The $10,000 Bill
Let's talk about the highest denomination banknote that circulated publicly in the US. The first $10,000 bills were issued in the 1870s. Most notes were Gold Certificates and were used in bank transfers, overseas settlements, and payment of export/import duties. However, some notes were held privately and used as stores of value or, in the days before checks or credit cards, were used in high-value transactions like the purchase of land.
Since 1928, the $10000 note has had the portrait of Salmon P. Chase who was Secretary of the Treasury in the Abraham Lincoln administration. Chase would resign in 1864 over a patronage dispute with Lincoln, perhaps with an eye to run against Lincoln in the Presidential election of that year. Lincoln parried Chase by appointing him Chief Justice of the Supreme Court.
The last $10000 bills were printed in 1945, and issuance ceased in 1969. This happened because the Fed believed that cash was on its way out. People, they believed, would just write checks and use credit cards by the 1970s. Also, the Fed did not want to pay to have a new set of plates engraved for these notes. The argument was also put forward that only criminals used high-denomination notes. However, there was no evidence to support this position.