Does he tend to hold all the company shares he gets or does he exercise his options and sell as soon as he can, keeping his exposure to his own company’s stock to a reasonable level while freeing up cash?
Did he have a reason for needing to raise cash - new mortgage, new boat, new girlfriend, new alimony payments?
Unfortunately since is a Canadian company we can’t just go to the SEC filings and check it out. Don’t know what the rules are in Canada but someone probably has records of his sales.
In Canada it is customary to update one’s porfolio in February for tax purposes, as the deadline for tax-deductible retirement savings contributions is March 1.