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Times when teams should have cashed in?

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Was speaking to a friend the other day, and he mentioned that United should've cashed in on De Gea when we had the chance. I'm not sure what the fee was when Madrid came in for him, but it was a decent offer plus Navas. I don't completely agree as he was still quality for 1-2 seasons.

It did get us talking about other times when clubs should've cashed in. I'm thinking Spurs in the last 5 years probably should've cashed in on Alli and Rose. Rose is struggling to find a club now when at one...

Times when teams should have cashed in?

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