Who would’ve guessed the king of hot takes could beat a former NBA player in a free-throw contest? Stephen A. Smith, ESPN’s outspoken commentator, bested Kenny Smith, the two-time NBA champion and current TNT analyst, in a surprisingly one-sided free-throw battle during the NBA Cup semifinal pregame show.
The Contest: Trash Talk Meets Awkward Execution
The matchup was simple: five shots each, trash talk mandatory. Stephen A. went 3-for-5 at the line, while Kenny, a career 82.9% free-throw shooter in the NBA, managed just 1-for-5. In fact, Kenny took an extra sixth shot, which also clanked off the rim, much to the delight of Stephen A. and the crowd.
With Shaquille O’Neal providing lively commentary, the contest wasn’t without its moments of confusion. Stephen A. technically clinched the win after four rounds, but Kenny insisted on taking his fifth shot, sinking it and declaring, “Now I’m warm!” The declaration seemed to reset the stakes, but his sixth (and unofficial) shot was another miss, cementing Stephen A.’s victory.
Stephen A., ever the showman, was ready to keep shooting if needed, showing the same intensity he brings to debates on First Take. “Shooters shoot,” he joked, basking in his unexpected victory.
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A Former Pro Falls Flat
TNT’s decision to pit Kenny Smith, a player with a respectable free-throw percentage during his 10-year NBA career, against Stephen A. seemed like a surefire win for the former pro. However, it became clear that Kenny’s shooting touch hasn’t aged well since his playing days ended in 1997. His stiff form and inconsistent aim provided fodder for Shaq’s playful ribbing and Stephen A.’s post-win gloating.
Shaq himself wasn’t spared from comparisons. Known for his notoriously poor free-throw shooting (52.7% career average), the Hall of Famer quipped that “Hack-a-Shaq” might be a better alternative than watching Kenny’s current form.
Stephen A. Keeps the Momentum in a 3-Point Shootout
The fun didn’t stop at free throws. Stephen A. and Shaq later faced off in an impromptu 3-point contest, which quickly devolved into a comedy of air balls. Shaq missed his first four attempts, and both men began wildly firing shots in what turned into an endurance test of embarrassment.
Finally, Stephen A. sunk a 3-pointer, earning a victory in front of a crowd that was clearly enjoying the spectacle. Kenny Smith, ever the good sport, sweetened the stakes by offering $10,000 to charity if either competitor could simply hit the rim, a challenge they eventually met.
Cross-Network Fun and NBA Nostalgia
The contest was part of the NBA Cup festivities, and the blending of ESPN and TNT personalities was a notable moment ahead of TNT’s Inside the NBA crew joining ESPN next season as part of a new media rights deal. While it’s rare to see such collaborations, the lighthearted event was a refreshing change from the typical analysis-heavy pregame shows.
Stephen A. brought more than just his fiery personality, surprising fans and colleagues alike with his shooting skills, honed during his brief college basketball career at Winston-Salem University before a knee injury cut his playing days short.
A Lighthearted Win for Stephen A.
Though the contest was all in good fun, Stephen A. Smith walked away with bragging rights and plenty of ammunition for future debates. His victory over Kenny Smith and his scrappy 3-point duel with Shaq made for an entertaining diversion during the NBA Cup pregame festivities.
For Kenny Smith, it was a humbling reminder that even former pros can have off nights—or, in his case, off decades. For Shaq, it was proof that not all basketball legends are built for free-throw or long-range glory.
As the dust settled, everyone involved returned to their day jobs—providing analysis and, when needed, taking shots on air rather than on the court.
