Chesapeake Asset Management Begins Investing in Ryder System. Is the Stock a Buy?

What happened

Chesapeake Asset Management LLC disclosed a new position in Ryder System (NYSE:R), according to a quarterly report filed with the Securities and Exchange Commission on October 15, 2025 (SEC filing). The fund purchased 19,350 shares during the period, bringing the position’s value to approximately $3.08 million as of June 30, 2025. This trade represents an estimated 2.78% of the fund’s $110.74 million in U.S. equity holdings.

What else to know

This is a new position for the fund, representing 2.78% of 13F reportable assets under management following the trade.

Chesapeake's top five fund holdings after the filing are:

• NASDAQ:MSFT: $11.41 million (10.0% of AUM) as of 2025-06-30
• NYSE:LLY: $6.94 million (6.2% of AUM) as of 2025-06-30
• NYSE:SPOT: $6.27 million (5.6% of AUM) as of 2025-06-30
• NASDAQ:AAPL: $5.99 million (5.4% of AUM) as of 2025-06-30
• NYSE:JPM: $5.52 million (5.0% of AUM) as of 2025-06-30

As of October 14, 2025, Ryder System shares were priced at $182.01, up 20.07% over the past year, outperforming the S&P 500 by 6.68 percentage points over the same period

Company Overview

Company Snapshot

Ryder System, Inc. is a leading provider of logistics and transportation solutions, operating globally with a diversified service portfolio. The company leverages its scale and expertise to deliver integrated fleet management and supply chain services to enterprise customers.

The company generates revenue through leasing and maintenance contracts, rental fees, logistics services, and the sale of used vehicles, offering integrated solutions to optimize clients' transportation and supply chain operations.

IMAGE SOURCE: GETTY IMAGES.

Ryder System provides fleet management, supply chain solutions, and dedicated transportation services, including full-service leasing, commercial vehicle rental, and logistics management.

It serves businesses across industries with large-scale transportation and logistics needs, targeting corporate clients seeking efficiency, reliability, and scalability in fleet and supply chain management.

Foolish take

Chesapeake Asset Management starting a new position in transportation giant Ryder System is noteworthy. The investment isn't small; Ryder stock sits just outside the financial management company's top five holdings at the number six position.

Ryder had a rough 2023 with sales down 2% year over year, but it undertook changes to its business, bouncing back strong in 2024 with 7% year-over-year revenue growth to $12.6 billion. However, sales results in 2025 have been mixed. Through the first half of this year, revenue of $6.3 billion was flat compared to 2024.

But that's not the whole story. Ryder expects its free cash flow (FCF) for the year to reach between $900 million and $1 billion. This sum far outpaces the $133 million in FCF produced last year, and will allow it to continue paying its robust dividend.

Moreover, the company adopted cost-saving initiatives that helped it increase diluted earnings per share (EPS) by 11% year over year to $3.15 in the second quarter. That's the third consecutive quarter of double-digit EPS growth.

Ryder's transformation from its difficult 2023 is delivering benefits to shareholders through higher EPS and FCF even though topline sales have not been impressive in 2025. These factors probably contributed to Chesapeake's decision to begin investing in Ryder, which looks like a solid stock to buy for income investors.

Glossary

13F reportable assets: Assets that investment managers must disclose quarterly to the SEC if they exceed $100 million in U.S. equity holdings.
Assets under management (AUM): The total market value of investments managed on behalf of clients by a fund or firm.
Position: The amount of a particular security or investment held by an investor or fund.
Stake: The ownership interest or share an investor holds in a company or asset.
Top five holdings: The five largest investments in a fund's portfolio, usually by market value.
Outperforming: Achieving a higher return than a specific benchmark or index over a given period.
Dividend yield: A financial ratio showing how much a company pays in dividends each year relative to its share price.
Fleet management: Services that oversee and coordinate commercial vehicles for businesses, including maintenance, leasing, and logistics.
Supply chain solutions: Services that help businesses manage the flow of goods, information, and resources from suppliers to customers.
Full-service leasing: A leasing arrangement where the provider handles maintenance, repairs, and other services for the leased asset.
Logistics management: The planning and coordination of moving goods and resources efficiently through a supply chain.
TTM: The 12-month period ending with the most recent quarterly report.

JPMorgan Chase is an advertising partner of Motley Fool Money. Robert Izquierdo has positions in Apple, JPMorgan Chase, and Microsoft. The Motley Fool has positions in and recommends Apple, JPMorgan Chase, Microsoft, and Spotify Technology. The Motley Fool recommends the following options: long January 2026 $395 calls on Microsoft and short January 2026 $405 calls on Microsoft. The Motley Fool has a disclosure policy.