Terry has become a legend at Stamford Bridge since joining as a youngster in 1998, winning four Premier League titles, five FA Cups, one Champions League and several other major honours at the club.
It could have been very different though, having initially started his career at Upton Park, where he was in the youth setup between 1991 and 1995.
He was clearly a major loss for the Hammers, and Tony Carr admits that he is the one player who he regrets missing out on most.
“We had some good players such as Matt Holland and Ray Houghton,” he told the Mirror.
“But John Terry was the one. Chelsea got into him and courted him. So you just shrug your shoulders and got on with it. John was one that got away.”
It certainly would have been interesting to see how Terry may have developed had he stayed at West Ham.
He will certainly have no regrets about his decision to move considering he has won everything during his time at the club.
He is unlikely to have managed the same had he stayed at Upton Park given the two clubs' varying fortunes over the years, although the gap could be set to close as the Hammers prepare for a bright future at the Olympic Stadium.