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The Milwaukee Bucks changed the NBA landscape, pulling off a blockbuster deal to acquire Damian Lillard. They hope it leads to their second championship in four years. But their primary motivation was working to keep Giannis Antetokounmpo with the only franchise he's been a part of beyond this season and, ideally, the rest of his career.

The cost of their efforts to bring that to fruition included sending two-time All-Star Jrue Holiday to the Portland Trail Blazers. They knew the risk in doing so, understanding the point guard on their 2021 title team would quickly get rerouted.

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Wednesday, at Holiday's introductory press conference with the Boston Celtics, he admitted trying not to get his hopes up about landing with his top choice and one of, if not the last place the Bucks wanted to see him end up.

The five-time All-Defensive team selection described the process of going from envisioning spending the rest of his career in Milwaukee to working with Trail Blazers' general manager Joe Cronin to send him to a destination on the five-time All-Defensive team selection's wish list while netting a satisfactory return that wound up including Robert Williams and multiple first-round picks as a "whirlwind." 

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But Holiday says he's grateful to Cronin for how well he communicated with him as everything unfolded and for trading him to the place he wanted to be more than any other.

What separated Boston from the other franchises on his list?

"I mean, you just look at the resume, right? You look at the history that this place has had. You look at the organization and everything that I've always heard about it. You look at how competitive they've been in the last five, six years, and even before that."

After recounting his multiple playoff battles against the Celtics, dating back to when he was the Philadelphia 76ers and that also includes the two's seven-game slugfest to go to the Eastern Conference Finals in 2022, Holiday stated, "Ever since I've been in the league and even before that, this has been a championship-caliber organization."

The franchise's pedigree, commitment to winning, and knowing who he's joining, including former Olympic teammate and two-time All-NBA First Team member Jayson Tatum and Charles Lee, an assistant coach who was with the Bucks when they lifted the Larry O'Brien Trophy in 2021 and was with Holiday as the latter went through a post-practice workout at the Auerbach Center on Wednesday, have the California native, who noted he has family who are Los Angeles Lakers fans that are "probably hurt" by his decision, believing Boston is the ideal landing spot for him.

"I feel like coming here is definitely my best chance of winning and being able to help the guys here that have made big moves and done great things in this league. So, I'm here to help step up that game and become a champion."

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Of course, there's also the added motivation of joining the top Eastern Conference threat to his former team.

"Going against Milwaukee, it should be fun," he conveyed with a smile across his face.

And, when asked about lessons learned or reinforced to him when the Bucks won the title in 2021 that he can impart to his new team throughout this journey, Holiday expressed the following to Inside The Celtics.

"That it's hard. It's harder than everything you've ever done before. You're going to be tired, (and) exhausted, but it's about who has the mental toughness, who can fight through it and make plays toward the end of games, end of (a) series, but who's the most connected? The team that wants it the most will go after it and get it."

From ownership to president of basketball operations Brad Stevens to the coaching staff and his new teammates, Boston believes it's put itself in the best position to do so by sacrificing what it took to acquire Holiday.

Further Reading

Under Joe Mazzulla, Celtics Rebuilding Brotherhood Between Past and Present

Celtics Excited to Learn from, Play Alongside Jrue Holiday: 'He Understands What It Takes'

Determined to Deliver Banner 18, Jayson Tatum's 'Looking Forward to Doing More, And So Should Everybody Else"

Kristaps Porzingis Says His Foot's 'Perfectly Fine' and He's Ready for Training Camp

Celtics ‘Eager’ to Extend Jrue Holiday

Jayson Tatum Preparing for Point-Guard Role This Season

Candace Parker on Celtics Trading Marcus Smart, Maximizing Tatum-Brown Tandem, Pat Summitt, and the Sports Matter Initiative

Brad Stevens Discusses Differences in Joe Mazzulla Entering Year 2 as Celtics' Head Coach

Here's What to Know About Celtics' 2023-24 Schedule

Dwyane Wade Discusses Jayson Tatum's Next Step, Him and Jaylen Brown's Challenge, Heat Culture, Pat Riley, Damian Lillard, and Life After Basketball

Why Celtics Should Enter 2023-24 Season Optimistic About Most Important Area of Improvement