AIZ ASSURANT, INC. Insider Trading

EVP Robert Lonergan sells 7,000 AIZ shares at $262.71 under pre-arranged 10b5-1 plan; retains 27,373 shares.

Robert Lonergan, EVP and Chief Strategy Officer, sold 7,000 shares (7.0K shares) of Assurant at $262.71 on 2026-06-22, reducing his holdings by 20.4% from 34,373 shares to 27,373 shares. This transaction was executed under a pre-arranged 10b5-1 trading plan adopted on 2026-03-20, meaning it was scheduled rather than discretionary. His prior sale at AIZ on 2025-03-20 posted a 30d return of -11.0% and 90d return of -8.0%, providing limited evidence of consistent execution timing at this ticker. The company shows solid fundamentals with $3.4B revenue, $274.1M net income, and annual revenue growth of 7.9%, trading at P/E 13.14.

SVP/CAO Dimitry Dirienzo sold 2,000 shares of AIZ at $255.68 for $511.4K; holdings drop from 4.7K to 2.7K.

Dimitry Dirienzo, SVP and Chief Administrative Officer, sold 2,000 shares at $255.68 on 2026-05-26, reducing his holdings from 4,741 to 2,741 shares. The current price of $252.06 is -3.4% from the 52-week high of $260.96, and the stock has advanced +8.3% over 30 days and +9.9% over 90 days. At a market cap of $12,488,977,382.22 and net income of $274,100,000.00, Assurant remains solidly profitable with annual revenue growth of +7.9%. The sale represents a substantial reduction in Dirienzo's proportional stake and occurs within the context of recent upward price momentum.

CFO Keith Meier sold 25,000 shares of AIZ at $254.31; scheduled 10b5-1 plan execution

Keith Meier, EVP and CFO of Assurant, sold 25,000 shares (representing 57.4% reduction in his holdings from 43,552 to 18,552 shares) on 2026-05-15 at $254.31 per share under a 10b5-1 trading plan adopted on 2026-02-13. This was a pre-arranged, scheduled transaction rather than a discretionary trade, and therefore reflects no timing signal or conviction-based positioning decision. The stock has appreciated 13.4% over the preceding 30 days and 16.8% over 90 days, trading near the 52-week high of $257.17, suggesting a period of strong momentum in the security. While the sale represents a material reduction in the CFO's direct holdings, the planned-trade framework limits the evidentiary value for inferring management confidence or concern about valuation.

AIZ EVP Rosenblum sells 2,000 shares at $251.77; holds 12.8K post-trade as stock approaches 52-week peak of $254.43

Jay Rosenblum, Chief Legal Officer, sold 2,000 shares at $251.77, reducing his holdings from 14.8K to 12.8K shares. The sale occurred near the stock's 52-week high of $254.43 (current price $254.61 is +0.1% from that peak), and AIZ has appreciated 17.1% over the prior 90 days. Rosenblum's single prior sale at AIZ (August 2025) posted a 90-day return of +8.4%, meaning the stock rose after that sale—not a pattern of well-timed exits. With a P/E of 12.61 and solid fundamentals (revenue $3.4B, net income $274.1M, annual growth +7.9%), the company's valuation remains reasonable even at current price levels. The sale itself does not carry strong directional signal given the modest reduction in holdings and the insider's limited history of market-timing success on this ticker.

Demmings Keith (CEO) sold 13,725 shares for $3,026,652.01 at $220.52 blended price; holds 84.6K shares post-sale.

Keith Demmings, President and CEO of Assurance Inc., executed 2 separate sales totaling 13,725 shares for $3,026,652.01 on 2025-10-03, reducing his holdings by 14.0% from 98,372 to 84,647 shares. The sales were executed at a blended average price of $220.52 per share, slightly below the current price of $221.69 and within the 52-week range. His prior sale at AIZ on 2025-08-29 showed a 30d return of -2.1%; with AIZ trading +5.0% over the past 30 days and +16.5% over 90 days, this current sale occurs in a rising price environment. Fundamentals remain solid with $3.2B in latest quarterly revenue, net income of $235.3M, and a P/E of 15.60, providing no evident operational red flags motivating a large executive liquidation.

CEO Demmings sold 4,275 AIZ shares at $220.27 for $941.7K; retains 98,372 shares post-sale

Demmings Keith, President and CEO of Asssurant, sold 4,275 shares for approximately $941.7K on 2025-08-29, reducing his holdings by 4.2% to 98,372 shares. The sale occurred at $220.27 per share, which sits 6.2% below the 52-week high of $228.68, within the stock's typical range. With a P/E of 15.10 and recent quarterly net income of $235.3M supporting a $10.8B market cap, the company shows stable fundamentals; the stock has gained 15.1% over the past 30 days and 5.2% over 90 days. The transaction represents a routine partial reduction in his substantial remaining position, consistent with ongoing portfolio management at a mid-sized scale relative to his 98.4K-share holding.

EVP and CLO Jay Rosenblum sold 3,900 shares of AIZ at $208.53; holdings reduced 33.1% to 7,875 shares

Jay Rosenblum, serving as EVP and CLO, sold 3,900 shares at $208.53 on 2025-08-12, reducing his holdings from 11,775 shares to 7,875 shares—a 33.1% reduction in his position. The transaction value of $813,256.47 represents a material divestiture by a senior legal executive. At the time of sale, the stock was trading $5.06 below its current price of $213.59, though it remains 6.6% below the 52-week high of $228.68. The company's fundamentals show solid performance with quarterly revenue of $3,158,400,000.00, net income of $235,300,000.00, and 6.7% annual revenue growth, supporting a reasonable P/E of 15.03. The context—sale timing, position reduction magnitude, and executive role—warrants review of regulatory filings to determine whether this reflects portfolio activity or other material considerations known to the insider.

Chief Marketing & Risk Officer Lonergan sells 3,500 AIZ shares at $212.39 for $743.4K; retains 25.7K shares

Robert Lonergan, Chief Marketing & Risk Officer, sold 3,500 shares of Assurant at $212.39 on 2025-03-20, generating total proceeds of $743,354.15. The sale reduced his holdings by 12.0%, leaving him with 25,731 shares post-transaction. The stock has declined 8.4% from its 52-week high of $228.68 and is currently trading at $209.44, roughly 1.4% below the transaction price. Assurant's financial position remains solid with quarterly revenue of $2,967,700,000.00, net income of $133,800,000.00, and a P/E of 12.39, suggesting the sale does not occur against a backdrop of obvious fundamental distress. The transaction represents a material but non-controlling reduction in a senior executive's stake; significance is moderate given the stable capital structure retention (25.7K shares remaining) and the absence of additional red flags in the earnings or valuation data.