweak things a little bit, but I always found him to be reasonable. There were small changes, and to be honest, I do the same thing.”

· An Eastern Conference Assistant GM: “First, you have to understand that we talk trades every single day. Someone is texting someone with a question like ‘How do you guys feel about…?’ or sometimes it’s a more straight-forward ‘Are you willing to move…?’ almost all day, every day.

For me, I spend a lot of time talking to my counterparts around the league, which includes Mike Zarren for Boston. The single biggest thing I learned with Zarren is that you have to make sure your idea meets the trade rules. I swear he’s got a computer for a brain and knows immediately if something is off.

After that, my boss and I would talk to Mike and Danny together. The bosses may change things slightly, but they knew where we were generally headed. At that point it’s picks or protections or something, rarely the players involved.”

· A Western Conference Executive: “They’re tough. Danny pushes hard and Zarren knows every cap trick there is. I make sure my whole team is in the room, because I figure I am missing something. What I didn’t like was when I thought we were there a couple of times and Boston would ask for something else. We eventually got there, but it felt like a lot more work than it had to be.”

· An Eastern Conference GM: “I hate talking trades with Danny because I feel like I’m gonna lose on something. One time, he called me about a guy who wasn’t in our rotation. This guy had played like five games in two months. I immediately panicked and called my team and our scouts and asked them ‘What are we missing? Why does Boston want him?’. That’s the sort of stuff you second-guess when talking trades with Danny.”

· A Western Conference Assistant GM: “Easiest conversations we have, because they don’t mess around. You ask about a guy and they don’t want to talk about him, they’ll tell you right away that you are wasting your time. Danny and Mike are also up front if you call and they don’t want anything from your roster. Once, at the draft, they told us ‘You better be talking picks, because we don’t want any of your players’. That may sound harsh, but draft day is so crazy and time is so short, that you appreciate the honesty.”

· An Eastern Conference Assistant GM: “I find it depends on timing. Near the draft, Boston wants to move and move quickly. Everyone does, but they are in warp speed. I guess that’s because of trading so many picks on draft day over the years.

During the offseason, it’s ok until they need to do something because of a deadline or a player is signing or something. Same thing at the trade deadline. We’ve been involved in stuff with them and Danny and Mike change and evolve terms so quickly that it can be hard to keep up. Me and my boss can tell you every player on every team. With Boston, Mike knows their salary within a few bucks. I need our cap guys for that. That allows them to move really quickly and to tweak things on the fly without having to spend time checking. I’m still having our cap guys run it through our models, and Zarren is telling me the results and our cap situation for the next three years.

In-season is the best. Things are calmer. You can bat around ideas for a while. They are good partners in just talking through things. And because they’ve made so many deals, Boston is good about pulling in third teams they trust. There is a comfort there.”

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Does Danny Ainge drive as hard a bargain as is often portrayed in the media?

· A Western Conference Assistant GM: “(laughs) Yes! In my experience yes. I don’t think it’s the whole thing that he has to win the deal, but he wants everything he can get. One time our GM hung up the phone and said ‘I think I just gave Ainge the right to pick our next jerseys and the right to swap first-born children of future draft picks’. (laughs) It’s a little unnerving.”

· An Eastern Conference Executive: “Absolutely. We’ve walked away from deals with Boston because they push too hard for an extra piece. Sometimes it’s a player, sometimes it’s a pick. Once, it was draft rights for a guy we didn’t think would amount to anything, but we stuck to our principles. Damn sure if that player didn’t end up coming over and having a nice career. Sadly, we traded him for less than Ainge was willing to give for him.”

· A Western Conference Executive: “I don’t think Ainge is tougher than anyone else. We all push hard. But he’s not unreasonable. We did a deal once that took roughly a month to come together. We’d talk, walk away and come back every four or five days. It was never contentious or ugly. Eventually, we gave a little, they gave a little and we got there. That’s usually how it works. Another time, at the trade deadline, we tried to do a deal and couldn’t make it work. There just wasn’t the right match. It wasn’t about Danny pushing too hard.”

· An Eastern Conference Executive: “I once talked to our buddies with the football team in town and asked about dealing with the New England Patriots. When they asked why I was asking, I said ‘Because there is something about Boston. They set a walk-away price and can’t be budged!’. My buddy laughed and said that’s how the Pats are. I find with the Celtics that they know what they want and don’t move off of it. It’s both infuriating and refreshing. At least you don’t waste time.”

· A Western Conference GM: “Yes. We’ve done some deals with Boston, but sometimes it’s taken a third team. I think Danny knows what he wants and he trusts Zarren to figure out a way to make the cap work. More often than not, they have been correct. So, I can’t blame them. But it does get frustrating when you think you’ve made a fair offer and Boston pushes for more. You have to have the guts to just walk away.”

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How often do you think Boston has really been “close” to trading for a star player?

· An Eastern Conference Executive: “Look, trading away a star or trading for a star is the hardest thing you can ever do in this league. It’s pretty rare that you don’t give up too much or get too little. Because Boston has had so many extra picks and good, young players on good contracts, I bet they have gotten close a lot.”

· An Eastern Conference Assistant GM: “Close is so hard to define. We don’t call something close until we are running it by our owner. I guess it matters what you consider close. I think sometimes we say ‘We got close’ when what we really meant was ‘We tried”. For example, we made an offer when Anthony Davis was on the market. Were we close? No. Did we try? Yes. But it’s all about how you define it.”

· An Eastern Conference Assistant GM: “You know how the game works. We offer a top-55 protected second round pick for an All-NBA guy and we can tell the media and fans ‘Well, we tried to trade for him, but couldn’t make a deal’. That’s probably some of what is going on with Boston. Maybe not that extreme, but you get it. It’s about looking good and in some markets that matters. Especially when you’ve been around for as long as Danny has.”

