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How to Go All In (or Not), According to Danny Ainge

The Celtics architect has built a super-good team, but can he get it to the next level? And does he need a star to do it?

AP images/Ringer illustration
AP images/Ringer illustration

After a long summer of topless championship parades, free-agency meetings in the Hamptons, Snapchat mishaps, and gold medals, the NBA is finally, truly, really, almost back. The start of training camp marks the beginning of our NBA Preview.

This is Squad Goals Week. We’re looking at a bunch of teams and asking one question: What constitutes success for this franchise?

“Go with Danny Ainge. He’s just lucky.”

This was Red Auerbach’s advice to Celtics co-owners Wyc Grousbeck and Steve Pagliuca during their search for a president of basketball operations in 2003. “That’s a high compliment from Red,” Grousbeck told me last week. “Sometimes things just happen, other times you make your own luck.”

Ainge learned a great deal from the man who drafted him in 1981. “I liked Red because he was a risk-taker by nature,” Ainge told me last month. The 2016–17 Celtics are as good as a team can be in this league without a superstar to carry them to the top. Yet some fans would be willing to blow it up if it meant bringing in that singular, big-name talent. The Celtics do need to go from good to great, but they can’t do it by making rash decisions. Luckily, Ainge has some experience in these matters.

During his tenure in charge of the Celtics, Ainge has accumulated assets, assembled the Big Three, helped the Celtics win Banner 17, and slammed the reset button while Paul Pierce and Kevin Garnett still had perceivable value. He is now considered one of the NBA’s most astute team builders, but it wasn’t always this way. The Celtics won an average of 34.5 games during the first four seasons of Ainge’s reign. It was a fallow period, but Ainge proved himself something of a draft-day savant, adding Al Jefferson, Kendrick Perkins, and Tony Allen with no pick higher than no. 15. It was hard to get Celtics fans to see the bigger picture, though. In 2007, he and then-head coach Doc Rivers had to weather public calls for their jobs.

“Danny had done the best he could with the draft picks. Doc had coached the best he could with a team that wasn’t ready to win games,” Grousbeck said. “We couldn’t ask any more of those guys.”

Unbeknownst to the general public, Ainge was working on the KG Plan, concocted three or four years before the summer of ’07. Maybe if fans had known, they wouldn’t have marched down Causeway Street with pitchforks and torches in hand. “‘We’ll be ready. We’ll have enough assets to trade for him if he becomes available. I don’t know if Minnesota will renew him.’ That’s exactly what Danny said,” Grousbeck recalled. “So through all the tough times, the assembling of picks, playing the kids, Doc taking the losses on his record as we lost — it was all toward a goal of building those kids up so they’d become tradable assets where we’d keep some, trade others.”

After years of asset hoarding, Ainge acquired Garnett from Minnesota, pulling off the first 7-for-1 in league history. The Celtics went on to win their 17th NBA title in 2008, came up short the following season, competed for a few years after that, and then tore it down in 2013 by trading Pierce and KG to the Nets for a bazillion unprotected first-rounders and assets.

Now the Celtics are positioned to pounce on the next star player who becomes available while building a team that’s tied for fourth-best title odds this season. Boston got to this point by making opportunistic moves: trading for Isaiah Thomas, Jae Crowder, and Jonas Jerebko; signing Evan Turner for a bargain; and flipping overachievers like Jordan Crawford for assets. While Ainge said, “I don’t really look at them as assets,” those players have undeniably positioned the team to get in the same room as the summer’s best free agent, Kevin Durant, and actually sign the second-best free agent in Al Horford.

“Nobody has ever done it better in the history of the league than how Danny did it, ever. Nobody’s ever done that,” Blazers president of basketball operations Neil Olshey told NBA TV’s Open Court this summer. “It’s unprecedented, the assets, from where that team would’ve been in 18 to 24 months and what it is back to today.”

AP Images
AP Images

Nobody is forcing Ainge to build this way. “Ownership not only supports us, but they’re involved with our plan,” he said. “They are involved to a great extent in where we are today and our plan moving forward.”

Grousbeck bought the team in December of 2002 after organizing an investment group called Banner 17 LLC. “I made it clear to everybody that we could win Banner 17 and there would be no dividends or anything else,” Grousbeck said. “Our first priority was to go and win, and the financials would take care of themselves.”

