I bet against Donald Trump, and lost. I got ahead, anyway.
In the final days of the 2024 US election, the “ Trump trade ” was getting woolly. Investors who thought Trump would win or lose the presidential race were betting for or against the impact his economic policies might have. New tariffs on imports might be bad for shippers and good for domestic producers. Tax cuts could generate larger deficits and higher interest rates. Deregulation could yield more corporate mergers.
The most direct Trump trade was a bet on the shares of Trump’s own company, Trump Media & Technology Group, known by its ticker symbol DJT . A Trump win could boost the fortunes of the flagging Truth Social network, while a Trump loss could doom the money-losing venture. The stock price was yo-yoing based on every hint that Trump was up or down in the polls.
I decided to sample the action. I wanted to place an options trade on DJT, because that’s the way many other Trump traders were playing it. I’m a plain vanilla investor, so I asked Eric Hale, founder and CEO of Trader Oasis, to guide me through an options trade. I didn’t know if Trump would win or lose, but I thought shares of DJT, which had been trading around $50, were seriously overpriced. The company was a social media pipsqueak with barely any revenue, yet the stock price gave it a market value of $8 billion. That seemed way too high under any election outcome.
I bought a put contract with a strike price of $25, which meant I could sell 100 shares at a profit if the price fell below $25 before my contract expired on Nov. 15. The contract cost $3.90 per share for 100 shares, so $390 in total. I’d make a profit of about $1,110 if the price dropped to $10, and $2,500 if it went to 0. If the price never fell below $25 by Nov. 15, I’d be out the full $390.
For a few days, it looked promising. The stock closed at $40 the day I bought my put. It fell to nearly $30 the following day, which pushed the market value of the put higher than what I paid for it. I could have closed the trade then for a small profit. But I wanted to go the distance.
Trump won, of course, which should have demolished my Trump trade. But instead of soaring after Trump’s win — which was the expectation trading action had been signaling — the stock languished. There was a brief uptick once the election outcome was clear, but then the stock fell to $30, then $27. A couple of bucks lower and I’d get back at least get some of my money.
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On Nov. 15, the day my put expired, the stock crawled back to about $28. I was out of luck and my $390 was gone. It was my second failure to capitalize on an investing fad. In 2021, I tried my hand at meme stock investing by buying shares of BlackBerry. I went underwater right away and ended up losing $1,760.
Other Trump traders hit the jackpot. The “French whale” who wagered $70 million on a Trump win on the betting site Polymarket took home an $85 million profit . Big bank shareholders saw handsome gains on the likelihood of softer regulation. Anybody who owned the beaten-down shares of Fannie Mae or Freddie Mac enjoyed a 70% pop on hopes that Trump will privatize the two federal housing agencies.
I should swear off trendy investing ideas, except I got it right once. I bought a bit of cryptocurrency during the heady days of 2017, when bitcoin was starting to garner mainstream attention. A year or two later, I bought stock in a crypto-related company. Trump’s win in 2024 turned out to be bullish for crypto, since he’s promised friendly policies. I didn’t plan it this way, but my crypto gains offset the $390 loss, and then some, and then some more.
My Trump trade also gave me a rudimentary understanding of how to place option trades. My main takeaway: Leave it to the pros. But if I get laid off and decide to become a day trader, I got a wee bit of starter education.
I also paid closer attention to Trump’s company than I would have if I'd had no stake in it. The stock jumped after Trump said on Nov. 8 that he had no plan to sell his shares , as some of the company’s backers had feared. But other company insiders did sell shares , which seemed to drag down the stock. Three days after my Trump put expired, worthless, the stock was back to around $27, close, once again, to my strike price. I may have guessed right about the direction of the stock, even if I lost money on my bet.
Rick Newman is a senior columnist for Yahoo Finance . Follow him on Twitter at @rickjnewman .
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