TheChek News Flow

What we predicted: Amazon Will Buy Lyft

What happened: A deal between the two companies seemed to make sense: Lyft is a distant No. 2 in traditional ride-hailing to Uber, which makes a deep-pocketed partner like Amazon appealing. Despite its also-ran status, Lyft still has enough scale to help Amazon bring its autonomous vehicle taxi service, Zoox, to the masses. Oh, and Lyft’s CEO David Risher is a former longtime Amazon executive. But for now, Lyft and Amazon are on their own separate paths.—Nick Wingfield

Grade: F

What we predicted: Elon Musk Will Try to Buy TikTok

What happened: There was also a logic to this prediction. President Donald Trump was eager to find American investors to buy TikTok from its Chinese parent ByteDance to avert a shutdown of the app in the U.S. due to a law passed by Congress. Musk at the time was a close ally of Trump’s and already had a stake in social media through his ownership of X. But Musk in February said publicly that he wasn’t interested in buying TikTok. And he wasn’t on the broader list of investors in a new U.S.-based TikTok entity that the app’s management shared with its employees last month.—N.W.

Grade: F

What we predicted: Nvidia Will Make Several Significant Acquisitions

What happened: The AI chip giant announced one bona fide blockbuster deal in 2025, although it was not a traditional acquisition: its $20 billion agreement in December to hire most of the staff of the chip startup Groq and pay for a nonexclusive license to Groq’s technology. It struck a similar deal with the networking startup Enfabrica a few months earlier, but that agreement was much smaller at around $900 million. Nvidia may have a more sizable deal in the works: Earlier this week, Calcalist, an Israeli financial publication, reported that Nvidia is in advanced talks to buy an Israeli AI startup, AI21 Labs, for as much as $3 billion. If that deal happens, it will be in 2026.—N.W.

Grade: B+

What we predicted: Microsoft Will Do a Deal With Anthropic

What happened: We nailed this one. We posited that Microsoft and Anthropic would cozy up as the former company sought to lessen its dependence on OpenAI, still its most important AI partner. Sure enough, in November, the companies announced a strategic partnership through which Anthropic committed to spending $30 billion to buy computing capacity from Microsoft’s Azure cloud service. Microsoft also pledged to invest up to $5 billion in Anthropic, and Anthropic made its Claude AI models more broadly available to Microsoft customers as part of the agreement.—N.W.

Grade: A

What we predicted: Amazon Will Launch Its Own Version of Ozempic

What happened: We were wrong. Amazon didn’t launch its own version of a GLP-1, the category of weight loss drugs that includes Ozempic and Wegovy, in 2025. It did, however, expand its pharmacy business in other ways, including by launching same-day medication delivery in more U.S. cities and adding medication kiosks to One Medical offices. The wait for an “Amazon Basics” version of GLP-1 drugs continues.—Theo Wayt

Grade: F

What we predicted: Telegram Will Launch a Stablecoin

What happened: Didn’t happen. The Dubai-based messaging app is popular among crypto traders and users, and we predicted that the allure of launching its own stablecoin would be irresistible for Telegram. Instead, the first wave of noncrypto firms issuing stablecoins turned out to be payment and fintech related firms, such as Western Union, Klarna and SoFi. Social media and communications apps could join that crowd, but they haven’t yet.—Yueqi Yang

Grade: F

What we predicted: An AI Agent Will Cause Chaos for a Blue-Chip Company

What happened: We were pretty close. In early December, The Information reported that a chatbot launched by the retailer Gap Inc. to field product-related questions went off the rails, discussing a bunch of questions outside its purview including about sex toys and Nazi Germany. The chatbot was powered by enterprise AI startup Sierra, cofounded by former Salesforce co-CEO Bret Taylor.

