Birmingham City will always feel lingering overpayment regret from £5m Everton transfer agreement | OneFootball

The Scotsman failed to justify such a hefty price-tag at St. Andrew's

Throughout the 2000s, Birmingham City became what has since been stereotyped as a 'yo-yo' club between the Premier League and the Championship.

In fairness to Blues, after regaining top-flight status for the first time since 1985 under Steve Bruce through a dramatic penalty-shootout success over Norwich City in 2002 at Cardiff's Millennium Stadium, they were able to maintain their position until the summer of 2006, when developments became far more tumultuous.

Indeed, after a relegation campaign was followed by a first-time promotion from the Championship in 2006/07, Bruce would depart St. Andrew's @ Knighthead Park after six years in the hotseat, joining divisional rivals, Wigan Athletic.

Former Rangers and Scotland boss, Alex McLeish, was then handed the vacancy by David Sullivan and David Gold on 28th November 2007, with the remit of initially reconsolidating Birmingham's top-flight position before progressing up the table once again.

Unfortunately for the Scot, he wasn't fully able to do so throughout his tenure, despite the fact he was in charge of the club's historic EFL Cup triumph against Arsenal at Wembley Stadium in February 2011, before earning 'Judas' status in B9 after quitting to join Aston Villa.

Several of his transfer calls at Blues were also of mixed success too, with one always likely to leave a sense of overpayment in particular.

James McFadden's move to Birmingham City from Everton FC

That came in the form of McLeish's compatriot, James McFadden, who was lured to the Second City from Everton for a reported £5m sum during the first transfer window of the Scot's stint at St. Andrew's in January 2008.

The ex-Motherwell striker had been on the books at Goodison Park under David Moyes since a £1.25m agreement in 2003, but failed to net his first goal for the club until 2005, with it eventually coming in a 5-2 defeat to Tottenham Hotspur.

During what was a relatively successful period for the Merseyside outfit, which included a fourth-place finish in the 2004/05 season, McFadden struggled to assert himself as a first-team regular behind the likes of former Birmingham striker, Andrew Johnson.

The highest number of appearances and goals during his first spell at Goodison came during the 2005/06 campaign, in which he netted seven times in 41 appearances across all competitions.

Despite such inconsistencies and a mixed injury record, McLeish had full faith in the 49-time international to become a success in the West Midlands, saying the deal was "worth every penny."

Alex McLeish got James McFadden, Birmingham City verdict wrong after £5m transfer

Whilst McLeish's ambitions were understandable, they couldn't have been much more different from reality, as McFadden's frustrations continued in Small Heath.

In truth, four goals in his first 12 appearances was a respectable return, although Blues would be relegated on the final day of the season, with a draw against Blackburn Rovers not enough to see them leapfrog Fulham, who mounted a well-documented escape act under Roy Hodgson.

The striker would remain a part of an experienced side tipped for an immediate bounce back in the Championship, but McFadden once again struggled to maintain his fitness and regularly oust the duo of Cameron Jerome and Kevin Phillips from the starting lineup, scoring just four times and posting a further five assists in just 30 league appearances.

His best season at St. Andrews would, ironically, come in what was the club's best season, statistically speaking, since 1958/59. After scoring the opening goal of Blues' season against Portsmouth, a further four strikes and three assists helped the club finish ninth, before his injury demons returned in the Autumn of 2010.

The Scot was sidelined for a lengthy period after sustaining knee ligament damage just weeks into the most mixed of seasons in B9, as Blues won the second major trophy in their entire history, but were relegated months later under a cloud of financial uncertainty under Carsen Yeung.

After making 88 appearances, in which 14 goals and 15 assists were racked up, it proved to be the end of the road for McFadden in Brum, as a contract extension wasn't exercised. He then returned to Everton on a free transfer, before the final Premier League stint of his career came with Sunderland.