The majority of successful signings he has made have been more by luck than judgement. He's paid top dollar (invariably the asking price) for every player he's signed, and sells at knock-down prices.
His inability to negotiate effectively meant that we lost out on his 'first choice' replacement for Kompany, the decidedly average Koulibaly, and he pretty much panic bought Dias. Classic TB fluke.
If he hadn't been instrumental in getting Pep to City, he'd probably have been kicked out years ago, and have slithered off to some other comfy DoF old pals job in La Liga.
From what I've seen of him since he arrived, I can only imagine that if he's involved in his own pay negotiations at City, he's probably only on about £75 a week.
He's what us FOCs used to call a spiv. I certainly wouldn't buy a used car off him.