If there was one certain throughout Danny Ainge’s run as the Celtics’ chief front office figure, it’s that if there was a big fish to be caught, Ainge and the Celtics were out there fishing pole in hand.
It didn’t always lead to that next great Celtic — it was always going to be hard for the Celtics to come through with a sequel to the Kevin Garnett trade, all things considered — but it did always lead to the Celtics being one of the first teams mentioned whenever any top-tier talent became available.
One of the greatest examples of that was the C’s being mentioned, and on more than a few occasions, during the Jimmy Butler sweeps during Butler’s time with the Bulls.
But that ultimately turned out to be one of the best non-trades Ainge made during his Boston tenure, Ainge revealed in an interview with Quentin Richardson and Darius Miles on the Knuckleheads podcast.
BOSTON, MASSACHUSETTS – JULY 17: Celtics President of Basketball Operations Danny Ainge reacts during a press conference introducing Kemba Walker (not pictured) and Enes Kanter (not pictured) at the Auerbach Center at New Balance World Headquarters on July 17, 2019 in Boston, Massachusetts. (Tim Bradbury/Getty Images)
“Red [Auerbach] once told me when I first got the job in Boston, he said, ‘Some of the best trades I ever made were the ones I wasn’t able to make,'” Ainge said when asked about any notable trade that didn’t come to be in Boston.“There was a time when I was trying to get Jimmy Butler from Chicago when I was in Boston, but [the Bulls] wanted a lot, so we didn’t do it.”
A Bull from 2011 through 2017, the trade rumors involving the 6-foot-7 wing during his time in Chicago seemed to hit a fever pitch during the 2016 NBA Draft, when Butler was considered an almost certainty to be moved.
The Celtics, who at that point still possessed an absolute ton of assets and in possession of the No. 3 overall pick in that year’s draft, were one of the more popular teams bandied about during that time.
So, what was the ask from the Bulls that made Ainge & Co. pivot off a player they loved?
“And it ended up [that] it would’ve been Jaylen [Brown] and Jayson [Tatum]. Both those draft picks that we got Jaylen and Jayson with,” Ainge revealed. “Like, I loved Jimmy and I was trying to get him. Could’ve drafted Jimmy late [in 2011]. I liked him even then, but like now he had proven how good of a player he was.
“So yeah, that was probably one.”
MIAMI, FLORIDA – MAY 17: Jaylen Brown #7 of the Celtics and Jimmy Butler #22 of the Heat look on during the third quarter in Game One of the 2022 NBA Playoffs Eastern Conference Finals at FTX Arena on May 17, 2022. (Michael Reaves/Getty Images)
Heavy price tag and all, it’s a move that Celtics fans appeared to want at the time (though they likely didn’t know the complete asking price), as the selection of Brown with the No. 3 overall pick was booed by those in attendance at the team’s draft watch party. The Celtics also booed the Guerschon Yabusele and Ante Zizic selections that came 13 and 20 picks later respectively (can’t blame ’em there, as time proved).
Brown, for what it’s worth, has remembered the booing of his selection over half a decade later.
“They booed me,” Brown recalled in an interview with Slam Magazine’s Deyscha Smith earlier this year. “Wyc [Grousbeck] was calling my name and he’s up there saying, ‘Jaylen, he’s gonna be one of the best players the city has ever seen. He’s up there, like defending the pitch. We’re sticking with it, y’all get over it. This is who we’re going with.’”
Whether or not the Celtics were booing Brown himself or the fact that the Celtics didn’t move the pick for what would be considered more of a ‘win-now’ piece remains up for debate.
MIAMI, FLORIDA – MAY 17: Jimmy Butler #22 of the Miami Heat talks with Jayson Tatum #0 of the Boston Celtics during the third quarter in Game One of the 2022 NBA Playoffs Eastern Conference Finals at FTX Arena on May 17, 2022. (Eric Espada/Getty Images)
But the fact that the Celtics didn’t move all of that for Butler remains one of the greater what-ifs throughout Ainge’s run with the Celtics, especially when looking at Chicago’s insistence that the C’s included both the Brown and Tatum pick, both of which were acquired via the Celtics’ swindling of the Nets for Garnett and Paul Pierce.
That’s also without getting into what else would’ve had to be thrown in on the part of the Celtics to complete the deal, which almost certainly would’ve been more than two draft picks given the NBA’s trade structure.
Jimmy Butler of the Miami Heat is defended by Jayson Tatum of the Boston Celtics during Game 6 of the 2023 Eastern Conference Finals. (Mike Ehrmann/Getty Images)
What’s interesting is that the Celtics did ultimately decide to part with some of the assets Stewart mentioned in his 2016 scoop on the Bulls-Celtics talks, but they used ’em to acquire Kyrie Irving from the Cavaliers and Marcus Morris from the Pistons in 2017.
Would a Kyrie-Butler-Horford trio been enough for Kyrie to want to stay with the Celtics (it was once rumored that Butler and Kyrie had interest in a potential team-up together somewhere in the East), and more importantly, would it have been enough for the Celtics to ultimately win a championship?
That, like all hypotheticals, is a complete unknown.
But Ainge and the Celtics’ genius behind opting not to move the 2017 Brooklyn pick honestly goes without saying.
With that pick, the Celtics got a legitimate superstar in Jayson Tatum. And there’s no denying that Tatum has a greater ceiling than Butler, and that the Celtics’ window to win a championship is greater with Brown and Tatum than it would’ve been with Butler and (insert other big pieces here).
BOSTON, MASSACHUSETTS – MAY 29: Jimmy Butler #22 of the Heat dribbles against Jaylen Brown #7 of the Celtics during the third quarter in Game 7 of the Eastern Conference Finals at TD Garden on May 29, 2023. (Maddie Meyer/Getty Images)
Of course, there’s tremendous irony in Brown and Tatum nearly being traded for a player they’ve gone head-to-head against in three of the last four Eastern Conference Finals (and with Butler’s heat emerging victorious in two of those three playoff meetings), but this remains a clear-as-day win for the Celtics.
When the Bulls ultimately decided to move Butler, it was to Minnesota and in exchange for Zach LaVine, Kris Dunn, and the rights to Lauri Markanen. 17 months later, Butler was on the move again, this time to Philadelphia and in exchange for Jerryd Bayless, Rob Covington, Dario Saric, and a second-round pick. As the trade returns dwindled in terms of high-ceiling impact, and as Butler ultimately decided to walk to Miami via free agency, there’s no denying that gifting Chicago two franchise cornerstones for Butler would’ve aged like milk for Ainge’s club.
Maybe Red was onto something.
