Agree with most of your post but had to address: "we KNOW there won't be any dilution because all the shares are already out!"
If Sean wanted to issue additional shares, all he has to do is to reverse split the O/S let's say 1 for 10. Then:
O/S becomes 20,000 A/S remains 200,000.
Then Sean can play the game one more cycle.
This being said, if the current merger project doesn't materialize, who would buy new shares from Sean. There shall be plenty of shares available from current shareholders trying to get rid of them.