I am afraid you do not get a "Gold Star" for tax / financial...

I am afraid you do not get a "Gold Star" for tax / financial planning.

I do not have an opinion on TAH or Wilson's reasons for selling - however you are missing the following pionts. Apart from the fact it is not uncommon for Directors to cash out of a company when they retire.

If Wilson has exercised 2,694,500 options @ $10.18 he would have to come up with $27,430,010 - the only way he could fund this is probably by selling the shares once the options have been exercised.

He would be taxed on the full amount of the profit as the purchase date is the date the options are exercised and converted to shares - not the date of the options being issued.

Assuming Wilson could fund the $27,430,010 exercise price and hold the shares he would not be taxed at 48.5% on the dividend due to imputation credits.