We recently published a list of Unknown Billionaire Phill Gross’ 10 Stock Picks with Huge Upside Potential. In this article, we are going to take a look at where Delta Air Lines, Inc. (NYSE:DAL) stands against unknown billionaire Phill Gross’ other stock picks with huge upside potential.

Phillip “Phill” Gross is a seasoned investor and influential figure in the world of institutional asset management, best known as the Co-founder, Managing Director, and Healthcare Portfolio Manager of Adage Capital Management. While Robert Atchinson, his longtime collaborator and fellow Co-founder, serves as the firm’s Portfolio Manager, Gross’s leadership and strategic vision have played a foundational role in shaping Adage’s long-term investment philosophy and reputation. The two met in the mid-1980s while working as Harvard University’s endowment analysts. Their professional synergy led them to leave Harvard Management Company in the 1990s, following public scrutiny over performance-based bonuses. With the backing of an initial $1.8 billion investment from Harvard and an agreement for the university to receive 10% of the firm’s earnings, they launched Adage Capital Management in 2001 alongside an 18-person team.

Under Gross’s co-leadership, Adage has become a key player in managing assets for prominent institutional clients such as Harvard University, Dartmouth College, Northwestern University, the American Red Cross, and the Getty Foundation. The firm specializes in long/short equity strategies guided by fundamental analysis and engages in risk arbitrage and event-driven opportunities when market conditions are favourable. Adage Capital Management and its predecessor, the Select Equity Group at Harvard Management Company, have consistently outperformed broader market benchmarks by an average of 3.5% over the past 15 years. This is a testament to the disciplined, research-driven investment framework that Gross helped instill.

Gross himself brings a deep background in healthcare investing, having served for nearly two decades at Harvard Management Company in various roles, including Healthcare and Retail Analyst, Equity Research Director, and Partner. His academic credentials include a B.S. in finance and economics (1982) and an M.S. in investments (1983), both from the University of Wisconsin. He remains actively engaged with his alma mater, serving on the advisory boards of the Steve Hawk Center for Applied Securities Analysis and the Nicholas Center for Applied Corporate Finance. In recognition of his professional accomplishments and ongoing contributions, Gross received the Distinguished Alumnus Award from the University of Wisconsin Business School in 2006.

Beyond finance, Gross is a committed philanthropist. He co-founded Strategic Grant Partners, an organization focused on driving systemic change in education and family services throughout Massachusetts. He also serves as Vice President of the Board of Directors for Youth Enrichment Services, a nonprofit that provides urban youth with outdoor recreational experiences. In addition, he holds board positions with the U.S. Ski and Snowboard Association, where he is Vice-Chair of the Investment Committee, and with the T2 Foundation.

Adage Capital Management’s latest 13F filing for Q4 2024 reported $57.19 billion in managed securities, with the top 10 holdings comprising 31.7% of the total portfolio, demonstrating a strategic yet diversified approach to asset allocation. While Atchinson oversees day-to-day portfolio management, Gross’s enduring influence and expertise, particularly in healthcare investing, continue to shape the firm’s long-term success and institutional credibility.

Our Methodology

We searched through Adage Capital Management’s Q4 2024 13F filings to identify unknown billionaire Phill Gross’ stock picks with the highest upside potential. We compiled the equities with upside potential higher than 34% at the time of writing this article and discussed why they stood out as strong potential investments. Finally, we ranked the stocks based on the ascending order of their upside potential. To assist readers with more context, we mentioned the hedge fund sentiment around each stock using data from 1,009 hedge funds tracked by Insider Monkey in the fourth quarter of 2024.

Why are we interested in the stocks that hedge funds pile into? The reason is simple: our research has shown that we can outperform the market by imitating the top stock picks of the best hedge funds. Our quarterly newsletter’s strategy selects 14 small-cap and large-cap stocks every quarter and has returned 363.5% since May 2014, beating its benchmark by 208 percentage points (see more details here).

Delta Air Lines, Inc. (NYSE:DAL)

Number of Hedge Fund Holders as of Q4: 84

Adage Capital Management’s Equity Stake: $184.78 Million 

Upside Potential as of May 2: 44.58%

Delta Air Lines, Inc. (NYSE:DAL) is one of the leading U.S. airlines, operating nine hubs with Hartsfield–Jackson Atlanta International Airport as its largest in passenger volume and flight departures. In the face of shifting economic conditions during the first quarter of 2025, the airline managed to deliver steady profitability, aligning with results from the previous year. Delta reported operating revenue of $14.0 billion and an operating income of $569 million, reflecting a 4.0 percent operating margin. Earnings per share stood at $0.37, while the company generated $2.4 billion in operating cash flow. Delta also made significant progress on its financial obligations, with $531 million in payments toward debt and finance lease obligations, bringing total outstanding debt to $15.8 billion at the quarter’s end.

CEO Ed Bastian acknowledged the quarter’s unexpected challenges but praised the workforce’s dedication, emphasizing Delta Air Lines, Inc. (NYSE:DAL)’s position of strength moving forward. He projected a June quarter profitability between $1.5 billion and $2 billion. However, he noted the economic uncertainty makes it premature to revise the full-year outlook. Despite the cautious tone, Bastian expressed confidence in Delta’s capacity to deliver solid profitability and free cash flow for the remainder of the year, citing the company’s proactive strategy, improved cost environment from declining fuel prices, and a focus on financial durability and differentiation in the competitive airline industry.

Although Delta Air Lines, Inc. (NYSE:DAL) expects total revenue in the June quarter to range from 2% below to 2% above the same period last year, the airline sees continued resilience in premium, loyalty, and international segments. This strength is helping offset some softness in domestic and main cabin performance. Hauenstein noted that while 2025 is unfolding differently than initially expected, Delta Air Lines, Inc. (NYSE:DAL) remains focused on long-term strategic goals while adapting to evolving market conditions.

Overall, DAL ranks 2nd on our list of unknown billionaire Phill Gross’ stock picks with huge upside potential. While we acknowledge the potential of these stock picks, our conviction lies in the belief that AI stocks hold greater promise for delivering higher returns and doing so within a shorter time frame. There is an AI stock that went up since the beginning of 2025, while popular AI stocks lost around 25%. If you are looking for an AI stock that is more promising than DAL but that trades at less than 5 times its earnings, check out our report about this cheapest AI stock.

READ NEXT: 20 Best AI Stocks To Buy Now and 30 Best Stocks to Buy Now According to Billionaires.

Disclosure: None. This article is originally published at Insider Monkey.