It's only a smart investment if he gets a profit on it. At the moment, he doesn't. And if he gets out for roughly what he paid, he'd have been better off putting the dough in a premium bond.
I'm not trying to be all doom and gloom here. It's just the way I understood it off that podcast. Clearing our debts + the deadwood being off the wage bill + the new stadium is enough to be potentially upbeat about. But the first bit seems a way off at the moment.