WHILE THE TEAMS GET TOGETHER Before training camp in September, a surprising piece of information emerged in NBA rumor mills: Not only were the Milwaukee Bucks in play to acquire Damian Lillard in a trade; They had become favorites.
How were they going to do it? This is what the team's leadership was trying to solve. It was a transaction that could disrupt the league and there were bound to be consequences.
With a clogged roster, limited draft assets and only a couple of tradeable young players, the Bucks had no easy way to achieve such success. Khris Middleton and Brook Lopez, two big-salaried stars who could have possibly been in a bid to help Milwaukee match Lillard's $45.6 million salary, had just signed new contracts and were not allowed to be traded during months.
The Portland Trail Blazers had done a good job all summer keeping details of Lillard's trade talks private. But now there was a blitz to get details. As cap strategists and executives examined the situation and talked among themselves, many began to come to a conclusion:
Jrue Holiday was in play.
That turn of events ended up having a big impact on the season, although not in the way many expected. Eight months later, after a five-day pit stop with Portland, the player who spent last summer thinking about returning to the top of the mountain with the Bucks is four wins away from helping the Boston Celtics hang up the elusive banner number 18 in a key role as one of the final players in their championship puzzle.
“I mean, [winning a title] “It takes everything,” Holiday said after 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 by being able to go out there and fight and leave everything on the court, you have a better chance of getting that win.”
VACATION WAS NAMED an All-Star in 2022-23, although it was a season that ended in disappointment as his top-seeded Bucks were defeated in the first round by the Miami Heat. Still, there was great interest in him throughout the league. Holiday, a defensive wizard, locker room rocker and postseason specialist, had been such a desired player that the Bucks gave up three first-round picks to acquire him from the New Orleans Pelicans in 2020 after a bidding war.
The prospect of the Bucks acquiring Lillard certainly caught the attention of the league.
But at 33 years old and expected to hit free agency after the season, Holiday wasn't a player likely to stick around in Portland's rebuild if he was in the deal, and teams knew it.
“I think we were wondering if Portland would end up getting someone they would then part ways with as a result of Dame moving,” Celtics president Brad Stevens said in October. “So we were monitoring it like the rest of the league.”
But when the monster trade dropped, it hit Holiday out of nowhere. He was taking a nap the afternoon of September 27 when he missed a call from Bucks general manager Jon Horst. His agent contacted him a few minutes later to inform him that he had been traded by Lillard.
“I was shocked,” Holiday later said on Draymond Green's podcast. “I had no idea.”
A few days earlier, Holiday had given an off-season interview to the Milwaukee Journal Sentinel in which he declared: “I'm a Buck for life, and I mean it from the bottom of my heart. I don't want to play for any other team.” , making it clear that he hoped to sign a long-term extension and stay.
His new reality came quickly. The Blazers, trying to maximize the return on what would become a sequence of deals, made two things known to all parties involved.
First, Portland intended to trade Holiday back and allow him to participate in the process. Sending him to a team he would be willing to re-sign with 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 to have won the future Hall of Famer lottery 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, without delaying Lillard's release before training camp.
This aspect of the trade was potentially negative for the Bucks. Numerous Eastern Conference contenders, now facing the prospect of having to defend Lillard in a playoff series, viewed Holiday as an ideal option against his now-former team.
But Milwaukee had just made the biggest move of the offseason, creating a tantalizing star duo that had ignited its fan base. More importantly, the deal thrilled franchise player Giannis Antetokounmpo, who rode the wave of enthusiasm to sign a three-year, $186 million extension a month later that instantly made any risk in the trade worth it.
Now, just an hour after waking up to the news, Holiday and his wife, Lauren, found themselves on a call with agent Jason Glushon and a list of the remaining 28 teams to review. With his next team getting his Bird rights and the chance to sign him to an extension before he became a free agent next year, Holiday was thrust into making a version of free agency and having to quickly select a list of places where he could finish. his career.
When the call ended, there was a list of five or six teams. Portland found out and the bidding began. Several teams armed with draft pick assets that would have been attractive to the Blazers called only to be told they weren't on the roster.
This included the Pacers and New York Knicks, teams that later made big changes during the season and had long playoff runs. But the Blazers stuck with Holiday's roster.
“Portland blessed me,” Holiday said when it was all over. “[Blazers general manager] “Joe Cronin did a great job communicating with me about how he wanted to proceed.”
WITHIN A COUPLE During the days of Lillard's initial 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 searching for a point guard for months, ironically almost reaching 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 up the Blazers' books. But Portland pushed for more, seeking trades of draft picks and unprotecting those picks.
The Clippers' proposal generated the type of strong offer from the Celtics that Portland was hoping for. The Celtics, heavily committed to doing everything they can in the short term after trading for Kristaps Porzingis earlier in the offseason, came in with an offer that the Clippers couldn't match.
The Celtics also offered two first-round picks, their own in 2029 and a pick from the Golden State Warriors in 2024 that ended up becoming a lottery pick, one that Boston had obtained from the Memphis Grizzlies in the three-team deal that He also got them Porzingis. The Blazers pushed and landed two giant late acquisitions: Boston agreed to take the 2029 pick unprotected and included defensive big man Robert Williams III along with Brogdon.
Less than five days after becoming a Blazer, Holiday was a Celtic. It was a high price, but Boston had not only seen it as an opportunity to add an ideal defensive specialist, but also as a way to slow 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 at and that you think are a great fit,” Stevens said after signing Holiday. “And Jrue is one of those guys.”
Holiday ended up starting 69 games and was a core player on a 64-win team that captured the first overall playoff seed 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 ends. Porzingis and Jayson Tatum are signed through 2025-26, and Tatum is eligible to sign 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 only championship of his career.
It's a total you'd like to increase this month… and beyond.
“Once I got here, or even once I knew I was going to be traded here, this was part of what I wanted, what I envisioned,” Holiday said after signing the extension. “I want to be here… I want to win multiple rings.”
