He joined Arsenal in 1996, and having spent 18 years revolutionising the club and developing a never-ending stream of talented young players, he's preparing to say goodbye -- hopefully with an FA Cup victory.
No, not Arsene Wenger -- who has repeatedly indicated he'll sign a new contract and lead Arsenal into next season -- but Liam Brady, the club's longstanding head of youth development. A genuine Arsenal legend, having been among the most popular players at Highbury in the 1970s, Brady is finally set to leave his post. Wenger praised his "consistent contribution to the success of the club," while describing his departure as a "big loss."
When recently quizzed by the Arsenal matchday programme about the best players he'd developed during his time at Arsenal's academy, Brady had one standout name. "We managed [to bring through] a number of players," he said. "But most notably to date, Ashley Cole. Nobody made the impact that Ashley did. He was -- and still is -- outstanding."
So much happened at Arsenal in the couple of seasons after their last trophy, the FA Cup in 2005, that it's difficult to know precisely when the watershed was. You can say that Arsenal haven't won a trophy since they lost the pace of Thierry Henry, the guile of Dennis Bergkamp, the wing play of Robert Pires or the power of Patrick Vieira. You can point to the move from Highbury to the Emirates as the defining moment, or the departure of David Dein as vice-chairman.
Cole's departure wasn't as significant for the team, but it was arguably one of the most damaging things for the club and its supporters. The aforementioned quartet of players were in the autumn of their careers, the stadium move was long-planned and economically successful, while Dein's departure was, ultimately, a simple backroom reshuffle.
Cole, however, was a key representation of Arsenal. He was born four miles away from Highbury, grew up supporting the club and progressed through the ranks to become a dependable left-back, having been a forward in the youth system. He was a true local hero, an Arsenal regular and one of the first names on the England teamsheet at an amazingly young age. Among a plethora of more talented teammates, Cole was the most "Arsenal" player at the club.
His departure to Chelsea was a game-changer for the Gunners. It was the first time they'd lost a key player to a genuine rival -- and not just any rival, but Chelsea. The West London side, traditionally considered a smaller club than Arsenal, were now capable of poaching Arsenal's key players in the Roman Abramovich era. It was a genuinely symbolic blow to Arsenal, partly because of the protracted, ugly nature of the transfer itself and partly because it suggested Arsenal were, at that point, unable to compete with the top clubs financially.
Arsenal fans rarely used to jeer their ex-players, partly because there was never a great sense of bitterness upon their return. Cole changed this -- his return prompted an unprecedented angry reaction from Arsenal supporters, perhaps understandable given the circumstances of his departure.
Nevertheless, it seemed to alter the attitude of many Arsenal fans, and now booing has become de rigueur, having previously been a trademark of mid-table clubs perennially frustrated that their best assets are always determined to move elsewhere -- Aston Villa or West Ham, for example. Robin van Persie? Understandable. Samir Nasri? Perhaps. But when Gael Clichy collects possession and there's a smattering of half-hearted boos, it feels a little silly. Emmanuel Adebayor is unquestionably spurred on by the taunts, and puts in extra effort against the Gunners. In this sense, Cole's departure seems the turning point.
"Saint Totteringham's Day," when Arsenal supporters celebrate the point at which Tottenham can no longer finish above them in the league table, also feels rather defeatist. Allegedly created in the 1990s, the fact that its popularity has ballooned throughout Arsenal's trophyless years suggests a nervous shift in perspective -- looking over the shoulder to mock local rivals, rather than ahead to genuine title challengers.
In truth, Cole's departure was only a minor problem on the pitch. Initially, Clichy was superb in that role, while Cole struggled to adapt swiftly to Chelsea, although the Frenchman's form declined after his error at Birmingham in 2008.
Arsenal were compensated with William Gallas in the Cole transfer, and although the Frenchman was a good defender (never given full credit for the way his pace worked perfectly with Thomas Vermaelen's proactive style during the Belgian's debut season), he was hardly an Arsenal man, being more associated with Chelsea and eventually leaving for Tottenham. His captaincy was particularly problematic -- again, the Birmingham match in 2008 was a key moment.
Another problem was the fact Arsenal had lost their English spirit. Cole's departure came at the same time Arsenal moved to the Emirates, and they started that uncertain new era with barely any homegrown players. Only two Englishmen: Justin Hoyte (18 starts) and Theo Walcott (five starts) featured for Arsenal in the Premier League that season, and at a time when, in hindsight, neither were yet ready.
Is this an issue? Well, not necessarily. Wenger always signed lots of foreign talent, generally with fantastic success. But fans like local lads; they appreciate their club developing talent. It's especially important when a club changes its stadium and loses its most influential backroom figure, too -- they act as an important symbol of the club.
It's interesting, considering Wenger imported so many foreigners during the first half of his tenure at Arsenal, that the club has recently emphasised its newfound British core so strongly. It's something absent during the initial post-Cole years.
"It is not by coincidence, it is down to the work that we have done, that we have more good English players," said Wenger, a nod to Brady, even if many of those players were recruited from elsewhere. "If the quality is local, it is even better because it gives you more guarantee of stability -- the players who are English ... are more likely to stay for a longer term than foreign players."
Cole didn't, of course, despite once saying he dreamed of captaining the club. Interestingly, Cole has retained links with Arsenal -- on his first return he admitted he still "loved the club"; he's shown respect when dealing with members of Arsenal's backroom staff; and, bizarrely, he turned up at Arsenal's recent Christmas party too, days before he faced them with Chelsea.
Aside from Mathieu Flamini, a six-month overlap with Walcott's Arsenal career and a couple of players he might know from England duty, there's really no one left at the club with any reason to invite him.
Perhaps most peculiarly, Cole was voted 25th in a list of 50 all-time Arsenal greats in 2008, less than two years after his incredibly bitter departure, at a time when he was Arsenal's public enemy number one. That, more than anything, reflects the bond he should have had with the club.
Whatever the rights and wrongs of Cole's departure, and both sides probably made errors, his decision to join Chelsea has proved correct from his perspective. He's won a league title, four FA Cups, a League Cup, a European Cup and a Europa League, while retaining his place at international level. He's England's fifth-most capped player behind Peter Shilton, David Beckham, Bobby Moore and Steven Gerrard -- and the amazing fact that 106 of his 107 caps were as a starter means he's actually played more minutes than Beckham and Gerrard.
It's somewhat fitting that Arsenal might end their trophy drought in the same week Cole's career as a genuinely top-level footballer comes to a close. Finally omitted from an England squad and likely to be released from Chelsea this summer, only now -- eight years after his departure -- can Arsenal boast of being in a better position than their former left-back, should they lift the FA Cup this weekend.
Arsenal are excellent at recognising their proud history at the Emirates -- club legends depicted on the outside of the ground, trophies won depicted on the inside. So far, they've had no cause to add an extra entry in either category -- Brady is one of those celebrated, but sadly none of his fledglings have joined him. Cole would have been the first Emirates-era legend; instead, Arsenal will have to win their first Emirates-era trophy.