Cy Young Award Winners
With victories by Greg Maddux (1992) and Jake Arrieta (2015), the Cubs have etched two names into Cy Young history, turning a once-elusive dream into a celebrated reality.
The Cy Young Award stands as baseball's crown jewel for pitchers, a singular honor recognizing the absolute best on the mound each season. Born in 1956 with one winner for all of MLB, it split into separate National and American League trophies in 1967 to better honor excellence across both leagues. For the Chicago Cubs—a franchise steeped in pitching lore from the dead-ball era to the modern age—this trophy represents a rare but celebrated summit of mound dominance. While the North Siders' history with this specific award is marked by scarcity, two legendary arms have managed to lift the hardware while wearing the pinstripes.
- Award Name
- Cy Young Award
- League Affiliation
- Major League Baseball (National & American Leagues)
- Cubs Winners
- 2
- Winners List
- Greg Maddux (1992), Jake Arrieta (2015)
- First Award Year
- 1956
- Selection Body
- Baseball Writers' Association of America (BBWAA)
- Status
- Active Annual Honor
Lore & Background
The Cubs' quest for the Cy Young finally culminated in two historic victories, breaking a long-standing drought. The first breakthrough came in 1992 with Greg Maddux, who secured the National League award while anchoring the Cubs' rotation before his legendary run with Atlanta began. Decades later, the franchise added to its mantle when Jake Arrieta dominated the league in 2015, becoming only the second Cub to claim the honor. These two triumphs stand as testaments to elite pitching excellence within Chicago, proving that while rare, the Cubs' mound dominance has indeed been recognized at the highest level.
In Their Own Story
The wind whipped off Lake Michigan, biting at the exposed skin of an October evening at Wrigley Field. In the bleachers, a lone fan clutched a faded program from 1972, the paper soft with age. He remembered the roar that shook the brick walls when Fergie Jenkins struck out his thousandth batter—a moment where the collective hope of Chicago seemed to crystallize into certainty that *this* was the year he would be crowned king. The scoreboard flashed stats so undeniable they felt majestic, yet deep in the front office, the trophy case remained stubbornly empty of that specific gold-plated honor. He smiled sadly, a bittersweet expression known well by Cubs fans: while the team had legends who could stop time with a curveball or silence a crowd with a slider, the Cy Young Award seemed to slip through their fingers like sand, always just out of reach.
Reader's Guide
Introduced in 1956 to honor Major League Baseball's most outstanding pitcher, the Cy Young Award has eluded the Chicago Cubs for over six decades. This zero-winner record is particularly striking given that Cubs pitching staffs have frequently led the National League in ERA and strikeouts during championship-contending years. The narrative of this drought is defined not by a lack of talent, but by historic near-misses: Fergie Jenkins finished second in voting twice while with Chicago, and more recently, Kyle Hendricks garnered significant attention without securing the trophy. Voted on by the Baseball Writers' Association of America (BBWAA) based on regular-season performance, the award highlights the razor-thin margins of the sport; a single injury, a trade deadline departure, or a rival's once-in-a-generation season can sever the path to glory. For Cubs fans, this history represents a unique blend of frustration and enduring respect for pitchers who performed at an elite level even if the hardware never arrived.
Did You Know?
- Greg Maddux won his first Cy Young Award in 1992 while playing for the Chicago Cubs, just one year before beginning his historic four-year streak with Atlanta.
- Jake Arrieta became the second and most recent Cubs pitcher to win the award, capturing the National League honor in 2015 after a dominant season that included a no-hitter.
- Fergie Jenkins remains the only other Cubs pitcher to finish as a runner-up for the Cy Young Award twice (1967, 1968).
- Despite boasting multiple Hall of Fame pitchers in their history over a century-plus existence, the Cubs have produced exactly two Cy Young winners.