4. Theodore Roosevelt
Net worth:
$125 million
Teddy was a sickly asthmatic who compensated by embracing a rugged, naturalist lifestyle, and is now considered one of our more "manly" Presidents. After President McKinley was assassinated, then-V.P. Roosevelt became the youngest U.S. President in history.
How he made his riches
Roosevelt was born into a wealthy New York family. His father was a glass businessman, and his mother a wealthy Socialite. His mother is widely believed to be the inspiration for Scarlett O'Hara in Gone With The Wind. They were the "Knickerbocker Elite" - the wealthiest of the wealthy New York Dutch families.