Ryan Dempster Net Worth: Ryan Dempster is a $50 million net worth Canadian retired professional baseball player. Ryan Dempster was born in May 1977 in Gibsons, British Columbia, Canada. He was a right-handed pitcher who batted and threw. As a baseball player, he was a part of the Chicago Cubs team that won the World Series in 7 games in 2016. After his career as a baseball player, Dempster started a sports management company. He played college ball for the University of Washington from 1995 to 1999, where he led the Huskies to the National Championship in 1998. In 2000, he was drafted by the Cubs with their first pick (number one overall) in the draft. That year, he made his debut against the San Diego Padres, getting knocked out early after giving up four runs in only two innings. He had another poor season in 2001, finishing with a 5.14 ERA. However, in 2002, he had a better season, going 17-6 with a 3.38 ERA. He continued to improve each year, reaching 200 innings pitched for the first time in 2005 and winning 20 games twice more (2006, 2007). After several trade rumors in 2008, Dempster finally decided to leave Chicago during Spring Training. He signed with the Texas Rangers, but was traded at the end of March to the Boston Red Sox.