Ex-Warriors Star Roasts Stephen A. Smith Over Nephew’s $20000 Loss in Bet

It is no secret that Stephen A. Smith loves being raw, even if that means inviting beef. LeBron knows it, Luka knows it, and all for his opinions. So Gilbert Arenas didn’t hold back when he once said to Smith, “You are not important, you are a vessel for information. You are a preacher, not God,” for calling out media figures with his signature fire. But this time, the tables turned—Gil stepped into the role of “god,” preached his way, and walked away with something SAS would mind sharing.

A few days ago, the ex-Warriors star Arenas posted a video on Instagram with Josh Smith, Stephen A. Smith’s nephew, who challenged him to a Madden NFL showdown—the popular football video game series. The wild part? A $20K bet. Josh agreed to pay if he loses, using his uncle’s company credit card. Gil captioned it, “Madden 2026 on the Company Credit Card of Uncle SAS 😂😂🗣️ I accept, sir. See u tomorrow night 😎” In the clip, he hilariously declared, “okay my team is rams but I will play with Baltimore.” He stuck with Baltimore, and the game’s outcome had Gil dancing live on stream.

Gil shared a hilarious screenshot of Jace Smith, Josh’s son, DMing him: “Yerrr. This Jace. Soooo….what you was saying👀 Don’t tell my pops😅😂😪” Josh got completely crushed in Madden, scoring 0 points while Gil’s Baltimore racked up 18. Gil laughed through a video, saying, “Mr. Stephen A. Smith, you see that name up there, I beat your nephew so bad, his son had to DM me…18-0 in Madden…he scored 0, son was so upset, he had to DM me telling what’s up, what’s up pops.” Yes, $20K straight from SAS’s company credit card, while Stephen A. sat back with zero involvement. Second chance? Gil is kind.

He added jokingly, “He needs to get it together, and if he wants to keep that 20 grand, *ahem coughs* round two or game two, coming soon, it’s gonna be the same thing…he couldn’t even kick a field goal, that’s how bad he was. Welcome to the family.” Gil captioned it: “@josmith776 u might wanna have another kid, u lost this one with that 0 point performance last night 😂😂 20k on the line and that’s how u play MADDEN ✌🏾 @stephenasmith JACE is under the Arenas Brand now 🤷🏾‍♂️😂”

Well, Gilbert Arenas has never shied away from throwing out challenges. Back in September, he put up $1,000 on the line as he, Malik G, and the Gil’s Arena Crew set the stage for an epic Monday Night Tailgate. The highlight was a legendary 1v1 in Gil’s own backyard, where two subscribers went head-to-head for the cash prize. But this time the stake was $20K! Still, the playful back-and-forth just got wilder after Arenas’ “Madden curse” dig—this time, the Smith family felt it firsthand, with the nephew taking the full brunt of the fallout.

Gilbert Arenas takes on Stephen A. with ‘Madden Curse’ and legal drama

Gilbert Arenas didn’t hold back during a recent livestream of No Chill Gil, poking fun at ESPN’s Stephen A. Smith while playing EA Sports College Football 26. “Hey Stephen A. man, we’ve got to talk brother. Because it ain’t a damn coincidence that everybody you know is going to jail,” Arenas joked, referencing recent legal troubles surrounding Marcus Morris, Shannon Sharpe, and even himself. “I ain’t saying you know, nobody snitched. I’m just saying, hey Stephen, you know how to pick them. I’m just going to be honest. It’s like the Madden curse, just the other way around.” The comments, full of Arenas’ signature humor, set the tone for what’s quickly become a high-profile, ongoing back-and-forth between Gil and SAS.

The drama hits closer to home for Arenas, who’s now federally indicted for allegedly running an illegal gambling operation from his Encino mansion, alongside a suspected Israeli crime figure. The indictment says Arenas hosted high-stakes poker games targeting wealthy players and celebrities, operating the ring for months. Meanwhile, Marcus Morris recently faced legal trouble over unpaid casino markers, and Shannon Sharpe exited ESPN following a civil lawsuit settlement. Even though Smith himself hasn’t been implicated, Gil’s playful “curse” comment highlights just how tangled the web has gotten.

Stephen A., for his part, wasn’t having too much fun with the jokes. On his show, he addressed a clip of Arenas poking fun at the ongoing drama: “Bro, I need you not to play around. My brother, I do not want to see you in jail at all. It’s not a good look. It’s nothing to laugh about.” He reminded Arenas of the serious stakes, noting that sponsors, advertisers, and business partners all share the same concern, and it is no joke. But is Arenas listening? Time will tell.