Gareth Barry. Thought he was villa through and through and then left for a club who actually finished below us that season. Obviously the right decision for him in the end but at the time I was shocked and it all happened pretty suddenly and the fee wasn’t even good either
Perhaps not quite the same but when the news about Petrov having cancer broke that was pretty heartbreaking, not the same as a transfer but was obvious he would never play again
Gareth Barry for me, purely because we looked like we were on the verge of something big at the time and breaking into the top 4 .
Once Barry had been sold for me that marked the start of the decline under MON , well that and the fateful Moscow trip and adjacent collapse v Stoke
Selling Cahill was majorly annoying
Buying bent for £23m and selling him for £250k was painful
Buying Curtis Davies for £10m and selling him for £200k was also painful
Giving away Daniel Johnson and Callum Robinson was sheer lunacy
I was upset by the sale of Nathan Baker
Sad to see Olof Melberg leave, saw through MON I think. Understand that he wanted one big move but he remained a better defender than those that followed. Apart from that Southgate to Middlesboro, Gray, Yorke, Milner, Barry. All top class footballers whose ambition wasn't matched by the club.
As a kid, Gidman and Andy Gray. As an adult, I’d been a fan of Luc Nilis for a while and was amazed when he came to us. So gutted he only played, I think, three games. Of those that departed in the usual way, in more recent times I’d have to say either Yorke or Milner. I was living in Germany when Yorke left and, shortly after he did, on the ferry on the way back to visit I wanted to punch an eight-year-old wearing a Man U top with Yorke on the back.