Ishaug Anthony D, chief financial officer of Winmark Corporation (WINA), has filed 36 Form 4 transactions with the SEC, all involving the single Minneapolis-based retailer. The pattern is heavily skewed toward selling: open-market sales total roughly $4.72 million, while there are zero open-market purchases. The remaining activity consists of compensation-related grants and option exercises, which together account for about $4.11 million in acquired shares but are mechanical in nature rather than discretionary investments.
The most recent cluster of filings, dated May 30, 2025, shows the heaviest selling. On that day, Ishaug executed five separate open-market sales totaling approximately $1.71 million, with individual transactions ranging from $77,390 to $1.22 million. A week earlier, on May 6, 2025, he sold another $586,712 across four transactions. Those sales followed an option exercise on May 30 valued at $618,732, suggesting the shares sold were sourced from that exercise. The most recent filings, from June 1, 2026, and April 30, 2026, are an award grant worth $916,139 and an option exercise worth $323,537, with no accompanying sales.
The selling bias is consistent across the entire filing history. In October 2024, Ishaug sold $880,110 across three transactions after exercising options worth $481,262. The only open-market purchase in the entire record is zero, meaning every discretionary transaction has been a sale. The compensation grants—$804,334 in June 2024, $825,998 in December 2024, $802,060 in June 2025, and $761,052 in December 2025—are annual equity awards that vest over time, and the option exercises appear to be routine conversions of previously granted awards. The pattern is one of a long-tenured executive steadily monetizing equity compensation, with no recent indication of accumulation or conviction buying.
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