Conservative icon rages at Donald Trump over $20m stocks loss and brands tariffs chaos ‘Orange Monday’

‘Orange is the new black,’ according to Dave Portnoy – and a recent rant from the conservative Barstool Sports founder when it came to Donald Trump’s tariffs.

His remarks were made during a Monday morning live stream he manned for nearly an hour on X, as markets opened to general unrest.

The stream quickly devolved into an anti-Trump rant, when Portnoy revealed he had suffered some $20 million in losses since the trade obstacles were announced last week.

He proceeded to tear into Trump while referencing swirling fears of another ‘Black Monday’ – an unexpected stock market crash seen on Monday, October 19, 1987.

In doing so, Portnoy also panned the president’s complexion – rechristening April 7, 2025, ‘Orange Monday’ in his honor.

‘This is a decision that one guy made that crashed the whole stock market,’ Portnoy raged, hours after losing $200,000 in parlay that included Duke in the ticket. ‘That’s why we’re calling it Orange Monday.’

‘The stock market is getting crushed. I’ve lost 20 percent of my net worth,’ he continued, before bringing up how Trump over the weekend bragged about being ‘a very low handicap’ at a senior-aged golf tournament in Jupiter, Florida, Sunday.

‘And you’re out on the golf course,’ Portnoy, who has a reported net worth of more than $100million, raged. Indexes have since recovered some losses, with the Dow Jones down about 1.9 percent as of midday.

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‘You think if I’m losing money, if the stock market is tanking that only affects rich people?’ Portnoy nonetheless continued, in a spiel that saw him openly pan the president’s policies for the first time.

‘We’re probably affected the least.

‘Yeah I’m losing $20 million, but I still have plenty of money… it all shakes down,’ he went on, before using experience he’s garnered running his own company to provide some purported expertise.

‘Look at Barstool Sports, alright? This economy tanks. Our advertisers, who do business overseas and sell products and advertise with us. They sell less products. It gets more expensive. What’s the first thing they cut? Ad budgets. Ad budgets that we get.

‘Suddenly we’re not getting as much money,’ he went on, juxtaposing the two business models to make his point. ‘Suddenly I have to fire Nate [a Barstool staffer] and lay people off.’

‘That’s how it works,’ he continued, offering some full-throated confidence. ‘The rich people are probably the least affected… It affects you whether you have money in the stock market or not.’

Major indexes, meanwhile, have lost around 10 percent of their value since last week, when Trump unveiled the controversial ‘liberation day’ tariffs he says will boost US manufacturing.

Many, however, have argued it will only spur stagnancy, while thrusting the US in the throes of what could become a self-induced recession. 

Defenders of the president, meanwhile, have argued the pains that come in the short-term – including slumping 401(k) savings – will be worth it in the end.

‘Sometimes you have to take medicine to fix something,’ told reporters aboard the presidential plane on a flight back to DC from the senior golfing championship he said he had ‘won’.

‘I think your question is so stupid,’ he added, after being asked whether American consumers have the necessary ‘pain threshold’ to deal with plummeting stocks and prospective price hikes.    

Critics appearing on networks such as CNN and MSNBC have insisted as such, arguing Trump is causing unnecessary chaos for ordinary Americans at a time where the economy was already facing unrest.

Others have question whether the infrastructure even exists to achieve the type of manufacturing boom Trump is looking for, as he seeks to jumpstart domestic operations.

Treasury Secretary Scott Bessent pushed back against such concerns over the weekend,telling  NBC’s Meet the Press there was ‘no reason’ to expect a recession. 

‘This is an adjustment process,’ he said of losses seen over the past week or so and how they should not be a cause for alarm

Commerce Secretary Howard Lutnick similarly told CBS News Trump’s 10 percent ‘baseline’ tariffs – bolstered by additional obstacles against country’s with high tariffs against the US – on all imports, will be ‘stay[ing] in place for days and weeks.’ 

Portnoy, meanwhile, referenced a new term being coined by the  president to refer to those expressing fear over his aggressive approach during his ‘day trading’ stream Monday.

He said he is not a member of the ‘PANICAN’ party just yet, after Trump introduced the term for naysayers he deems are ‘weak and stupid’, as a play on the word panic and the suffix found at the end of the words used to reference both political parties.

Others, pointing out what they perceived as panic from Portnoy, disagreed.

‘Dave Portnoy’s reaction to losing 20 percent of his net worth because of Trump’s tariffs’ wrote former Republican rep Clara Harlow, calling him out for voting Republican in the primaries and the general election.’

‘Portnoy voted for Nikki Haley in the primaries and Trump in the general,’ she wrote, as other, more money-minded individuals criticized the self-made millionaire for suddenly changing his tune due to what they presented as characteristic dips.

‘Dave Portnoy just said that if Trump lets it goes until the Midterms and refuses to budge that he thinks “I would become a member of the panicking party,”‘ said Tahra Jirari, director of economic analysis The Chamber of Progress, a trade group that represents tech companies.

‘lol,’ she wrote in response, as several others continued to poke fun at Portnoy for concerns aired about his portfolio’s post-tariff performance.

‘It’s very hard to feel sorry for people like Dave Portnoy saying he is losing millions from Trump’s tariffs,’ wrote one such onlooker, with others panning him for his apparent lack of ‘diamond hands.’

‘Sir we[‘]ve lost dave portnoy,’ joked someone else, speaking from the perspective of the political camp Portnoy had previously claimed to be a part of.

‘Too many people hit the panic button. Probably shouldn’t be trading in the first place,’ added another user.

‘Diamond hands” is a slang term popularized by cryptocurrency enthusiasts, which refers to holding a volatile investment amid stark pressure to sell.

Such pressure was seen in spades Monday, as what can only be called a post-tariff selloff continued.

U.S. stocks bounced between gains and losses in what amounted to a particularly unpredictable trading session Monday, as traders continue to speculate about what the future holds in terms of finance.

After some losses seen early in the day, Portnoy, 49, raged: ‘I’m down $7 Million today… Trump has put his tariffs all over the place… everything is in the sh*tter.’

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