The Milwaukee Bucks never gave up on Jrue Holiday.
It was never quite that simple.
Last October, six months after they’d been bounced in the first round by Miami and went looking for ways to upgrade the roster, they saw a chance to pair Giannis Antetokounmpo with a fellow living legend in Damian Lillard and decided to do the deal. In fairness to the Bucks, who surely had mixed emotions as they watched Holiday dominate Game 2 of the NBA Finals for the Boston Celtics on Sunday night in their 105-98 win over Dallas, let’s not forget that the move was almost universally praised at the time.
But the secrecy with which Milwaukee’s front office operated in those weeks leading up to the trade, including the extremely unorthodox decision to spend those final three days using the team’s home locker room at Fiserv Forum as a temporary headquarters of sorts so as to avoid the possibility of any media leaks, spoke volumes about how much they still revered the two-time All-Star who played such a massive part in their 2021 title.
In the off chance the Lillard deal with Portland didn’t get over the finish line, there was a strong preference that Holiday never know that he had almost been moved. What’s more, there was still an internal confidence that the Bucks could win the whole thing with Holiday for a second time if the roster remained intact.
These are the kinds of tricky, and often sensitive, situations that come with running an NBA team. But the deal went down, of course, and the 33-year-old Holiday spent just four days as a member of the Trail Blazers before landing with this Celtics team that is halfway toward its goal of winning the franchise’s 18th championship (which would break their tie for the league lead with the Lakers).
To hear Holiday reflect on it all after his remarkable Game 2 showing, when he had 26 points (11 of 14 shooting), 11 rebounds and three assists while helping hold the Mavericks below 100 points in back-to-back games for the first time in this postseason, was to understand that he’s at peace with it all. And no, as he insisted, that’s not the case because he’s still in the hunt for the Larry O’Brien trophy and the Bucks have been home since early May.
“I’m close to (Bucks general manager) Jon (Horst),” Holiday told The Athletic after Game 2. “Obviously, we’ve been through a lot, and we’ve won together. But I’ve never really been the type to get my feelings hurt. I would even tell you that on this trade, my feelings weren’t hurt.
“It was just that for me, personally, and I can’t speak for my wife and my kids, but it was a shock. It was a shock, right? You’re waking up out of a nap and getting a call and five minutes later, you’re going somewhere else. Would it have been nice to know, maybe like a day ahead? Yeah, but I understand Jon’s point of view — 100 percent. It’s not an easy thing to do.”
His wife, Lauren, had been vocal with her frustration about how the deal was handled back then. But time heals all wounds, and Jrue now finds himself in a better basketball place than he was before. As he remembered, the Trail Blazers’ handling of his uncertain future played a pivotal role along the way.
“Portland was in communication with me about what I wanted to do,” Holiday said. “They told me their timeline, and how they saw the team and what I would bring and all that. But they also asked if I wanted to be (traded). So they gave me the options, which I truly respect, because I’ve never gotten that before. (Trail Blazers head coach) Chauncey (Billups) and the GM (Joe Cronin) did a great job of just communicating with me, and honestly putting me in a place to be here now. So after we had that conversation, there was three or four days of just not knowing where I was going to go. (But) there was an understanding that (his next team) would be competitive. There was an understanding, and they sent me all the way back here.”
When Holiday arrived in Boston, that meant going from a decorated 54-year-old veteran coach in Mike Budenholzer to a 35-year-old in Joe Mazzulla who was entering his first full season in charge of the Celtics. Holiday and Mazzulla had only spent time together once, during the 2023 All-Star weekend in which Holiday saw just nine minutes of playing time in Team Giannis’ 184-175 win over Team LeBron.
“I actually appreciated him playing me just (nine) minutes in the All-Star game,” Holiday said. “I’m just not as good as the other people, and we won the game. So yeah, he coached well.
“And I actually talked to him more about his faith and more like outside of basketball, and got to know him a little more, at the All-Star game. That was cool, kind of getting to know somebody and building a relationship and not even knowing that in the future, he’d be my coach.”
But even before they’d connected that weekend, Mazzulla said he felt like he knew Holiday because of their shared Christian faith. More specifically, Mazzulla would often use a mobile app that featured Holiday reading bible verses to users.
“His voice is on the app, reading verses, and I would listen to it,” Mazzulla told The Athletic. “So I’ve always had, like, a spiritual connection to him.”
The connection grew as their first season together went on, with Holiday’s two-way talents giving the Celtics the sort of perimeter defense that no team in the league could claim. With Jayson Tatum and Jaylen Brown leading the way, and Holiday joining Kristaps Porziņģis as the new additions who make this Celtics team so much more potent than the one that fell to Golden State in the Finals two years ago, Boston ran away with the regular season. And after it all went so well, Holiday was rewarded with a four-year, $135 million contract extension in mid-April that will make him a mainstay of this Celtics era.
As we were reminded in Game 2, the Holiday influence isn’t always front and center. He was the undisputed star of the latest Finals affair, having made the Mavericks pay on this night when Tatum and Brown were average by their standards, but spent his postgame news conference making sure the basketball world knew where he stood in the Celtics’ power rankings. After saying on a SiriusXM interview that he agreed with Dallas coach Jason Kidd’s assessment that Brown was Boston’s best player, he took the time to clarify that he saw Tatum and Brown as the team’s co-leaders.
Truth be told, it was Holiday who looked like the Celtics’ best player on Sunday night. And for Mazzulla, who has seen his impact up close all season long, he couldn’t be happier that the Bucks decided to move him along.
“I felt his impact in moments throughout the season,” Mazzulla said. “He’s so good, and so nice, that he doesn’t want to step on people’s toes. But there’s been like 10 to 12 times where he’s taken the reins of the game, and you’d be like, ‘Okay, that’s the guy.’ He picks and chooses his spots really, really well, and it’s priceless to have.”
(Top photo of Jrue Holiday: Mercedes Oliver / NBAE via Getty Images)
