Ashley Cole to Cesena among nine most bizarre first manager jobs | OneFootball

We did not have Ashley Cole rocking up at Cesena for his first job as a head coach on our bingo cards for 2026, but here we are.

Moving into management has long been a common route for players without much of a clue what awaits in the real world after they retire. Often, those players get a chance with one of the clubs they played for because DNA. But some take a more unconventional pathway.

Here are some of the most curious first managerial jobs taken on by former players.

Ashley Cole at Cesena

What’s particularly intriguing about Cole’s first managerial job is that he has gone back to a country where he failed as a player.

One of the best left-backs of his generation, Cole enjoyed success in most places, but his Serie A spell with Roma was an obvious exception. He remains a derided figure in the Italian capital to this day.

But he has taken on the challenge of guiding Cesena in Serie B after cutting his teeth as an assistant to some of his former teammates like Frank Lampard and Wayne Rooney.

Cesena are currently eighth in Serie B, which already has a six-team play-off system like the one that will be introduced in the Championship next season. Their players include former Fiorentina midfielder Gaetano Castrovilli and ex-Juventus full-back Gianluca Frabotta, as well as goalkeeper Jonathan Klinsmann, son of Jurgen.

Cesena were in Serie A when Cole was a player, but these days are a phoenix club after going bankrupt in 2018.

Bringing in a high-profile name like Cole is a bold move designed to boost the current regime’s profile. He will be backed up by an all-Italian coaching staff, none of whom he has worked with before.

Cole intended to learn Italian when he joined Roma, but there was never any evidence of him speaking the language in public, so it remains to be seen how well he will be able to communicate with the squad he has inherited as he begins to form his own tactical ideas.

Edgar Davids at Barnet

If we’re talking random, it doesn’t get much more random than Edgar Davids at Barnet.

Yes, he was a player-manager rather than just a manager, but he took the job a couple of years after he last kicked a ball around for Crystal Palace, serving as an Ajax board member in between.

No matter how much time has passed, it still takes some mental gymnastics to get your head around the concept of a three-time Eredivisie and three-time Serie A winner ending up at the helm of a League Two club.

Discipline issues affected Davids’ impact on the pitch for Barnet. As the manager, he resigned in January 2014 with a record of 25 wins, 25 losses and 18 draws.

His next job as a head coach didn’t come until January 2021, when he was appointed by Olhanense in the Portuguese third tier; Davids was sacked that July.

A year later, he was an assistant coach to Louis van Gaal at the World Cup with the Netherlands.

Pascal Chimbonda at Skelmersdale United

Chimbonda played for four different clubs in the Premier League, but later spent some time playing in non-league…where his managerial career began.

In 2023, Skelmersdale United of the ninth-tier North West Counties League appointed Chimbonda as their new manager. He later registered himself as a player too.

But Chimbonda oversaw their relegation and he was dismissed at the end of the season; we like to think that Chimbonda had his own resignation letter tucked down his sock.

Gary Neville at Valencia

Neville’s doomed spell at Valencia is the epitome of disastrous decisions to derail what might have been a promising managerial career.

Neville had been working as an assistant coach with the England national team for three-and-a-half years when Valencia appointed him in December 2015.

The former Manchester United right-back didn’t speak Spanish, so it was seen as a risky move by Valencia, who failed to win any of his first nine La Liga games in charge, and also suffered a 7-0 thrashing by Barcelona in the Copa del Rey for good measure.

By March 2016, Neville was sacked by Valencia after just 28 games in charge. Since then, he has returned to punditry and shown no interest in resuming a managerial career.

Would things have unfolded differently if he’d started out somewhere in English football instead? Maybe, maybe not. But it’s hard to look back at his Valencia stint and think it was a good choice for either party.

Sol Campbell at Macclesfield

All but one of Campbell’s league appearances as a player were in the top flight, but his managerial journey began in League Two after serving as an assistant manager for Trinidad & Tobago.

According to the man himself, it took seven years and around 15 job applications to become a manager before getting his breakthrough.

Macclesfield Town appointed Campbell in November 2018 whilst bottom of the league. He eventually guided them to safety, but left at the end of the season amid their financial troubles.

The former Tottenham and Arsenal defender then got a job in League One with Southend United, but hasn’t managed since leaving them in 2020.

David James at Kerala Blasters

Former England goalkeeper James finished his playing career as the player-manager of Kerala Blasters in the newly-formed Indian Super League in 2014.

He led them to the final of the play-offs to decide the league title, but suffered defeat and then left the club.

In 2018, James returned for a second spell in charge of Kerala Blasters, this time without combining any playing duties, but he was sacked that December after going on a run of 11 games without a win.

James spoke in 2010 about his desire to find a coaching job in England in 2020, but none has ever materialised.

Kevin Phillips at South Shields

Phillips’ most memorable achievement was winning the European Golden Shoe for his 30-goal Premier League season with Sunderland in 1999/00.

Across his career, the striker scored 92 Premier League goals. After retiring, he spent time on the coaching staff of clubs like Leicester, Derby and Stoke.

But his first job as a manager in his own right, assigned in January 2022, was in the seventh tier of English football with Northern Premier League side South Shields (who had already enjoyed the services of his former Sunderland teammate Julio Arca as a player a few years previously).

Phillips won promotion to the National League North after two seasons with South Shields before being succeeded by Arca. He has since managed Hartlepool United and AFC Fylde, but is yet to get an opportunity in the EFL.

Albert Riera at Olimpija Ljubljana

Spain has become a hotbed of managerial talent in recent years, currently represented in the Premier League by Mikel Arteta, Pep Guardiola, Unai Emery and Andoni Iraola. All are regarded as some of the best footballing brains in the league.

But former Manchester City and Liverpool winger Riera has taken a path less travelled.

After finishing his playing career in Slovenia with Koper in 2016, Riera began his managerial career in the same country with Olimpija Ljubljana.

Two spells with another Slovenian side, Celje, have set him up for opportunities in the bigger leagues. He got the Bordeaux job in between those spells until their bankruptcy, and was appointed by Bundesliga side Eintracht Frankfurt earlier this year.

Steven Taylor at Gulf United

Former Newcastle United defender Taylor took charge of Gulf United – a club founded in 2019 in Dubai as an academy pathway – when they entered the UAE Third Division in 2022.

He guided them to back-to-back promotions to reach the top flight before making way for another, non-related ex-player with the same surname: Neil Taylor.

Taylor remained in the UAE for his next job with Al Qabila, achieving another promotion with a bit of help from his old teammate Papiss Cisse playing up front.

He is still working in the Middle East now, but as part of a project he co-founded known as The Player.