Will high risk lead to high reward? How Danny Ainge's bold moves made Boston a title contender

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On a late June morning, maybe not coincidentally around the same time that rumors were swirling about future of disgruntled San Antonio Spurs star Kawhi Leonard, Boston Celtics coach Brad Stevens popped into the trainer's room at the team's old practice facility where Gordon Hayward was navigating his daily rehab. The conversation quickly shifted to the life of an NBA general manager.

"I was telling Gordon, I can't ever see myself wanting to be a front-office guy," said Stevens, who has plenty of input in Boston's roster building but prefers to leave the heavy lifting to president of basketball operations Danny Ainge and his small front office circle featuring Mike Zarren, Austin Ainge, and Dave Lewin. "I just think it's the amount of things that you're always bouncing around and balancing. And having to make those hard decisions about moving guys. I think that would be really hard to do.

"I think Danny Ainge is obviously great at his job. And his staff, they're all really good at their jobs. They work really hard and, because of that, we're in really healthy shape here as we move forward."

Stevens will enter his sixth NBA season with a roster brimming with talent, in large part due to the bold decisions that Ainge routinely made during roster construction. It seems impossible that, five years ago this month, Stevens trotted out a starting five of Avery Bradley, Gerald Wallace, Jeff Green, Brandon Bass, and Vitor Faverani for his first NBA game. 

Ainge and his NBA remodeling company quickly went to work, completing 22 trades and roughly 75 major transactions over the next four years, reshaping the team multiple times until Ainge was certain it was a legitimate contender.

Which is exactly what the Celtics are as they prepare to host the Philadelphia 76ers in the NBA's season opener on Tuesday night at TD Garden.

* * * * *

The 2013 blockbuster trade with the Brooklyn Nets that returned one of the most prized hauls in NBA history is often lauded as Ainge's masterpiece. And yet it wouldn't be nearly as romanticized if not for the way Ainge parlayed the pieces of that deal into both the talent on the current roster, and the future assets that should allow Boston to contend deep into the future.

Ainge did it all in a very Red Auerbach-like manner, with a healthy dose of risk associated with most transactions. While some general managers tread with caution, Ainge routinely made tough calls while shrugging off the magnitude of such decisions.

"It's just basketball," Ainge often shrugs when asked about his boldest moves.

Now, after all that high risk, the Celtics are hoping for high reward.

"Danny's not afraid to take chances," said Al Horford, a smile forming as he looked around Boston's sparkling new practice facility that bears Auerbach's name and marveled at how much this team has changed even since he signed a four-year, $113 million deal in the summer of 2016.

"Danny is a risk-taker. And I definitely appreciate that."

A closer look at four of Ainge's most risky moves while building the core of this current roster in the aftermath of the Nets trade:

The Kyrie deal: A lot to give up with little guaranteed

It's easy to sit here now and say the Irving deal was a no-brainer. But rewind to the night of that jaw-dropping swap with the rival Cavaliers and there was genuine outrage from many Celtics fans that the team gave up All-NBA guard Isaiah Thomas and Jae Crowder and Ante Zizic AND the Nets' 2018 first-round pick. 

Even Horford admits the deal left his head spinning.

"To be completely honest: I was like, ‘What's going on with that?'" Horford said of a swap that capped Boston's unexpected summer overhaul. "The Gordon [Hayward pursuit], I knew about because I was in it and we were making the pitch for him. The Kyrie stuff was shocking, I would have never seen that coming. 

"But Danny told me before I signed here, ‘We're going to get people around you and we're going to contend. We have the assets, we have everything to make that a reality.' It's one thing to say it, it's another thing to deliver it. I didn't know specifically how it was going to happen, that's why it was so surprising to me to see how it all unfolded."

The real risk in the swap was the possibility of giving up all those assets with the very real possibility that Irving could opt out of the final year of his deal and sign elsewhere next summer. Which is why Celtics brass, including Ainge, had to feel a sense of victory when Irving unexpectedly announced his intentions to re-sign here in the summer of 2019.

Even Irving recognized the risk the Celtics took bringing him here.

