John R. Gallagher, chief operating officer of Trupanion (TRUP), has filed 85 Form 4 transactions, all in that single company. The pattern is one-sided: he has recorded zero open-market purchases and zero acquisitions for cash, while his total open-market sales reached $514,808.19. The most recent three sales occurred on May 28, June 29, and July 28, 2026, with values of $78,153.39, $10,925.85, and $10,809.48 respectively.
The bulk of his recent filings are not discretionary trades. They are code F transactions, shares withheld to cover tax obligations, and code M exercises, which are mechanical conversions of options. For example, on August 25, 2026, he had multiple F transactions valued at $318.40, $3,502.40, and $191.04, each paired with an M exercise valued at zero. Similar clusters appear on August 22, May 25, and May 22, 2026, with F values ranging from $153.02 to $25,725.60. These are automatic events tied to compensation vesting, not market timing.
The only discretionary signal in the data is the sell side. Gallagher has sold TRUP stock in each of the last three months, with the largest single sale in late May. There is no corresponding purchase activity to offset those sales. The total sell value of roughly $515,000, combined with zero buy value, gives the record a clear selling bias. The recent trades, however, are dominated by tax withholding and option exercises, which do not reflect a change in his position.
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