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John joined Town at the start of the 1994/1995 season after signing professional terms following the step up from the youth team. John never made the team until the 96/97 season having a run of 26 games and 3 goals, and he did this in such a fantastic way, that despite the club being relegated John was sold for £1.5million to Everton at the end of the season.
Oster was used very much as a fringe player at Goodison Park and was seen as a devoloping youngster. Everton seemed keen to put time into Oster and let him develop as a player and so the player was kept there until 1999 when he was transfer listed and sold on to Sunderland for £1million. Oster made 50 apperances for Everton, scoring 3 times.
Oster dipped and dived in and out of Sunderlands regular bunch on a regular basis, often playing a quarter of the season as a first team player, the next quarter as a reserve and then bouncing back for the rest of the season.
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With Sunderland moving up in the Premiership and with the club now being considered as a top 8 side, Oster was no longer required in the first team and was sent out on loan to Barnsley where he only made 2 apperances in 1 month at Oakwell.
The following season Sunderland were struggling to get to grips with the Premiership and sunk to the bottom. Despite this Oster still was over looked and in October 2002 Paul Groves pulled of a dream move for Town fans as Oster arrived back at Grimsby on 3 month loan.
John made an impression straight away scoring on his debut in a 1-1 home draw with Gillingham. He continued to dazzle the fans and to be honest along with Georges Santos,looked a class above everyone else.
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With this in mind however Oster re-signed for The Mariners on loan again this time for 2 months. He made 7 apperances and scored once. Osters last touch in his last game for Grimsby was his volley to make it 1-0 away at Rotherham in the 91st minute.
Groves attempted again to sign Oster permanently but the player refused and Grimsby were relegated, as were parent club Sunderland.
Sunderland took Oster of the transfer list and he became a regular as the he was re-added into first team action as the club went through the 03/04
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Oster started the current season of as a regular for Sunderland but was loaned to Black Cats rivals Leeds United on a 3 month loan. It was reported that Oster was on loan to aid a permanent move to Elland Road. However the cash strapped South Yorkshire club could not afford Oster and his loan was cut short as he was arrested twice, for a drunken brawl in Durham, and the again at the Leeds United christmas party.
John returned to Sunderland and was released for his actions. The small number of Town fans rumoured it was possible he could return to Blundell Park on a short term deal and the club was going to scrape every penny out the piggy bank to pay his wages, but before anything could become of it Oster moved
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In my eyes Oster is one of the awesome talents I have seen at Blundell Park, he is a true legend and I would welcome this player back to the club even if he did get arrested twice a month. A superb product of the club and has a fantastic footballing brain.