Ryan Dempster
A durable and witty Canadian starting pitcher who anchored rotations for two World Series champions a decade apart.
Born 1977 (age 49)·Canadian baseball player·Birthday: May 3·Generation X
Biography
Ryan Dempster's career was a study in reinvention and resilience. Breaking in as a hard-throwing but wild closer for the Florida Marlins, he saved games for their 2003 World Series winner. His career then hit a trough, with control issues threatening to derail it entirely. Dempster's pivotal move came with the Chicago Cubs, where he was converted into a starter—a gamble that yielded an All-Star season in 2008. He became the reliable, innings-eating anchor of the Cubs' rotation for five years, known for his sharp slider and veteran guile. In a storybook twist, he was traded back to the American League in 2012 and, returning to a relief role, became a key setup man for the Boston Red Sox' 2013 championship. Off the mound, Dempster was a beloved clubhouse presence, famed for his pranks and impressions. His journey from flamethrowing closer to crafty ace and back to playoff-tested reliever showcased a rare baseball intellect and adaptability.
Generation X
1965–1980
The latchkey kids. Raised during divorce, recession, and the end of the Cold War. Skeptical, self-reliant, media-literate. They invented indie culture, grunge, and the early internet — then watched the Boomers take credit.
Ryan was born in 1977, placing them squarely in the Generation X. The events that shaped this generation — economic uncertainty, the end of the Cold War, and the rise of personal computing — shaped the world they entered and the choices available to them.
#1 When Ryan Was Born
The biggest hits of 1977
#1 Movie
Star Wars
Best Picture
Annie Hall
#1 TV Show
Happy Days
Ryan's Life & Times
The world at every milestone
1977Born
Star Wars premieres; Elvis dies
Gas: $0.62/galHome: $31,800Min wage: $2.30/hrPresident: Jimmy Carter"Tonight's the Night" — Rod StewartBest Picture: Annie Hall
1982Started school
Michael Jackson releases Thriller
Gas: $1.22/galHome: $55,200Min wage: $3.35/hrPresident: Ronald Reagan"Physical" — Olivia Newton-JohnBest Picture: Gandhi
1990Became a teenager
Hubble Space Telescope launched; Germany reunifies
Gas: $1.15/galHome: $79,100Min wage: $3.80/hrPresident: George H.W. Bush"Hold On" — Wilson PhillipsBest Picture: Dances with Wolves
1993Could drive
European Union officially established
Gas: $1.11/galHome: $86,600Min wage: $4.25/hrPresident: Bill Clinton"I Will Always Love You" — Whitney HoustonBest Picture: Schindler's List
1995Could vote
Oklahoma City bombing; Windows 95 released
Gas: $1.15/galHome: $96,500Min wage: $4.25/hrPresident: Bill Clinton"Gangsta's Paradise" — CoolioBest Picture: Braveheart
1998Turned 21
Google founded; Clinton impeachment
Gas: $1.06/galHome: $107,300Min wage: $5.15/hrPresident: Bill Clinton"Too Close" — NextBest Picture: Shakespeare in Love
2007Turned 30
iPhone released; Great Recession begins
Gas: $2.80/galHome: $172,600Min wage: $5.85/hrPresident: George W. Bush"Irreplaceable" — BeyonceBest Picture: No Country for Old Men
2017Turned 40
#MeToo movement; solar eclipse crosses the US
Gas: $2.42/galHome: $195,000Min wage: $7.25/hrPresident: Donald Trump"Shape of You" — Ed SheeranBest Picture: The Shape of Water
2026Age 49 today
Gas: $3.91/galPresident: Donald Trump
Key Achievements
- Won a World Series as a closer with the Florida Marlins in 2003 and as a reliever with the Boston Red Sox in 2013.
- Selected as a National League All-Star in 2008 after transitioning successfully to a starting role with the Chicago Cubs.
- Pitched over 200 innings in four consecutive seasons (2008-2011) as a workhorse starter.
- Recorded 87 saves as a closer for the Marlins and Cincinnati Reds early in his career.
- Won a Gold Glove award in 2013 for his defensive excellence as a pitcher.
Did You Know?
He is a member of the Canadian Baseball Hall of Fame.
Dempster is an accomplished impressionist, famously impersonating Harry Caray and other broadcasters for teammates.
He hosted "The Offseason with Ryan Dempster," a comedic baseball talk show on MLB Network.
He pitched for Team Canada in the inaugural 2006 World Baseball Classic.
After retirement, he worked in the Chicago Cubs front office as a special assistant.
“I've been a starter, I've been a closer. I've just never been a hitter, thankfully.”
