Sir Simon Robey had his career planned out. He wanted to become a professional opera singer and his dream was to sing on stage at the Royal Opera House, but he accidentally stumbled into investment banking. It’s a decision he occasionally regrets while singing in the shower in the morning. But Robey, 60, turned out to be a pretty good banker, and has been described as the City’s “trillion dollar man” for the cumulative size of the mega-deals he has worked on, including advising the Cadbury board on the sale of the 197-year-old chocolate company to America’s Kraft in 2010. His sought-after advice has earned him at least £137m in the last seven years alone. He is spending this lockdown at Bramfield Hall, a Grade II-listed, 16th-century country estate in Suffolk, which was owned by the Rabett family for 450 years until Robey spent a chunk of his bonus on it. It was at Bramfield that Robey, a lifelong Arsenal fan, this week signed up a new recruit for his boutique investment bank Robey Warshaw. His old friend and former chancellor of the exchequer George Osborne will become the only person to join the bank as a partner since Robey founded it with fellow investment banking superstars Simon Warshaw (an heir of the Molton Brown beauty empire) and Philip Apostolides in 2013. Osborne will be giving up his elective portfolio of roles, including editor-in-chief of the Evening Standard newspaper, but the new job is set to propel the former chancellor – best remembered for ushering in a decade of austerity and public spending cuts – even higher into the ranks of the top 1% of high earners. Robey Warshaw has paid out £207m in profits to partners over the last six years, according to accounts filed at Companies House. Most of the money has gone to Robey, who is understood to hold the biggest equity chunk in the partnership. The accounts show that the bank, which operates out of a townhouse on Grosvenor Square in Mayfair, turned over £255m in the six years to March 2020, but has not paid any tax. Robey Warshaw said it was not liable for tax because of its structure as a limited liability partnership, and that it is “the responsibility of the individual members to settle any liability arising from their share of partnership profits”. A spokesperson for the bank declined to state how much tax the partners had paid on their share of the profits, but said: “All Robey Warshaw partners are UK registered taxpayers and pay all taxes required under UK law.” “It’s all very cosy, isn’t it?” said Richard Burgon, a Labour MP and former economic secretary to the Treasury. He sees Osborne’s move as an example of the “revolving door” in British public life between government and the financial sector. “He [Osborne] was in charge of putting the banks in order after the financial crisis, but instead he embarked on the austerity drive that transferred wealth from the majority to the top 1%,” Burgon said. “Now he has got an incredibly lucrative job as a result, it is a reminder that the political elite runs our society in the interest of the economic elite.” Robey was adopted and grew up in Cambridge. He has described himself as “an odd child”. “Anorak, glasses, listening to classical music and watching birds. It was a fairly nerdy upbringing in Cambridge,” he told the Evening Standard. He boarded at Reed’s School, an independent private school in Cobham, Surrey, before winning a choral scholarship to read English at Magdalen College, Oxford. It was while performing in a cabaret at Oxford’s Randolph Hotel that he accidentally stumbled into banking. A so-called “milk round” presentation for the investment bank Lazard was taking place next door. He wandered in on a whim, and won a place as a graduate trainee. “When I joined Lazard in 1983, it was very English, very old-fashioned and a bit like being back at boarding school. We shared one computer, had long lunches and drank champagne after work,” he wrote in an FT magazine article celebrating 30 of “the City’s most influential people”. “Lots of things were wrong with this set-up: it was a bit clubby, male and public school.” As he progressed in his career and joined Morgan Stanley, where he worked for 25 years before starting out on his own, Robey became – to his own admission – a difficult and demanding boss. His colleagues once gave him a T-shirt with “Get This Right or I’ll Kill You” printed on it, which he proudly wore at the gym. He had uttered the words “half in jest” to a colleague during a deal in 1996. He now claims to have “mellowed a lot”. Robey has worked on some of the biggest deals in British, European and worldwide business. He advised Marks & Spencer on its defence against a takeover attempt by Sir Philip Green; helped AstraZeneca’s defence against a takeover by the US’s Pfizer; and worked with the London Stock Exchange on its aborted merger with Deutsche Börse. He was also involved in Halifax Bank of Scotland’s emergency merger with Lloyds TSB during the financial crisis in a deal hammered out in a three-bedroom flat in Mayfair. And he advised the Treasury on Bradford & Bingley’s nationalisation. Osborne is not the first person from politics that Robey has brought into banking. He recruited Jonathan Powell, Tony Blair’s former chief of staff, and Lord Heywood, the former cabinet secretary, during his time at Morgan Stanley. His love of opera has not left him, and he finally got to grace the Royal Opera House’s main stage when he became chairman in 2008. Soon after he took the job Robey appointed Lord Heywood’s wife, Suzanne, to the board. He stepped down himself soon after being knighted for services to music in 2016. Robey is married to Victoria, a former banker and the ex-wife of the incoming BBC chairman Richard Sharp. He has three children from a previous marriage, and is stepfather to Victoria’s three children. He still sings, but says he has to be “very drunk” to do so in public. But he did once take to the stage in a piano bar in the Swiss resort of Klosters. “He was fabulous,” a PR executive recalled. “Unfortunately the Swiss tourists didn’t realise that they were being sung to by one of the City’s best investment bankers.”