I don't think he's half the business man he and the press like to portray.
He sacked Pochettino because he'd dreamt of appointing Mourinho since he took over the club and Mourinho was the dogs bollocks.
Also he spunked £1.2Billion on a stadium he was offered a guaranteed price of 800m on, which he turned down because he thought he could deliver under budget. Several hundred million of that was to secure a £5m a year NFL deal which is questionable on its own, but on top of that it's unlikely to last the distance because everyone knows Shahid Khan is dead set on buying Wembley for the Carolina Panthers and the FA are not going to be able to foot the £150m refurbishment/upkeep bill on the stadium due in a few years.