Former Celtics guard’s influence reportedly swayed Damian Lillard to choose Portland Trail Blazers over Boston Celtics during free agency decision.

Damian Lillard’s decision to spend the bulk of his NBA career with the Portland Trail Blazers rather than joining the Boston Celtics—a franchise steeped in championship pedigree—has long puzzled many league insiders. Now, a new report suggests that the persuasive influence of a former Celtics guard played a pivotal role in that career-defining choice.

The Mystery Behind Lillard’s Loyalty to Portland

Lillard, a seven-time All-Star and one of the most lethal scoring point guards of his generation, had options early in his career. While the 2012 NBA Draft placed him with Portland, multiple sources over the years have confirmed that other franchises, including the Boston Celtics, had serious interest in acquiring him—either via draft-day trade, subsequent offers, or free agency flirtations.

With the Celtics consistently in playoff contention, many speculated that a Lillard–Jayson Tatum pairing could have forged a perennial Eastern Conference powerhouse. But despite the allure of Boston’s storied history and bigger market visibility, Lillard remained firm in his commitment to Portland—until his eventual move to the Milwaukee Bucks in 2023.

Recent reports suggest that former Celtics point guard and fan favorite Rajon Rondo may have been one of the voices who helped solidify Lillard’s decision to stay put in Portland in the earlier stages of his career.

Rondo’s Words Carried Weight

According to sources close to both camps, Lillard sought the counsel of several veteran point guards during his early years in the NBA, and Rondo was among those he trusted most. At the time, Rondo was still in his prime and widely respected for his high basketball IQ, playoff pedigree, and leadership qualities.

The conversations reportedly took place during summer offseason training sessions and pick-up runs, where NBA players often gather and exchange insights. Rondo, who had his own battles with the Celtics’ front office during his tenure in Boston, is said to have advised Lillard to “build something lasting” rather than chase legacy by joining a team like Boston.

Building a Legacy vs. Chasing One

Rondo’s influence stemmed not just from his words, but from his experience. While he won a championship with the Celtics in 2008 and made multiple deep playoff runs, his time with the franchise wasn’t always smooth. From contract tensions to being involved in trade rumors, Rondo had seen the ruthless business side of the NBA up close.

By the time he crossed paths with Lillard in a mentorship setting, Rondo had already played for multiple teams and was vocal about the toll that instability can take on a player’s legacy and mindset.

“Dame was never about the flashy market,” one source told Bleacher Report. “He wanted to create something that was his. Rondo’s advice resonated with him—be the guy that elevates a franchise, not one that jumps to the next big thing.”

Loyalty Became Lillard’s Brand

What followed was a decade of commitment. Lillard became not only the face of the Trail Blazers franchise but also a rare symbol of loyalty in a league increasingly defined by super-team formations and player mobility.

Throughout the years, he had chances to move—especially after Portland failed to surround him with championship-caliber talent. Yet time and again, Lillard emphasized his belief in loyalty, culture, and legacy—values that mirrored the sentiments Rondo is known for sharing with younger players.

Rondo, even after retirement, continued to be an advocate for personal growth and building something meaningful in one place, often using Lillard as the prime example of how to do it the right way.

Celtics’ Pursuit and What Could’ve Been

Boston’s interest in Lillard has spanned years. Multiple trade rumors surfaced involving then-Celtics president Danny Ainge exploring the possibility of acquiring Lillard to pair with budding stars like Jaylen Brown and Jayson Tatum.

However, the Celtics never got close to finalizing a deal. According to insiders, it wasn’t because Portland wasn’t willing to listen—it was because Lillard never pushed for the move.

“Boston made calls. Portland listened. Dame didn’t entertain it,” said one NBA executive.

This loyalty, now possibly attributed in part to the early influence of Rajon Rondo, shifted the trajectory of both franchises. The Celtics moved forward with their young core and made multiple deep playoff runs. The Blazers, meanwhile, tried and failed to build a contender around Lillard, ultimately leading to his departure to Milwaukee in 2023.

Rondo and Lillard: Similar Souls?

Though very different in playing styles—Rondo a pass-first, cerebral maestro and Lillard a dynamic scoring machine—the two point guards share key traits: toughness, leadership, and a willingness to speak out.

Both men were often described as the heartbeat of their respective teams, and both preferred substance over style.

It’s no surprise, then, that Lillard might have gravitated toward Rondo’s mentorship. In fact, several trainers and former players noted that Lillard often mimicked Rondo’s routine of breaking down film and organizing offseason training schedules with surgical precision.

“Dame didn’t just want to score—he wanted to lead,” said one former Blazers assistant. “Rondo was the perfect influence for that.”

Could History Have Been Different?

If Lillard had taken a different path—say, joined Boston when Kyrie Irving departed or asked for a trade in 2021—it’s likely that the Celtics’ championship timeline would have accelerated.

Pairing Lillard with Tatum could have created the most explosive offensive backcourt in the East. It may also have impacted the team’s decision to trade for Jrue Holiday in 2023 or restructure around defensive players like Derrick White and Marcus Smart.

And yet, as the dust settles, it’s clear that Lillard’s path—though unconventional—was deeply intentional. Whether Portland ever gave him enough to compete is another debate. But his impact there, like Rondo’s in Boston, is undeniable.

In today’s NBA, where player movement and social media often dominate narratives, it’s rare to find stories about mentorship and behind-the-scenes influence. But the story of Rajon Rondo helping guide Damian Lillard’s early choices is a reminder of how vital player-to-player wisdom can be.

Rondo may not have worn green when he advised Lillard to stay put, but his Celtics legacy—and experiences, both good and bad—certainly shaped what came next.

In the end, both point guards stayed true to themselves. One helped revive the Celtics’ golden era of the 2000s. The other carried a small-market team on his back for over a decade. And both, in their own way, defined what it means to lead.