What if ... Roberto Carlos’ Chelsea transfer had not collapsed at the last minute?

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.

Photo by Martin Rickett - PA Images/PA Images via Getty Images

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!

Photo by SEZAYI ERKEN/AFP via Getty Images

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.

“With Chelsea, it got very close. It was literally agreed and I just had to go there and sign the contract. It was just a week before I signed for Fenerbahce and I had been to Paris to meet both Roman Abramovich and (former chief executive) Peter Kenyon.

“Unfortunately, in the final moments something didn’t work out just before finalising, which happens a lot in football. There was an issue with the lawyer.

“It was all agreed, though, and I am 100 per cent sure I would have done well in the Premier League and it would have suited my characteristics.”

-Roberto Carlos; source: Goal

Roberto Carlos may have been 34 by then, but he would not have been expected to carry the load by himself. After all, Chelsea had solved the left back problem a year prior by signing Ashley Cole. But just imagine for a second Ashley Cole backed up by ... Roberto freaking Carlos. A 34-year-old Roberto Carlos, but still! The Roberto Carlos who would go on to collect nearly 200 more professional appearances for Fenerbahce, Corinthians, and Anzhi Makhachkala over the next five seasons! There was plenty of juice left in the tank.

Would his signing made the telling difference in a most dramatic 2007-08 season? Maybe save Mourinho from getting sacked out of boredom? Maybe make just the tiny bit of difference that would’ve been needed to win either the League Cup final or the Champions League final, which Chelsea lost in extra-time and on penalties, respectively?

Or later on, would he have bonded with some of the other coaches, including his compatriot Luiz Felipe Scolari, and the attacking-minded Carlo Ancelotti and André Villas-Boas? Would he have joined the likes of Michael Ballack or Cesc Fàbregas, who had joined Chelsea late(r) in their careers only to become associated very strongly with the Blues?

Obviously, we’ll never know. But it’s fun to imagine for a second.

Photo by Alexander Hassenstein - UEFA/UEFA via Getty Images