The County Treasurer of New York at the Broadway Bank Checks, 1866

Paid: 10 Dollars for five.
Insurance Value: 300+ dollars, based on this.

From Scripophily the World's #1 Buyer and Seller of Original Stock and Bond Certificates:
"Beautifully engraved check from the County Treasurer of New York - National Broadway Bank issued in 1868. This historic document has an ornate border around it with a vignette of an old sailor, an indian, a ship and an eagle. The check is signed by the New York City Mayor John Thompson Hoffman (who later became Governor), City Comptroller Richard B. Connolly, and the Clerk J.P. Touny. John Thompson Hoffman ( 1828-1888) who also signed the check was Mayor of New York from 1866-1868 and Governor of New York (Elected Twice) from 1869-73. He joined the Tammany Society in 1859. As mayor of New York City and governor of New York the activities of Tweed Ring were at their height. His political future was ruined by conviction of Tweed, although there was never any proof he was involved."


The thing I like most about this check is the primitive security feature. It's a cross-hair pattern; it's very non discrete so I held it up to the light to help you see it.
Beautiful engraving indeed. Fine penmanship too. Everyone wrote in calligraphy back then.
I love that 5 people signed each one of these checks: the mayor, the clerk board supervisor, the comptroller, the county bookkeeper (that's him turned ninety degrees on the left side) AND the payee (on the back).