Recent news that the U.S. Treasury Department is considering replacing Alexander Hamilton’s image on the $10 bill with that of a notable American woman has ignited some discussion about the famous men on our money, particularly this controversial seventh President. Jackson, remembered both as a man of the people and the man responsible for the Trail of Tears, has long held the coveted spot on the $20, one of the most commonly circulated bills—but he hasn’t always held that place of honor. In fact, Jackson’s face has only graced twenties since the 1920s; prior to that, Old Hickory had his humble beginnings on the $10 bill.

National Museum of American History via Wikimedia Commons

The first-ever run of Federal Reserve notes didn’t come out until 1914, when Jackson’s portrait featured prominently on the $10, with Grover Cleveland holding pride of place on the $20. In 1928, federal money went through a design do-over; Cleveland ascended to the space vacated by Alexander Hamilton on the $1000 bill—which astute readers will realize is no longer in circulation—while Jackson settled into his now-familiar place on the $20, with Hamilton demoted to the $10. Why the dramatic reshuffling of Presidents? Not even the Treasury Department itself seems to remember, claiming that their absence of documentation on the subject means, “It’s a mystery to us as well.”

The great irony of Jackson’s visage prominently featuring on a banknote is, of course, that he disdained paper money, preferring the tangible value of gold and silver—it’s debatable whether Jackson would consider his commemoration on the $20 bill any sort of honor at all.