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Brian Windhorst, ESPN Senior Writer
AS TEAMS GATHERED ahead of training camp in September, a surprising piece of information came down the NBA rumor mill: The Milwaukee Bucks weren’t just in play to acquire Damian Lillard in a trade; they had become the favorites.
How were they going to do it? This is what team front offices were attempting to figure out. It was a potentially league-altering transaction, and there was sure to be fallout.
With a jammed payroll, limited draft assets and only a couple of tradable young players, the Bucks didn’t have a simple way to pull off such a blockbuster. Khris Middleton and Brook Lopez, two large-salary stars who plausibly could have been in an offer to help Milwaukee match Lillard’s $45.6 million salary, had just signed new contracts and weren’t permitted to be traded for months.
The Portland Trail Blazers had done a good job all summer of keeping details of the Lillard trade talks private. But now there was a blitz to scrounge up details. As the cap strategists and executives examined the situation and spoke among themselves, many started coming to a conclusion:
Jrue Holiday was in play.
That turn of events ended up having a major impact on the season, though not in the way many expected. Eight months later, after a five-day pitstop with Portland, the player who spent last summer thinking about returning to the mountaintop with the Bucks is four wins away from helping the Boston Celtics hang elusive banner No. 18 in a key role as one of the final players in their championship puzzle.
“I mean, [winning a title] takes everything,” Holiday said following Boston’s Game 4 victory over the Indiana Pacers in the Eastern Conference finals. “I think it’s one of the hardest things I’ve ever done.
“I think being able to go out there and fight and leave everything out on the court, you have the best chance of getting that win.”
HOLIDAY WAS NAMED an All-Star in 2022-23, though it was a season that ended in disappointment, as his top-seeded Bucks were upset in the first round by the Miami Heat. Still, there was significant interest in him from around the league. A defensive wizard, locker room rock and postseason specialist, Holiday had been such a desired player that the Bucks gave up three first-round picks to get him from the New Orleans Pelicans in 2020 after a bidding war.
The prospect of the Bucks acquiring Lillard certainly had the attention of the league.
But at age 33 and expected to hit free agency after the season, Holiday wasn’t a player who was likely to stay with rebuilding Portland if he was in the deal, and teams knew it.
“I think we were wondering if Portland was going to end up getting somebody that they would then move on from as a result of moving Dame,” Celtics president Brad Stevens said in October. “So, we were monitoring it like the rest of the league.”
But when the monster trade went down, it hit Holiday out of the blue. He was taking a nap on the afternoon of Sept. 27 when he missed a call from Bucks general manager Jon Horst. His agent reached him a few minutes later with the news that he’d been traded for Lillard.
“I was in shock,” Holiday later said on Draymond Green‘s podcast. “I had no clue.”
Just a few days earlier, Holiday had given an offseason interview to the Milwaukee Journal Sentinel in which he declared: “I’m a Buck for life, and I mean that like deep in my heart. I don’t want to play for any other team,” making it clear he hoped to sign a long-term extension and stay put.
His new reality arrived fast. The Blazers, trying to maximize the return on what would turn into a sequence of deals, made two things known to all parties involved.
First, Portland indeed intended to re-trade Holiday and would allow him to be involved in the process. Sending him to a team with whom he’d be willing to re-sign would increase his trade value.
Second, the Blazers made it clear to the Bucks that they planned to make the Lillard trade and the subsequent Holiday trade two separate transactions. The Bucks, elated they’d won the sweepstakes for future Hall of Famer in Lillard, would not be involved in Holiday’s final destination part of a three- or four-team trade. The Blazers didn’t know how long it would take to find Holiday’s new team and wanted to let a market develop, while not delaying moving on from Lillard ahead of training camp.
This aspect of the trade was a potential negative for the Bucks. Numerous Eastern Conference contenders, now facing the prospect of having to defend Lillard in a playoff series, saw Holiday as an ideal option against his now former team.
But Milwaukee had just made the biggest move of the offseason and created a tantalizing star duo that had ignited its fan base. More importantly, the deal thrilled franchise player Giannis Antetokounmpo, who rode the wave of excitement into signing a three-year, $186 million extension a month later that instantly made any risk in the trade worth it.
Now, just an hour after being awoken with the news, Holiday and his wife, Lauren, found themselves on a call with agent Jason Glushon and a list of 28 remaining teams to go through. With his next team getting his Bird rights and the ability to sign him to an extension before he became a free agent the next year, Holiday was plunged into doing a version of free agency and having to rapidly select a list of places where he might finish his career.
When the call was over, there was a list of five or six teams. Portland was made aware, and the bidding commenced. Several teams armed with draft pick assets that would’ve been attractive to the Blazers called only to be told they weren’t on the list.
This included the Pacers and the New York Knicks, teams that later made big in-season trades and had long playoff runs. But the Blazers stuck to Holiday’s list.
“Portland blessed me,” Holiday said when it was all over. “[Blazers general manager] Joe Cronin did a great job of communicating with me on how I wanted to proceed.”
WITHIN A COUPLE of days of the initial Lillard trade, two teams emerged as favorites to land Holiday: The Celtics and the LA Clippers. Both teams were on Holiday’s list.
The Clippers had been aggressively looking for a point guard for months, ironically nearly coming to a deal with Boston for Malcolm Brogdon around the draft in June. To get Holiday, they were willing to send multiple first-round picks and expiring contracts that would help clean the Blazers’ books. But Portland pushed for more, looking for draft pick swaps and having those selections be unprotected.
The Clippers’ proposal drew out the type of strong offer from the Celtics that Portland was hoping for. The Celtics, heavily committed to going all-in on the short term after trading for Kristaps Porzingis earlier in the offseason, came with a bid the Clippers couldn’t match.
The Celtics also offered two first-round picks, their own in 2029 and a 2024 Golden State Warriors selection that ended up becoming a lottery pick — one Boston had gotten from the Memphis Grizzlies in the three-team deal that also landed them Porzingis. The Blazers pushed for and got two giant final acquisitions: Boston agreed to make the 2029 pick unprotected and included defensive specialist big man Robert Williams III along with Brogdon.
Less than five days after he became a Blazer, Holiday was a Celtic. It was a big price, but Boston not only had seen it as a chance to add an ideal defensive specialist but also as a way to blunt the Bucks’ acquisition of Lillard.
“There’s a list of guys in the league that you always think you’ve never had a real chance to get that you think are perfect fits,” Stevens said after landing Holiday. “And Jrue is one of those guys.”
Holiday ended up starting 69 games and was a core player of a 64-win team that captured the No. 1 overall seed in the playoffs and had the third-best defensive rating in the league. In April, he signed a four-year, $134.4 million extension, keeping him in Boston through the 2027-28 season, the same year Jaylen Brown‘s contract is up. Porzingis and Jayson Tatum are both signed through 2025-26, with Tatum eligible to ink a five-year supermax extension this summer.
That quartet has Boston back in the NBA Finals for the first time since 2022. During the Eastern Conference finals against the Pacers, Holiday averaged 18.5 points, 7 rebounds, 5.8 assists and 1.5 steals. His steal in the final minute of Game 3 clinched the game and essentially the series — and evoked memories of a similar play in Milwaukee’s Game 5 win during the 2021 Finals against the Phoenix Suns that helped Holiday claim the lone championship of his career.
It’s a total he’d like to increase this month — and beyond.
“Once I got here — or even once I knew I was getting traded here — this was a part of what I wanted, what I envisioned,” Holiday said after he signed the extension. “I want to be here … I want to win multiple rings.”