I honestly think Levy's primary mistake was not seeing he was simply being used as leverage by MGW, Eze, and Palace this summer.
MGW and Eze had no real desire to come to Spurs, sure they would have if it were the only way they could up their wages and/or move, but it was really about using Spurs as a lever to get more money from their desired club.
Palace had no real interest in selling to Spurs, Parrish is closer with the goons and they're hoping to do business on a CB to replace Guehi. Sure, they would have sold to us if given no alternative, but really they just used us as a lever to get more money from woolwich. The negotiations drug out so long because they kept moving the goalposts and back channeling with the goons, same with Eze's negotiations.
And to me thats the worst thing about the saga. Levy didn’t lose this time because he was cheap - he lost because he got played by 3 different parties that had no real interest in doing business with him but used the threat of dealing with him to achieve their individual goals at his/our expense. It's worse than missing out by being cheap.