Placing the financial aspect of an NBA team “way down the list,” in Grousbeck’s words, is striking compared to other franchises or even businesses. Other teams might panic to make a splash signing for the sole purpose of having fans fill the seats. That doesn’t make the Celtics better, it just makes them different. Grousbeck said they’re not at the same level as the Patriots, but that’s who they aspire to be. “I think that money just doesn’t come into the conversations very often,” Grousbeck added. “What we’re trying to provide those guys [with] is patience. It’s another twist on financial. We’ll say that we’ll take two, three, or four years, whatever it takes to rebuild.” The Celtics are a legacy franchise with a massive local and worldwide audience. They have some wiggle room that the Pelicans or Hornets might not have to take calculated risks on overlooked players.

“The biggest thing that I appreciate about Danny is he doesn’t look at guys as finished products,” Celtics head coach Brad Stevens said in an interview with Boston’s 98.5 The Sports Hub. “I think it’s the ‘glass is half full’ kind of way at looking at things. It’s obvious who the superstars are and there are a lot of other people in this league that are asked to play a role to help their teams be the best they can be, and that’s most of the league. So can we find guys that, for whatever reason, have been undervalued because maybe their role has been a little different than we would play them.”

The patience of ownership and the front office has put the Celtics in a unique position. Last season they became only the 10th team over the last 40 years to win more than 45 games and select a player in the top five of the NBA draft, choosing Jaylen Brown from Cal. With Nets picks still in their possession (the rights to swap in 2017, and unprotected in 2018), they could conceivably do it for a second and third season in a row.

Here are the other instances in league history when this has occurred:

Based on my research, history doesn’t guarantee future success, but that list provides a strong track record for franchises adding a top pick in addition to their already productive teams. Two franchises became dynasties (’80s Celtics and Lakers) and two won a title (Bullets and Pistons), and four of those players are Hall of Famers. The two busts (Bowie and Darko) were sandwiched between future Hall of Famers. All of this is to say the Celtics don’t need to duplicate the ’07 mega-trade fireworks. “When you make mistakes is when you say you have to do something,” Ainge explained. “There’s a lot of names out there that we’ve talked with about trying to acquire, but we wouldn’t pay the price. We’re prepared to build on what we have if that’s the best path.”

In other words, there’s no rush. They have a perfectly viable Plan B that emphasizes talent development and building through the draft. The Celtics won’t settle for a double that drives in a few runs when they can load the bases and hit a grand slam. That’s a surprise to Kevin McHale, Ainge’s teammate of eight seasons and trade partner in the Garnett deal. “Danny is one of the most impulsive people I know, and I’m shocked he doesn’t make a trade every week,” McHale said during a recent conference call. “He’s a disciplined general manager, which is funny because he’s a very undisciplined person.”

Close followers of the Celtics rumor mill will recognize the person McHale is describing. Boston often finds itself at the center of trade chatter. That charged atmosphere is partially self-created. Ainge and Isaiah Thomas both said the Celtics weren’t done even after signing Horford. Grousbeck said “there could be some fireworks” in 2014 when the target was Kevin Love. A fan can be left feeling duped if they don’t read past the tweet or headline.

Take this past draft night for example. The Celtics were in deep trade discussions with the Bulls for two-time All-Star Jimmy Butler. When Adam Silver came to the podium, Celtics fans expected to hear the name of Providence point guard Kris Dunn, since he was the player Chicago wanted. Then Jaylen Brown was announced. Fans unleashed a Darth Vader–style “Nooooooooo” before booing ferociously. Maybe the anger comes from great expectations. Maybe it’s the “long wait” after not winning a title since 2008. No matter, it’s the same story as 2007, months before Ray Allen and KG were acquired: It’s hard, if not impossible, to judge teams’ decisions to either make moves or stand pat when the facts are unknown.

The Chicago Tribune reported the partial terms of trade discussions this summer: Butler to Boston for Crowder, the no. 3 pick (Dunn), and the no. 16 pick. A league source with knowledge of the situation indicated to me that Chicago also demanded an additional starter-level player in the deal. It’s unclear what was and wasn’t discussed, but what we do know is that the Bulls weren’t prepared to go full rebuild (though that could change by the trade deadline).

