The 54-year-old former British Olympic Association chief executive, who, as insidethegames reported yesterday, takes over from departing American Jim Scherr as chief operating officer for the inaugural European Games to be held in the Azerbaijani capital next year, has a career pedigree as impressive as any winner of Crufts. But he reckons this move is one which presents arguably the greatest challenge.
"I'm very clear about what my role is," he told me as we chatted in a Surrey hostelry on the eve of his departure. "When you consider it normally takes seven years to organise an Olympic Games, to deliver an event of this magnitude within a matter of months is no mean undertaking, particularly for a country with no great record of staging major events.
"You go to Azerbaijan feeling slightly apprehensive but you come away completely blown away by the investment they are making not only in sport but the whole nation for the quality of life for its people.
"So I have no doubt that Baku will produce something of which the city, the nation and Europe will be very proud."
Britain too, as the UK involvement is substantial.
Baku was chosen only in December 2012 to host the Games which were the brainchild of European Olympic Committee president Patrick Hickey. Up to now Clegg, originally hired in a special advisory capacity as executive director of the Games, had been spending a week every month in Baku.
He now moves there full time to assume the chief operating officer post following former United States Olympic Committee chief Scherr's surprise decision to return to the US to spend more time with his own marketing company.
One of Clegg's first tasks will be to help find a replacement for another American, the Games' prospective communications director Darryl Siebel, who did an outstanding job in a similar capacity for the BOA but following a disagreement with Baku over his commitment to the Sochi Winter Games opted out and has now become assistant director of sport at the University of Las Vegas.
Siebel had worked as chief communications officer at the United States Olympic Committee under Scherr between 2003 and 2009.
Few sports administrators have had a career as varied as former Army major "Cleggy", never one to dip his toe in at the shallow end. This ranges from managing the British biathlon team to becoming deputy general secretary and then chief executive of the BOA for 12 years, directing an IOC session in Birmingham, overseeing the 48-nation European Youth Olympic Festival in Bath and running Ipswich Town FC as its chief executive from 2009 to 2013 where daily dealings with one of the game's more combative managerial figures, Roy Keane, surely armed him for any confrontations that Baku might bring!
While at the BOA he led their political lobbying campaign to persuade a then reluctant British Government to back a bid for the 2012 Olympics. On returning from Singapore in 2005, where he was one of three British signatories on the 2012 host city contract, he led a meeting of Olympic national governing bodies and national agencies to set a target of aspiring to finish fourth in the 2012 medal table, one met in stunning fashion four years early.
Clegg, who was made a CBE in 2006 for his contribution to London's successful bid, also managed British teams at 12 Olympic Games, six as Chef de Mission, but in 2009 decided that a restructuring at the BOA left him no option but to leave in "bittersweet" circumstances after a total of 20 years.
However, he did secure a walk-on part in 2012 as the official Olympic attaché for the Pacific island of Guam!
Subsequently he became a consultant to Madrid's 2020 Olympic bid and is currently chairman of Great Britain Badminton and a member of the BOA executive board under new chairman Sebastian Coe.
And so to Baku, where he reminds us there are now only 13 months before curtain-up. "There have been Asian and Pan American Games since 1951 and All-African Games since 1976, but despite the athletic prowess and commercial strength of Europe there has never been a European Games," he says.
"This has been talked about for some years and it seemed a natural opportunity for Azerbaijan, who have twice bid unsuccessfully for the Olympics, and surely will bid again, to grasp with both hands as they were building the facilities anyway."
The Games are expected to attract some 6,000 athletes from 49 countries - including Team GB - competing in 19 sports.
Some state-of-the-art stadiums exist, including the 60,000-seater national stadium are well under construction and others like the multi-purpose venue designated for archery, are being refurbished.
Guess who the archery centre is named after? The name Tofiq Bahramov will certainly be familiar to English and German football fans. For back in 1966, when Azerbaijan was part of the Soviet Union, it was the famously moustachioed figure of Bahramov who signalled the contentious third goal which secured England's World Cup victory at Wembley, unhesitatingly insisting Geoff Hurst's shot in extra time had crossed the line.
He remains Azerbaijan's most celebrated sporting figure.
"Think Paul Deighton [former LOCOG chief executive] but on a slightly smaller scale," is how Clegg describes his own role. "These are not a replica of the Olympic Games but they are important to the Olympics because several sports that will be ranking events for Rio 2016.
"The programme will be meaningful and dynamic, with some sports that are not currently in the Olympics such as karate and beach soccer.
"There will also be beach volleyball, boxing, judo, taekwondo, shooting, gymnastics, wrestling, volleyball, road and mountain cycling, BMX - and street athletics along boulevards with a background of the Caspian Sea. A tremendously atmospheric environment.
"This is a fantastic opportunity to be involved in moulding an event which will have a profound impact on European sport.
"For the past nine months I have been working closely with the Minister for Youth and Sport, Azad Rahimov. We have confidence in each other and complementary skills which we believe will deliver a very successful event on time.
"But we must remember this is not a marathon. It is now a sprint for the next 13 months."
Father-of-two Clegg will be joined by his wife Hilary for the duration in Baku where there are familiar faces among the administrative staff of 350, many recruited from LOCOG including another American, Doug Arnot, who was 2012's director of Games operations. Their jobs range from commerce to ceremonies.
"There is a great team in place and the opportunity to create something new is really exciting," adds Clegg, who once said of his own career: "There are a lot of people who talk the talk in British sport. I hope I walk the walk."
As far as staging prestigious international events is concerned, Baku is probably best known as host city for the 2012 Eurovision Song Contest, in which the UK's Engelbert Humperdinck finished a dismal 25th. The high expectation is that Simon Clegg's production number will be an infinitely bigger hit for Britain's reputation.
Alan Hubbard is an award-winning sports columnist for The Independent on Sunday and a former sports editor of The Observer. He has covered a total of 16 Summer and Winter Games, 10 Commonwealth Games, several football World Cups and world title fights from Atlanta to Zaire.