Peter Fankhauser, chief executive of Thomas Cook, has splashed out £50,000 buying shares in the travel operator.
He paid 29p per share, according to disclosures made to the stock market today.
He is already sitting on a paper loss on that purchase as the shares are off 4% today at 27p.
Over the past 14 months the shares have crumbled from 120p after a series of profits.
The latest leg down may be fuelled by a report over the weekend that the families will be advised not to book holidays after March because of Brexit. Downing Street has denied the suggestion.