Three big questions: Chelsea’s Willy Caballero and swan songs

3. Will this be his last season and will he join the Chelsea staff after?

Whether or not Caballero is second or third choice will play into whether he stays as a keeper beyond the next season. But then what? Does he continue as a player or does he go ahead and retire with a top European club as his final contract?

Every time Chelsea has brought in a much older keeper in the last few years, it has come with a certain belief that the Blues were signing them for more than just their play on the field. After all, most of these older keepers were third choice and not expected to play a single minute. The implication is that Chelsea had plans beyond just their playing days.

It is a bit romantic for a player to retire and immediately join the coaching staff or the staff of the club in some other way. In fact, it really has not happened with Chelsea without at least some delay in between. But these are different times at the club and the implication of an older keeper retiring and entering the staff seems as likely as ever.

Where Chelsea has an open spot or if they create one is a conversation for another day. But with four years at the club, the Blues should at least see what they can do for the Argentine should this be his last season. He has been an admirable performer and he is surely important behind the scenes with much younger keepers around him. That experience may not translate directly into coaching, but surely there is a place for him somewhere in the hierarchy should he want to continue in the game.

What questions do you think need to be asked of Willy Caballero ahead of next season? Let us know in the comments and on Twitter!