Richard Lorrison, who had read about a similar scam in a newspaper article, sent out hundreds of letters using false names to claim that waiters had spilt wine on his suit.
Southwark Crown Court in London was told yesterday that he pocketed pounds 1,300 from restaurants that paid up before the fiddle was halted.
He admitted five charges of deception and asked for a further 316 similar charges to be considered. He also admitted obtaining two bank loans for pounds 10,000 each in the name of Andrew Smith and to obtaining property by deception - a passport in the same name. Lorrison, 30, of Old Basing, Hampshire, was jailed for 18 months.
The court was told he had abandoned his career with a leading law firm because he felt that his City job would never allow him to settle his spiralling debts.
Judge Mota Singh said that Lorrison had created a series of false identities to carry out the frauds. Restaurants in the City and east London that paid out for cleaning bills included: the Mustard Smithfield Brasserie, the Prospect of Whitby public house, Rudland and Stubbs, the Simpsons Tavern, and Pascal's Restaurant.
Stephen Winberg, for the prosecution, said Lorrison began writing to restaurants in the name of Christopher Brown, claiming that some wine had been spilt on his suit by a waiter, and enclosing a forged copy of a dry-cleaning receipt.
Mr Winberg said restaurants would reply with an apology and cheques for up to pounds 30. In May last year, Lorrison was stopped in a car registered in the name of Brown and complaints by restaurateurs later led back to the defendant.
Max Hill, for the defence, said his client had trained as a solicitor with the "top-10" firm Herbert Smith and with another firm before deciding to leave the profession.
As a trainee, Lorrison had earned up to pounds 25,000, but he abandoned his career and offended - creating a "labyrinth" of false identities.
"The great mystery is why a young man with all the education that can be thrown at him would reject his chosen profession at such a time," Mr Hill said. Lorrison had despaired of clearing his debts.