#14: Gloria C. MacKenzie
Prize Money: $590.5 million
Gloria C. MacKenzie was 84 when she won the $590.5 million Powerball jackpot in Florida in 2013. A widow from Zephyrhills, she bought the ticket at a Publix supermarket after another customer reportedly let her go ahead in line. At the time, it was the largest single-ticket lottery jackpot in U.S. history.

MacKenzie chose the lump-sum option, which was about $370.9 million before taxes. She later made major donations, including a large gift connected to education in Maine, but her fortune also led to legal disputes over financial management. Her story became a reminder that even historic wealth can bring complicated decisions.
