RYAN RYAN SPECIALTY HOLDINGS, INC. Insider Trading

Director Anthony J Kuczinski bought 3,000 RYAN shares ($104,960) across 2 purchases; holdings increased 29.8% amid 4-insider cluster buy

Anthony J Kuczinski, a director at Ryan Specialty Holdings, executed 2 separate purchases totaling 3,000 shares for $104,960.00 between June 11–12, 2026, at prices ranging from $34.83 to $35.77. This represents a 29.8% increase in his pre-transaction holdings from 10,072 to 13,072 shares. The current price of $35.34 is only marginally above his blended average price of $34.99, but the stock is -49.1% from its 52-week high of $69.49, suggesting Kuczinski is accumulating during a significant drawdown. His prior buy at this ticker on 2025-05-12 delivered a -16.9% 90-day return, establishing a poor track record of timing at RYAN specifically. However, this filing is part of a cluster pattern in which 4 other insiders also purchased within the past 14 days, indicating broader insider appetite despite recent price weakness and Kuczinski's own history of ill-timed entries at this security.

Director John W Jr Rogers purchased 7,500 RYAN shares at $35.16; cluster buy pattern with 3 other insiders within 14 days.

John W Jr Rogers, a director of Ryan Specialty Holdings, purchased 7,500 shares at $35.16 on 2026-06-10, increasing his holdings by 6.8% from 110,433 to 117,933 shares. This transaction occurs within a coordinated cluster, with 3 other insiders also buying within the past 14 days—a pattern that typically indicates collective internal assessment of value. The purchase price of $35.16 sits between the 52-week low of $29.28 and far below the 52-week high of $70.08; the stock is currently trading at $34.49, down 50.8% from its peak. Rogers' cross-ticker track record shows mixed outcomes: 2 prior buys with an average 90-day return of -6.4% and a 50% win rate, suggesting his prior open-market purchases have not consistently preceded positive performance. The simultaneous buying by multiple insiders merits investor attention as a coordinated signal, though the weak historical outcome pattern of Rogers' prior transactions tempers the conviction this particular trade would normally imply.

Executive Chairman Patrick G Ryan buys 120,000 shares of RYAN at $32.50; stock down 55.1% from 52-week high amid cluster buying.

Patrick G Ryan, Executive Chairman, purchased 120,000 shares at $32.50 on 2026-06-05, bringing his holdings to 13,817,859 shares. The purchase occurs while the stock trades at $32.56, down 55.1% from the 52-week high of $72.50 but up 10.8% over the past 30 days. His prior buy at RYAN on 2025-09-12 generated a +4.5% 90-day return, and his cross-ticker track record shows 1 prior buy with 100.00% win rate at the 90-day mark. The transaction coincides with a cluster pattern: 2 other insiders bought within the past 14 days. The company shows strong revenue growth of 21.3% year-over-year with $795,229,000.00 in latest-quarter revenue, though the stock's P/E of 32.89 and current 90-day decline of 18.0% warrant attention to underlying momentum.

CFO Janice M Hamilton buys 6,300 shares of RYAN for $200,292.75, increasing holdings by 76.1% to 14,574 shares

Janice M Hamilton, CFO of RYAN Specialty Holdings, executed a $200,292.75 purchase of 6,300 shares at $31.79, substantially expanding her equity stake by 76.1%. The transaction occurs with the stock trading 57.4% below its 52-week high of $72.50, and after a 90-day decline of -21.6%, creating a window where the CFO chose to add material exposure. The company's fundamentals show solid revenue growth of 21.3% year-over-year to $795.2M with a market cap of $3.4B, though the current P/E of 31.17 remains elevated. This purchase by the company's chief financial officer may indicate selective conviction in the business at current valuations relative to recent highs, though the trade's timing relative to broader market or company-specific developments cannot be determined from the filing alone.

EVP & General Counsel Mark Katz buys 3,215 shares of RYAN at $31.07; holdings rise 287.8% to 4,332 shares

Mark Katz, EVP & General Counsel, purchased 3,215 shares (3.2K shares) at $31.07 on 2026-06-03, boosting his total holdings from 1,117 to 4,332 shares—a 287.8% increase. The transaction occurred when the stock was trading at $30.86 and down -57.4% from its 52-week high of $72.50, having declined -21.6% over the prior 90 days. His same-ticker history at RYAN shows mixed timing outcomes: 2 of 4 prior sells were well-timed at the 90-day mark, while 2 were not. The company maintains solid revenue growth of +21.3% year-over-year with $795.2M in quarterly revenue, though it trades at a P/E of 31.17. This buy represents a significant accumulation relative to his prior position size, occurring during a period of material stock weakness.

