Stephen A. Smith and Donald Trump’s relationship is one of those media-world connections that’s easier to describe as friendly, familiar and complicated than a traditional friendship. They are both loud, New York-coded, camera-ready personalities who understand attention better than most walking this Earth. But their public history is not some deep buddy-buddy saga with years of vacation photos and courtside selfies. It is more like a long-running collision between sports, politics, TV, and ego.
Still, there is definitely history there. Stephen A. has acknowledged knowing Trump; Trump has spoken about Stephen A. in surprisingly warm terms at times; and the two have circled each other through Fox News appearances, political commentary, 2028 presidential speculation, and, most recently, the Knicks’ NBA Finals run. That last part is where things went from “friendly media acquaintances” to full-on public back-and-forth.
The latest drama came after Trump attended Game 3 of the NBA Finals at Madison Square Garden, where the Knicks lost to the Spurs, ending their 13-game winning streak. Stephen A., a lifelong Knicks fan, blamed Trump’s presence, security, road closures and overall disruption for messing up the team’s “mojo.” Trump clapped back by questioning Stephen A.’s IQ and presidential qualifications, and Stephen A. responded by mocking Trump for appearing to fall asleep at the game. So, yeah — whatever friendship existed, the Knicks might’ve effectively ended it.
Early Connections: Stephen A. & Trump Move In The Same Media Universe
There is no clear public “first meeting” moment between SAS and Donald Trump, but the connection makes sense when you look at their worlds. Trump has been a New York celebrity/business figure for decades, and Stephen A. built his career as one of the loudest and most recognizable voices in sports media. Both also mastered the art of turning TV appearances into headline-generating moments.
Love 105.3 RnB? Get more! Join the 105.3 RnB Newsletter
Thank you for subscribing! Please be sure to open and click your first newsletter so we can confirm your subscription.
Stephen A. has publicly spoken about advice he once received from Trump, specifically framing it as business advice on leverage. That alone suggests their connection predates the current political drama and was rooted more in media, money, and New York celebrity culture than party politics.
October 2024: Stephen A. Pushes Back On Trump Defenses During A Hannity Appearance
Before the latest Knicks drama, Stephen A. had already shown he was not afraid to criticize Trump, even while appearing on conservative media spaces. In October 2024, he went on Hannity and sparred with Sean Hannity over Trump’s mental sharpness, saying they “can’t be watching the same stuff” if Hannity was bragging about Trump’s clarity. He also made it clear that while he was critical of Kamala Harris, that did not mean he was automatically in Trump’s corner.
That moment is important because it shows the difference between Stephen A. having relationships with right-leaning media figures and actually being a Trump loyalist. He has been comfortable criticizing Democrats, but he has also been willing to call out Trump when he feels like the conversation is getting ridiculous.
November 2024: Stephen A. Says He Saw Trump’s Win Coming
After Trump’s 2024 election win, Stephen A. became one of the most talked-about sports personalities in political media because he was willing to say Democrats missed the mark. He appeared on shows like The View and Hannity, breaking down why Trump’s victory did not shock him, even though he did not present himself as some MAGA surrogate.
This is where some people started reading their relationship differently. To some, Stephen A. was just being honest about why Trump connected with voters. To others, his frequent appearances in conservative spaces made him look too comfortable around Trump’s orbit.
January 2025: Stephen A. Says He Felt Like A “Damn Fool” For Voting For Kamala Harris
Stephen A.’s political commentary got even louder in early 2025 when he said on Real Time with Bill Maher that he felt like a “damn fool” for voting for Kamala Harris. His criticism was aimed more at the Democratic Party’s process and messaging than at a direct endorsement of Trump, but the comment still drew a lot of attention for how blunt it was.
This added another layer to the Trump/Stephen A. conversation. Stephen A. was not saying Trump was his guy, but he was openly saying Democrats fumbled badly enough that he understood why voters rejected them.
