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Somebody got rich quick on Monday morning. Just 16 minutes before President Donald Trump’s surprise decision to pause the bombing campaign against Iran, market records show traders bought about $1.5 billion in S&P 500 $SPX futures and sold about $500 million in crude oil $CRUDE futures.
After President Trump’s 7:06 a.m. social media post, the S&P futures rose between 0.9% and 1.3%, while oil futures fell about 15% even before the markets opened. That’s a potential profit of $40 to $50 million on the oil, and $18 million or so on the S&P futures. Did someone have advance knowledge of the market-moving announcement? To understand what happened and whether this was insider trading, BBTW Editor Peter Green spoke with Ben Schiffrin, a former SEC enforcement attorney who now runs securities policy for good-government group Better Markets.
There’s been a lot of chatter about those massive oil and S&P futures trades that hit just before President Trump announced he was pausing the bombing campaign in Iran. Was this insider trading?“Certainly, the timing of the trade is highly suspicious. The age-old question on insider trading is, what are the chances that someone just happened to make the right trades at exactly the right time? It’s possible, but lots of times it’s unlikely. Normally, agencies like the Commodity Futures Trading Commission would go in and investigate to find out whether it was just coincidence or whether somebody actually had inside information and traded on it illegally.”
“Unfortunately, these days, the CFTC seems more interested in supporting prediction markets than in regulating the market. There’s really nothing preventing it from trying to figure out what happened here—the CFTC has long gone after insider trading. The problem is enforcement capacity. They’ve lost a lot of personnel and focus.”
How would regulators actually track down who made these trades?“The CFTC can investigate, look at trading records, and then build up through the intermediaries that help facilitate the trade. There’s definitely a way they can trace it back… This is what makes it a little different from the potential insider betting sites like Polymarket where everything’s in crypto and anonymous. It would be very hard to figure out the identity of an insider bettor on those sites. But with these traditional commodities trades, the CFTC has experience unraveling that. They can subpoena records. Even in a digital age, there’s always a paper trail.”
“In garden‑variety insider trading cases, you often find a message or a text — some ‘Hey, you should be aware of this’ type note. That’s what investigations look for. As for whether it was a single trader or multiple entities? I don’t think anybody knows at this point. It’s just too early.”
You mentioned prediction markets like Kalshi and Polymarket — where users bet on political or military events — and how some have profited ahead of major actions.“I think you have to separate what’s going on in prediction markets versus traditional commodities markets. On prediction markets, people don’t necessarily think there’s anything preventing them from using confidential information to bet. Up until recently, even Kalshi hadn’t said it would police for insider betting… You could easily see a trader saying, ‘I’ve got this intelligence, and there’s nothing stopping me from profiting off it.’”
“You need rules that prevent people from doing that — and then, of course, enforcement of those rules. With traditional markets like oil futures, the rules already exist; the problem is they’re not being enforced. The CFTC and the SEC have both been much less active in the last year. The CFTC, in particular, lost a lot of enforcement personnel and morale. So, I think it’s not that there aren’t rules to prevent insider trading — it’s that nobody seems to be focused on enforcing them. The leadership at the CFTC needs to get back to its core mission rather than being preoccupied with crypto and prediction markets. There’s no question the appearance of insider trading has become more frequent… from bets on strikes in Iran to wagers on Venezuela’s leadership changes. It’s all part of a pattern. ‘
Watch Big Business This Week on Cheddar—and YouTube!Big Businesses mentioned this week:$META ( ▼ 8.01% ) $GOOG ( ▼ 3.03% ) $EL ( ▼ 5.23% ) $RGR ( ▼ 3.33% ) $TSLA ( ▼ 3.36% ) $UBER ( ▼ 3.41% ) $RIVN ( ▼ 2.66% ) $LCID ( ▼ 7.35% ) $AMZN ( ▼ 1.99% ) $HMC ( ▼ 0.67% ) $SONY ( ▼ 2.51% ) $DIS ( ▼ 1.12% ) $WBD ( ▼ 0.48% ) $NXST ( ▲ 0.75% ) $YOU ( ▼ 1.4% ) $DAL ( ▼ 1.8% ) $UAL ( ▼ 0.09% ) $BA ( ▼ 2.42% ) Why the “Tehran TACO” trade is so much spicier than previous TACOsEat too many tacos and you need relief. But when you’re an investor, and the TACO is another move by U.S. President Donald Trump in his month-long bombing campaign against Iran, that relief is hard to find.
