The Boston Celtics, fresh off their record-setting 18th NBA championship in 2024 and a stellar 61-win season in 2024-25, face a critical offseason with their payroll pushing against the NBA’s punitive “second apron” threshold. To avoid severe financial penalties and roster-building restrictions, many expect the Celtics to trade high-priced talent, with veteran point guard Jrue Holiday frequently mentioned in rumors. A bold proposal from Barstool Sports’ Dan Greenberg on June 12, 2025, has sent shockwaves through NBA circles: a potential swap sending Holiday to the Sacramento Kings for six-time All-Star DeMar DeRozan. Backed by insights from NBA analyst Jake Fischer, this trade could reshape both teams’ futures. Let’s unpack the financial logic, roster implications, and fan reactions to this blockbuster rumor.
The Celtics’ Payroll Predicament
The NBA’s second apron, a salary cap threshold that imposes heavy luxury tax penalties and restricts trades and signings, looms large over the Boston Celtics. With a star-studded roster featuring Jayson Tatum, Jaylen Brown, and Jrue Holiday, the Celtics’ payroll is among the league’s highest. Despite reports that Boston isn’t “desperate” to slash costs, the consensus among experts and fans is that shedding salary is inevitable to stay competitive under the NBA’s stringent financial rules.
Trading high-salaried players like Holiday, who will earn $32.4 million in the 2025-26 season, is the most direct path to getting under the second apron. Holiday, a 16-year veteran acquired before the 2023-24 season, was instrumental in Boston’s 2024 championship, averaging 11.1 points, 5.4 assists, and elite defense. His five top-eight finishes in Defensive Player of the Year voting highlight his value, but at 34, his contract makes him a prime trade candidate. Moving Holiday could provide financial relief while allowing Boston to retool around Tatum and Brown, but it risks disrupting the chemistry that fueled their recent success.
The Proposed Holiday-DeRozan Swap
Barstool Sports’ Dan Greenberg sparked intrigue with his June 12, 2025, prediction: “Feels like we’re headed for a Jrue for DeRozan swap.” This one-for-one trade would send Holiday to the Sacramento Kings and bring 35-year-old DeMar DeRozan, a six-time All-Star, to Boston. DeRozan, who signed a three-year, $73.89 million deal with the Chicago Bulls before being traded to Sacramento, will earn $24.75 million next season—$7.65 million less than Holiday. The swap would leave the Celtics $13.3 million above the second apron, a significant step toward compliance, while keeping the Kings $19 million under the first apron, giving them flexibility for further moves.
The trade aligns with Sacramento’s needs, as outlined by NBA analyst Jake Fischer. The Kings, under new general manager Scott Perry, have prioritized playmaking after a lackluster 2024-25 season. Fischer notes that Sacramento has explored guards like Holiday, Washington’s Marcus Smart, and Malcolm Brogdon, with Holiday’s championship pedigree and defensive prowess making him a top target. DeRozan’s departure would sting, given his 22.2 points per game last season, but Holiday’s two-way impact could stabilize the Kings’ backcourt alongside De’Aaron Fox and Domantas Sabonis.
Trading Defense for Offense: Roster Implications
The proposed swap would force both teams to recalibrate their identities. For the Celtics, DeRozan’s arrival would shift their focus toward offense. Averaging 22.2 points on 47.4% shooting in 2024-25, DeRozan is a mid-range maestro and clutch scorer, complementing Tatum and Brown’s perimeter game. His playmaking (5.3 assists per game) could offset Holiday’s loss, though his defensive limitations—compared to Holiday’s lockdown ability—could expose Boston against elite guards like Tyrese Haliburton or Damian Lillard. DeRozan’s fit in Brad Stevens’ system, which emphasizes versatility, raises questions, but his scoring punch could keep Boston’s offense humming.
For the Kings, Holiday would be a defensive anchor and floor general. His 33.3% opponent field goal percentage as the closest defender in the 2025 playoffs (per The Lead) showcases his ability to neutralize threats. Pairing Holiday with Fox would create a dynamic backcourt, with Holiday’s veteran savvy balancing Fox’s explosive scoring. However, losing DeRozan’s offensive firepower could strain Sacramento’s scoring depth, forcing players like Kevin Huerter or Malik Monk to step up. The Kings’ playoff aspirations hinge on Holiday’s ability to elevate their defense while maintaining offensive flow through playmaking.
Financial and Strategic Considerations
Financially, the trade is a win-win. For Boston, shedding $7.65 million in salary brings them closer to second apron compliance, potentially unlocking the taxpayer mid-level exception ($5.7 million) for free agency signings. The Celtics could also explore additional trades—perhaps involving Derrick White or Al Horford—to fully duck under the apron, preserving flexibility for future moves. Sacramento, with $19 million under the first apron, gains room to pursue complementary pieces, such as a stretch big or wing defender, to round out their roster.
Strategically, the trade reflects differing priorities. Boston, aiming to sustain a dynasty, must balance cost-cutting with maintaining a championship core. Trading Holiday, a fan favorite who embodied the 2024 title team’s grit, risks backlash but aligns with long-term financial health. Sacramento, desperate to break their playoff drought, sees Holiday as a veteran leader to push them into contention. The Kings’ willingness to part with DeRozan, a proven scorer, signals confidence in their young core and a shift toward defensive identity under coach Mike Brown.
Challenges and Fan Reactions
The trade faces hurdles. Holiday’s emotional ties to Boston, where he won his second championship, could complicate negotiations, and his no-trade clause gives him veto power. DeRozan, a California native, might resist leaving Sacramento, where he’s embraced a leadership role. Both teams must also consider chemistry: Boston’s cohesive 2024-25 squad could falter with DeRozan’s ball-dominant style, while Sacramento risks disrupting their offensive rhythm without DeRozan’s scoring.
Fan reactions on social media are mixed. Celtics fans lament losing Holiday’s defense, with one X user writing, “Jrue for DeRozan? We’re trading heart for buckets—bad move.” Others see DeRozan as a scoring boost, noting, “DeMar with Tatum and Brown? That’s a nightmare for defenses.” Kings fans are torn, with some excited for Holiday’s defense but others reluctant to lose DeRozan’s clutch gene. The rumor has sparked heated debates, reflecting the high stakes for both franchises.
The Jrue Holiday-for-DeMar DeRozan trade rumor, fueled by Dan Greenberg and Jake Fischer, is a fascinating glimpse into the NBA’s complex financial and strategic landscape. For the Celtics, swapping Holiday’s defense for DeRozan’s offense could ease their second apron woes while keeping them in title contention. For the Kings, Holiday’s arrival could solidify their playoff push at the cost of DeRozan’s scoring. As the offseason unfolds, this blockbuster proposal has NBA fans buzzing with anticipation. Will Boston and Sacramento pull the trigger, or is this just offseason speculation? Share your thoughts—would you make this trade if you were running the Celtics or Kings?