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 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