A native of Buffalo, New York, Speicher, studied at the Art Students League in New York in 1907 and spent his summers in Woodstock studying landscape painting under Birge Harrison. Through his friend, George Bellows, he was brought to Robert Henri's evening classes in New York. Soon after, Speicher was able to support himself with portrait commissions and became quite successful. Speicher, however, opted not to continue in this vein but instead, like his teacher Henri, produced non-commissioned portraits of people whom he found fascinating.

Speicher chose local Woodstock residents such as Maureen and Red Moore (lot 28), and created portraits composed of strong forms with simplified modeling of contrasting light and dark. This technique not only drew the sitter abrublty infront of the viewer but simultaneously unveiled psychological and emotional characteristics. Speicher was also influenced by the Woodstock modernists and employed certain techniques such as flattened spatial construction in his works. Allusions to these progressive elements can be seen in Maureen's spotted blouse which is void of dimension.