At the age of 30 he gave up sales and marketing to pursue his calling as a coach and ended up in the MLS for two years. He's now moved to Seoul to start again...
There are key differences - largely off the pitch - but Liverpool fan Sam Drury has spotted five things that are similar five years on. A big sale, a big Italian arrival...
1) For which club - who play at Nuevo Colombino - was Santi Cazorla playing when he received the Spanish Player of the Year award in 2007?
Recreativo de Huelva.
2) Christian Benteke was signed by Aston Villa from which club?
3) Juan Mata won the European Under-21 Championship in 2011. Name either of his two teammates who are also playing in the Premier League.
Cesar Azpilicueta and David De Gea.
4) Marouane Fellaini has won the Ebony Shoe. What is the Ebony Shoe?
It's the award given every year to the best player of African origin in the Belgian league.
5) Name either of the two players to have broken up Dimitar Berbatov's domination of the Bulgarian Footballer of the Year between 2002 and 2010.
Stilian Petrov or Martin Petrov.
6) Against which team did Luis Suarez make his Premier League debut and score in a 2-0 win?
7) Pablo Zabaleta won Olympic gold in 2008. Which of his teammates also plays in the Premier League?
8) Robin van Persie was one of six Dutch players who started the 2010 World Cup final who have played in the Premier League. Name the others.
John Heitinga, Giovanni van Bronckhorst, Nigel de Jong, Arjen Robben and Dirk Kuyt.
9) Which manager deemed Demba Ba surplus to requirements at Watford in 2005?
10) Which manager signed Sebastien Bassong for Newcastle?
11) Name two of the three strikers who scored more goals than Adel Taarabt in the Championship season of 2010/11. All three are now in the Premier League.
Danny Graham, Grant Holt and Shane Long.
12) Name three of the four clubs Nicky Shorey played for between spells at Reading.
Aston Villa, Nottingham Forest, Fulham and West Brom.
13) Aside from Southampton's Adam Lallana, who is the only other player called up by England in 2012 who is yet to make his debut?
14) At which overseas club did Ryan Shawcross have a loan spell while at Manchester United?
15) Steven Fletcher is a two-times winner of the SFWA Young Player of the Year. Name either of the players who won the award in 2009-10 and 2010-11 and then flopped at Premier League clubs.
Danny Wilson (Liverpool) or David Goodwillie (Blackburn).
16) Name Michu's hometown club. Clue: He joined many others in helping them out this year.
17) Jan Vertonghen was named Eredivisie Player of the Year last season. Which curent Premier League player won it two years before?
18) Claudio Yacob's nickname at Racing was La Flaca. Does that mean a) 'The Destroyer' b) 'Skinny Girl' or c) 'Silly Boy'.
b) Skinny Girl.
19) From which Madrid side did Wigan sign Momo Diame?
20) With which club did James McCarthy win the Sottish First Division?