Simon Greenberg was a 25-year-old sports reporter at The Mail on Sunday when, in February 1995, he landed the scoop that cost George Graham his job as manager of Arsenal. Greenberg revealed that Graham had accepted a “bung”, or illicit payment, of more than £400,000 from a Norwegian soccer agent in relation to the transfers of two players. Graham insisted that it was an “unsolicited gift”, but the Football Association saw differently and handed him a one-year ban.
That the story brought down the manager of Arsenal, arch-rivals of Greenberg’s beloved Tottenham Hotspur, was not lost on those close to him. As his younger brother Daniel wryly remarked, Graham’s departure from Arsenal “did not work out so well for Spurs in the end”: Arsenal later hired Arsène Wenger and went on to even greater glory while Graham, having served his ban, turned up as manager of Tottenham.
Greenberg, who won a pair of industry awards for the story, found himself fêted by Fleet Street and was entrusted with co-writing the autobiography of Les Ferdinand, the former England player. Yet in 2004 the poacher turned gamekeeper, becoming communications and public affairs director at Chelsea, overseeing all aspects of the club’s communications including Chelsea TV, the website, magazine, match programme and social media.
He arrived at about the same time as José Mourinho, Chelsea’s new manager, and the pair became known for their furious bust-ups, with Greenberg telling the manager the truth, no matter how awkward or unpleasant. Mourinho called Greenberg the “shadow”, because he was always there, helping to keep him out of trouble. In press conferences Mourinho seemed to relish dropping bombshells, winking at Greenberg as he disappeared, leaving him to pick up the pieces.
All this proved useful experience for Greenberg, who in 2011 joined News International (now News UK, publisher of The Times) as director of corporate affairs. This was at the time of the phone-hacking crisis that would engulf, and ultimately close, News of the World, and he was responsible for articulating the company’s response to the affair. It was a gruelling couple of years, including an interview with Jon Snow of Channel 4 News that was more of a mauling than a grilling.
Yet far from bemoaning his thankless task, Greenberg relished getting involved in the minutiae of a complex issue. According to reports at the time he was among those proposing that part of the solution to the company’s problems might include closing the Sunday title. As he put it in an email that was later made public: “Unparalleled moments need unparalleled action.”
Simon Marc Greenberg was born in north London in 1969, the son of Benson Greenberg and his wife Judy (née Ashley) who ran a small rag-trade business. While never overtly religious, he was proud of his Jewish roots and prone to pepper light conversation with Yiddish references, “schluff” (a nap) being a favourite.
He was educated at Christ’s College Finchley and read history at the University of Exeter, where an obsession with facts made him pretty much unbeatable in football quizzes. Despite being a member of the university’s second XI, he resolved that if he could not play the game at the highest level he would instead write about the sport and took the postgraduate journalism course at City, University of London.
He joined the Hornsey Journal in 1991, but his story-getting abilities soon attracted the attention of The Mail on Sunday, where he rose to deputy sports editor by his mid-twenties. Six years later he was approached by Max Hastings to join the Evening Standard, becoming the youngest sports editor on Fleet Street.
While always a football fanatic, Greenberg discovered that his sporting strength lay in the pool. Broad-shouldered and well over 6ft tall, he had the ideal build for a swimmer and took up the sport competitively, training with Mark Foster, the former world champion. In 2009 he won bronze for Britain in the veterans’ division at the 2009 Maccabiah Games, known as the “Jewish Olympics”, in Tel Aviv.
That same year his enduring relationship with the mercurial Mourinho provided him with an opportunity to present Will Lewis, his closest friend, with an unusual 40th-birthday gift. Mourinho was by then managing the Italian club Inter Milan and Greenberg hatched a plot to lure Lewis, then editor of The Daily Telegraph, to Milan to speak at an Italian newspaper event.
The morning after a jolly night out in the city, Lewis expected to be taken to a conference centre. Instead, they pulled up at Inter’s Angelo Moratti training ground. After lunch with Mourinho and his squad, Greenberg explained to a tired and emotional Lewis that he was about to be put through his paces by Rui Faria, Inter’s assistant coach. Rather than a kickabout with superstars such as Zlatan Ibrahimovic and Patrick Vieira, he was led to a treadmill and hooked up to a heart monitor. With a grin spreading across his face, Greenberg enjoyed a cool drink as his friend spent the next hour pounding on the running machine.
The previous year Greenberg had taken the advanced management programme at Harvard Business School, later wearing his Harvard hoodie with pride. After a spell running England’s ill-fated bid to host the 2018 Fifa World Cup, backed by the Duke of Cambridge and David Beckham, he joined News International.
As the dust settled on the phone-hacking scandal Greenberg once again found sanctuary in sport, becoming News Corp’s global head of rights, setting up Dow Jones Sports Intelligence, dedicated to providing sports brands and their sponsors with data. The company’s intranet briefly described him as “global head of rites”, prompting him to joke that he had been appointed either its chief rabbi or head druid.
Meanwhile, after a couple of relationships including seven years with Harriet Messenger, he married Fran Jefferson, a music industry executive, in 2013, the Glastonbury Festival having provided their first date. She survives him with their son, Sam, as well as Coco and Sukie, Fran’s two daughters from a previous marriage. At their family home in Queen’s Park the couple hosted dinner parties and children’s penalty shoot-outs with equal aplomb.
Simon Greenberg, journalist and football executive, was born on July 26, 1969. He died after a short illness on August 30, 2021, aged 52
