His millionaire lifestyle, built in the early 1980s on trading in Japanese bonds, included the obligatory executive jet, Rolls-Royces, homes around the world, and the ownership of a football club.
His gambling record was the envy of every trackside punter - a regular winner both on the racecourse and at the bookies. He was a true Eighties self-made man with his cockney vowels and shoulder length hair.
Yet Terry Ramsden, 46, looked anything but a high-flying, city whizz- kid yesterday as he stood in the dock at the Old Bailey. A bankrupt with debts of more than pounds 100m, he was jailed for 21 months for trying to conceal about pounds 300,000 from his creditors.
Ramsden's roller-coaster career began in the City at the age of 16 as an insurance clerk. He quickly realised he could make more money by working for himself and set up his own business, making pounds 25,000 in the first month.
But the vehicle for Ramsden's career was a company in Edinburgh called Glen International which he bought in 1984, when it had a turnover of pounds 18,000.
By 1987, the figure had risen to pounds 3.5bn and Ramsden was said to be the nation's 57th richest man.
The venture was based on his knowledge of the specialised and volatile market in Japanese warrants. These were options to buy shares in Japanese companies. He gambled on a rising market and got it right. After hitting the jackpot, he was quick to adopt a suitably flamboyant and high-flying lifestyle to go with the new-found wealth.
Along with his Porsche, Ferraris and Rolls-Royces, he was interested in racehorses - lots of them. At one stage he owned 75. One of his biggest successes on the racecourse was when his horse Not So Silly won the Ayr Gold Cup in 1987.
Small of stature, but invariably accompanied by minder, he was a regular visitor to the winner's enclosure. "I'm a stockbroker from Enfield. I've got long hair and I like a bet," he once said.
He also owned a Georgian mansion on a luxury estate in Blackheath, south- east London, where he could relax in a swimming pool with hologram shark fins beamed on to the water, before flying by helicopter to Walsall Football Club, of which he was both owner and chairman.
He lived with his wife, Lisa, and their son, Jake. They also had homes in Scotland, Bermuda and Portugal.
But in 1986 the market and Ramsden's luck changed.
The 1987 crash knocked hundreds of millions of pounds off the value of his securities. He started to run out of cash to keep the huge and complex portfolio of securities afloat and his marriage was on the rocks.
Added to this, he was estimated to have lost pounds 58m at the racetrack - there were even stories of him parting with pounds 2m in a single day.
Within a year, Glen International crashed, owing pounds 98m, and he moved to the United States.
In September 1991, a warrant for his arrest was issued on fraud charges and he was detained in a jail in Los Angeles until his return to Britain in February 1992. The next month, Ramsden was declared bankrupt - with the Inland Revenue demanding pounds 21.5m and other creditors bringing the total debt to near pounds 100m.
Ramsden escaped with a two-year suspended sentence in November 1993 after he pleaded guilty to offences of recklessly inducing fresh investment in his empire.
As a bankrupt, Ramsden was required to disclose all his assets and income but failed to reveal the existence of a hidden trust and concealed his ownership of three million shares in the Silversword Corporation, a Canadian company in which he had a controlling interest.
Thousands of pounds was paid from the trust fund to Ramsden's mother, Florence, a former cleaner, which she passed on to her son. He also failed to mention winnings of pounds 77,000 in 1992, from an accumulator bet involving five horses and a dog.
Last year, the Serious Fraud Office announced that Ramsden was to be prosecuted for failing to disclose assets.
At his trial, Ramsden admitted failing to disclose about pounds 300,000. It was also revealed that the fund had also helped pay for a house worth pounds 323,800 for his wife and son.
Jailing Ramsden for 21 months, Judge Peter Beaumont QC also ordered him to pay pounds 10,000 towards prosecution costs.
He told Ramsden: "You broke the law and must now be punished." The judge said he would serve at least half the sentence in prison.
Ramsden, of Fulham, south-west London, pleaded guilty to three charges of breaching the Insolvency Act by failing to disclose all his assets.
Anthony Arlidge QC, for the defence, said: "He was motivated by a desire to win back his wife and restart his family life. He accepts now that is no longer possible."
He added: "He is a man of considerable talent, who for a long time was extremely successful. Rightly or wrongly, he felt his failure was not his fault but due to the misguided views of others."