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    Home»NBA»“The Buddy With The Orange Hat Look Like Chauncey Billups”: NBA Fans Crack Up Seeing Diddy’s Prison Photo With Chauncey Billups Lookalike
    NBA

    “The Buddy With The Orange Hat Look Like Chauncey Billups”: NBA Fans Crack Up Seeing Diddy’s Prison Photo With Chauncey Billups Lookalike

    Dan AgultoBy Dan AgultoNovember 3, 2025No Comments4 Mins Read
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    Portland Trailblazers, Chauncey Billups
    Apr 13, 2025; Portland, Oregon, USA; Portland Trail Blazers head coach Chauncey Billups (right) listens to Trail Blazers’ general manager Joe Cronin answer a question during a press conference before Portland plays their last season game against Los Angeles Lakers at Moda Center. Mandatory Credit: Jaime Valdez-Imagn Images
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    The internet once again proved that NBA Fans can turn any situation into comedy gold. TMZ dropped what it called the “clearest photo” of music mogul Diddy as an inmate, and while the picture itself was serious, the comment section had other plans.

    Chauncey Billups
    Apr 6, 2025; Portland, Oregon, USA; Portland Trail Blazers head coach Chauncey Billups watches from the sideline during the first half against the San Antonio Spurs at Moda Center. Mandatory Credit: Soobum Im-Imagn Images

    @big_business_ shared the post on X, saying, “Now TMZ just dropped the clearest photo of Diddy as an inmate in prison.”

    Now TMZ just dropped the clearest photo of Diddy as an inmate in prison https://t.co/5FITGwWbDU pic.twitter.com/W6wXCvg3gN

    — Ahmed/The Ears/IG: BigBizTheGod 🇸🇴 (@big_business_) November 1, 2025

    That alone stirred reactions, but it was @Eyeof__TygerV4 who broke the internet with one line: “I’m crying because buddy with the orange hat look like Chauncey Billups.”

    The resemblance between the man beside Diddy and the Portland Trail Blazers coach set NBA Fans off. Memes flooded the timeline within minutes, with jokes comparing “inmate Chauncey” to the real Billups pacing the sidelines in Portland.

    @LAClippersFilm joined in, tweeting, “The accuracy is insane lmaoo,” which summed up everyone’s reaction.

    It didn’t take long before NBA Fans were editing side-by-side photos of the two, with captions like “Coach Billups after another loss” or “Chauncey scouting from a new location.” The mix of pop culture, hoops humor, and perfect timing made it one of the funniest crossovers of the week.

    What started as a serious TMZ release quickly turned into another example of how NBA Fans can find humor anywhere—even in unexpected headlines. They don’t just follow the game; they shape the internet’s reactions to it, one viral moment at a time.

    NBA Fans Keep Joking About Chauncey Billups

    Even as the Portland Trail Blazers quietly put together a surprising run, NBA Fans still can’t resist taking shots at Chauncey Billups. After the Diddy photo meme, the Blazers coach found himself trending again—this time for basketball reasons.

    USATSI 19349419 scaled
    Nov 2, 2022; Portland, Oregon, USA; Portland Trail Blazers head coach Chauncey Billups and guard Damian Lillard (0) pay tribute to the late NBA player and coach Bill Russell before a game against the Memphis Grizzlies at Moda Center. The Memphis Grizzlies won the game 111-106. Mandatory Credit: Troy Wayrynen-USA TODAY Sports

    @shaesharpeshow posted, “The Trail Blazers are now 4-1 in the Tiago Splitter era. How we feeling about him as a longterm coach #RipCity?” referring to assistant coach Tiago Splitter temporarily handling coaching duties. The tweet immediately sparked debate, with many joking that the team’s sudden improvement was no coincidence.

    The Trail Blazers are now 4-1 in the Tiago Splitter era

    How we feeling about him as a longterm coach #RipCity ? 🤔 pic.twitter.com/wZRfoxHj4f

    — RIPCITYY🌹 (@shaesharpeshow) November 1, 2025

    @lansingmoore14 didn’t hold back, writing, “Chauncey Billups you sold us the f*ck out,” while @tallntalented13 added, “This team was poised to be good defensively with jru. But Chauncey!!!!!! You did that sh*t.”

    Despite the jokes, the Blazers’ recent wins show that the team still has potential under Billups—or at least when he’s not the main story. Yet NBA Fans love consistency, and if there’s one thing they’ll always be consistent about, it’s finding ways to roast a struggling coach.

    The timing of the Diddy meme and the Blazers’ slight turnaround made it all too perfect for NBA Fans. For them, it’s not just about the scoreboard—it’s about the storylines that make the sport endlessly entertaining.

    And right now, whether it’s memes or missed rotations, Chauncey Billups remains one of NBA Fans’ favorite topics—both on and off the court.

    Portland Trailblazers, Chauncey Billups
    Apr 13, 2025; Portland, Oregon, USA; Portland Trail Blazers head coach Chauncey Billups (right) listens to Trail Blazers’ general manager Joe Cronin answer a question during a press conference before Portland plays their last season game against Los Angeles Lakers at Moda Center. Mandatory Credit: Jaime Valdez-Imagn Images

    For more sports content:

    Follow us @HardwoodHeroics for your NBA and college basketball reading fix. You can reach out to Dan Agulto through email at papadanph@gmail.com. To read more of our articles and keep up to date on the latest sports news, click here!

    Dan has been active in sports since 2016 and has worked behind the scenes as a scriptwriter for basketball, volleyball, and other sports. At a time, Dan has also been working as a sports commentator for CBA Pilipinas. During the pandemic, he has also been actively writing betting articles for CashBet and BetNow.

    Chauncey Billups Sean Diddy
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    Dan Agulto

    Dan has been active in sports since 2016 and has worked behind the scenes as a scriptwriter for basketball, volleyball, and other sports. At a time, Dan has also been working as a sports commentator for CBA Pilipinas. During the pandemic, he has also been actively writing betting articles for CashBet and BetNow.

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