On Wednesday, Dave Portnoy, the founder of Barstool Sports, indicated that he might lean towards supporting Democrats in the upcoming 2026 midterms if the economy and stock market fail to recover. Although he initially backed Trump, stating he was never an extreme MAGA supporter, he has grown increasingly vocal about his concerns regarding the president's tariff policies, particularly their detrimental effect on the market.

During his "Davey Day Trader" livestream, Portnoy referred to the week’s trading commencement as “Orange Monday,” a nod to the hefty losses he’s faced due to tariffs, claiming a dip of around $20 million in his investments. Despite his frustration, he conveyed a sense of loyalty to Trump, acknowledging the president's intelligence and expressing hope that his economic strategies would eventually yield positive outcomes. Aware of the critical nature of the approaching midterms, Portnoy believes that electoral outcomes will be strongly influenced by economic recovery or continued decline.

Furthermore, he reflected on the heightened volatility in the stock market and speculated that the perception of potential tariff pauses could have a significant impact on investor confidence. While Portnoy’s political stance has shifted over the years, he emphasized that he does not strictly align himself with one party, indicating that his vote will depend on the political landscape and economic circumstances. He also remarked on his audience's strong sentiment towards Trump, noting their belief that the left is more intolerant, thus influencing their reluctance to abandon the president despite ongoing economic challenges.