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. Which club did Sebastien Bassong join on loan from Spurs in January 2012?
2. From which club did QPR sign Djibril Cisse in January 2012?
3. Name the midfielder Manchester City signed on loan from Roma in January 2012.
4. Which Argentine midfielder did Blackburn sign from Newell's Old Boys in January 2011?
5. Who did Aston Villa midfielder Stephen Ireland join on loan in January 2011?
6. Against which team did Andy Carroll make his debut after joining Liverpool for £35million in January 2011?
7. And against which team did Fernando Torres make his debut after joining Chelsea in the same window?
8. How many goals did Torres score in 18 appearances for Chelsea in the 2010/11 season?
9. Which former Liverpool defender did Sunderland sign on loan from Wolfsburg in January 2011?
10. Which former Arsenal midfielder did Man City sign in January 2010?
11. Name the winger Real Madrid signed on loan from the Premier League in January 2010.
12. Which striker did Chelsea sign from Bolton in January 2008?
13. Which other London club did Alex Song join on loan from Arsenal in January 2007?
14. In which year was the first January transfer window?
15. Which World Cup winner rescued Birmingham from relegation after signing for the club in January 2003?
16. Who helped to save West Brom from relegation after joining on loan from Manchester United in January 2005?
17. Name the winger who will join PSG this month after a £35million deal was arranged in the summer.
18. Who is the third most expensive January transfer in Premier League history behind Fernando Torres and Andy Carroll?
19. Name Manchester United's most expensive signing in the January transfer window.
20. Which two words are associated with Sir Alex Ferguson when discussing the January window?
Come this way for the answers...