Jordan gained a reputation as a manager-killer early in his Palace reign, though this changed as his reign progressed. Between 2000 and 2003 no fewer than the following five managers departed the manager's post: Steve Coppell (August 2000), Alan Smith (April 2001), Steve Bruce (November 2001), Trevor Francis (April 2003), and Steve Kember (November 2003). Of these, only Coppell and Bruce left of their own accord, with Coppell's departure brought about by a personality clash and Bruce's resignation leading to a high court case.
Iain Dowie was appointed in December 2003 and the club bounded up the table from the relegation zone to win promotion in May 2004, beating West Ham United at Cardiff's Millennium Stadium in the play-off final, fulfilling Jordan's promise of promotion within five years. However, the club remained in the Premier League for just one season before being narrowly relegated in 2005. In May 2006, having accepted Dowie and Jordan had differences but the same goal, Dowie left the club by mutual consent. However, towards the end of the month Dowie joined Charlton Athletic as their new manager, prompting Jordan to issue a legal writ against him, claiming Dowie had lied about his reasons for departure.
Peter Taylor, an ex-Palace player was installed on 13 June 2006. However, his reign would last just 16 months, ending on 8 October 2007 with the sack. Jordan stated he wanted Taylor to be remembered as a good player for Palace rather than a bad manager. On 11 October at a press conference he unveiled Neil Warnock as the new manager, which failed to surprise many as the two were reported to be good friends. Jordan's choice appeared to have been a good one, since the club embarked on a superb run of form that saw them move from the relegation places into the 2007–08 season play-offs, but the relationship between the pair ended in a dispute after Warnock left the club to join Queens Park Rangers following the Eagles' entering administration.
Dowie Court Case
Jordan succeeded in his High Court battle against Dowie, with The Hon. Mr Justice Tugendhat ruling that Dowie had lied when negotiating his way out of his contract at Palace. Dowie won the right to appeal against that decision, leading to it being heard in the Court of Appeal. In April 2008, Crystal Palace F.C settled out of court with Iain Dowie, and issued the following statement.
"Prior to appeal being heard a mutually satisfactory settlement of all matters has now been reached on terms acceptable to Crystal Palace Football Club"