I originally posted this on the blog section but some surfer deleted my comment for telling the truth "Not this **** again Portsmouth broke even on transfers while Harry was the manager. The manager does not have control over finances unless the chairman and/or owner allows him to. How likely is it that all the chairmen and owners (in some cases, like Portsmouth, multiple chairmen and owners) allowed Harry to access their wallets Which one of David O'Leary and Peter Ridsdale is responsible for the collapse of Leeds?"
Do you think Arsene Wenger gets involved on the financial side of transfers or do you think he tells the chairman who he wants and the chairman does his best to get the players?
As noted above Harry was not responsible for finances, and you'd have to compare the wages of the players sold vs the wages of the players bought There was around 110 million brought in by all the sales of players after Harry left and television money but that only halved the debt. A large part of the remaining debt was loan repayments and unpaid taxes