James M. Cracchiolo, chairman and CEO of Ameriprise Financial (AMP), has been a consistent net seller of company stock over the past year, with Form 4 filings showing no open-market purchases during the period. The most recent cluster of transactions occurred on July 28, 2026, when he executed two open-market sales totaling approximately $9.8 million, alongside an option exercise valued at $8.76 million and a large tax-withholding disposition of $19.1 million. That pattern—selling shares while simultaneously exercising options and having shares withheld for taxes—repeats a structure seen in his February 4, 2026 activity, when he sold roughly $23.9 million across eight separate open-market trades.
Across all 47 filings since early 2025, Cracchiolo has sold $57.4 million worth of AMP stock, with zero buy-side transactions. His only acquisitions have been compensation-related: equity awards and option exercises totaling $843,750, including a $425,000 grant in February 2025 and several zero-value awards tied to performance vesting. The February 2026 sales were particularly dense, with nine individual transactions ranging from $972,547 to $8.61 million, all executed on the same day. The January 2026 filings show a similar rhythm—large tax-withholding events ($9.06 million and $1.09 million) paired with option exercises and equity grants.
The data reveals a steady, mechanical pattern rather than opportunistic timing: Cracchiolo sells on vesting dates, uses a portion to cover tax obligations, and disposes of the remainder in the open market. His most recent activity on July 28, 2026, mirrors this cadence, with the $10.4 million in gross sales offset by the $8.76 million option exercise, leaving a net cash outflow of roughly $1.6 million after accounting for the tax withholding. Over the trailing 12 months, his selling has been consistent but not accelerating—the February and July 2026 clusters are comparable in size, suggesting a regular portfolio rebalancing schedule rather than a directional bet on the stock.
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