Having started his career at Chelsea, there were great hopes for Jason Cundy, but he failed to make a regular place in the starting line-up at Stamford Bridge, so moved on to Tottenham, who were struggling at the time.
Brought in by Terry Venables for manager Peter Shreeve to shore up the leaky Spurs defence in March 1992, Cundy played a part in turning things around, when it looked bleak for Tottenham for a while. Initially joining on loan, at the end of that season, his move was made permanent in the summer of 1992 for £750,000.
However, his performances were slightly erratic and his size sometimes made him vulnerable to nippy forwards, who could out-pace him. He fell out of favour when Gerry Francis took over, not helped by a number of injuries that rule him out of contention for the team. Farmed out on a succession of loan deals, it was perhaps unsurprising when Jason left Tottenham to join Ipswich Town in 1996, following a spell there on loan.
Ironically, the thing he will be remembered most for as a Spurs player came at Portman Road, where he made a strong challenge to get to the ball ahead of Jason Dozzell (then playing for Town) on the halfway line and the ball was carried on the wind over Ipswich keeper Craig Forrest, who was off his line and flew into the net for Cundy's only goal in a Tottenham shirt.
Alan Ball bought the defender at the start of the 1999-2000 season and his physical presence made a difference, as Pompey's defensive record improved, but the defender was rocked by being diagnosed with testicular cancer His fight against the condition was successful and he continued to play at Fratton Park until he retired through injury in 2000.
Moved into the media and is a regular presenter on TalkSport radio and is seen on GMTV and Chelsea TV.
Was married to Lizzie - an actress/presenter/model - and lived in Upton Grey, Hampshire with their two sons (Josh and James), before leaving his wife for opera singer Hannah Pedley.