Intriguing group lot relating to then-New York Police Commissioner Teddy Roosevelt (1894-1896) and Inspector William F. Boettler. Lot consists of six items, including: Mr. Theodore Roosevelt’s imprinted business card, trimmed to 2.75 x 1.5, with the following ALS written on the card in pencil, in Roosevelt’s hand: “This is to introduce to whom it may concern, Roundsman W.F. Boettler, whom I appointed on the police force and who has just been assigned as Roundsman as reward for special gallantry in stopping a runaway team. T. Roosevelt”; a metal I.D. policeman’s medallion, approximately .75 x 1.5, with the engraved “Wm. F. Boettler, 27 Police Pct. New York, 321” on the wing of an eagle on the obverse, and “One dollar reward” on the reverse; a lieutenant’s tribute medal or coin, dark chocolate patina, 1.25” diameter, with Roosevelt’s profile on the obverse; a large, color Memorial card, 5 x 8, laminated, with the Twenty-Third Psalm on one side, and the New York Times obituary for William F. Boettler on the other. The obituary reads, in part: “Dead at 90; Police Inspector of Bygone Era. Remarkable record…In 1899 he stopped a runaway horse and was decorate and promoted…at the appointment as inspector in 1909, he was the youngest man on the force who had ever attained that rank…” An original program for the Memorial Service to Bro. Theodore Roosevelt under The Lodges of the Sixth Masonic District of New Jersey, February 9, 1919, 6.5 x 5, six pages, with a tipped-in portrait of Roosevelt; an original issue of Spring 3100, the Policeman’s Magazine for the NYC police department, October 1958, 7 x 9.5, 48 pages, which lists on page 19 the surviving “Teddy Boys” 19th Century Rough Riders, listing William. F. Boettler. In overall fine condition, with loose cover and pages to the magazine, chipped edges to Roosevelt’s Memorial Program cover. COA John Reznikoff/PSA/DNA and R&R COA.