MK Dons chairman Pete Winkelman is not averse to taking a risk or two - moving the club 50-odd miles from their Wimbledon roots springs to mind - and the appointment of Roberto di Matteo is another huge gamble for both parties.
There is no doubting Di Matteo has an impressive football pedigree, with 37 caps for Italy, a successful spell with Lazio and five-and-a-half years spent with Chelsea on his CV.
But it is his lack of managerial experience that has raised more than a few eyebrows.
The 38-year-old was competing against the likes of Lee Sharpe and Sir Steve Redgrave in Channel Five's Superstars and working as a pundit for Swiss television on Euro 2008 when he first got word of Winkelman's interest.
"It was a bit of a peculiar situation," Di Matteo, who had never applied for a job in management, told BBC Sport.
It's an ambitious club and personally I am very ambitious
Roberto Di Matteo
"I was working in Switzerland on Euro 2008 for Swiss television and Christian Smith got in touch.
"He knew the chairman here and they got in touch for something else, my name was thrown in and here I am."
Smith - a senior commercial executive for the Professional Footballers' Association - informed the Dons chairman that Di Matteo, having completed his Uefa A Licence qualification, was looking for his first step into management.
Winkelman was instrumental in persuading Paul Ince to come to Milton Keynes and the appointment of Di Matteo is another coup for the enigmatic Dons chairman.
Like his successor, Ince was a relative novice when he took over the Dons hot-seat in the summer of 2007, having spent just six months at the helm at Macclesfield.
But Ince's success in winning promotion to League One and capturing the Johnstone's Paint Trophy saw the former England captain depart for the Premier League with Blackburn.
In offering only a one-year deal to Di Matteo (with an option of a further 12 months), Winkelman has placed the Italian under great pressure to prove he is capable of filling Ince's shoes.
As well as a gamble for his employers, Di Matteo's appointment is also risky for himself. If he succeeds, he could conceivably follow Ince into the Premier League - but failure could condemn him to the managerial scrapheap.
Comparisons with his predecessor are bound to be drawn, but whereas Ince surrounded himself with an experienced backroom team, including former Wigan boss Ray Mathias, Di Matteo's staff have considerably fewer miles on the clock.
Di Matteo has appointed former Chelsea colleague Eddie Newton, who was part of the youth coaching set-up at Stamford Bridge, as his assistant and ex-Great Britain sprinter Ade Mafe, who was also involved with the Blues, as his fitness coach.
"We've known each other for 12 years and gone through a few things as players and coaches," said Di Matteo.
"We've done our coaching badges together and we have the same philosophy of how football should be played.
"Eddie's got loads of experience in terms of coaching and me too. Obviously not as much as some managers who have been in the job for 20 years but we've got enough."
A triple leg fracture sustained in September 2000 effectively ended Di Matteo's playing career and he officially called it a day 18 months later.
Di Matteo's playing career ended after he suffered a triple leg break
He spent the intervening years gaining his coaching qualifications and when the call finally came, he had no hesitation at taking the chance for his first taste of management.
"I love the set-up here, it's great," he said.
"It's an ambitious club and personally I am very ambitious so I like that and hopefully we can work on the longer term."
But Di Matteo will get a crash course in some of the problems of managing in League One.
Following promotion, the squad has already been depleted, several key members of the backroom staff also left in the wake of Ince's departure and despite appearances, with the Dons moving into a new 22,000 all-seater stadium last season, there is little money to spend.
Add to this the high expectations of the club's fans and it is understandable why Di Matteo is playing down the club's ambitions.
"I think it won't be easy," he added. "We will try to establish ourselves in this league.
"I've lost a couple of important players who were here last season so we will have to see how well we can replace them and get on with them.
"There is a little bit of money available to spend but in League One the financial resources are limited."
Although the management game is new to Di Matteo, he says he has learned from the managers he has worked under during his playing career.
Ruud Gullit brought him to Chelsea, while he also played for the likes of Gianluca Vialli and Arrigo Sacchi.
"I guess everybody has his own personal touch but you try to gain from your experience that you had as a player and from the good coaches you had during your career," he added.
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