Aidan Rave, who served as deputy to Mr Winter during a turbulent few years at Doncaster Council, has been appointed as interim chief executive of South Kesteven District Council in Linconlshire.
Mr Rave announced the news on Twitter, posting: "I'm proud and honoured to have been confirmed as chief executive of @southkesteven and look forward to the hard work ahead #skgoingplaces."
He has been handed the job on a 12 month interim basis with the possibility of extending the role further based on performance and progress made.
It marks a return to local government for Mr Rave who served as deputy under Mr Winter from 2002-06.
In recent years he has held a number of business, consultancy and charity roles.
Mr Rave stepped down as deputy in February 2006, telling a press conference that he could no longer work alongside Mr Winter, who himself stood down in 2009 after pressure grew on him to quit after a number of clashes with key allies and the Doncaster social services scandal.
In his resignation speech, Mr Rave said: "I tendered my resignation because of a mismatch of values and I don't believe my position in the cabinet is tenable any longer."
He later took another swipe at Mr Winter adding :"The town deserves so much better than what it is getting at the moment. There are good people working hard in the council for this borough, as much as there are good people in the Labour Party, trying to maintain the values of fairness and social justice in our borough's politics.
"Unfortunately, at the moment they are the lions led by donkeys, a change needs to take place sooner rather than later."
Former rugby league player Mr Winter became the first directly elected mayor of Doncaster in 2002 and successfully defended the position in 2005.
But he was forced to complete his final term as an indepedent following his removal from the Labour Party after serious failings were exposed within the council.
A no confidence vote in Mayor Winter was passed in July 2008 but he refused to stand down.
Further calls for his resignation followed in January the following year after DMBC was deemed to be seriously failing in its delivery of social services following the deaths of seven children that were on the local "at risk" register.
Later that year, he said he would not be standing for re-election and in June 2009 was replaced when English Democrat Peter Davies won the mayoral election.
In 2015, Mr Winter released his autobiography, revealing his time in charge of the council, but the book proved to be a flop and since stepping down from his role, he has kept a relatively low profile.