Loyal MAGA ally Dave Portnoy has strayed from his close ties with Donald Trump in recent weeks following the president’s controversial tariff policy that sent the stock market plummeting.
While Trump’s administration has been scrambling to smooth over backlash to its economic strategy, and Portnoy wasn’t satisfied with Treasury Secretary Scott Bessent’s explanation.
Bessent spoke at the American Bankers Association on Tuesday morning and said the administration was focused on ‘Main Street,’ and not ‘Wall Street.’
Portnoy responded to a clip of Bessent speaking on X and fired back at the secretary, ‘Isn’t Bessent worth like hundreds of millions of dollars because of his work on Wall Street hedge funds and s***?’
‘Now that he’s left Wall Street after making infinity money he is saying the stock market is bad? When did he work on Main Street?’ Portnoy added.
Bessent served as the CEO and Chief Investment Officer of a hedge fund in New York and previously worked for Soros Fund Management before assuming the position as Trump’s Treasury Secretary. He has an estimated net worth of $500 million.
Portnoy has been vocal about his financial hits due to the stock market dips, admitting last week that he ‘didn’t understand’ the tariffs, but was down $7 million.
Then on Monday morning, Portnoy revealed he lost close to $20 million, and wished that he could go back to when he was only down $7 million.
‘This is a decision that one guy made that crashed the whole stock market,’ he said about Trump. ‘That’s why we’re calling it Orange Monday.’
He went on to say that he lost 20 percent of his net worth and slammed Trump for going golfing last weekend in Florida while the country’s economy was in turmoil.
Portnoy also publicly criticized the Trump administration for the humiliating mistake that led to the inclusion of Atlantic editor Jeffrey Goldberg in a classified group chat disclosing war plans in Yemen.
Despite his recent rants, Portnoy said that he would continue to support Trump and trusted that the president had a plan.
He presented a calmer demeanor during a Wednesday afternoon interview on CNN with Dana Bash.
Portnoy admitted that even though he was ‘uncomfortable’ with the stock market crashing, he knew that Trump would implement tariffs if elected.
The Barstool Sports CEO confessed that he ‘didn’t know’ the stock market would crash as a result of tariffs and claimed that he ‘didn’t think most people did.’
‘I’m willing to still give him time,’ Portnoy added.
Even though Portnoy reaffirmed his MAGA support, he doubled down on his disapproval of Bessent’s comments about Wall Street taking a back seat to ‘Main Street.’
Portnoy’s remarks came before Trump’s stunning announcement on Wednesday afternoon that the administration would be pausing the tariffs for 90-days, except for China.
Trump reduced the tariff tax to 10 percent for a majority of the US’s trade partners, while he simultaneously increased China’s tax to 125 percent.
Bessent told reporters after the announcement that the reduction was Trump’s strategy, ‘all along.’
‘It took great courage — great courage — for him [Trump] to stay the course until this moment,’ Bessent added.
The secretary explained that 75 countries had renegotiated trade agreements with the US after Trump’s reciprocal tariff strategy.
‘It is going to take some time, and President Trump wants to be personally involved. So that’s why we’re getting the 90-day pause,’ Bessent said.
He added that China was the ‘biggest source’ of trade issues for the US, but refused to call the conflict a ‘trade war.’
As a result of the pause, the stock market soared on Wednesday afternoon with the S&P 500 up 7.5 percent, Dow Jones up 6.5 percent, and Nasdaq up 9.6 percent as of 3 pm EST.
Portnoy was quick to change his tune after the pause, sharing a video of himself on X reacting to gaining $8.2 million in investments.
‘I’M UP 8.2 MILLION TODAY! WHERE ARE ALL THE PEOPLE IN MY MENTIONS NOW!’ he wrote alongside a clip of himself dancing.
‘All these left people “You voted for this,” “Oh he’s crying,” I’m dancing! I said it’s the time to buy. I said “Give him [Trump] some time,” Portnoy said in the clip.
He went on to defend Trump, saying that the president knows what he’s doing and is negotiating with other countries.
‘The stock market is tied in with Main Street, Wall Street, let it eat! Let me eat! And they let me eat, and I’m eating pizza, burgers,’ Portnoy concluded.