But, lo and behold, Spurs were waiting in the wings to pluck him away from West Ham. After just 4 months there, Jermaine must be cursing the day he met David Pleat!
Clearly dejected by life at White Hart Lane, Defoe has realised that his only chance of not fighting against relegation in North London, other than signing for Arsenal, is for his employers to snap up Claudio Ranieri if Chelsea decide to ditch him in the summer.
Speaking to BBC Radio London, Defoe said "I think it is unbelievable that he will go from Chelsea. He is a great manager and he has done well there.
"It is really strange and I don't think it is fair. But if Tottenham get Ranieri, that will be great for the club because he's a great manager.''
It must also be noted that Jermaine recently got up to G in his English Dictionary, spotting the word "great" and deciding it would be, erm, great to use it in an interview as many times as possible!
Great stuff Jermaine!