Chelsea forced me to sign for Tottenham but I dislike Spurs as much now as I did then
As Chelsea and Tottenham prepare to reignite one of London’s fiercest rivalries tonight on talkSPORT, former defender Jason Cundy’s allegiances remain steadfastly blue despite his brief detour to White Hart Lane.
The broadcaster’s colorful career path – from Chelsea youth product to reluctant Tottenham player – provides fascinating insight into a derby that still makes his blood boil with partisan passion nearly three decades later.
Cundy’s transfer to Tottenham in 1996 remains a sore point, described by the pundit himself as “terrible” during a candid appearance on talkSPORT’s Inside Chelsea.
The circumstances surrounding his move paint a picture of football’s less player-friendly era: “I’d just signed a four-and-a-half year contract in November, and by March, Chelsea accepted a bid,” Cundy recalled. “Ian Porterfield called saying Terry Venables would phone me that afternoon. Back then, if the club wanted you gone, you went.”
This forced transition from boyhood Chelsea supporter to Tottenham player created cognitive dissonance that still resonates today. While making 18 Premier League appearances across four years for Spurs before moving to Ipswich, Cundy never assimilated into the Lilywhites’ culture.
“They wanted the money more than me,” he stated bluntly about Chelsea’s decision to sell him to their arch-rivals.
Tonight’s clash promises to continue the recent tradition of explosive encounters between these sides. Last season’s 4-1 Chelsea victory at Tottenham Hotspur Stadium featured two red cards (Cristian Romero and Destiny Udogie), while December’s seven-goal thriller saw Spurs surrender a 2-0 lead in a match that encapsulated both teams’ chaotic tendencies this campaign. These fiery meetings align perfectly with Cundy’s description of a rivalry that “will crackle” under the lights.
The talkSPORT host’s disdain for Tottenham extends beyond professional courtesy. Even comparing the derby atmosphere to Chelsea’s more recent west London rivalry with Brentford, Cundy leaves no doubt about where the real intensity lies:
“Brentford under the lights or Spurs under the lights? Let me tell you, you can’t compare the two.” This visceral reaction stems from childhood experiences in Chelsea’s youth system where, as Cundy explained, “It was ingrained in you what this game meant.”
Modern footballers might struggle to comprehend Cundy’s generation having minimal control over their career trajectories. His story highlights how the power dynamic has shifted – today’s players wield significant influence over transfers, while in the mid-90s, clubs could ship out academy products to bitter rivals without consultation. Yet through this unwanted transition, Cundy’s Chelsea roots never withered.
As both teams enter tonight’s match with European ambitions hanging in the balance, Cundy’s perspective adds historical context to a rivalry that transcends table positions.
His journey from the Stamford Bridge terraces to the White Hart Lane pitch and back again to Chelsea media circles represents the kind of career arc that makes derby days so emotionally charged.
While Tottenham seek revenge for December’s collapse, Cundy will be watching as he always has – through blue-tinted glasses, proving some footballing allegiances run deeper than paychecks or playing contracts. In the cauldron of a London derby, where tribal loyalties outweigh temporary employers, Jason Cundy remains Chelsea to the core.