The Harsh Truth Celtics Fans Knew All Along: What Blazers Fans Are Struggling to Accept About Jrue Holiday

In the summer of 2025, the Boston Celtics made a bold move that sent shockwaves through the NBA: trading veteran guard Jrue Holiday to the Portland Trail Blazers in exchange for Anfernee Simons and a pair of second-round picks. At the time, reactions were mixed. Celtics fans mourned the departure of a key piece from their 2024 championship team, while many Blazers supporters saw it as a coup—acquiring a proven winner, elite defender, and locker room leader to mentor their young core. Holiday himself expressed gratitude toward Celtics president Brad Stevens for his transparency, and early in the 2025-26 season, he delivered, posting impressive numbers like 16.7 points, 8.3 assists, and 5.3 rebounds per game in limited action.

But as the season has progressed into January 2026, a different narrative has emerged. Holiday, now 35, has been sidelined since mid-November with a lingering calf injury, missing over a month and a half of action with no clear return timetable. The Blazers, hovering around .500 despite his early contributions, have struggled in his absence. And voices from the Celtics side—particularly writers and analysts who watched Holiday closely during his two-year stint in Boston—are pointing out realities that some Portland fans seem reluctant to fully embrace.

The core of this disconnect boils down to one uncomfortable truth: Jrue Holiday, for all his intangibles and championship pedigree, is an aging player on a declining trajectory, carrying a hefty contract and increasing injury risk. Boston recognized this and moved on proactively to avoid luxury tax penalties and roster inflexibility. Portland, in contrast, absorbed those risks in hopes of accelerating their rebuild. Now, with Holiday’s injury exposing those vulnerabilities, a Celtics perspective highlights what many Blazers fans hoped to ignore: the trade carried significant downside that the Celtics were wise to avoid.

The Trade Context: Why Boston Moved On

To understand the current discourse, it’s essential to revisit the trade’s origins. The Celtics were staring down severe salary cap constraints under the NBA’s second apron rules. Holiday was entering the later years of a four-year, $135 million extension he signed in 2024, with salaries escalating to around $32-37 million annually, including a massive player option for 2027-28. While Holiday was instrumental in Boston’s 2024 title run—earning All-Defensive honors and providing steady two-way play—his 2024-25 season showed signs of wear.

In his final year with the Celtics, Holiday averaged a career-low-ish 11.1 points and 3.9 assists on reduced usage, playing fewer minutes as younger players like Payton Pritchard ate into his role. He dealt with nagging injuries, appeared to play with “heavy legs” at times, and his production dipped noticeably compared to his prime years in Milwaukee or even his first season in Boston. Analysts noted that the taxing championship run followed by Olympic duty in 2024 likely contributed to this fatigue.

Brad Stevens, ever the forward-thinker, prioritized financial flexibility. Trading Holiday not only shed salary but brought in the younger, higher-upside Simons (then 26) on an expiring deal, plus draft assets. It was a calculated reset, allowing Boston to dodge the second apron while injecting scoring punch and youth. Celtics writers praised the move as necessary, even if painful—Holiday was beloved, but unsustainable long-term.

Portland, meanwhile, viewed Holiday as the perfect veteran to pair with emerging talents like Scoot Henderson, Shaedon Sharpe, and Donovan Clingan. General manager Joe Cronin targeted him specifically, seeing his defense and leadership as catalysts for a playoff push. Early returns seemed promising: Holiday elevated the Blazers’ play, instilling a defensive identity and providing on-court poise. Fans celebrated, with some even declaring Portland the stealth winners of the swap.

The Celtics Writer’s Perspective: Bobby Krivitsky’s Blunt Assessment

This is where the titular “Celtics writer” comes in—Bobby Krivitsky of Hardwood Houdini, a prominent Boston-focused outlet. In late 2025 pieces, Krivitsky articulated what many in Celtics circles had observed: Holiday’s decline was real, and Boston’s decision to trade him was prescient.

Krivitsky pointed out that even at 34 (Holiday’s age during his last Boston season), signs of slowdown were evident—heavy legs, reduced explosiveness, and injury niggles that limited his impact in high-stakes moments. “Seeing Holiday play with heavy legs and watching his production dip may have signaled to the Celtics that, as much as they love the person and the player, it was in their best interest to trade him,” Krivitsky wrote. He emphasized that Holiday’s value stemmed heavily from intangibles—leadership, defense, clutch play—but his on-court output was no longer elite enough to justify the cost for a cap-strapped contender.

Fast-forward to January 2026: Holiday’s prolonged calf injury has validated this view. He’s played just 12 games for Portland, and the team has gone 7-13 without him. Blazers fans, initially optimistic, now express concern over his $100+ million remaining commitment and how his contract might age poorly. Krivitsky and others argue this is the “brutal reality check” Boston avoided—paying premium dollars for a 35-year-old with mounting injury risks.

What Blazers fans “refuse to believe,” per the framing in Portland media echoing Krivitsky, is that Holiday isn’t the needle-mover he once was. His early hot streak in Portland masked underlying issues: increased role inflated his stats temporarily, but sustainability was questionable. Celtics observers saw this coming; they knew Holiday thrives best as a complementary piece on a contender, not a primary option on a developing team.

Why Some Blazers Fans Resist This Narrative

Portland supporters aren’t blind—many acknowledge the risks. Reddit threads on r/ripcity show mixed emotions: hope for Holiday’s leadership mixed with worry over injuries and cap implications. But there’s resistance to fully accepting the “decline” label. Holiday’s strong start fueled belief that a bigger role unlocked his “fountain of youth.” His veteran presence was seen as invaluable for a young roster needing culture-building after years of rebuild turbulence.

Moreover, intangibles are hard to quantify. Holiday’s defense, playmaking, and off-court mentorship can’t be captured in box scores. Blazers writers note his seamless adjustment and positive impact when healthy, arguing the trade’s value transcends stats. Some fans point to Boston’s own struggles post-trade (if any) or Simons’ fit issues as proof Portland didn’t overpay.

Yet, the injury reality bites. With no firm return date, questions loom: Will Holiday hold up over a full season? Can Portland contend with him as a high-usage guard? His contract hampers flexibility, especially in a loaded West.

The Broader Implications: Lessons for Both Franchises

This saga underscores the NBA’s harsh business side. Boston prioritized sustainability, trading a fan favorite for youth and flexibility. They’ve navigated cap challenges while remaining competitive. Portland bet on acceleration, but injuries have exposed the gamble.

Krivitsky’s take resonates because it’s rooted in close observation: Celtics staff and media saw Holiday’s limitations up close. Blazers fans, excited by the acquisition, hoped for a different outcome. Now, with Holiday sidelined and the team treading water, acceptance is creeping in—that Boston knew something Portland is learning the hard way.

Holiday remains a class act. He praised Stevens, denied unhappiness rumors, and embraced Portland. When he returns, he could still contribute meaningfully. But the Celtics writer’s point stands: at this stage, Jrue Holiday is a high-risk, high-reward asset—one Boston wisely offloaded.

As the trade deadline approaches, Portland faces decisions. Flip Holiday for assets? Ride it out? Whatever the path, the conversation sparked by Celtics voices like Krivitsky highlights a timeless NBA truth: Father Time is undefeated, and even champions feel his touch eventually.