Sierra said the episode was caused by a “bad actor” trying to “jailbreak over a dozen of our customers’ AI agents.” The company said its abuse detection systems caught all but the Gap one, although the problem was fixed. As we noted at the time, it wasn’t the only such embarrassment. In July, Elon Musk’s xAI had to apologize after its Grok chatbot praised Adolf Hitler in a series of X posts.—Martin Peers

Grade: A

What we predicted: Marc Lore’s Wonder Will Acquire FreshDirect or Gopuff

What happened: Wonder didn’t acquire FreshDirect, Gopuff or another grocery business in 2025. It made two other acquisitions though: Tastemade, a media business, and Spyce, the robotics company that manufactures Sweetgreen’s automated salad-making machines.—Ann Gehan

Grade: F

What we predicted: Tim Cook Will Extend His Apple Tenure for Another Half-Decade

What happened: It’s hard to say definitively whether Apple’s CEO has committed to remain at Apple for another five years, but it seems unlikely. Apple’s most senior executives are at-will employees, without employment contracts, the company says in its filings with regulators. If Cook had made an explicit promise to the company’s board to stay at the company through a particular date, there’s a good chance Apple would have disclosed such a detail.

There’s also been considerable buzz lately about Apple stepping up its CEO succession planning, as we and others have reported. Nothing appears to be imminent on that front, but five years is a long time in a tech industry moving very quickly.—N.W.

Grade: F

What we predicted: College Athletes Will Become University Employees

What happened: We were premature. Alabama football players, Duke basketball stars and other college athletes didn’t start earning wages from their schools in 2025. It may be a question of when, not if, that happens. Last month, a bill backed by the NCAA and the U.S. Olympic and Paralympic Committee hit a wall in Congress; it would prevent college athletes from being classified as employees.

Another part of our prediction did come to pass though—namely, that the flood of name, image and likeness dollars into colleges athletes’ pockets would prompt some of them to choose college over the pros. Just last week, on Christmas Eve, Baylor University announced it signed seven-foot Nigerian center James Nnaji, who was a second-round draft pick for the NBA’s Detroit Pistons in 2023. Colorado College this week added a former minor league professional hockey player to its roster. Both developments are a sign that, for some athletes, playing college sports and landing blockbuster sponsorships is starting to look like a more appealing financial bet than grunting it out in minor leagues or sitting on pro benches.—Sara Germano

Grade: C

What we predicted: A Buyout Wave Will Hit Consumer Companies

What happened: None of the direct-to-consumer brands that we named in this prediction as likely buyout candidates—such as ThredUp and Allbirds—ended up being taken over by private equity firms in 2025. There were, however, some notable deals that weren’t that far off from the ones we predicted. For example, Rent The Runway’s longtime lender and other investors took control of 86% of the company’s shares in August and restructured its debt obligations. But Rent the Runway remains a publicly-traded company. Meanwhile, Grove Collaborative conducted a strategic review in 2025 after one of their shareholders pushed for it, but a buyer hasn’t yet materialized for the business.—Ann Gehan

Grade: C

What we predicted: AI Chatbot Companies Will Face Hundreds of Lawsuits

What happened: We were way off. Chatbot companies have faced lawsuits, to be sure, but most likely in the dozens, not the hundreds. Plaintiffs filed seven lawsuits against OpenAI in November alone alleging that the company’s ChatGPT pushed their family members into delusional conditions that drove some people to kill themselves. Just a month ago, the New York Times sued Perplexity for copyright infringement, adding to a suit the Times filed against OpenAI a couple of years ago. Amazon and the Chicago Tribune also sued Perplexity in recent months, while Reddit sued the firm in October. Other similar lawsuits in 2025 included Advanced Local Media suing Cohere in June. The lawsuits are coming, just not that many.—Martin Peers

Grade: C

What we predicted: Cisco CEO Chuck Robbins Will Leave

What happened: We whiffed badly on this one. Not only is Robbins still running Cisco, but the networking giant’s business performed well in 2025 thanks to the AI boom. The company’s stock hit an all-time high in December and closed the year up nearly 31%.—N.W.

