Bill Ackman, Billionaire investor and founder of Pershing Square Holdings, has had quite the busy 2025, making some notable buys and sells while also considering the next steps to potentially create a “modern-day” version of Berkshire Hathaway (NYSE:BRK-B). As Warren Buffett retires, perhaps it’s Ackman that could be the big-money manager to follow as he makes big, bold bets to take his hedge fund to the next level.
Just over a week ago, the 13-F filing confirmed that Ackman had bought up shares of ride-hailer Uber Technologies (NASDAQ:UBER | UBER Price Prediction) while selling out of fallen sneaker maker Nike (NYSE:NKE) in the first quarter. Now, Ackman shined light on his latest bets, announcing that he bought up shares of e-commerce juggernaut Amazon (NASDAQ:AMZN) while dumping shares of Canadian railway Canadian Pacific Kansas City (NYSE:CP).
Bill buys up Amazon, sells out of CPKC
Personally, I’m a huge fan of selling out of Nike and CPKC (wonderful businesses, but their shares have been less than timely of late) and buying into Uber and Amazon.
Upon announcing the new position, Ackman remarked that AMZN shares appeared “extremely attractive” at his price of admission. Undoubtedly, the Magnificent Seven titan hasn’t looked this cheap in years, now going for 32.7 times trailing price-to-earnings (P/E) or 31.5 times forward P/E.
Though Amazon stock didn’t really gain any sort of “Ackman premium” following the news, I do think that investors looking to get back into the Mag Seven trade stand to do very well by riding on Ackman’s coattails. The stock sold off just north of 1% on Friday’s session, as Trump’s latest tariff comments (now directed at Apple (NASDAQ:AAPL)) weighed heavily on the S&P 500. A regulatory filing rejected by shareholders also likely didn’t help the cause for AMZN shares on the rough Friday session.
Of course, CPKC is still a fantastic railway to hang onto for the long haul, even as it races into tariff headwinds. But in light of tariff disruptions, I’d argue that Amazon is the much better bet, especially since I’m even sure you can consider the Canadian railway a cheap stock at just over 26.6 times trailing P/E. It’s certainly not the cheapest rail stock in the world. And while it’s a good name to hold for the long haul, perhaps it’s not the best name, especially if you’ve got a chance to pick up of a Mag Seven stock at a double-digit percentage discount.
Amazon stock certainly looks “attractive” at current levels
Sure, Amazon faces its own tariff troubles. But its stock has already crumbled close to 30% from peak to trough. After a month or so of relief gains, AMZN shares have regained close to half of the ground lost, now down just over 15% from their February 2025 all-time highs.
As big retail starts to steadily step away from the direct-to-consumer (DTC) route (has the DTC bubble burst?), Amazon could stand to gain as it offers a greater selection of branded merchandise on its platform. Whether we’re talking about Nike sneakers or Armani perfumes, I think the trend that sees big retailers going towards Amazon is just getting started, as they explore options to boost sales in what could be a harsher economic environment.
Beyond retail, Amazon stands out as a strong horse to bet on in the AI race. The e-commerce titan is poised to spend $100 billion on AI infrastructure this year alone. There’s no question that Amazon’s AI powers stand to gain at an explosive rate over time. As more robots step into the warehouse, while AI coders get to work in the offices, Amazon stands out as a prime automation play (pardon the pun) for the agentic AI era.
At current multiples, I do think the Mag Seven stock is way too cheap, given the AI-driven catalysts that may not be all too far off from giving quarterly numbers a serious boost. Perhaps Ackman is right to buy despite the tariff jitters and public scrutiny from Trump after Amazon’s now-scrapped plans to show tariff costs.
Top Gaining Stocks
Top Losing Stocks