“We’re trying to find deals. And sometimes you have to make small deals in order to be able to have big deals,” Ainge said. “You have to put yourself in position with good young players and good contracts and future assets. It puts us in the game if there’s a player that becomes available in the trade market, but they have to like those young players and assets,” he continued. “In the meantime, we’re not sitting around and waiting for something like that to happen. We’re trying to make something like that happen, but we’re not just chasing every player out there.”

The possible Butler trade raised an interesting question: What player is worth a coffer-emptying offer? A seismic trade is the preferred path for the Celtics, but Butler isn’t quite in the same class as the league’s indisputable superstars, like Paul George, Russell Westbrook, or Anthony Davis. “Our goal is clear, which is Banner 18,” Grousbeck said. “Sometimes there may be quick ways that can accelerate us there. Other times you have to be patient or slow.” They may not quite be on Cleveland’s level, but Cleveland is an injury or two away from being on theirs. The Celtics are opportunists in the trade market, but they could be in the playoffs as well.

“If there’s a mega-trade in the future, great. Otherwise we’ve got room for a max free agent this summer,” Grousbeck said. “I like where the team is but I feel that we are a significant step below where we need to be. … There’s more to do, and we’re not kidding ourselves that we’re there yet.”

With a projected salary cap in 2017 of $102 million, Boston has a simple path to max space by declining nonguaranteed options of multiple players. You and I don’t need league sources to know who the max-level free-agent targets are. The list is short. Options are scarce. It’s reasonable to assume that Kevin Durant will stay with the Warriors, but Boston hasn’t stopped dreaming just in case Golden State turns out to be a single-season fling. The Celtics also expressed interest in Blake Griffin this summer, so it’s conceivable they’d have interest when he hits free agency.

To be clear, those conversations were merely exploratory since the Clippers had no interest in retooling, per a league source. Gordon Hayward received interest from Boston in 2014 when he was a restricted free agent; Hayward and Brad Stevens also have unfinished business after experiencing a heartbreaking national championship loss at Butler. Beyond that, there is no star, max-level, unrestricted free agent available in 2017 who is both reasonably acquirable and enticing to the Celtics.

Boston’s path forward is easy to project if the Celtics add a superstar. They’d have their contending core, so when Thomas and Avery Bradley hit the market in 2018, Boston would go into the luxury tax to retain them. Grousbeck did that during the Big Three era and admitted that he told Durant that he’ll do it again. “We’ve paid the tax, and this isn’t about money,” Grousbeck said in a radio interview. However, if the Celtics are unable to land a star, the bargain contracts of Thomas (average remaining annual value of $6.4 million) and Bradley ($8.5 million) could become problematic since the team would have enough to renegotiate and extend one or both of their deals.

While the Celtics would eventually like to lock up the guard tandem, the order of operations matters. If it weren’t for those cheapo contracts (or Crowder’s, at $7.1 million), they never would’ve had the space to add Horford and pursue Durant in the first place. Signing them before acquiring a star would limit Boston’s flexibility to pounce on a star if one becomes available.

In the meantime, Ainge will continue to practice the lessons learned from Auerbach. “He was a master of just managing personalities. It was one of his greatest gifts as a real people guy. I loved that about Red,” Ainge said. “Red saw the little things in the game that make the players good.” These were the overlooked details of the game — screening, hustling, and closing out. “It wasn’t just about how many points and rebounds you got.”

Ainge played 14 years in the NBA, coached the Suns for four seasons, and has been in charge of the Celtics since 2003. Despite that résumé, Ainge leans on other voices within his front office. “He’s a teammate, not a sole operator,” Grousbeck said. “That’s an important characteristic of a general manager.” This is a lesson Ainge learned from Red: “He was smart and thought things through, and he had a lot of people he trusted and confided in. It wasn’t like he was working on an island.”

The first thing Auerbach ever asked Ainge was, “You know why I got you, Ainge?” Ainge, then a bright-eyed 22-year-old, figured it was simply because he was a good player.

“No, I got you because you’re an instigator.”

As a general manager, Ainge has instigated with purpose, taking aggressive steps to achieve the team’s goals. Only three years ago, after trading Pierce and Garnett, the future was murky. Today, it’s clear: a contender in the East with arguably the most assets in the league. I asked Grousbeck if he would have believed me had I, back in 2013, told him the Celtics would be where they are today. He laughed.

“I don’t believe it today.”