Phil Hellmuth held the title of youngest World Series of Poker’s Main Event champion for almost 20 years following his victory in 1989 at age 24.

But since the rise of online poker, there have been multiple champions in their early 20s who bettered that record.

Here are the youngest Main Event champions in history:

Joe Cada

The 2009 Main Event winner remains the youngest champion at 21 years, 11 months and 23 days old, a record that will be difficult to beat. The Michigan native defeated a field of 6,494 entrants to win more than $8.5 million.

Pius Heinz

The first German to win the Main Event, Heinz was 22 years, five months and 28 days old when he captured the bracelet in 2011, making him the second-youngest champion. His victory was worth more than $8.17 million.

Peter Eastgate

He ended Hellmuth’s 19-year run as the youngest winner by taking down the 2008 Main Event at age 22 for more than $9.15 million. The Dane enjoyed the record for one year before it was broken by Cada.

Jonathan Duhamel

The 2010 Main Event champion was 23 when he defeated John Racener heads-up. Duhamel owns three WSOP bracelets total, and the Canadian has more than $14 million in career WSOP earnings.

Ryan Riess

The Michigan State graduate rolled over the final table at the 2013 Main Event, defeating Jay Farber for the $8.36 million first prize. Riess was 23 at the time of his victory, about four months older than Duhamel.

Contact David Schoen at [email protected] or 702-387-5203. Follow @DavidSchoenLVRJ on Twitter.