As teams prepared for training camp in September, a surprising rumor circulated: the Milwaukee Bucks were not only in the mix to acquire Damian Lillard but had become the favorites.
The question was how they could make it happen. The Bucks had a tight payroll, limited draft assets, and only a few tradable young players. Khris Middleton and Brook Lopez, two high-salary stars, had recently signed new contracts and couldn’t be traded for months.
Throughout the summer, the Portland Trail Blazers kept details of the Lillard trade talks under wraps. As executives analyzed the situation, they realized Jrue Holiday might be the key piece in the trade.
This revelation had a significant impact on the season, though not as expected. Eight months later, after a brief stint with Portland, Holiday is now on the verge of helping the Boston Celtics secure their 18th championship, playing a crucial role in their lineup.
"Winning a title takes everything," Holiday said after Boston's Game 4 victory over the Indiana Pacers in the Eastern Conference finals. "It’s one of the hardest things I’ve ever done."
Holiday, named an All-Star in the 2022-23 season, faced disappointment as his top-seeded Bucks were upset in the first round by the Miami Heat. Despite this, he remained highly sought after due to his defensive skills, leadership, and postseason experience. The Bucks had acquired him from the New Orleans Pelicans in 2020, giving up three first-round picks after a bidding war.
The prospect of Milwaukee acquiring Lillard caught the league’s attention. At 33 and nearing free agency, Holiday wasn't expected to stay with a rebuilding Portland if included in the deal.
"When the trade happened, it shocked me," Holiday said. He had recently expressed his desire to stay with the Bucks long-term.
After the Lillard trade, the Blazers intended to re-trade Holiday, involving him in the process to maximize his trade value. They informed the Bucks that the Lillard and Holiday trades would be separate, not delaying Lillard’s move before training camp.
This strategy posed a challenge for the Bucks. Eastern Conference contenders saw Holiday as an ideal player to counter Lillard in playoffs. However, Milwaukee’s acquisition of Lillard created a star duo that excited fans and pleased franchise player Giannis Antetokounmpo, who soon signed a three-year, $186 million extension.
Within an hour of being traded, Holiday and his wife, Lauren, were on a call with his agent, Jason Glushon, listing potential teams. Portland honored his preferences, leading to a focused bidding process.
Two teams emerged as favorites: the Boston Celtics and the LA Clippers. The Clippers, seeking a point guard, made an aggressive offer, but the Celtics' bid was stronger. Boston, committed to short-term success after trading for Kristaps Porzingis, offered two first-round picks and included Robert Williams III and Malcolm Brogdon.
Five days later, Holiday was a Celtic. The Celtics saw him as a perfect defensive fit and a way to counter the Bucks' Lillard acquisition.
Holiday started 69 games, becoming a core player for the Celtics, who achieved a 64-win season and the top playoff seed. In April, he signed a four-year, $134.4 million extension, aligning his contract with key players Jayson Tatum and Jaylen Brown.
Boston is now back in the NBA Finals, aiming for their first title since 2022. During the Eastern Conference finals, Holiday averaged 18.5 points, 7 rebounds, 5.8 assists, and 1.5 steals. His crucial steal in Game 3 was reminiscent of his game-winning play in the 2021 Finals with Milwaukee.
Holiday envisions multiple championships with Boston. "Once I got here, this was part of what I wanted," he said. "I want to win multiple rings."
