While you were enjoying the $5 payout from your scratch-off ticket, one well-timed bet by an anonymous Polymarket user locked in a $400,000+ payout. The user placed a $20,000 bet on Venezuelan President Nicolás Maduro’s downfall just hours before President Trump ordered his capture, raising concerns over insider trading in a wildly unregulated market.

Last year, sportsbooks, financial platforms, and even media organizations like CNN signed deals with existing prediction markets or announced their own, further legitimizing the industry. Monthly bets placed on Polymarket and Kalshi jumped from less than $100 million in early 2024 to more than $13 billion last November.

You can bet on anything. We have $20 on you reading this sentence, but only after you speedrun the puzzle at the bottom of the newsletter. Polymarket, which currently bans users in the US (that can be circumvented with a VPN), gives bettors the ability to wager on things like the January Fed rate decision, the 2026 Super Bowl winner, the next US presidential nominees, and the fall of the Iranian regime:

• Kalshi, which is regulated by the government and allows US users, said it doesn’t list contracts on war, but does have related bets, like whether or not Greenland will become a part of the US.
• Polymarket, meanwhile, now offers contracts on whether the US will strike Cuba, Colombia, or Somalia.

The Commodity Futures Trading Commission (CFTC), which regulates Kalshi (and will oversee Polymarket once it’s approved for use in the US), has long been considered under-resourced, leading critics to argue that prediction platforms can be manipulated by deep-pocketed bad actors. Kalshi and Polymarket have both said that they have systems to root out market manipulation and insider trading.

Big picture: Polymarket is in hot water with gamblers who thought they’d get massive payouts from the more than $10.5 million in bets they collectively placed on a US invasion of Venezuela. The platform said that the capture of Maduro does not technically qualify as an invasion.—MM

Senate votes to block Trump from attacking Venezuela. In a largely symbolic 52–47 vote, five GOP lawmakers joined Democrats in advancing a resolution that would limit President Trump’s ability to launch further military strikes on Venezuela, less than a week after the US conducted an operation that killed dozens and captured the country’s president, Nicolás Maduro. The measure still requires a final vote in the Senate and would need to pass the House, too. (Even if it gets through Congress, Trump is certain to veto it.) Trump said that the five Republicans who backed the resolution “should never be elected to office again.”

Two people shot by immigration officers in Portland, OR. A man and a woman were shot by ICE officers yesterday in a car in Portland and taken to the hospital with injuries, authorities said. The Department of Homeland Security said the car’s passenger was associated with the Venezuelan Tren de Aragua gang and that the driver had tried to run immigration officers over. Portland Mayor Keith Wilson called on ICE to cease operations in the city until an investigation is completed. The shooting comes a day after a federal immigration officer fatally shot a 37-year-old woman, Renee Nicole Good, in Minneapolis. Local officials said video evidence contradicted DHS’s claim that the shooting there was in self-defense. Minneapolis Public Schools late Wednesday announced the cancellation of classes for the rest of the week as anti-ICE protests swelled in response to the shooting, although the protests have reportedly remained peaceful. Meanwhile, Minnesota officials said they were being blocked from accessing evidence by the FBI, which has assumed control of the investigation into the shooting.

Paramount won’t take no for an answer. If you didn’t like our original offer, perhaps you’ll like the exact same one, but with more oomph? That appears to be Paramount Skydance’s approach to its attempted hostile takeover of Warner Bros. Discovery (WBD) after it reaffirmed its $30 per share tender to buy WBD yesterday, arguing it’s still superior to Netflix’s bid. In a statement, Paramount said it has “diligently and constructively addressed each concern raised by WBD,” which includes how the deal is financed. For now, the WBD board is moving ahead with Netflix’s offer, while Paramount still hopes to win over the WBD shareholders.—AE

Uncle Sam suddenly moved closer to achieving the foreign trade equivalent of nirvana. The US trade deficit—calculated as imports minus exports—unexpectedly shrank by 39% last October from the prior month, according to government data released yesterday.

Economists were surprised to see the deficit fall to $29.4 billion, the lowest reading since 2009 as exports rose 2.6% and imports fell 3.2%, which will bolster the GDP for Q4.

Tariffs are working?

Reducing the export-import gap was the main motivation behind President Trump’s tariffs. With tariff whiplash causing trade balance fluctuations last year, the trade deficit from January to October was still 7.7% higher than a year prior. The month-to-month contraction in October was largely due to swings in a handful of products:

• Surging gold shipments abroad accounted for nearly 90% of the rise in exports.
• The import decline was largely led by falling pharmaceutical purchases after drugmakers spent the previous month stockpiling foreign medicines in preparation for tariffs Trump had threatened to impose on the industry by October 1 (though deals with drug makers mostly provided tariff relief).

Meanwhile, computer equipment imports rose, likely reflecting the AI boom.

There might be more trade turbulence ahead…as the Supreme Court determines the legality of tariffs that Trump issued under emergency powers, with a decision expected as early as today.—SK

A challenger emerges in the fight against your extended family’s 77-thread email exchange: As part of an AI makeover for Gmail, Google is introducing a secondary smart inbox with message summaries and broadening access to other Gemini-powered Gmail features, the company announced yesterday.

Still in beta mode, the new AI Inbox presents a personal assistant-like rundown of your unread mail, along with suggested to-dos. It will roll out to “trusted testers” in the US before expanding “in the coming months,” Google said.

Meanwhile…

• All consumer Gmail accounts will gain access to Suggested Replies personalized for tone, AI summaries atop email threads, and the Help Me Write tool for generating and polishing messages—features that were previously only available to premium Google subscribers.
• The new features for paid users include a proofread tool that dances on Grammarly’s grave and an AI-enabled search bar that lets you find an email by asking questions like, “Who was the plumber that gave me a quote for the bathroom renovation last year?” per Google’s launch video.

Google is crushing the AI race. Its parent company, Alphabet, surpassed Apple in market capitalization this week for the first time since 2019, buoyed by optimism around its latest Gemini model and its custom chips. Alphabet is now the second-most valuable company in the world behind Nvidia.—ML

Who needs doctors when you can ask a robot if your nagging cough is just a cold or, far more likely, a rare 18th-century pulmonary disease? OpenAI says there are hundreds of millions of you doing the latter.

The AI company behind ChatGPT said that 230 million users ask the chatbot health questions every week. That’s about 29% of the app’s total user base (as of late last year). Health is such a popular topic on ChatGPT that OpenAI announced it’s launching a dedicated experience with “enhanced privacy” to store all of your health-related questions.

The new platform, ChatGPT Health, allows users to connect their medical records and wellness app info. OpenAI stresses that it’s meant “to support, not replace, medical care.” It added that ChatGPT Health is not intended to diagnose or treat illnesses. For that, you still need to be a human with a medical degree.—AE

The feeling of getting a 5/5 on the Brew’s Weekly News Quiz has been compared to when a 40-degree day feels like spring because it’s been 20 degrees every day for a month.

It’s that satisfying. Ace the quiz.