Looking into the sale by James he shared in his form 4 filing that his sale was to cover the transaction cost in exercising his non-qualified stock options (NSO). This sale results in closing part* of his NSO grant and acquisition of 477,011 shares. The net cash value of the sale comes out to $196k. This should result in ordinary income tax of roughly $42M.

* I’m not actually sure how NSOs work here. It’s unclear to me if there are still exercisable options in this grant or any other outstanding grants.

The shares were sold to cover the exercise price relating to the exercise of stock options to purchase 531,787 shares, which are scheduled to expire in 2025.

https://www.sec.gov/Archives/edgar/data/1318605/000177134025000004/xslF345X05/edgardoc.xml

Some of these are incorrect. Amazon didn’t acquire iRobot, and the planned acquisition was terminated in January 2024.

https://media.irobot.com/2024-01-29-Amazon-and-iRobot-agree-to-terminate-pending-acquisition