In the first few years of the Roman Abramovich Era, Chelsea were regularly linked with the crème de la crème of world football — and with good reason. The new owner’s millions were seemingly limitless, Financial Fair Play (FFP) had not been invented yet, and Chelsea CTEO (that’s Chief Tapping-up Executive Officer) Peter Kenyon was splashing the cash wherever, whenever, and however he could.

Despite the money, the trophies, and the Special One, Chelsea weren’t perfect. Left back was a particular problem area. Mourinho ended up converting William Gallas to great effect, but unlike future conversion project César Azpilicueta, Gallas was not too keen on that, to say the least. Others, like Asier Del Horno, Wayne Bridge, Celestine Babayoro, and Paulo Ferreira rotated through, but proved to not be long-term or even good solutions.

 It certainly wasn’t for a lack of trying though, and one of the big names often mentioned had been a certain Roberto Carlos, then at Real Madrid. But somehow, that never materialized.

In 2004, all that was missing was a fax.

“We’re waiting for a fax from Chelsea confirming they will pay the £20m fee in order to complete the deal.”

-Jorge Valdano; May 2004

In 2006, all that were missing were the house keys.

“I can’t deny the rumours about me going to Chelsea next season. They are reality, and contacts have taken place. Chelsea have been on my trail for a long time and Jose Mourinho would be delighted to have me in his squad next season. Although I haven’t yet bought a house in London, I will buy one if I need to…”

-Roberto Carlos; May 2006

The legendary left back’s contract expired the next summer. Third time the charm. Surely, nothing would stop things then!

 But as the man himself revealed this week, there was some trouble with the lawyers at the last minute. And so in swooped Fenerbahce, who had been hot on his trail for some time as well.continue reading

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