Born in Wuerttenberg on March 3, 1890, Otto Esswein started his military career with the ground forces before transferring to aviation in 1915. Assigned to Jagdstaffel 26, one of Imperial Germany's "hunting groups", in 1917, Esswein scored twelve confirmed kills to become a "double ace", also receiving the Iron Cross and Military Order of Merit in the process. In July of 1918 he successfully parachuted out of a burning aircraft, only to meet his end in another burning plane 5 days later on July 21. Measuring 3 3/4 inches wide and 7 3/4 inches tall, the goblet is of hammered silver construction, prominently featuring a design of two eagles fighting over the inscription "Otto Esswein/15.11.1917/Jasta 26", November 15 being the date of his first confirmed kill and "Jasta" being short for "Jagdstaffel". At the bottom are a set of 4 ball legs, with "Dem Sieger im Luftkampft" (The Victor in Air Combat) around the base, and a small silver disc marked "CHEF DES FELDFLUGWESENS" (Chief of the Field Air Forces) on the underside. Included with the goblet is some research material provided by the consignor and a set of 9 World War I-vintage photographs, including pictures of German military men (none explicitly identified as Esswein) and aerial photographs of the countryside and battlefields.

Very fine, with a deep well aged patina on the silver and a few minor handling marks overall. The photographs show mild foxing and ageing.