When president of basketball operations Brad Stevens and the rest of the front office sat down after last season to piece together their next steps following Boston's Eastern Conference finals loss to Miami, a question hovered over them.
How much were they willing to shake up the core of a team that had lost in the NBA Finals in 2022 and then came up a game short of returning the following season?
In the end they opted to swing big, trading longtime point guard Marcus Smart as part of the deal that netted 7-footer Kristaps Porzingis. Then, after Milwaukee traded Holiday to Portland to get Damian Lillard, the Celtics pounced, dealing former NBA Sixth Man of the Year Malcolm Brogdon and big man Robert Williams III to get Holiday.
The bold moves have proven to be exactly what the Celtics needed, helping produce a 64-win regular season, a romp through the first three rounds of the playoffs and a 2-0 lead over the Dallas Mavericks in the NBA Finals.
For the defensive-minded Holiday, whose defense limited Kyrie Irving, combined with a 26-point,11-rebound effort helped Boston salvage its 105-98 Game 2 victory, it's the latest example that Holiday is where he is meant to be.
"I think that this is what was supposed to happen. And I'm glad that I'm here and I'm glad that I'm in this moment," Holiday said prior to the start of the Finals.
"(Celtics coach) Joe Mazzulla has talked about that a lot, especially this season is being in the moment, and that's what I've tried to do."
Part of what's made Holiday so effective for the Celtics is the 33-year-old's willingness to adapt his game to fill whatever his team has needed this season.
A No. 3 scoring option in Milwaukee behind Giannis Antetokounmpo and Khris Middleton during the Bucks' 2020-21 championship season, Holiday has accepted being the fourth or fifth option in Boston. His 12.5 points per game average this regular season was the lowest since his rookie season.
But there have been times, such as in Game 2, when Dallas doubled up on All-Star Jayson Tatum, put more pressure on Jaylen Brown or Porzingis struggled, when Holiday had to increase his output.
He's done it, while maintaining intensity on the defensive end this season. He was selected to the NBA All-Defensive second team. It was the sixth time he was picked for the first or second team in his career.
Holiday believes it's a byproduct of the collective unity the team has been building throughout the season.
"I think when you sacrifice together and you do something together, it brings you closer," he said. "I think being able to go through wins and losses and to build something, it means a lot. ... From (roster spots) 1 to 15, somebody's sacrificed something."
Part of what's helped ease Holiday's transition to Boston has been the familiarity he already had with Tatum, with whom he played alongside on the 2020 U.S. Olympic basketball team that captured the gold medal during the Olympics in Tokyo.
Tatum said that relationship made periodic check-ins he had at times this season with Holiday easier.
"I would just check in or always remind him to be yourself and, we're going to need you in big moments, obviously like (Game 2)," Tatum said.
It's allowed Holiday to play to his strengths, most notably his ability to bring a measure of calm to the court in Mazzulla's controlled chaos.
Holiday's also been able to provide stability in crunch time for a team that in recent playoff runs sometimes wilted in those moments, often trying to lean on one-on-one play or committing turnovers.
And while a player such as Smart was a dominant alpha on the court, Holiday knows what it's like to play alongside a star such as Antetokounmpo, and coax the best out of them.
Asked to imagine what position the Celtics might be in without Holiday on the roster, Tatum didn't want to entertain the thought.
"Good thing we don't have to find out," he said.
No matter what happens over the remainder of the Finals, this won't be a one season-and-done stop for Holiday, who signed a four-year extension in April.
"From here on it's like — I'm supposed to be here," Holiday said. "And I'm supposed to be with my teammates. And we're supposed to do this together."
But there's only one way he'll feel as if his arrival in Boston can be deemed a success.
"It's been great and the journey's been awesome, but at the end of the day, the job is not done," he said.