"What more can you ask for from an organization than taking a chance and getting me out of Cleveland? Really taking a chance regardless of whether I signed back or not," said Irving. "They had the same attitude. They just wanted to show me what being a Celtic is about, and hoped I would come around, and I absolutely did."

Trading back from No. 1, drafting Jayson Tatum in 2017 draft

Identifying Tatum as the best player at the top of the 2017 draft board was bold enough given the fact that Markelle Fultz was widely anointed the surefire top selection. But having the chutzpah to move back and be fully confident that neither of the teams in front of you would have a sudden change of heart and steal Tatum took some confidence as well.


The reward for taking that chance? The Celtics are set to collect the Sacramento Kings' 2019 first-round pick, so long as its not the top overall selection. Boston could have as many as four first-round picks in next year's draft and is well positioned to maintain a pipeline of young talent for the foreseeable future.

Last we saw Tatum in a meaningful game, he was putting the exclamation point on his rookie season by dunking on LeBron James and nearly willing Boston to the NBA Finals. After a summer working out with Kobe Bryant and Penny Hardaway, Tatum might just be poised to make a leap to NBA All-Star, and, you might have heard, he's still only 20 years old. Said Terry Rozier this preseason: "He's got that like, ‘I'm the man,' look." 

Drafting Jaylen Brown at No. 3 in 2016 draft

Celtics fans peppered co-owner Wyc Grousbeck with boos when he announced to season-ticket holders at Boston's 2017 draft party that the team had selected Brown with the No. 3 pick.

With Thomas and Crowder injecting new energy into this Celtics team, there was a palpable desire for Boston to use its treasure trove of assets to acquire a more established talent. Fans yearned for Jimmy Butler, which is funny now when you juxtapose the drama and uncertainty in Minnesota with the tranquility that exists now in Boston.

Heck, some fans would have settled for Boston drafting Kris Dunn over Brown, particularly given how some analytics suggested Brown had high-bust potential based on statistical comparisons to past draftees. 

Brown has been proving the scouting reports wrong ever since. And he made a pronounced leap last season in the aftermath of Hayward's season-ending injury, asserting himself as an impact player and leaving many reassessing his NBA ceiling. Given the mixed return on the players selected after Brown (Dragan Bender, Dunn, Buddy Hield, Jamal Murray, and Marquese Chriss were the next five picks) and considering the way his skill set has only added to Boston's versatility, it seems Ainge's gamble paid off.

And Brown isn't content with the strides he's made. He's forever motivated to prove those doubters wrong.

"I think I was born with [a desire to get better]," said Brown. "I had that will and that fire to continue to get better, move forward and be the best version of me I can be."

Not trading up for Justise Winslow, drafting Terry Rozier at No. 15 in  2015 draft

Ainge likes to note how some of the best advice Auerbach ever gave him was how the best moves are often the ones you don't make. Overflowing with future assets entering the 2015 draft, the Celtics made a well-publicized push to move up with their eyes on Justise Winslow. Ainge would have parted with some of the team's most prized picks but the Charlotte Hornets ultimately elected to keep their selection (taking Frank Kaminsky) before the Heat snagged Winslow.

When that deal fizzled, Ainge could have gotten conservative with the team's pick at No. 16. Instead, he drafted the unheralded Rozier, earning scathing reviews from those that had Rozier pegged as a late first-round talent at best.

Ainge showed unwavering faith in Rozier and that confidence was rewarded last season when Rozier dazzled in the playoffs in place of an injured Irving. Now Rozier is a household name, his "Scary Terry" brand exploding on a postseason stage. He's in line to command a monster payday next summer as a restricted free agent but this season he'll be a key cog for a Boston bench that could dictate just how successful this team will be.

Ainge loves Rozier's personality and is forever joking around with him. When Rozier gloated about his new shoe deal with Puma this month by saying he was "trying to have some drip," the not-so-hip Ainge playfully responded by asking Rozier on social media, "If I could get one drop off that drip, would I be cool?"

Rozier's response?

"He can get some boss drip," said Rozier. "I'll give him some boss drip. I'm not about all that other drip."

Ainge has most certainly earned that boss drip. But it's another championship ring that would really add to his swagger.