· A Western Conference Assistant GM: “Probably not, but that’s more about it being really hard to make a trade. I’m not exaggerating to say that maybe 1% of the trades we talk actually happen. And I mean trades that are real, not just asking about someone. Trades that are actually legal and could be done.

Do the math. That means we aren’t close very often. In terms of numbers, Boston probably isn’t close. But if Danny or Mike or anyone there says they were close, it probably means they got it past just exchanging names.”

· An Eastern Conference Executive: “I’m sure they got close a lot of the times Danny said they did. But you have to understand, sometimes those are things we say to pacify the media and fans. No one wants the GM who just sits on their hands. That works in San Antonio, because they win all the time. Anywhere else, the fans expect you to be active. And with a million extra picks, I’m sure Danny was under pressure to make moves.

Here’s the thing though: I’m not sure getting close and not making the deal has missed for Boston. Trade for a couple of guys and you don’t have (Jayson) Tatum or (Jaylen) Brown. Make a deal for AD (Anthony Davis), and you’re out players and picks, and he probably leaves anyway. I think Danny has been right to walk away and not overpay.”

· A Western Conference Assistant GM: “People love to say ‘Sometimes the best trades are ones you don’t make’ and that’s kind of true. But Boston had all those picks. They landed some really good players and moved some to get Kyrie (Irving), but so many others were kind of wasted. I think Danny could have pushed a deal or two through if he had been willing to give up some of his picks. I bet last year, they wish they had traded for some extra bench guys at least.”

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Do you think Danny Ainge has actually “won” most of his trades?

· An Eastern Conference GM: “Didn’t you say he’s made like 60 trades in almost 20 years? You don’t get to make that many trades over that many years if you don’t win most of them! (laughs)”

· A Western Conference Assistant GM: “He got KG (Kevin Garnett) and Ray (Allen) and won a title. Now he has two young stars. I know that’s only a couple of trades, but those were two huge moves. And they were risky both times. I think he wins plenty.”

· An Eastern Conference Executive: “You don’t stay in the job as long as Danny has without doing well in most of your deals. I think what he did in 2014, when he rebuilt that team on the fly to give Brad (Stevens) his first playoff team, was remarkable. They made something like 12 trades (note: it was actually 10) that season. Each one was small, but each one was really good.”

· A Western Conference GM: “I think Danny has nailed the big trades he’s made. The smaller ones are a little rougher. They tried to fill out that bench around KG (Kevin Garnett), (Paul) Pierce and Ray (Allen) for so many years and he never hit the right mix.

More recently, they had to have chances to move picks for players, but didn’t. Now what do they have? Young players blocked on the roster and they used good picks to dump salary. Those are misses.”

· An Eastern Conference Assistant GM: “He’s won the ones that mattered most. They’re kind of the Buffalo Bills of getting close, but not getting there, but at least they’re in the mix every year. That’s mostly because Ainge and Zarren made the right trades and signings.”

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Do you enjoy talking trades with Boston?

· An Eastern Conference GM: “Yes. They are easy to deal with. Danny tells you when he’s not interested, switches to something he is interested in right away or walks away. My team loves Mike Zarren because he’s not arrogant. He might tell them something doesn’t work cap-wise or something, but he’s not a dick about it. And Boston is great about finding a third team for deals if you need one.

Oh, and they are up front if they plan on flipping the guy you trade them. I personally don’t care what you do after our deal. He’s not my player anymore. But some of my peers hate it. I think they worry about ‘Could I have gotten that deal?’. It’s not something I worry about, but Boston does tell you if that is their plan.”

· A Western Conference Executive: “Ummmm…no comment. (laughs). Not really. It’s hard to get anything done with them and they push hard for answers. We prefer to take our time. We’re not going to rush into anything. We’ve done deals with them, but we make them wait until we’re comfortable. That’s how Boston gets you. They make you make the mistake.”

· A Western Conference Assistant GM: “I love it, but that’s because it’s me and Mike (Zarren). He’s easy to work with. I think my boss has it a little bit harder with Danny, but we’ve done deals with them. And they’ve always been almost the exact framework that Mike and I worked out.”

· An Eastern Conference Executive: “Nope. Not at all. I feel worried that they know things I don’t know, especially at the draft. Maybe I’m just paranoid, because they’ve always been honest with me. But I start wondering what they see in a player that I don’t see.”

· An Eastern Conference GM: “I do. There’s no (expletive) with Boston. Get in, get out. It might take a bunch of conversations, but they aren’t wasting your time. And you get brutal honesty. Once we asked them what they thought of one of our players and the response was ‘You’re asking because he can’t play. Why would we want him if you don’t?’. And they were right. He couldn’t play.

Mostly, I appreciate guys who want to work with you. Need something they don’t have? They’ll get a third team. Want in as a third team? They’re happy to listen. When they call you, they get to what they want right away. If you tell them a guy is off limits, they might push a bit, but not too much. They’ll circle back to see if anything has changed, but not every couple of days like some others do. They respect you when you tell them no, because that’s what they expect in return.

Look at this year. Charlotte didn’t have to do Gordon Hayward as a sign and trade. They weren’t dumping salary and still had to eat (Nicolas) Batum’s salary. But they did it because the year before, Boston helped them get Terry Rozier in the double sign and trade with Kemba Walker. That’s how you build equity and good relationships.

I think Danny has made so many deals with everyone because there’s no (expletive). No one feels like information is being withheld or that they are being lied to. That’s important in our business. You have to have trust and I trust Boston when making a trade.”