Darren Bent was caught off-guard by Ashley Cole's first managerial role and claimed he'd have been better off at a Championship side.
Cole was appointed manager of Serie B side Cesena until the end of the season on Sunday, although he could secure a prolonged stay in northern Italy should certain criteria be met.
Ashley Cole celebrates his commemorative England caps
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Cole has done it all as a player, but can he enjoy success as a manager?Credit: Getty
It marked the 45-year-old's first senior managerial role of his coaching career having cut his teeth as an assistant at Chelsea, Everton, Derby County, Birmingham City and England.
Speaking on talkSPORT Drive, Bent pointed out Cole has 'got the credentials' having learned his trade in England and working with some impressive players.
It's why the Chelsea great's decision to take the managerial plunge in the Italian second tier was all the more perplexing.
Cole 'earned his stripes', but Cesena move still surprising
"It does surprise me that he's gone to a second division team in Italy," Bent said.
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"I thought he's got the credentials, certainly with his coaching career.
"He's not one of these who, as soon as they've retired, has jumped into a job. He's almost earned his stripes with coaching roles.
"He and Lee Carsley work quite well together as well."
Bent then proposed a scenario where if he was presented with the Cesena role or taking over Championship outfit Hull City, who sit fifth in the second tier, the former Premier League marksman wouldn't look too far away from home.
Hull or Cesena?
"I'd rather take the Hull job," Bent said.
"There's a chance to get into the Premier League next year. If a play-off team in the Championship can get into the Premier League, I'm going there."
Ashley Cole with England
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Could Cole have kicked off his managerial career closer to home?Credit: Getty
Bent added: "Northern Italy sounds beautiful.
"But if he was to go to Hull, he's in the Premier League if they get promoted next year.
"Even if they don't get promoted, he's still in a very, very good league."
Although Hull stand a chance of returning to the English top flight for the first time since 2017, Cole could still feel the rush of promotion at Cesena.
How are Cesena performing this season?
Cesena sit 8th in Serie B, which would be good enough to secure a spot in the league's preliminary round for the promotion play-offs.
In Serie B, the top two teams in the 20-team division are automatically promoted to Serie A, with third and fourth progressing straight to the promotion play-offs semi-finals.
Ashley Cole stands alongside Lee Carsley before an England match
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Cole has worked across several clubs and even for England under former interim boss Lee CarsleyCredit: Getty
It means teams that finish 5th, 6th, 7th and 8th will have to take the longest route possible should they want to rub shoulders with the likes of Juventus and Inter Milan next season.
Teams in the Championship will soon become familiar with Serie B's play-off system as the EFL confirmed they will expand the play-offs from four teams to six, beginning with the 2026/27 campaign.
Although a surge to the top four of Serie B may be too difficult amid Cesena's surprising record, European football expert Andy Brassell believes the expectation for Cole will be to reach the play-offs.
Why Cole has a chance to 'make it his own'
"If you look at Cesena and where they are at the moment, they have a losing record," Brassell told talkSPORT.com.
"They've lost more games than they've won. So he's not expected to get into the top four. I think that would require an absolutely crazy run and a couple of teams above falling to bits.
"But it does mean that he needs to not just assure they make the top eight, but prep them for going into those playoffs.
Ashley Cole and Wayne Rooney at Birmingham
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Cole has been an assistant for five different teams but is finally making the step upCredit: Getty
"So it's quite a big job where he'll get a lot of time to work on the team and make it his own between now and the end of the season."
Despite the difficulty of the task that awaits, Brassell reserved special praise for Cole and his willingness to take the path less travelled to kick-start his managerial career.
"Look, Ashley Cole has proved so far by doing a variety of different jobs that he's a thoughtful coach," Brassell said.
"He's someone who's not turned his nose up at stuff that other big players would consider a bit menial. He's been really keen to learn the whole way.
"I think if you look at some people he knows, and I think you look at Cesc Fabregas and Dennis Wise, for example, there are people involved in Italian football who will speak for him, who know him. And I think that will have played a big part in him gettng involved there.
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"But nevertheless, seeing a young English coach going there and having a go and trying to carve something out is really interesting."
Cole's first match in charge of Cesena is a trip to 15th-placed Mantova on Tuesday, with kick-off scheduled for 7pm.