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Reading: Damian Lillard Sends ‘Jackpot’ Message To His Doubters After Entering Free Agency
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Home > NBA News & Analysis > Milwaukee Bucks News & Analysis > Damian Lillard Sends ‘Jackpot’ Message To His Doubters After Entering Free Agency

Damian Lillard Sends ‘Jackpot’ Message To His Doubters After Entering Free Agency

As Damian Lillard hits the free agency market, the former Milwaukee Bucks star had something to say to those who doubt his abilities.

Siddhant Gupta
Jul 4, 2025
3 Min Read
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Mandatory Credit: Kevin Jairaj-Imagn Images

Former Milwaukee Bucks guard and 9x All-Star Damian Lillard finds himself in an odd position heading into the offseason. Amid the doubts about the 34-year-old guard’s ability to bounce back in free agency, Lillard shared a comment in response to these naysayers. He said:

“If they call it a gamble at this stage… Tell them this is the jackpot.”

After being waived and stretched by the Milwaukee Bucks, Damian Lillard has inevitably found himself on the free agency market. While some reports suggest that Lillard was happy about leaving the Bucks, the future outlook isn’t completely in the guard’s favor.

At 34 years old, Lillard is entering the last stages of his career. While his averages of 24.9 points, 4.7 rebounds, and 7.1 assists per game from last season were impressive, there are more pressing concerns surrounding the 7x All-NBA guard.

Lillard tragically tore his Achilles during the first round of the playoffs against the Indiana Pacers this year. Although the Bucks were already backed up against the wall, the injury sustained by Lillard saw Milwaukee make an early exit from the postseason.

The Bucks’ offseason was marked by rumors revolving around a potential move for their superstar, Giannis Antetokounmpo. Instead, Milwaukee stunned the league by waiving Lillard’s contract, a decision that even Antetokounmpo hasn’t been too happy about.

As things stand, the Bucks will be stretching Lillard’s $112.5 million contract over the next five years, effectively paying the guard approximately $22 million each season. With this move, the 9x All-Star is free to assess the quality of the teams in the league and potentially also join on a short-term, team-friendly contract.

The immediate obstacle in Lillard’s journey is recovery. Given that the guard is expected to be sidelined for the majority of the season, if not the entire season, teams may be cautious about indicating an interest in signing the 34-year-old.

As the star guard recovers close to his family in Portland, he will have a lot of time to think about his prospects. 

If winning titles is a priority, Lillard would be best served by entertaining veteran minimum deals or MLE contracts to join a title contender. But if the primary outlook is to sign a large contract, the veteran guard may face more challenges along the way.

Currently, Lillard still has some suitors interested in his services. As a competent point guard with tremendous shooting ability, he immediately increases the offensive firepower of any roster he’s on. 

The Golden State Warriors and the Los Angeles Lakers have emerged as potential landing spots for the 9x All-Star. Should he sign a contract with either team, he would undoubtedly strengthen the backcourt once he returns from injury.

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TAGGED:Damian LillardMilwaukee Bucks Archive
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BySiddhant Gupta
Siddhant Gupta is a basketball columnist at Fadeaway World, based out of Mumbai, India. He combines firsthand playing experience with thoughtful analysis to report on the NBA's ever-evolving world. A lifelong athlete, Siddhant's perspective is rooted in years on the court, giving his work a unique edge that resonates with both casual fans and seasoned ones.Before joining Fadeaway World, he spent two formative years at Sportskeeda, where he sharpened his skills and had the opportunity to interview NBA legend Ray Allen during his time in India. A diehard Los Angeles Lakers fan since 2008, Siddhant doesn't just report on the game—he lives it. Beyond his work, he is a student of the game, constantly learning, debating, and engaging with the local and global basketball communities.
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