He lost his job at the lobbying firm GPC Market Access; his column was then excised from The Express; and the refuge that was Talk Radio showed him the door when he claimed to be phoning a show from a Dutch brothel.
It would not be surprising if, at this point, Draper took time out to cope with depression, and try to refocus. But he is not a man to be idle and last month his latest venture, which comes replete with a few well- spun column inches, emerged - Draper the Adman.
Some might say that, having been so royally burnt in other media sectors, he should leave this particular sector well alone. But Draper has launched his own advertising agency, Farm Communications, claiming that it is a new concept in advertising - a brave bid for a man who openly professes to know nothing about the industry.
His agency, set up with Paul Jeffrey and Robert Smith - who join him from BDDH & Partners and who have worked with clients such as BT, British Gas and The Guardian - is one of a new breed that aims to work project by project. It will farm out each piece of work to a team of creatives, hence the name. Draper said at its launch: "I don't know much about advertising at all. I'm on a huge learning curve; I want to learn something new."
Learning something new is likely to be the least of his problems. After the Draper publicity machine wound down, it emerged that Farm is not in fact unique, as was first thought. In London alone there at least three companies using the name "Farm" that already trade in the media sector. At least two of those have expressed concern over Draper's use of the name, and there is talk of a nasty legal battle - a legal battle that could bring Draper's venture to a premature end.
The Farm, based in the converted Truman brewery in Brick Lane, London, is a graphics agency run by Daniel Cigman and Fergus Partridge, specialising in branding. The director, Danny Cigman, says that since coverage of Draper's agency emerged last month, they have been plagued with calls from journalists looking for Draper. Worse still are calls from disgruntled clients.
"One of our major clients rang us and asked when we had been bought out by Draper, and asked why we hadn't told them of the tie-up," says Cigman. "It was very annoying and we have had to explain to people that we have nothing to do with him."
The Farm has been trading (with its definite article) for almost two years and is talking to lawyers about Draper's use of the name. The letterheads of both companies feature farm animals. Draper's company is unrepentant, and has declared that it will not be changing its name.
Cigman's problem lies in the way a court would view the word "the", and whether an ad agency can infringe on a design agency's trade.
Over in Covent Garden is another ad agency, Farm, with big-name clients such as the Tate Gallery, Selfridges and Channel 4, which is very much in Draper's sector. It, too, has been plagued with calls from journalists. Its director, Ben Weaver, is becoming increasingly irritated.
Farm, Covent Garden, is of a similar mould to Draper's Farm. It too is an outsourcing specialist, retaining a small staff and using a network of creatives based on client demand. Besides the names, the similarity between the two agencies will, say advertising sources, be where Draper's next battle lies.
"It is exactly the same premise as we are working under," complains Weaver. "It is causing confusion, and within days of the first press reports of Draper's new company we were inundated with calls from journalists and others wondering where he was. We have nothing to do with him, and wouldn't want to, either. We have worked exceedingly hard over the past two years to bring this type of agency into the market-place, and then suddenly up pops Draper saying he has a unique new idea which is not only the same as ours but has the same name."
Although he has registered his new agency at Companies House as Farm Communications Ltd, truncated references by Draper and others to his company as Farm may be legally unacceptable.
But, typically, the row, which is currently confined to letters and lunches and has not involved lawyers, has cut no ice with the ever-determined Draper. His partner, Paul Jeffrey, says: "We're not trying to pass ourselves off as these other companies. When we searched Companies House we found no trace of these other crowds. We are getting a lot of coverage and they are just being arsey about it. To be frank, they're a pain in the butt and to expect us to change our name is quite ridiculous."