Jrue Holiday’s path from Trail Blazers to Celtics was short but worthwhile

PORTLAND, Ore. – Jrue Holiday barely spent any time as an official member of the Portland Trail Blazers organization.

He never put on their jersey. He never appeared in a game or even practiced for the team. Before Portland, which had acquired him in September from the Milwaukee Bucks, dealt him to the Boston Celtics four days later, Holiday didn’t even have enough time to binge a great television show, never mind to fully digest the ramifications of his stunning trade from the place where he won a championship.

But as he lined up the next steps for his career during a whirlwind stretch for him and his family near the end of this past offseason, Holiday did have enough time for a meaningful conversation with Blazers head coach Chauncey Billups.

Before the Celtics blasted the Blazers 121-99 on Monday night, Holiday said he admired how Billups handled the situation by prioritizing the player’s desires over anything else. During that brief window when Holiday was technically with the Trail Blazers, Billups, one of the few people who could understand the emotions of such a transition, supported Holiday’s wish to join a different organization and dished out advice on how to handle the move from Milwaukee to whatever would come next for the guard.

“It meant a lot,” Holiday told The Athletic. “Being able to see a coach that has my best interests (in mind). And you could see it and you could hear it, which a lot of times maybe some players don’t get a chance to see that from a coach. So he definitely had my best interest (at heart) from the beginning. And he just always looked out for me.”

Though Holiday (left knee tendinopathy) did not suit up for the Celtics as they pounded the Blazers, the matchup brought up a reminder of the hectic 96-hour window during which he was traded twice in a series of transactions that reshaped a pair of Eastern Conference contenders.

The Bucks landed Damian Lillard in the first Holiday trade. The Celtics, who had been preparing for the possibility that an impact player would shake free in the Lillard deal, quickly pounced to scoop Holiday from Portland for Malcolm Brogdon, Robert Williams and two first-round picks. How different would Boston’s roster look without Holiday? He has completed one of the league’s best starting lineups by fitting in seamlessly and providing toughness on both sides of the ball. The 50-14 Celtics, currently on pace for 64 wins, simply would not have been the same without him.

Portland coach Chauncey Billups, shown at Monday’s game against the Celtics, counseled Jrue Holiday after he was briefly traded from the Bucks to the Trail Blazers. (Alika Jenner / Getty Images)

It was between the two trades, when the Celtics were among several contenders pursuing Holiday, that he met with Billups to discuss his future.

“I had a great conversation with him,” Billups remembered. “I did. I love Jrue, man. I love Jrue. And we got him very briefly obviously. And I had a conversation — a long, good conversation with him — just about I know it was a little tough spot for him, being traded, kind of being blindsided by that. I’ve been there before. So just being able to rap with him like that because I know him. And it was important for me that a good person like him, who’s been great on every team and every community that he’s lived in, for him to be treated properly and be put in a great position and a great spot.”

During that chat, Holiday said he told Billups that he wanted to join a contender rather than stay on the rebuilding Portland roster. Billups, a five-time All-Star during his days as a player, understood Holiday’s urge to compete for another championship. On a deeper level than that, Billups also identified with the complex thoughts swirling inside of Holiday’s head. Billups, who was traded from the Pistons in 2008 after winning a title there four years earlier, understood what it was like to be uprooted from a team he helped build into a champion.

“I think the biggest thing was just there’s not a lot of people that actually have been through that, that can kind of talk him through it, that he’s actually seen and he respects,” Billups said. “So just I wanted to hear him out, listen to him, and understanding that I know how he feels, I know where he’s at in his career. He’s not 25 where he can just (be patient). I know what he wants to play for. So it was actually a really good conversation that we were able to have even though, and obviously, I didn’t know where it would end up. But our intention was to make sure that he was going to be in a great position, a great situation. And happy for him (that he landed with the Celtics), man. He’s just being Jrue. All he does is (be) a winner.”

At the time of his heart-to-heart with Billups, Holiday was rocked by the Bucks organization’s decision to trade him in a package for Lillard. Holiday’s wife and kids were established in Milwaukee. He didn’t envision himself playing anywhere else. Shortly before the Bucks moved him, Holiday said he wanted to play for the team for the rest of his career. In a hurry, his reality changed. He would need to adjust to life somewhere else. He was still spinning from the shift in the aftermath of the trade.

Billups helped prepare Holiday for what to expect.

“Just him being real with me,” Holiday said. “Obviously because he’s been through just a lot. Being a Hall of Famer, being a winner, a champion, being a point guard. Him just being super honest with me and speaking from experience.”

What type of perspective did Billups share?

“One, the biggest thing was just to stay professional, man,” Billups said. “You can be very emotional in a situation like that when you get blindsided and you say some things that you can’t take back or act a way that you can’t take back. And also, whenever you get to the place that you’re going, just be who you are. Don’t show that hurt and that emotion that you just had to go through because whenever you show up, that’s how they’re going to judge you. So just giving him some of them type of little nuggets that you would think they’re easy but they’re not easy when you’re dealing with a lot of emotion in the moment and every time it’s a family, it’s tough on your kids and your wife, and it’s real. So Jrue, he’s obviously done a great job.”

Holiday said he felt like Billups understood everything he was going through. He said Billups was fully supportive of whatever decision he made. Days later, during Holiday’s introductory press conference in Boston, he said the Blazers organization and general manager Joe Cronin welcomed him with strong communication throughout the process. The Blazers facilitated a trade to one of Holiday’s preferred landing spots in the Celtics. He believed Boston gave him the best chance of winning another championship.

The Celtics have looked like one of the favorites so far. They methodically dismantled the Blazers on Monday, leading by double digits for most of the game. The win moved Boston to an impressive 19-1 against teams in the bottom 10 of net rating this season. It also gave the Celtics 50 wins for the third straight season, a milestone Jaylen Brown wanted the team to avoid taking for granted. According to Jayson Tatum, Brown gives a speech every year around the time Boston clinches a playoff berth. He did it this time after beating the Blazers.

“I’m going to keep saying it until I’m blue in the face,” Brown said. “I’m grateful to be on a team that’s winning, to be on a team that’s been playing the right way, has another opportunity to do something special. So that’s a blessing. I don’t care if they want to hear it or not, I’m grateful.”

Brown called it an honor to give that speech every year.

“You see what’s going on in different places of the league,” Brown said. “Team chemistry, locker room, teams that are in losing environments. That hasn’t been us. For the most part, I’ve won every step of my career and that’s been just (thanks) to great teammates, a great organization, and trying to build something special. So you don’t want to take that for granted.”

Holiday has accentuated that winning environment. He has been a dream for the Celtics so far, giving them consistently efficient production and competitive maturity on both ends of the court. Even while a significant percentage of his touches and shot attempts have disappeared, he has played without a hint of selfishness.

After the Bucks moved on from Holiday, it was clear the guard would make a big impact on another team. It just wouldn’t be in Portland. The Celtics won the bidding war for him in early October to solidify an already loaded roster.

“Y’all welcome,” Billups said.

(Top photo of Jrue Holiday from earlier this season: Bob DeChiara / USA Today)

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