Director Ryan Patrick G Jr. purchased 25,865 shares across 3 transactions for $1,033,974.65 at RYAN, raising stake to 428,295 shares.

Director Ryan Patrick G Jr. executed 3 separate purchases totaling 25,865 shares for $1,033,974.65 on February 20 and 23, 2026, at prices ranging from $39.94 to $41.41 and averaging $39.98. The stock now trades at $38.86, down 48.8% from its 52-week high of $75.93 and off 22.3% over the prior 30 days and 33.1% over 90 days—a significant drawdown during which this director chose to increase his position by 6.4%. His prior four purchases at RYAN show a mixed timing history, with only 1 of 4 resulting in positive 90-day returns, suggesting this ticker has not been a reliable predictor of his buy acuity. The company fundamentals remain solid with $754.6M in quarterly revenue and 21.3% annual revenue growth, though the elevated P/E of 114.29 reflects investor skepticism about valuation at present levels.

CEO Timothy Turner sold 129.6K RYAN shares (91.2% of holdings) at $53.61 for $6.9M on 2025-12-12

CEO Timothy Turner executed a substantial sale of 129.6K shares at $53.61, reducing his holdings from 142.1K to 12.6K shares—a 91.2% reduction in his stake. The sale occurred at a price $0.58 below the current market price of $54.19, and at a significant discount to the 52-week high of $75.93. His single prior sale at RYAN on 2024-08-09 occurred at a time when the stock subsequently gained 13.9% over 90 days, indicating the prior sale was poorly timed from a hindsight perspective. The magnitude and near-complete divestiture of his position warrants investor attention, as it represents a material shift in his ownership concentration, though the absence of scheduled trade flags in this record limits the degree to which timing can be characterized as deliberate strategic action.

Director Gerald W Schwartz sells entire 4,145,621 share stake in RYAN for $225.9M at $54.50

Director Gerald W Schwartz executed a complete liquidation of his position in Ryan Specialty Holdings, selling 4,145,621 shares (4.15M shares) at $54.50, reducing his holdings from 4,145,621 shares to 0 shares—a -100.0% reduction. This total elimination of the director's entire equity stake, worth $225,936,344.50 ($225.9M), represents a material change in insider exposure to the company. The magnitude and totality of this exit—moving from full ownership to zero shares—removes a significant insider from the cap table and may signal a fundamental shift in the director's continued involvement or confidence in the company's forward trajectory.

Executive Chairman Ryan Patrick G bought 276,634 shares of RYAN at $51.84 on 2025-09-12 for $14.3M; stock -31.9% from 52-week high.

Executive Chairman RYAN PATRICK G purchased 276,634 shares worth $14,340,263.95 at $51.84, increasing his holdings to 13,699,959 shares. This occurred while the stock trades 31.9% below its 52-week high of $75.93 and has declined 21.5% over the past 90 days. The company reported strong fundamentals with annual revenue growth of +21.1% and quarterly revenue of $855,170,000.00, though the elevated P/E of 101.39 suggests the market assigns significant growth expectations. The timing of this open-market purchase amid price weakness warrants attention regarding his assessment of current valuation relative to company trajectory.

Director Ryan Patrick G Jr bought 100 shares of RYAN at $55.54; stock -27.0% from 52-week high; prior buys at ticker underperformed at 90 days.

Director Ryan Patrick G Jr purchased 100 shares at $55.54, a routine acquisition that increased his holdings from 256,094 to 256,194 shares. The stock is currently down 30-day change: -4.2% and 90-day change: -20.9%, trading at $55.43, which is -27.0% from its 52-week high of $75.93. His prior three open-market buys at RYAN (2024-11-05, 2024-11-06, and 2025-03-10) all showed negative 90-day returns, with TIMING PATTERN: 0 of 3 prior buys were well-timed. This incremental purchase occurs amid a period of sustained stock weakness and follows a historical pattern where his prior accumulation at this ticker has not preceded price appreciation.