Reacher Gilt was a con man who lives in Ankh-Morpork and was the antagonist of Moist von Lipwig in Going Postal. He was the Chairman of the Grand Trunk a company he stole from the Dearheart family. He very appropriately dressed in the manner of a retired pirate, and lived as such, with a cockatoo named Alphonse which had been taught to say the phrase "12 and a half percent" (that is, a single piece of eight). Little is known about him except that he threw the most incredible and extravagant parties; at one party a troll stripper was hired resulting three people jumping out of the windows despite the fact that troll strippers actually don more clothing instead of removing them. He was rich enough to purchase his own ancestors as well as the services of an Igor. Some say he owned a gold mine. Others say he was a pirate, though considering the fact that he practically dressed up as one, most may have dismissed it out of hand. In reality he was a con artist of legendary skill; something Moist instantly recognized being one himself. He partnered with Messrs Nutmeg, Greenyham, Horsefry and Stowley to steal the Grand Trunk from the Dearhearts via a method called the "Double Lever"; purchasing the company with its own money. While head of the Grand Trunk, Gilt had his office in the Tump Tower (an obvious pun on Trump Tower), though as with everything that is "gilt", that was mainly for show.
Concerned only with making money, he started mismanaging the clacks, running them to the point of breaking, removing the dedicated maintenance period, sacking staff and making them dangerous to work on. This led to clacks breaking down on a regular basis, staff frequently dying on the job (1 death per 3 clacks towards the end) and a rise in prices for poorer quality. Had the Trunk failed and gone bankrupt, Gilt was the kind of person who would have sold off his assets in the company long before the bankruptcy and, through another shell company, re-bought them at rock bottom prices to proceed to run it into the ground once more.
Gilt, and his partners Greenyham, Horsefry and Stowley happily make money on the Grand Trunk until the resurrection of the Ankh-Morpork Post Office by Moist von Lipwig through the machinations of Lord Vetinari.
While both were at heart con artists, Gilt differed from Moist in being utterly ruthless and willing to resort to murder. Any obstacle tended to be removed, courtesy of a Mr Gryle, an inhumanly efficient killer who is a banshee. Gilt disposes of his rival, Adora Dearheart's brother when he attempts to start a rival Clack company, gets rid of his partner Mr. Horsefry when he begins to get cold feet and tries to kill Moist to stop the Post Office's resurrection. Gilt was a proud person and the constant humiliations he suffered at the hands of Moist eventually led him to become sloppy. Infuriated by Moist's jibes, he failed to anticipate Moist's plan and was caught in a trap when Moist revealed how he had taken over the Grand Trunk. He fled and assumed a new identity and changed his appearance after being exposed but was recaptured by Mr. Pump, the Golem probation officer who was relieved on his duty to watch Moist. When brought before the Patrician, he was offered the job of re-structuring the Royal Mint, which came with a salary, and some kind of hat an offer similar to the one Moist was offered at the Post Office. Like Moist, he was also freely given the choice to decline and walk out of the office. He declined, and it is inferred he walked out of the door with the treacherous first step, the second step many stories below. While he wasn't a believer in angels, he was a firm believer in (his) personal freedom, to the extent that he might well have been aware of the terminal consequences of his choice, but was determined to be the one to make the choice. Equally he may simply have not taken the precaution that Moist had done, and looked before he leaped.
Pratchett says, "Reacher Gilt certainly looked like a pirate, with his long, curly black hair, pointed beard, and eyepatch. He was even said to have a parrot." – The name "Reacher Gilt" is itself a pun on "Long John Silver" the pirate captain from Robert Louis Stevenson's novel Treasure Island, as in 'silver' and 'gold' (gilt). A 'reacher' is a type of foresail on a sailing vessel as well as a tool for helping disabled people (like Long John Silver with his wooden leg) reach something. It also connotes someone reaching to take everything that he can possible get, especially money (money grubber). Gilt's name, appearance and libertarian-capitalist ideology has stronger resonances with Ayn Rand's charismatic capitalist hero John Galt and pirate Ragnar Danneskjold, from Atlas Shrugged. The reference to him throwing lavish parties suggests The Great Gatsby by F Scott Fitzgerald. There may also be links and distant echoes to the plot and characters of Shea and Wilson's Illuminatus! trilogy which is also in this context and is a work of satire parodying Ayn Rand's right-wing libertarian and extreme free-market philosophy. In this book, a "book within a book" is a parody of Ayn Rand's polemic, called Telemachus Sneezed. Roundworld parallels might include English billionaire playboy-investor Richard Branson.