The Boston Celtics have made the first of what is expected to be many moves this offseason in an attempt to cut their overall tax bill entering the 2025-26 season. Before the 2025 NBA Draft on Wednesday, the Celtics struck a deal late Monday evening with the Portland Trail Blazers, trading veteran guard and two-time NBA champion Jrue Holiday for 26-year-old guard Anfernee Simons and two second-round picks.

These second-round picks going to Boston from Portland are in 2030 and 2031, league sources confirmed to ClutchPoints.

Holiday, who had been a leader in the Celtics' locker room over the last couple of seasons, was an instrumental part of the team's championship run in 2024. Brad Stevens, Boston's president of basketball operations, originally acquired Holiday from Portland in 2023 in exchange for Malcolm Brogdon, Robert Williams III, and two first-round picks.

Ultimately, the trade in 2023 proved to be a success, as it helped the Celtics achieve their primary goal of winning a championship.

Now, the script has flipped this summer for Stevens and Boston. New ownership taking over for long-time owner Wyc Grousbeck made it their agenda to decrease the team's league-high payroll and tax bill this offseason, and the entire organization, including Stevens, recognized the need to do so after the playoffs, sources said.

Along with Jayson Tatum suffering an Achilles tear that will sideline him for the vast majority, if not all, of the 2025-26 season, 2024 Finals MVP Jaylen Brown recently underwent right knee surgery. The team is optimistic that he will be ready for the start of the new year.

The Celtics are not done quite yet after trading Holiday.

This was the first domino to fall in Boston this offseason, as the team remains heavily restricted by the apron penalties. Stevens and the Celtics' front office, league sources said, are operating to utilize the upcoming year as a “reset” period to save money and retool the roster around Tatum and Brown.

Rival teams have inquired about the possibility of Brown and key guard Derrick White being available in trade talks, yet the Celtics have given zero indications that they intend to move either player, sources told ClutchPoints in May. Recently, ESPN insider Shams Charania reported that it would take an “insurmountable package” to convince Stevens to move either player.

Boston's next order of business: continuing to evaluate the trade market for Latvian big man Kristaps Porzingis.

Like Holiday, Porzingis was another addition the Celtics made before the 2023-24 season, which ended in them capturing their 18th championship in team history. Porzingis is entering the final year of his contract and will make $30.7 million before becoming an unrestricted free agent in 2026.

Over the last week, the Celtics have been engaged in trade conversations with several teams regarding Porzingis, sources said. There are playoff-contending teams in both the Eastern and Western Conferences that have expressed interest in the 29-year-old stretch big man despite the injury problems and mysterious illnesses he battled in his two years with the Celtics.

It does not appear that Boston would need to entice teams to take on Porzingis' remaining salary, contrary to popular belief. There is a belief that the Celtics could hold onto their 28th pick in the 2025 NBA Draft on Wednesday in a trade involving Porzingis. They now have two more second-round picks that could be utilized as collateral if need be in future deals.

So, why did the Celtics cut ties with Holiday?

This was a move made to save money and open up immediate flexibility in Boston.

As a result of trading Holiday and moving his $32.4 million salary (not to mention the other years remaining on his contract) in favor of Anfernee Simons, who is making $27.6 million in the final year of his contract, the Celtics will save themselves roughly $40 million between salary and taxes, according to ESPN front office insider Bobby Marks.

Why pick Simons over other assets? The young guard is in the final year of his contract and will be an unrestricted free agent in 2026. In 70 games this past year with Portland, the former 24th pick of the 2018 draft averaged 19.3 points and 4.8 assists per game while shooting 36.3 percent from 3-point range.

Between his playmaking abilities at the point guard position and his shooting, Simons will immediately slide into an important secondary scoring role next to Brown and White with Tatum sidelined at a cheaper price.

Should this fit not work the way Stevens and the Celtics like, Simons can easily be flipped at the trade deadline in February. The worst-case scenario is that his contract expires and Boston creates cap flexibility for themselves. At the cost of an aging veteran on a non-favorable contract, Stevens worked his magic once again.

The Celtics will continue discussing trade opportunities around the league ahead of free agency, as a trade involving Porzingis is expected to follow suit.

The writing had been on the wall for Simons' eventual departure from Portland.

In addition to the organization expressing a sense of hesitance to offer the young guard a new contract extension that would have made him the highest-paid player on the team, Portland had signaled to some teams around the league that they were interested in trading Simons before the trade deadline this past season, sources said.

Two of those teams the Trail Blazers had spoken with in February were the Orlando Magic and Miami Heat, sources said. Neither trade conversation ever reached a point where real traction was forming.

After winning eight of their final 15 games to end the 2024-25 season, many of which were played without Simons leading the charge, Portland and executive Joe Cronin saw a clear path forward without the young guard. Instead, a new core group of Deni Avdija, Scoot Henderson, Shaedon Sharpe, Toumani Camara, and Donovan Clingan had emerged for the Blazers.

Chauncey Billups' squad finished the second half of the season after the All-Star break ranking fourth in defensive rating, an area they will continue to make improvement in this summer.

That is why acquiring Holiday in place of Simons was a move that made sense for this organization, regardless of the price tag that comes with the veteran's contract.

At this time, the Trail Blazers are confident with keeping Holiday if another trade does not materialize, sources said. However, Cronin and the Trail Blazers are expected to continue trade dialogue with teams that had previously expressed interest in Holiday before Boston sent him to Portland.

The Sacramento Kings, Dallas Mavericks, and Los Angeles Clippers were among Western Conference foes that held trade conversations with Stevens and the Celtics regarding Holiday, sources said.

All focus in Portland now turns to the NBA Draft on Wednesday night, where the Trail Blazers will have a big decision to make with the 11th pick. Several prospects have been linked to this franchise in recent weeks throughout the pre-draft process: Derik Queen, Carter Bryant, Egor Demin, Collin Murray-Boyles, and Asa Newell.

After trading Simons, the Blazers are said to have a few backcourt talents at the top of their draft board. It is worth noting that Illinois guard Kasparas Jakucionis and Murray-Boyles recently had private workouts in Portland over the weekend. Jakucionis' workout was described as “impressive and rewarding,” league sources told ClutchPoints.

Much like Boston, the Blazers will continue to navigate the offseason with open arms regarding further trade discussions. Deandre Ayton and Robert Williams III have been made available in trade talks dating back to before this past season's trade deadline, sources said.

Previously, the Trail Blazers had signaled to rival teams that they valued Williams and would not sell low on him. Whether or not that line of thinking has changed now that the veteran big man is in the final year of his contract is yet to be determined.

There has also been growing speculation about the team feeling out the market for veteran forward Jerami Grant, who also has three years left on his contract like Holiday. Grant has been the veteran leader in Portland since joining the team in 2022.

The Blazers found their new identity on defense to end the 2024-25 campaign, and potentially keeping Holiday would signal that Portland is looking to contend for a playoff spot in the Western Conference with their youthful roster during the 2025-26 season.