Over the years some of the greatest players in the world have played for Leeds United. Unfortunately, so have some of the worst. When it comes to terrible transfer dealings, we’ve had more than our fair share of flops. Here’s a small selection of those badly scouted few that have graced the lush green lawn of Elland Road.

Roque Junior

When word got around that World Cup and Champions League winner, Roque Junior would be joining Leeds on loan from AC Milan, the fans were delighted. The thinking was that such a talented player would be able to help the struggling club climb back up the table and stave off relegation.

Unfortunately for Leeds, Roque simply couldn’t adapt to the English game and it soon became clear as to why AC Milan were so willing to loan him out. Roque made just five appearences for Leeds before we helped him pack and took him to the airport, just to ensure he’d left the city for good. These days, Roque seems to have found his true level at Third Division Montenegrin club, OFK Igalo.

Kevin Nicholls

£700,000 was the fee Leeds coughed up for Kevin Nicholls. Two injuries later, the genius that is Dennis Wise was at the helm of the club and whilst Nicholls was still recovering from his latest injury, Wise pulled a masterstroke by awarding him the club captaincy.

After just a handful of games (13 to be precise), Nicholls stuck two fingers up at the club that had stuck by him through two injuries and awarded him captaincy, by demanding a move back to Luton Town.

If there’s one thing Dennis Wise did do right during his time at Elland Road, it was recouping the money we’d spent on the disgraced midfielder. Wise stubbornly refused to let Nicholls leave unless Luton could come up with what we’d paid for him. When they couldn’t, Preston North End came in and took him off our hands for £750,000. 18 games later, he’d managed to get out of his contract and return to Luton.

Darren Huckerby

At an astonishing £3,000,000 per goal, Darren Huckerby’s 40 appearences for Leeds will be remembered by most as a total failure. As much as the Leeds fans wanted him to do well, he never really found his feet at Elland Road and struggled to force his way into a first team that included Mark Viduka, Alan Smith and Michael Bridges.

After a year and half at the club, Huckerby left for Manchester City where he rediscovered his scoring boots. Although relegated with the team, he stayed on and helped them regain their Premier League status, only to be pushed out of the team by the arrival of Nicolas Anelka.

Huckerby now seems to have retired after finishing his career in the MLS with Californian team, San Jose Earthquakes. In 2008, he was voted the MLS Newcomer of the Year. (Only in America)

For me, Darren Huckerby personifies Leeds United’s transfer dealings around that time. He added nothing to a squad full of talent and his purchase only served to add to the clubs increasing expenditure. When we should have been buying players of sheer quality that could help us take the next step, we bought average footballers fit for a mid-table side.

Paul Okon

A product of the doomed Terry Venables regime, Paul Okon had spent his career moving from club to club and failing to find a permanent place at any of them. After 21 games at Leeds, it became glaringly obvious why. Although he had suffered from injury and was initially lacking match-fitness, time failed to improve the Australian and he was constantly caught out of position and failed to keep up with the pace of Premier League football.

Tomas Brolin

For me, Tomas Brolin is by far the worst signing in the history of Leeds United. Leeds fought off three Italian clubs to secure Brolin’s signature and after a £4,500,000 fee was agreed, the fans were expectant.

Brolin failed to live up to the hype though and the overweight, slow and out-of-place looking Swede made just nineteen appearences for the Whites scoring four goals in the process. Google “worst Premier League transfers” and Brolin will feature prominently in every list you can find, such is the legacy the man left behind.

I’ll end with a quote from one such list. The following comes from The Times Online and tells you all you need to know about the legend that is, Tomas Brolin.

“Hard to imagine that Leeds United, normally a model of fiscal probity, paid £4.5m for the Swedish meatball in 1995. A good footballer treats his body like a temple. Brolin’s was a bouncy castle.”