General Discussion

The faces on bills are Washington, Jefferson, Lincoln, Hamilton, Jackson, Grant, and Franklin - five presidents and two founding fathers. I'm sure Trump thinks he's in the same class of Great Men (I wouldn't call racist Jackson great, but that's another story). The $500, $1,000, $5,000, $10,000, and $100,000 bills feature pictures of McKinley, Cleveland, Madison, Salmon Chase (Treasury secretary), and Woodrow Wilson. The $100,000 never circulated at all.

The Treasury stopped printing the larger notes in 1945, but most continued to circulate until 1969 when The Federal Reserve began destroying those that were received by banks. The few that still exist are legal to spend but are so rare that they are worth more than their face value to collectors. Apparently there never has been a $250 bill, and why should there be one at all? It's a weird denomination, but it puts Himself between Franklin and McKinley, and is more likely to be circulated than anything larger, though perhaps only as a MAGA collector's item which will never be worth more than its face value.

Also, it's illegal to print money with the face of a live person. McKinley got the privilege of being on the $500 bill by becoming dead in a rapid unscheduled disassembly caused by one Leon Czolgosz, so maybe he's not the best act to try to follow, all things considered. But if the bill is ever issued and I can get my hands on one, I will definitely draw horns and a mustache on it with a Sharpie.