Insurance Mogul Patrick Ryan Has Bought $78 Million and Sold $181 Million Across Aon and Ryan Specialty
Patrick G. Ryan, founder of Aon Corporation and CEO of Ryan Specialty, has filed 2,444 insider transactions including $181 million in sales and $78 million in purchases across 3 companies.
Patrick G. Ryan, founder of Aon Corporation and current CEO of Ryan Specialty Holdings (RYAN), has filed 2,444 insider transactions including $181 million in sales and $78 million in purchases across 3 companies. While his Aon selling is historical (dating to the 2000s), Ryan has been a massive open-market buyer at his newer company — purchasing $14.3 million in RYAN stock in a single September 2025 transaction.
The Numbers
| Metric | Value |
|---|---|
| Career Sell Value | $181 million |
| Career Buy Value | $78 million |
| Total Transactions | 2,444 |
| Companies Filed At | 3 |
| Last Filing | Dec 10, 2025 |
Recent Buys
| Date | Type | Ticker | Shares | Price | Est. Value |
|---|---|---|---|---|---|
| Sep 12, 2025 | Buy | RYAN | 276,634 | $51.84 | $14.3M |
| Mar 14, 2023 | Buy | RYAN | 208,100 | $37.39 | $7.8M |
| Nov 25, 2022 | Buy | RYAN | 43,089 | $39.17 | $1.7M |
Ryan's $14.3 million buy in September 2025 was one of the largest single insider purchases of the year across all U.S. public companies.
What It Means
Patrick Ryan's career arc shows a rare insider evolution: he sold $181 million in Aon stock after founding the insurance brokerage giant, then pivoted to build Ryan Specialty — and has been buying aggressively at RYAN with $78 million in open-market purchases. His September 2025 buy of $14.3 million was particularly notable: it represented one of the year's largest individual insider purchases, signaling deep conviction in the specialty insurance and wholesale brokerage business he's building.
Ryan Specialty has been a strong performer since its 2021 IPO, with the stock climbing from the low $30s to above $80 by late 2025. Ryan's willingness to buy $14.3 million at $51.84 — well above his earlier purchases at $37-39 — suggests he views the company's growth trajectory as far from exhausted.
What to Watch
- Whether Ryan makes another large open-market purchase at RYAN, which would extend his pattern of multi-million-dollar conviction buys
- Ryan Specialty's acquisition strategy in the fragmented specialty insurance market, which has been a key growth driver
- The insurance industry cycle — hardening commercial insurance rates have benefited specialty brokers like Ryan, and any cycle turn could impact the stock
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