Green’s Dictionary of Slang

(UK Und.) a senior criminal beggar, outranked, if at all, only by the ruffler n.. Such a villain held absolute power, demanding and receiving both cash and kind, including their women, from his inferiors and beating them without fear of revenge.

c.1561		Awdeley Fraternitye of Vacabondes in Viles & Furnivall (1907) 4: An Vpright man is one that goeth wyth the trunchion of a staffe, which staffe they cal a Filtchman. This man is of so much authority, that meeting with any of his profession, he may cal them to accompt, & commaund a share or snap vnto him selfe, of al that they haue gained by their trade in one moneth. And if he doo them wrong, they hane no remedy agaynst hym, no though he beate them, as he vseth commonly to do. He may also commaund any of their women, which they cal Doxies, to serue his turne. He hath ye chiefe place at any market walke, & other assembles, & is not of any to be controled.
1592		Groundworke of Conny-catching Ch. 19: A walking Mort. [...] when these get ought, either with begging bychery or bribery, as money or apparrell, they are quickly shaken out of all by the upright man.
1608		Dekker Belman’s Second Nights Walk B3: They take vpon them the names of Kinchin Coes, till they are growne Rufflers, or Vpright-men.
1610		Rowlands Martin Mark-all 7: One complaines that he could not trauell safely, nor cary any money without danger of the vpright man and Tinker, but that they would robbe and spoyle them of all.
1641		R. Brome Jovial Crew II i: Sir, if you are [...] Dispos’d to Doxie, or a Dell, / That never yet with Man did Mell; / Of whom no Upright man is taster.
1669		W. Winstanley New Help To Discourse 131: The Upright-man is the Chief or Prince of the rest, who commonly walks with a short Truncheon in his hand, which he cals his Filchman, he claims a share of whatsoever is gotten by any others, and can command any of their Morts or Doxies to leave another man, and to lie with him.
1674		Head Canting Academy (2nd edn) 35: When this Upright Man dyed (which was seldome otherwise than on the Gallows,) then all of this cursed Fraternity [...] chose the lustiest stoutest Rogue in the whole pack, to be their chief Leader, whom they called Upright Man.
1688		R. Holme Academy of Armory Ch. iii item 68b: Give me leave to give you the names (as in their Canting Language they call themselves) of all (or most of such) as follow the Vagabond Trade, according to their Regiments or Divisions, as [...] Upright Men, the same as Ruffelers.
c.1698		B.E. Dict. Canting Crew n.p.: Upright-men c. the second Rank of the Canting Tribes, having sole right to the first night’s Lodging with the Dells.
1707		J. Shirley Triumph of Wit 182: The Upright Man, who being chosen for his Strength, Archness, and Policy in bringing them off at a dead Lift, is stiled their Chief, whom all the rest obey, and amongst them his Will is a Law during Life, unless he be deposed in a General Assembly or Meeting, which is held twice a Year in great state in Places pre-appointed, and most commonly in the Suburbs of London.
1725		‘When My Dimber Dell I Courted’ in Farmer Musa Pedestris (1896) 49: Nor could th’ uprightman live without her, / She triumph’d over every one.
1725		New Canting Dict. n.p.: upright-men the First Rank of the Canting Tribes; As an Upright-man, signifies the Chief or Principal of a Crew. The vilest stoutest Rogue in the Pack, is generally chosen to this Post, and he has the sole Right to the first Night’s Lodging with the Dells, who afterwards are used in common among the whole Fraternity. He carries a short Truncheon in his Hand, which he calls his Filchman, and has a larger Share than ordinary of whatsoever is gotten in the Society. He often travels in Company with 30 or 40 Males and Females, Abram-men, and others, over whom he presides arbitrarily.
1737, 1759, 1760, 1776		Bailey Universal Etym. Eng. Dict. [as cit. 1725].
1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue n.p.: Upright man, the chief or principal of a crew.
1815		(con. 18C) W. Scott Guy Mannering (1999) 148: There was not one, from Johnnie Faa the upright man, of the gang to little Christie that was in the panniers, would cloyed a dud from them.
1828		Sussex Advertiser 14 Apr. 4/3: [We] soon passed a long string of gaggers, priggers, Adam Tylers, fancy coves, autum [sic] morts, gammoners, sweetners, uprightmen, bully huffs, lully priggers, star gazers, and coves of all sorts.
1834		(con. 1737–9) W.H. Ainsworth Rookwood (1857) 162: The upright man, the chief of the crew, arose from his chair, donned his gown of state.
1895		Crowe Aus. Sl. Dict. 91: Upright Man, the head of a gang of thieves.
1906		Minneapolis Jrnl (MN) 24 Jan. 19/3: Yes, gents, I’m a dimber-damber upright man.