The Pluto devil was first used by the Pluto Corporation of French Lick, IN in 1893. The company, at the time, sold Pluto mineral water for "medicinal purposes". The chip is probably from the turn of the century to about 1909.

The Anona Cigar was distributed by Y. Pendas and Alvarez. They had a shop on Pearl street (a couple of block from where I am right now) in NYC. The chip is from the same time period as the Pluto.

The word "Squeezers" was trademarked by NY Consolidated Card Co in 1906. It is assumed that the chip below is from that time period.

The Chauncey Olcott was distributed by W. Mulford & Son Cigar Company, Unadilla, NY. Chip is from 1926.