Further to that, he's one of BT's staff pundits. So it's not as if he gets a gig here and there... he's been on most weekends for them so a regular wage. Living beyond his means?
I first came across a certain player when he had to travel for training from the south coast to Manchester, whilst his wife lived in London. He was always skint and his wife would bail him out. The manager at one of the clubs also had a property scheme that players invested in. When the bubble burst, big money was lost, but as it was all off the books, nothing could be done and the players took a hit. I would not post the club, players or managers details but I have known about this for years as at one time my firm had court orders against several players, manager and chairman of a major club.