5 Ian Wright
Another ex-Gunner with cup and league medals to his name and by the time he signed for West Ham, in July 1998 at age 34, he had become Arsenal’s all-time top scorer with 185 goals from 288 appearances. He commenced his West Ham career with the only goal in an away win at Sheffield Wednesday and would finish the 1998/99 season as the club’s leading scorer with 9 league goals from 20 starts. Wright missed three months of the season after the New Year through injury but returned in mid-April with the Hammers still in the hunt for a top four finish. A disastrous 5-1 home defeat to Leeds, in which Wright was sent off along with teammates Hislop and Lomas, finally putting paid to those hopes. In the aftermath of the sending off Wright is said to have smashed up the referee’s room and left the ground still in his kit. He played his last league game the following week (a 6-0 defeat at Everton) and despite featuring in one Intertoto match at the start of the following season he left the club shortly after.
4 Nigel Winterburn
Part of the renowned ‘1-nil to the Arsenal’ defensive line-up, Winterburn had a collection of league and cup winner’s medals to his credit before arriving at West Ham, aged 36, in the summer of 2000. The move saw him become a teammate of Paolo Di Canio with whom he had clashed in the lead up to the infamous referee felling incident at Hillsborough two years previously. Winterburn was a regular feature in the side during his first two seasons at Upton Park, first under Redknapp and then as part of the Roeder revolution. He scored his only West Ham goal in the 1-0 win at Elland Road which was to be Rio Ferdinand’s last game for the club. In the 2002/03 relegation season Winterburn had begun as a regular but lost his place to Rufus Brevett after Christmas leading him to retire at the end of the season, six months short of his 40th birthday and having played over 90 games for the Hammers.
3 Liam Brady
An FA Cup winner at Arsenal, Brady had also picked up two Serie A titles with Juventus (as well as playing for Sampdoria and Inter) before he found his way to West Ham as a 31 year old in 1987. Brady had previously been in the Arsenal side beaten by West Ham in the 1980 FA Cup final. He stayed with the Hammers for three years, featuring in almost 120 games and scoring 10 goals prior to his eventual retirement. Brady was an elegant footballer noted for close control, passing and for a wand of a left foot. He became very popular during his time in the east-end even though he was unable to save the Hammers from relegation in 1988/89 or help steer them to promotion in the following year. In a fitting end to his career he scored a marvellous last goal in his final game; a 4-0 home victory against Wolverhampton.
2 Teddy Sheringham
When he signed for West Ham in July 2004, Sheringham was 38 years old and the proud owner of Premier League, FA Cup and Champion’s League medals; all earned in his 30’s at Manchester United. Sheringham joined West Ham during one of their sojourns in the second tier and was instrumental in helping the club regain its top flight status through the Play-Offs, even though he was unavailable for the Play-Off matches. Having scored 20 league goals from 33 appearances he is the last West Ham player to have reached this mythical milestone (although Marlon Harewood scored 22 the same season if all competitions are counted). Sheringham stayed at West Ham for two more seasons and although used rather sparingly he added further goals and made a substitute appearance in the 2006 FA Cup final, where he was the only Hammer to score in the penalty shoot-out. During this period he broke a number of records both as the oldest player to play and score in the Premier League. He left to join Colchester in July 2007.
1 Stuart Pearce
Pearce joined West Ham on a free transfer in August 1999 at the age of 37. A former England captain, his only major domestic honours were a brace of League Cup wins with Nottingham Forest. Bringing qualities of leadership, bravery and determination to Upton Park he unfortunately suffered a broken leg in only his fifth match in claret and blue, a home encounter with Watford. The injury kept him out for five months only for him to suffer a recurrence in his third game back, this time at home to Southampton where he is alleged to have wanted to play on despite the break. The following season was more positive, at least fitness wise even if the team did not perform so well on the pitch, with Pearce playing in all but four league games and earning himself recognition as Hammer of the Year. Overall he played 50 times and scored 3 goals for the Hammers before being signed by Kevin Keegan at Manchester City in the summer of 2001.