The Special One: Jose Mourinho – Tottenham Hotspur
Okay, so maybe this one depends a bit more on how long you’d be in quarantine for. I’m not sure whether I could last more than a week or two in a confined home with Jose Mourinho. A few days though, would be utterly fascinating.
You’d have to look really hard to find a more intriguing, entertaining character in recent football history than current Spurs manager Jose Mourinho. His press conferences continue to be the gift that keeps on giving, and some of the things he has said and done over the years will live forever in the memories of fans.
Apart from this, he has had a fantastic career and discussing some of his best and worst moments with him would actually be really cool, regardless of whether you love him or hate him. Jose Mourinho was an easy pick for this list simply based on his personality alone.
Mr Experienced: Carlo Ancelotti – Everton
Kaka, Cristiano Ronaldo, Ronaldo Nazario, Andrea Pirlo, Zinedine Zidane, Paolo Maldini, Fabio Cannavaro, Philipp Lahm, Alessandro Nesta, Gianluigi Buffon. Am I listing out a bunch of legends of the game? Yes. Does it also double up as a list of players Carlo Ancelotti has managed during his famous career? Yes!
Being in quarantine with a man who has worked alongside so many of the greatest players this world has ever seen would be an absolute dream come true, no question. Carlo Ancelotti has had a legendary footballing career, and while he is no longer managing such great players (since he is currently at Everton in the Premier League), he is something that would have endless stories and tales about the players and moments of the past.
His career path is priceless, and I’m sure any of us could sit and talk to him for hours on end without getting bored.