Terry Ramsden, 52
Terry Ramsden, 52
Who is he? One of the fastest risers of the 1980s, Ramsden, the son of a factory cleaner from Enfield, was a long-haired, flamboyant chancer who was among those who gave Thatcherism a bad name. He made his money on the international bond market and spent it on 100 race horses, gambling - up to £500,000 a stake - and football clubs, becoming briefly chairman of Walsall FC. At one point said to be worth £150m, making him the 57th richest man in Britain.
What happened to him? His spectacular fall began when the Japanese markets collapsed in 1987. Ramsden spent six months in prison in Los Angeles fighting extradition after being arrested at the request of the Serious Fraud Office. Bankrupt in 1992 with debts of £100m and given a two-year suspended sentence for fraud. Jailed in 1998 for concealing money from creditors.
What is he up to now? Released in 1999, he claims to have developed a new trading system for securities and currencies; has stakes in two Aim-listed cash-shell companies and City PR firm Hansard Group. He is buying race horses again and has acquired 200 acres of development land near the famous Sandy Lane resort in the Bahamas. He says: "I always thought I'd get a second chance, now I have and I've earned it."
Will he make it? Shares in the Aim-listed companies he is linked to fell sharply at the end of August after a fundraising for Hansard ran into difficulties. There is little to recommend any of them and his track record speaks for itself. Chances of success are slim.
Robert Montague, 56
Who is he? Montague was one of the first of the new breed of fat cats who profited from the boom of the 1980s as the flamboyant chairman and chief executive of the container-leasing group Tiphook. A fleet of luxury cars, a personal jet, a yacht, a Georgian mansion in Oxfordshire and a herd of pedigree cattle were among his assets. He earned £1.3m a year - an extraordinary salary at the time.
What happened to him? Tiphook's trailers failed to hold their value and the company simply lived beyond its means, growing too big too fast. It collapsed in 1994 with debts of £1.1bn. Montague was declared bankrupt with personal debts of £30m and was forced to sell the cars, the house, the cattle etc.
What is he up to now? Back in the transport rental business within a year of bankruptcy - after seeking permission of the receivers - he set up Axis, which is now the biggest business on the Alternative Investment Market (AIM). He was discharged from bankruptcy in 1997.
Last year he set up Trailerent, which leases new road trailers in Britain and last month he floated Intermodal Resources, which leases transport equipment mainly in mainland Europe, on AIM, raising around £500,000. His stake is around 40 per cent. Now living in a former mill house in Oxfordshire, Montague says: "My life has changed a lot, I'm very careful in what we do.''
Will he make it? Tiphook's demise and Montague's own bankruptcy means the warning light is rightly flashing over Intermodal. But a saving grace is the seven years he has spent building the business, so a truly chastened return in a sector that he knows well means chances of success are good.
Jim Slater, 74
Who is he? Hailing from an earlier generation of City high-flyers, Jim Slater profited from the 1960s stock market boom in the same fashion that Ramsden and others rode the 1980s. He turned an obscure £1.5m company called H Lotery & Co into the merchant bank Slater Walker in eight years. It was worth £200m, which today would make it a member of the FTSE 100.
What happened to him? Slater Walker collapsed in 1974 amid disclosures that he had loaned money to a "satellite company" to buy shares in the merchant bank. Slater ended up with debts of £3m and assets of £2m, which famously led to him describing himself as a "minus millionaire".
What is he up to now? Slater remains very active and interested in the ups and downs of the markets. He repaid his creditors and rebuilt his fortune by investing in property and then writing dozens of children's books. He also bought salmon fishing rights and turned them into timeshares. He successfully reinvented himself as a respected share tipster - which included a stint on The Independent - and, in conjunction with son Mark, he still patrols the market looking for good buys. In 2002 he returned as head of a publicly quoted company for the first time in 28 years when he took over the chair of BioProjects International, which backs biotechnology ventures. He said: "I do not intend to become chairman of any other public companies.''
Will he make it? Still respected by admirers of his 1990s stock market guide, The Zulu Principle, Slater certainly has experience on his side. Crucially he has already made one comeback, paying off creditors and rebuilding his private wealth after Slater Walker. With his biotechnology punts this wily septuagenarian has a better chance than most of success.
Andrew Regan, 38
Who is he? A corporate raider and former head of the food supply company Hobson. At the age of 31, he launched an audacious and ultimately unsuccessful £1.2bn bid for the supermarkets-to-funerals group Co-op, in 1997; he aimed to sell off parts of its business to other concerns such as Sainsbury's.
What happened to him? The Co-op bid collapsed spectacularly amid rumours of corruption after Regan was seen receiving internal Co-op documents in a pub car park from a senior executive of the company; both men were later condemned by a High Court judge as "patently dishonest'' and their conduct "a gross, wilful and disgraceful breach of confidence''.