Grade: F

What we predicted: Warner Bros. Discovery Will Rebrand Max

What happened: In July, Warner Bros. Discovery did indeed change Max’s name to HBO Max, which is what an earlier version of the service was called. The rechristening was just one episode within a much bigger drama involving the beleaguered company’s future, which reached new heights in December when Netflix and David Ellison’s Paramount made competing acquisition offers.—Abram Brown

Grade: A

What we predicted: OpenAI’s Chief Operating Officer, Brad Lightcap, Will Depart

What happened: The bottom line is that Lightcap, as of this writing, is still at OpenAI. However, leadership changes continued to chip away at his influence at the company. (Earlier such changes are what prompted our prediction.) In May, OpenAI hired then-Instacart CEO Fidji Simo to become the CEO of Applications. That role could have been a natural fit for Lightcap, who was running OpenAI’s day-to-day business operations at the time. Now, Lightcap reports to Simo, placing him a step further away from CEO Sam Altman.—Stephanie Palazzolo

Grade: F

What we predicted: Conservative-Favorite Industries Will Be Funding Hot Spots

What happened: We were right on the money in predicting defense tech and crypto would both get big investment bumps in the Trump era. Global venture capital investments in defense tech startups surged to $59 billion for the 12 months ended Sept. 30, 2025, compared to $25.2 billion for the comparable period in 2024, PitchBook estimates. Investments in stablecoins jumped too, buoyed by the Trump administration’s crypto-friendly policies, including his signing of the GENIUS Act in July, which provided the first regulatory framework for the industry. Circle Internet Group, the stablecoin issuer, pulled off a spectacular IPO in 2025 as well, though some crypto stocks and token prices cooled considerably in the latter half of the year.

There were fewer obvious signs of an investment bonanza in other startup categories on our list of potential beneficiaries. Funding in ed tech startups, for example, was flat through the end of November compared to the full year of 2024, according to CrunchBase. And there is sparse data on a funding boom for longevity startups. One exception was NewLimit, which was cofounded by Coinbase CEO Brian Armstrong and raised a $130 million Series B round from Kleiner Perkins and others in May.—N.W.

Grade: A-

What we predicted: Microsoft Will Stave Off the FTC’s Current Investigation

What happened: It’s too soon to say whether this prediction will age well or not down the road, but it didn’t come true in 2025. Andrew Ferguson, the Trump-appointed successor to Lina Khan as chair of the Federal Trade Commission, hasn’t moved to drop the agency’s far-reaching probe into Microsoft—instead, at least early on, Ferguson’s FTC continued its line of questioning by asking other companies about alleged anticompetitive behavior by Microsoft as of March 2025. That doesn’t necessarily mean the FTC will actually file a full-fledged antitrust lawsuit against Microsoft. Meanwhile, Trump himself has shown an appetite to go after Microsoft, including demanding that it fire its president of global affairs, Lisa Monaco, because she previously worked for the Obama and Biden White Houses. Microsoft has so far declined to do so.—Aaron Holmes

Grade: D

What we predicted: Trump Will Sign Child Online Safety Legislation Into Law

What happened: The president didn’t sign a comprehensive online safety law aimed at protecting children, such as the Kids Online Safety and Privacy Act, which passed the U.S. Senate in 2024 before stalling in the House. Such an event could be getting closer though. In mid-December, a House subcommittee advanced a package of 18 child online safety bills, including a new version of KOSA, for the full House Energy and Commerce Committee to consider. But compromises in that legislation have upset some lawmakers and it’s likely to face aggressive lobbying by the tech industry, making it hard to predict whether it will pass and in what form.—N.W.

Grade: D

What we predicted: Alibaba Will Acquire One of China’s Top AI Startups

What happened: Alibaba Group didn’t acquire Moonshot AI, as we predicted. The Chinese tech giant, however, did effectively acqui-hire some researchers from another major Chinese AI startup, 01.AI, which shifted its focus away from developing cutting-edge models.

Instead, the biggest event in China’s AI sector in 2025 was DeepSeek’s sudden rise to global stardom due to the release of R1, its highly capable open-source AI model. It prompted Moonshot and other Chinese AI startups to renew their focus on research and develop their own open-source models. In July, Moonshot launched a new model called Kimi K2, whose strong coding capabilities impressed app developers in the U.S. and elsewhere. On the back of Kimi K2’s success, Moonshot has been working on a new funding round at a valuation of $4 billion.—Juro Osawa

Grade: D

What we predicted: Josh Kushner Will Buy New York Magazine

What happened: In 2024, Kushner, the founder of investment firm Thrive Capital, made a handful of flashy media deals, including buying the rights to Life magazine and investing in the movie studio A24. So our speculation that he might snap up New York magazine wasn’t such a stretch. But we were wrong: Vox Media still owns the venerable magazine.—A.B.

Grade: F