When John Terry and Ashley Cole played for Premier League giants Chelsea, there was a long-running joke among staff about which of the pair was the most prolific womaniser.
Terry, the club captain, was a mainstay of the now very much defunct ‘kiss and tell’ pages of the tabloid press, including one confession in 2013 by a glamour model that they’d enjoyed a ‘tryst’ in a nightclub toilet even though she had broken her leg.
Cole, meanwhile, was caught cheating on his beautiful pop star wife Cheryl Cole with hairdresser Aimee Walton, who he had met in a London nightclub back in 2008. But more on their romantic misdemeanours later.
The pair became close after Cole joined Chelsea from Arsenal in 2006 – a move that prompted his nickname ‘Cashley’, courtesy of his high-wage demands (the star reportedly wanted £60,000 a week) – and lived just a stone’s throw away from one another in the footballer enclave of Cobham, Surrey.
Cheryl and Terry’s super-tolerant wife, Toni, also became such close friends that after the Aimee scandal Cheryl reportedly only trusted Cole to behave without her if Toni was there.
‘Ashley and John were both party boys,’ says my source. ‘They had a bromance but at times it could get very toxic. They had a lot in common. They had these two beautiful women who loved them, life was brilliant for them. They were rich, talented and very, very famous.’
Fast forward to this week and Ashley and John, both 45, reunited in Miami as they sat side by side and watched England’s 2-1 victory over Norway in the World Cup.
John Terry and Ashley Cole were sat together in the stands in Miami for England’s quarter-final with Norway
Cole and Terry playing for Chelsea in 2011… there was a long-running joke among staff at Stamford Bridge about which of the two was the most prolific womaniser
Terry lost a battle with the now-defunct News of the World newspaper over their scoop that he had had an affair with his Chelsea teammate Wayne Bridge’s wife Vanessa Perroncel
The men looked deep in conversation as the television cameras flashed up a shot of them on the stadium big screen. John, a failed football manager who has now turned his hand to punditry work on Piers Morgan’s World Cup 2026: Uncensored show, has barely aged since his heyday. Cole has recently ‘stepped down’ from managing the Italian Serie B side Cesena after just eight games and looked a little weathered.
But regardless, I was shocked to see them sitting together and looking so friendly – especially after the speculation I heard about them 16 years ago in the early months of 2010. A time which both men, I’m sure, would rather forget.
For in the January of that year, Terry, known as ‘JT’ among his teammates, had lost a battle to injunct the now defunct News of the World newspaper over their scoop that he had had an affair with his Chelsea teammate Wayne Bridge’s wife, Vanessa Perroncel.
It dominated column inches for weeks as Britain despised JT and sympathised with both his wife and Wayne – a longstanding close pal of his. The scandal led to Terry being sacked as England captain as his reputation fell into the gutter.
At the time there was perhaps only one thing that was ever going to shift the dial and the attention of the press: another footballer being caught out for cheating on his high-profile wife. So, step forward Cole, who in March 2010 was left reeling when it was his name plastered across the red-top papers.
The footballer’s life began to unravel when, that month, it was claimed he sent naked pictures of himself to model Sonia Wild, then 28 – something he profusely denied.
Then Vicki Gough, a 30-year-old secretary working for Chelsea’s rivals Liverpool, claimed she had sex with the former England defender on two occasions before big matches. Next up was American Ann Corbitt, who alleged that Ashley slept with her in his hotel room in Seattle while on a tour with Chelsea the previous summer.
So where was this flurry of stories coming from? Sources within the football community at the time told me to note the timing, suggesting that there were some friends within Terry’s circles that seized the opportunity to ‘drop Ashley in it’.
‘It’s certainly the theory we are working with,’ an associate of Team Cole told me at the time. ‘John and a lot of his friends knew much of what Ashley had been getting up to and then there you go, the focus turns from JT to Ashley.’
Terry with his super-tolerant wife Toni… Cheryl became such close friends with Toni that she reportedly only trusted Cole to behave without her if Toni was there
Ashley and Cheryl Cole in 2006… they divorced four years after getting married
Cole arrives at Westminster Magistrates’ Court in 2012, where he was a key witness in Terry’s trial for a racially aggravated public order offence
Indeed, even today, those familiar with the scandal suspect that it was those in JT’s camp who may have tipped off the press about Cole’s affairs.
‘John had hired a very well-connected and very aggressive PR team at the time,’ says my insider. ‘John was fuming that he couldn’t stop the barrage of stories but literally within weeks the world had forgotten about him and Vanessa and moved on to Ashley.
‘There’s obviously no suggestion that John did anything to cause Ashley upset but there were some of his associates who wanted to save him from the pile-on he was getting.
‘The next thing you know, Ashley was at the centre of it all and, given his wife Cheryl was a superstar, a national treasure, it was always going to be a big story that he had cheated on her. The timing was all very convenient.
‘It was enough to knock Terry off the news agenda. It was literally one after the other, like buses. Ashley was getting it from all quarters. It was a masterstroke by someone. John then had to watch Ashley go through what he had been through, you wonder how he felt about that.’
The accusations left Cheryl heartbroken and later that year she decided to end their four-year marriage. It was a move that devastated the Girls Aloud singer. ‘Ashley was the love of Cheryl’s life,’ a friend told me at the time. ‘She’s heartbroken, bereft, but she knows it has to end.’
While Cheryl ditched Cole, he and John remained friendly. And in July 2012, when Terry stood trial for a racially aggravated public order offence against Queens Park Rangers defender Anton Ferdinand, Cole attended Westminster Magistrates’ Court as a key witness for his teammate.
He told the court that he did not hear the alleged racial remark on the pitch at QPR’s Loftus Road stadium and stated that the incident was a minor dispute that ‘shouldn’t have come to court’. John was cleared but later suspended and fined by the FA.
But back to the Miami stadium on Saturday night where the former footballers were seen cheering their country on.
There would also have been plenty for the pair – both now dads – to reminisce about.
‘Well, they would have had an awful lot to talk about, wouldn’t they?’ says an associate of the two men from back in their heyday.
‘And we probably don’t know the half of it!’
