A Timeline Of Charles Barkley’s Beef With San Antonio

Charles Barkley’s beef with San Antonio is not exactly Drake vs. Kendrick. It is not a real, ugly feud built on actual hate, lawsuits, diss tracks or anything that serious. It is more like one of the longest-running inside jokes in BA television history: Chuck says something wild about San Antonio, the city gets mad, the Inside the NBA crew laughs, Spurs fans boo him, and somehow churros end up involved.

Still, after more than a decade of jokes about San Antonio women, the River Walk, the Alamo and the city as a whole, Barkley has basically become San Antonio’s favorite enemy. He has repeatedly insisted he is “just joking,” but the jokes have followed him for so long that local media, fans and even city officials have all gotten in on the back-and-forth. MySA notes that Barkley’s San Antonio jokes have been going for more than 15 years, with the churro jokes becoming one of the most recognizable parts of the bit.

The latest chapter came during the 2026 NBA Finals, when the Spurs’ return to the biggest stage put San Antonio back in the national spotlight — and gave the city a chance to confront Chuck on live TV. Mayor Gina Ortiz Jones appeared on ESPN’s Inside the NBA coverage before Game 1, roasted Barkley over his years of shots at the city, and even handed him churros as a peace offering/troll move. Barkley laughed it off, praised San Antonio, and again said the whole thing was rooted in fun. So, no, this is not a “real beef” in the traditional sense. But as far as NBA TV bits go, Charles Barkley vs. San Antonio has had a longer run than most playoff rivalries.

A TIMELINE OF CHARLES BARKLEY’S BEEF WITH SAN ANTONIO

Early 2010s — The “Big Ol’ Women” Joke Becomes A Thing

Barkley’s San Antonio jokes started gaining real traction on Inside the NBA when he repeatedly joked about there being no “skinny women” in the city. What probably started as a throwaway TNT wisecrack eventually became a full-blown recurring bit, especially whenever the Spurs were making deep playoff runs.

2014 — Chuck Introduces The Churro Lore

The whole thing hit another level when Barkley connected his San Antonio jokes to churros, acting out how he thought women in the city ate them during an Inside the NBA segment. The moment went viral and basically turned “San Antonio women” and “churros” into permanent Barkley/TNT lore.

2014 — San Antonio Keeps Winning Anyway

The funniest part about all the timing is that Barkley was talking all this noise during an era when the Spurs were still one of the NBA’s gold-standard franchises. San Antonio won the 2014 NBA championship, which only made the jokes hit differently: Chuck could clown the city all he wanted, but the Spurs were still collecting rings.

2017 — Barkley “Apologizes”…Then Immediately Makes It Worse

At one point, Barkley appeared ready to apologize to the women of San Antonio, but because it was Chuck, the moment quickly turned into more comedy. Sports Illustrated covered the clip at the time, noting that Barkley started with an apology before the segment went off the rails with more churro jokes.

2021 — TNT Reportedly Tells Him To Chill

By 2021, the joke had gotten big enough — and controversial enough — that Barkley said TNT told him he could no longer make the repeated “big ol’ women” comments on Inside the NBA. Barkley later blamed a MySA article for helping get the jokes shut down, which made the “feud” feel even more official between him and the city’s local media.

2024 — Chuck Takes Aim At The Alamo & River Walk

Barkly did not limit the jokes to the women of San Antonio. During an appearance on The Stephen A. Smith Show, he also took shots at the Alamo and called the River Walk a “dirty little creek,” making it clear that his San Antonio material had expanded into a full citywide roast.

2025 — Barkley Doubles Down At March Madness In San Antonio

Even after years of backlash, Barkley could not resist going back to the well while in San Antonio for the 2025 March Madness Music Festival. He praised the city and said he loved Gregg Popovich and the Spurs, but still finished by doubling down on his old joke about San Antonio women.

March 2026 — The Churro Jokes Still Has Legs

Even in 2026, the churro bit is still alive. ESPN posted a clip in March of Barkley having the Inside the NBA panel cracking up over another churro-related moment, proving the San Antonio joke had not fully gone away, no matter how many times Chuck said he was done with it.

June 2026 — The Spurs Make The Finals & San Antonio Gets Its Chance

The Spurs’ return to the NBA Finals against the Knicks put the whole thing in the spotlight. Since Inside the NBA was in San Antonio for Finals coverage, it was only right that the city finally got to answer Barkley on national television.

June 2026 — Mayor Gina Ortiz Jones Roasts Chuck & Brings Churros

Mayor Gina Ortiz Jones joined the broadcast, took a playful shot at Barkley’s “class” and “courage,” then handed him churros as a direct callback to his most famous San Antonio joke. Barkley took the moment in stride, laughed, praised the city, and again insisted the whole thing was a joke.

June 2026 — Chuck Turns The River Walk Into A Workout

As if the week needed another layer, Barkley was also spotted doing chair-lift workouts near the River Walk, the same place he had previously called a “dirty little creek.” The clip went viral because it felt like peak Chuck: roasting the city for years, then casually working out in the middle of one of its biggest tourist attractions.

At the end of the day, this is not a real beef as much as it is a long-running NBA comedy bit that San Antonio has learned to throw right back at him. Barkley has crossed the line plenty of times, and the jokes have definitely not landed with everybody, but the 2026 mayor/churros moment showed the city understands the assignment too. If Chuck is going to keep talking, San Antonio is going to keep clapping back.

RELATED: Michael Jordan & Charles Barkley Relationship Timeline