“Things are crazy right now,” said Chris Hodge, chief U.S. economist at Natixis. “I don’t know how you deploy capital with this amount of uncertainty. Nobody wants to get caught on the wrong side being too bearish when the president tweets out, ‘everything’s okay, we’re going to open up the Strait of Hormuz, the enemy is going to surrender.’”
Some of that rollercoaster ride is down to Presdient Trump’s mastery of the media, and the swift, if haphazard way his administration implements policy changes, like the day last April when Trump implemented his tariff regime. Markets react quickly to these moves, said Wendy Li, CIO at the alternative asset investment platform Ivy Invest.
“Where this term TACO has come about, is that Trump will make some dramatic statements or changes and policy shifts, and then pull back and recalibrate as necessary based on market reactions, and there’s this perception that has been generally validated by the ability to recalibrate when things have created excess volatility,” Li said in an interview. But she added, “With the war in Iran, I think we may see a different outcome.”
Right now, she said, as the president trumpets negotiations, oil prices quickly drop and stock prices rise as investors think a return to normal is in the cards. And then Iran comes back and says there are no negotiations, just an exchange of incompatible proposals. “There’s such a lack of clarity that markets are just responding very quickly to every piece of information that comes out.”
The problem, Li added, is that a war is qualitatively different from Trump’s peacetime policy switched, making this TACO trade a lot spicier.
“The expectation that things will resolve nicely and neatly, the buy-the-dip TACO mentality, is not necessarily the experience we’re going to have here, in large part because wars are unpredictable,” she said. “Someone can’t unilaterally decide to call an end to this. They can spiral out of control and last for far longer than it appears at the outset. Every week that goes by, there is an almost exponentially increased risk that we’re going to have the supply-side shock for longer, because it’s not like a flip of a switch and all this oil production comes back on.”
But the more the Administration threatens major changes, the less confidence investors and traders have that there will be a profitable bounce back from policies that are suddenly abandoned. In large part, that’s because Trump may have lost the upper hand in this conflict. As Hodge noted, it comes down to who’s really in charge: “Whatever the president says, it takes one party to start a war, it takes everybody to end it, right? So the enemy gets a vote here too.”
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Is this tech’s ‘Big Tobacco’ moment?Two juries ruled that Meta $META and Youtube $GOOG are bad for kids this week, in California and New Mexico, when they said the social media platforms’ parent company, Meta, got young users addicted and failed to protect them from sexually explicit content, solicitation, and human trafficking. In New Mexico, the jury stuck Meta with the max fine possible, $375 million. In Los Angeles, an unidentified woman was awarded $6 million after the jury found Meta and Alphabet-owned YouTube chose to make their apps addictive, leading her and others to have significant mental health issues. The New Mexico fine is only about 1/60th of Meta’s most recent quarterly profits, but it’s the verdicts that matter. They mark the first time a social media platform has been held responsible for the content it disseminates. Dozens of similar lawsuits are proceeding in state courts, after Congress declined to regulate social media companies. Meta faces some 2,000 similar suits in Federal courts, provoking a possible avalanche of industry-changing settlements like Big Tobacco had to make in 1998.
All bets, er, predictions, are off in NevadaState and federal officials are cracking down on Kalshi and Polymarket, the leading “prediction platforms” that dress up sports gambling and other forms of betting as federally (and loosely) regulated futures contracts. Nevada just got a court to order Kalshi that it needs a state gambling license to keep operating there, and it’s banned (for now) from offering so-called event-based contracts linked to sports, elections or entertainment. In Washington, Republican Sen. John Curtis of Utah and Dem senator Adam Schiff of California introduced a subtly-named bill called the “Prediction Markets Are Gambling Act.”
The short stackYou’re clearly into smart people talking about even smarter things. Lucky for you, that’s literally our whole deal at Cheddar. We interview the brightest minds in business, finance, and tech. If you’d like more in-depth analysis from interesting people, lcheck out our where to watch page and turn us on 24/7! Your wallet will thank you and so, more importantly, will your mind. But also your wallet. Remember that.
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