The affair led to a Serious Fraud Office investigation of allegations that he had earlier stolen £2.4m from Hobson to bribe Co-op executives to secure a food supply contract extension. Extradition from Monaco, where he was then based, by the SFO failed, but he returned voluntarily to face charges and was finally cleared last year after a three-trial marathon during which his lawyers told the court he knew nothing of the bribes. Two Co-op executives involved were convicted and sentenced to prison terms, but a civil case against him is still outstanding. He later claimed that he had been persecuted by the Government for attempting to buy a company which contributed £1.2m a year to the party.
What is he up to now? Now dividing his time between London and Geneva. Regan claims to have developed a computer system for identifying firms whose share prices do not reflect their cash flows or underlying assets and is reported to have come close to a takeover bid for Mothercare earlier this year, holding back when its price picked up. After taking a minority stake in the company, he returned to the stock market yesterday as chief executive of the investment vehicle Corvus Capital.
Who's behind him? John Duffield, a legendary City figure who was once married to Vivienne Duffield of the Clore family, is a key ally. His fund-management company Jupiter backed the Co-op bid and he has taken an 8 per cent stake in Corvus, through his New Star Asset Management vehicle.
Will he make it? : Regan still has it all to prove. The backing of Duffield gives him firepower but Regan faces huge competition in his chosen area of acquiring undervalued companies. His chances of large-scale success are slim. To most who meet him, Regan comes across as a plausible character; however, those in the City who are convinced of his abilities are in the minority. His track record of success in food manufacturing has long been overshadowed by the Co-op debacle and his backers are showing a huge amount of faith in a man whose early promise was cut short by the Co-op bid.
Greg Hutchings, 56
Who is he? Hutchings was a protege of Lord White (of Hanson fame) and the man who spent 17 years building the small and obscure Walsall buckle-making firm Tomkins into a £5bn multi-national conglomerate and member of the FTSE100 simply by eating up weaker enterprises; at its peak it employed 70,000 and owned both Rank Hovis McDougall and Smith and Wesson - hence the "buns to guns" tag.
What happened to him? Ousted from the Tomkins board in 2000 after a very public row over his use of company perks, including personal jets and household expenses, his two luxury London flats and for putting his wife and housekeeper on the company payroll. However, Hutchings was completely exonerated in a subsequent Ernst and Young report which said that he had broken no rules of corporate behaviour. Received £6m in shares as part of his settlement with Tomkins.
What is he up to now? Re-emerged this year by investing £2.1m to become chairman of Lupus Capital, an investment capital vehicle, aiming at acquisitions of around the £100m mark - essentially a repeat of the Tomkins formula but running it like a private equity house. He has a 12.5 per cent stake. Shares surged on news of his involvement and he will be well rewarded if he hits performance targets. Currently only one company on its books - Gall Thompson Environmental, which makes couplings for oil and gas lines.
Will he make it? Hutchings' track record at Tomkins gives him vast experience. His comeback plans have similarities to Regan's and most shrewd City watchers would back Hutchings, rather than the Co-op raider, to spot a winner.
John Gunn, 62
Who is he? A Cheshire railwayman's son who left Barclays to turn Exco International into the world's largest money broker by the mid-1980s, worth about £500m. After a boardroom row, he joined the former shipping line British and Commonwealth, which had diversified into aviation, hotels and, under Gunn, financial services.
What happened to him? A series of spectacularly bad deals - mainly the £400m takeover of a computer leasing business which turned out to be owing £550m - led to the collapse of B&C in 1990 with debts of £1.5bn. Gunn was heavily criticised in the subsequent 1994 Department of Trade report on the affair but fought back and was exonerated by the judge in the 1998 disqualification proceedings. City advisers have insisted that both verdicts are included in the prospectus every time Gunn sits on the board of a firm that will float. "Regulators, civil servants, they're all lying, cheating bastards. We were scapegoated.''
What is he up to now? Remains an active player and has set up a number of companies on AIM that develop green technology and use ideas stemming from university research, including Turbo Genset, which makes cheap electricity generators and Vert-Eco, involved in toxic waste clearance. Ceres Power, a fuel-cell company is expected to list next year. Sold stockbrokers Christows for £40m in 2000. Owns vineyard in California and house in Switzerland.
Who's behind him? The weathly Cayzer family backed him during the Exco and B&C years, while Nick Leslau and Nigel Wray, both property and stock market tycoons known in the City are said to be backing Vert Eco.
Will he make it? The B&C episode left Gunn with few powerful friends so he will struggle to win over mainstream backers. But his focus on trendy "green" technologies might just pay off.
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