In July 1997, Grimsby Town’s 18 year-old wideman, John Oster, rejected the advances of Manchester United to become a £1.6million addition to Howard Kendall’s Everton squad. A highly skilful flanker, boasting a low centre of gravity, tremendous balance and an electrifying turn of pace it seemed inevitable that the adopted-Welshman earned comparisons with Ryan Giggs.
Prodigious and mercurial, the baby-faced winger came straight into a woeful Everton team. But the burden of carrying his less gifted team-mates was simply too much: while Andrei Kanchelskis had done so just a year previous on the Everton right, he was a seasoned international. Oster, by contrast, was a 19 year-old with barely a season of third tier football to his name. Too often he was caught in possession or went missing. Sometimes when a trick failed to come off there was a noticeable drop of his head. Goodison’s unforgiving crowd took out its frustrations on the teenager, and his confidence waned.
Walter Smith, who showed little trust in Everton’s talented bunch of youngsters, virtually excluded him after his arrival as manager in July 1998. After transfer listing him at the end of the 1998/99 season, Oster joined Sunderland for £1million in August that year. He was, lamented Toffeeweb.com: ‘An enigmatic, problematic, idiosyncratic artisan in the Duncan McKenzie mould; perhaps there is no longer any room for such characters in the Premiership.’
Alas, Oster never really lived up to his potential in the north east. There followed a series of loan moves and free transfers that saw him play on the fringes of the top flight for some years, but the youthful promise was never realized.
Speaking later of his experience at Goodison, Oster highlighted the arrival of Smith as marking the beginning of the end. ‘We never spoke. Looking back, I went to the Premiership too early: I was only 20, and Everton was a different world to Grimsby. There, we'd play in front of 3,000, while there were 40,000 at Goodison. It was a different lifestyle as well; the lonely nights in a hotel in Liverpool have left their mark. I used to sit alone and worry about Everton, knowing I'd have to impress the fans, especially in the early games.’