July 4, 2024

The Milwaukee Bucks were determined to win the Damian Lillard sweepstakes last summer, even at the cost of trading Jrue Holiday, a crucial member of their 2022 championship team, to acquire Dame Time.

Fast forward to now, and Jrue Holiday has helped the Boston Celtics win the 2024 championship, leaving the Bucks puzzled over their decision.

Reflecting on the trade, Milwaukee’s forward Bobby Portis is still stunned that Jrue ended up with Boston when there were 28 other teams he could have joined.

“I remember when we first traded him, I was just hoping he wouldn’t go to the Celtics,” Portis shared on a recent episode of the Run it Back podcast on FanDuel TV.

The Bucks indirectly aided Boston’s success

Acquiring Lillard was a complex process. The Bucks and the Portland Trail Blazers needed the Phoenix Suns to facilitate the trade. In the three-team deal, Phoenix received Jusuf Nurkic, Grayson Allen, Nassir Little, and Keon Johnson, while the Blazers got Holiday and Deandre Ayton.

However, the rebuilding Blazers didn’t plan to keep Jrue. Boston quickly offered Malcolm Brogdon, Robert Williams, and two future first-round picks for Holiday. Portland accepted, making Portis’ worst fear a reality.

“Just 48 hours later, I saw that Jrue Holiday had been traded to the Boston Celtics. I was like, ‘Oh man, this is crazy’… Out of all the teams, he went to Boston. But it’s all good,” he said.

Jrue transformed the Celtics into serious title contenders

It wasn’t just Portis who was surprised by Holiday ending up in Boston. Even Celtics superstar Jayson Tatum was shocked that his team managed to pull off such a significant trade so quickly.

As the Celtics celebrated their 18th franchise championship on Sunday evening, it was the dynamic duo of Tatum and Jaylen Brown who spearheaded the victory. However, any Celtics fan would tell you that Jrue Holiday was the crucial addition that transformed them from a team struggling to clinch the title into the 2024 NBA champions.

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