5 Best Stocks to Buy According to Billionaire Richard Chilton

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1. Microsoft Corporation (NASDAQ:MSFT)

Chilton Investments’ Stake: $352 million 

Technology giant Microsoft Corporation (NASDAQ:MSFT)’s shares are among the weakest in the market this year as they are down by 22% year-to-date. The firm scored a win earlier this month when it announced on the 23rd that it had completed its first data center in Mount Pleasant. The data center is designed to support supercomputing and artificial intelligence, and Microsoft Corporation (NASDAQ:MSFT) continues to invest in the region until 2028. The firm also made inroads in the global clinical research sector in June after ICON plc selected it as a partner for its enterprise software needs. Through the deal, Microsoft Corporation (NASDAQ:MSFT)’s Microsoft 365 and Copilot software will be deployed by the firm.

Stifel discussed the firm on June 23rd as it reiterated a Hold rating and a $415 share price target. The coverage came after Microsoft Corporation (NASDAQ:MSFT) partnered with Chevron to support its power procurement needs.

Janus Henderson Global Sustainable Equity Fund discussed Microsoft Corporation (NASDAQ:MSFT) in its Q1 2026 investor letter:

“Microsoft Corporation (NASDAQ:MSFT) shares underperformed amid concerns over near-term returns from elevated cloud infrastructure investment and slower growth in the legacy software segment. While we trimmed the position in favor of more attractively valued opportunities, our long-term thesis remains intact. Microsoft benefits from powerful network effects and a deeply embedded ecosystem across productivity, cloud, and developer platforms, reinforcing its competitive moat. Its carbon-neutral Azure cloud platform plays a critical role in enabling businesses to decarbonize energy-intensive computing operations across sectors globally.”

While we acknowledge the potential of MSFT to grow, our conviction lies in the belief that some AI stocks hold greater promise for delivering higher returns and have limited downside risk. If you are looking for an AI stock that is more promising than MSFT and that has 100x upside potential, check out our report about the cheapest AI stock.

READ NEXT: 33 Stocks That Should Double in 3 Years and 15 Stocks That Will Make You Rich in 10 Years.

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