He was one of the main protagonists in the infamous ‘dentist’s chair’ incident in Hong Kong, joining Paul Gascoigne to down shots on England duty. Immediately ahead of a World Cup, he flitted to Portugal for a nightclubbing session and had to apologise to England manager Glenn Hoddle after being rumbled. In his playing days, Teddy Sheringham knew how to party. But even one of the Premier League's most renowned playboys believes Jack Grealish is gambling with his career with his off-the-field