2025-2026: Stephen A.’s Presidential Talk Puts Him On Trump’s Radar
Once Stephen A. started flirting with the idea of running for president in 2028, the dynamic with Trump got even weirder. Stephen A. said he had “no choice” but to consider the possibility after people encouraged him to do so, while making it clear he did not really want to be a politician.
Trump reportedly praised Stephen A.’s entertainment skills during a presidential conversation, which felt very on-brand. Trump knows TV presence matters, and Stephen A. has that in abundance. But that praise would not last once Stephen A. turned his Knicks frustration toward the White House.
June 2026: Stephen A. Begs Trump Not To Attend Knicks-Spurs Game 3
The current drama started before Trump even arrived at Madison Square Garden. SAS begged Trump not to show up to Game 3 of the NBA Finals between the Knicks and Spurs, telling him to stay at the White House because the city was already in championship-level chaos. Stephen A. stressed that his issue was not political — he said he would have felt the same way if Barack Obama were the sitting president attending — but he thought a presidential visit would create too much disruption around the Garden.
That warning ended up again like gasoline next to a match. Trump went to the game anyway, security was heavy, the atmosphere was tense, and the Knicks lost 115-111. Stephen A. did not need any more evidence. In his mind, the jinx had arrived.
June 2026: Trump Attends Game 3, The Knicks Lose, & Stephen A. Blames Him
After the Knicks lost Game 3, Stephen A. went off. He called Trump’s appearance selfish, said it disrupted New York, and blamed him for throwing off the Knicks’ energy. Trump became the first sitting president to attend an NBA Finals game, but instead of that being the headline, the story quickly became about boos, traffic, security and the Knicks’ streak ending.
June 2026: Trump Calls Stephen A. A “Nice Guy” — Then Questions His IQ
Trump’s first response had a little shade wrapped in a compliment. He called Stephen A. a “nice guy,” but then said running for president requires a certain aptitude and a high IQ, adding that he did not think Stephen A. had it. That was the moment the friendly/familiar dynamic turned into a very public roast session.
From there, Trump kept going. He later called Stephen A. an “arrogant fool” and “dumb as a rock” on social media, while also mocking the idea that Stephen. A Smith could run for office. At that point, the Knicks had officially turned a sports rant into a presidential beef.
June 2026: Stephen A. Fires Back & Mocks Trump For Appearing To Sleep
Stephen A. responded the only way Stephen A. knows how: loudly. He clapped back at Trump’s insults, challenged the idea that Trump should be questioning anyone’s intelligence, and mocked him for appearing to fall asleep during the Knicks game. The “Sleepy Joe” reversal was the kind of TV-ready line that made the story spread even faster.
June 2026: Stephen A. Takes The Argument To Hannity
The back-and-forth kept rolling when Stephen A. appeared on Hannity and defended his position. Hannity pushed back, but Stephen A. basically argued that sports fans understand momentum, vibes and superstition in a way political people might not. His point was not that Trump literally missed jumpers for the Knicks, but that presidential-level chaos was the last thing the team and city needed during a Finals game.
That appearance also showed why this relationship is so strange. Stephen A. can be cool with people in Trump’s media orbit, go on their shows, argue with them, joke with them, and still flame Trump when the Knicks are involved.
So, Are Stephen A. Smith & Donald Trump Actually Friends?
The safest way to put it: they appear to be friendly media acquaintances with a complicated public relationship, not inseparable personal friends. Stephen A. has known Trump, discussed advice he received from him, and moved through some of the same TV/political spaces. Trump has also spoken about him in a way that suggests familiarity.
But the Knicks drama showed the limits of that friendliness. Stephen A. may criticize Democrats and appear on Fox News, but when Trump got in the way of his Knicks, all that cordial energy went out the window. Their relationship is less “best friends” and more like two famous New York loudmouths who respect the game of attention — until one of them messes with the other’s team.
