Behind Ashley Cole's rise to his first managerial post

Behind Ashley Cole's rise to his first managerial post

Ashley Cole is widely considered the best left-back in Premier League history.

And, after years of building a dynasty on the pitch with some of England's biggest clubs in Arsenal and Chelsea, he has now taken his first step into football management.

Cole was yesterday announced as the new Cesena boss, a Serie B club currently fighting tooth and nail for a spot in the playoff places and a chance at glory.

The former England international has previously served as assistant manager for a few different clubs and setups but is now looking to replicate the greatness he created on the pitch with success on the touchline.

Cole's journey so far

Cole's journey in coaching management has been largely a supplement rather than a starting role thus far.

Since 2019, Cole has made his way through the levels, working as Frank Lampard's assistant at Chelsea and Everton and Wayne Rooney's backroom staff at Birmingham City in the Championship.

His most recent role was with the football association as an assistant for the English National Team, where he most commonly worked with the U21 squad but also played a role in Lee Carsley's time as interim with the England senior squad.

The Cesena job

Cesena sacked their manager Michele Mignani after a run of seven games without a win that saw them drop to the very bottom of the playoff picture.

🇮🇹 Ashley Cole has been appointed as manager of Italian side Cesena.

The 45-year-old has signed a contract until the end of the season.

Cesena are currently 8th in Serie B but are without a win in the their last seven matches. pic.twitter.com/62fOtTcszz

— English Players Abroad (@EnglishAbroad1) March 15, 2026

In the wake of the appointment, Cesena's club statement read, "The entire Cesena FC family is thrilled to welcome Ashley to lead the Bianconeri first team and extends a warm welcome to him and his staff in Cesena." We wish them all the best of luck in this new adventure."

Cole's side travel to 15th-placed Mantova on Tuesday night, with it not yet being confirmed if Cole will be in the dugout for the game or watching from the stands.

The former Chelsea man will be joined in Italy by Chelsea's academy coach Jack Mesure, who has a contract until June with a view to an extension if he meets certain criteria between now and the end of the season.

Cole's pedigree

To go alongside those valuable managerial experiences, Cole has an illustrious playing career that should bode well for leading a dressing room and getting the best out of players.

The England international earned more than 100 caps in an England shirt and made over 700 appearances in club football.

🗣️ Ashley Cole: “They look like mentality monsters, they're not giving anything up, after 20 years they should win it. It is theirs to lose!” 🏆
pic.twitter.com/NE9wGH2Ksd

— DailyAFC (@DailyAFC) March 12, 2026

He broke through at Arsenal, where he won two Premier League trophies, three FA Cups and two Community Shields.

Cole then moved to Chelsea, winning a plethora of trophies, including a Premier League title and four FA Cups, and reached the pinnacle of European football by winning the Champions League on one occasion.

During his playing career he also stepped foot on Italian soil, joining Serie A club Roma in 2014. He spent two years in the capital before moving on to LA Galaxy and then finishing his career at Derby County.

All of that success during his playing days is a great omen for what may be to come on the touchline.

Cole appears to be going about it the right way too, starting off with a club not as avidly in the spotlight and working his way up from there.