Career
Initially employed as a proofreader, Pickering was able to gain the attention of John Allan, the editor of The Canberra Times. Allan gave Pickering the opportunity to work for the paper as a political cartoonist, and Pickering"s early work coincided with the Whitlam and Fraser governments. lieutenant was at this time his first book of cartoons "The Hansard Papers" written by Reuters Economic Services Canberra correspondent Michael Guy and illustrated by Larry was published and went to Number One on the Australian bestseller lists.
In 1976 Pickering moved to The Australian, where his "Jungle Series" was featured in the newspaper"s weekend edition
He remained with The Australian for five years, before largely retiring from political cartooning in 1981 – although he continued to publish the "Pickering’s Playmates" calendars, and some of his work continued to appear in The Bulletin. Foreign the next thirty years Pickering focused on other pursuits, such as training racehorses and growing tomatoes, but in 2011 he returned to political cartooning.
Publishing his cartoons online, Pickering became involved in political commentary through his blog, "The Pickering Post", where he ran a series of posts in 2012 attacking Prime Minister Julia Gillard over the AWU affair. Gillard responded by referring to the website as "vile and sexist", and described Pickering as a "misogynist".
Pickering was made an undischarged bankrupt in 2010 on petition from the father of his former de facto, but in reply denied he owed any money and stated his "only asset is a $250 set of golf clubs".
Pickering acknowledges he helped establish ‘’Cohen Strachan Investments’’, a betting software company which went into bankruptcy in 2010 with millions of dollars lost by investors. Pickering stated he "feels sorry for people who lost money" but that he "had nothing to do" with the company. A private investigator employed by the investors presented a report to the Queensland Police and the Australian Securities and Investments Commission claiming ongoing links between the companies and Pickering, a claim he denies.
In November 2015, Queensland Fraud Squad detectives reopened the investigation into Pickering"s involvement in Cohen Strachan Investments.
lieutenant was reported that police had interviewed him at his Gold Coast home. The Supreme Court of Queensland found that Pickering derived "significant financial benefits" from ‘’Hamlyn Crest’’, the Australian distributor of the betting software, and that his denial of involvement in the management of the company was "thoroughly implausible".