When the Boston Celtics added Jrue Holiday and Kristaps Porzingis to the roster, there was a clear indication that they were throwing all in for the title. The Celtics had a maximum of a two-year window before they had to ship out players to avoid financial strain and possible penalties. Eventually, the Celtics pulled the trigger in the offseason. They traded Holiday to Portland.

Six months later, Holiday had a full-circle moment when he returned to TD Garden for the Celtics vs Blazers game on Monday. But he held no grudge for his second championship team. According to the two-time NBA champion, the Celtics president and general manager, Brad Stevens, had informed him before the trade.

“I knew I was getting traded,” Holiday told reporters. “Brad had told me that there was a possibility. And then whenever it happened, he was up front and told me what happened. So I felt like it was a great transition.”

This offseason was extremely crucial for Boston, given the choking financial burden that could have deeper repercussions. After Boston signed Porzingis and Holiday in 2023, they had four players earning over $30 million each in salary.

Luckily, the signings worked for the Celtics. However, in the same season, they were almost a million over the second apron line, and during the 2024-25 season, Boston went over $4.4 million over the second apron.

“Me and my family are doing well in Portland. A lot of people that we actually know love the organization from even before when they actually traded me here,” Holiday added. “But to circle back and get me means a lot to me, so I’ve been doing well.”

Entering this season, the Celtics had $227 million in guaranteed contracts. Had the Celtics chosen to keep the roster intact, they would have had to pay $500 million, including luxury-tax penalties. It would have made them the most expensive team in NBA history. Shipping key pieces was necessary for Boston, not just an option.

In the span of a few June days, the Boston Celtics pivoted from a looming financial nightmare to something closer to a controlled reset. By trading Jrue Holiday and Kristaps Porzingis, they didn’t just reshuffle the depth chart; they dramatically reshaped the balance sheet and bought themselves time around Jayson Tatum’s uncertain future.

Boston entered the 2025 offseason staring at an unprecedented combined payroll and luxury‑tax bill in the neighborhood of half a billion dollars, with some projections putting the number as high as roughly $540 million once all penalties were accounted for.

After sending Porzingis to Atlanta and Holiday to Portland, multiple cap analysts estimated that total obligation dropped to around $274–280 million, effectively cutting the bill almost in half.

ESPN’s Bobby Marks focused on the tax component, projecting about $180 million in luxury‑tax savings alone.

The timing of Jayson Tatum’s torn Achilles shifted the calculus as much as the new collective bargaining agreement did. With their franchise player expected to miss most or all of the 2025–26 season, the Celtics were no longer under the same pressure to maintain an all‑in, championship‑or‑bust roster at a punitive cost.

Instead of pushing further into second‑apron territory to defend a title window, they used Tatum’s lost year as a pivot point. Accepting short‑term pain on the floor to avoid long‑term financial handcuffs under the new CBA’s harsh apron restrictions.

That repositioning matters most when you look ahead to Tatum. He remains the centerpiece of the organization and a clear supermax‑level player when healthy, and the financial breathing room created by these trades makes committing to him long term more sustainable, not less.

Jrue Holiday gets honest about being back in Boston as Celtics fans show love to their former player

Holiday is a championship-caliber player for any team in the NBA. Well respected as one of the best defensive guards in the league, his arrival helped the Celtics fans celebrate a championship after 16 years. So when he returned to TD Garden on Monday, fans showed much-deserved love to their former player.

When Holiday stepped on the court for pre-game warm-up, fans gave him a standing ovation.

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It was all love from Holiday, too, who was asked about what it meant to play against his former team.

“It means a lot. Winning together, going through so many things together, even how it ended, doing that together, it was amazing, and I’ll never forget it,” said Holiday, in the interview on NBA on NBC.

According to ClutchPoints, when Holiday first learned of the trade, he was not happy. He wanted to stay and finish his career in Boston. However, having gotten to know the Celtics’ financial situation and an early heads-up from Stevens made the transition easy for them.

Holiday is happy with his family in Portland, but he understands the brutality of the NBA’s business. Who knows, he might be back in Beantown someday in the future.