Winning a Cy Young is basically like being knighted in the baseball world. It’s the highest honor a pitcher can get, named after Denton True "Cy" Young, a guy who won 511 games back when players were essentially built out of leather and grit. But here is the thing: the list of Cy Young award winners isn't just a collection of the best stats. It is a messy, evolving history of how we think about pitching.
Honestly, if you look at the 2025 results, you see how much things have changed. Tarik Skubal of the Detroit Tigers just went back-to-back, joining a super exclusive club of 12 pitchers who have ever repeated. Meanwhile, over in the National League, Paul Skenes—the kid everyone was obsessed with at LSU—unanimously snagged the award in just his second year.
It's wild. Skenes is only the third pitcher ever to pull off the Rookie of the Year and Cy Young combo within his first two seasons, following legends like Fernando Valenzuela and Dwight Gooden.
Why the Voting Is Often Controversial
People love to argue about this. For a long time, the BBWAA (Baseball Writers' Association of America) was obsessed with wins. If you won 20 games, you were basically a lock. But then 2010 happened. Felix Hernandez won the AL Cy Young with a 13-12 record. 13 wins!
Traditionalists lost their minds. "King Felix" had a 2.27 ERA and led the league in innings, but the "wins matter" crowd couldn't get over his team being terrible. That year changed everything. It shifted the focus toward ERA, WHIP, and eventually advanced metrics like FIP (Fielding Independent Pitching) and WAR (Wins Above Replacement).
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"The Cy Young Award represents the pinnacle of pitching achievement in baseball," says Robert J. Wood, PhD. He's right, but that pinnacle looks different every decade.
The Era of the Reliever
Can a relief pitcher win? Yes, but it is rare. It hasn't happened in over 20 years. The last one was Eric Gagné in 2003, who was basically a cheat code for the Dodgers. Before him, you had guys like Dennis Eckersley in 1992 and Rollie Fingers in 1981.
Usually, for a reliever to win, the starters in that league have to "falter." That doesn't mean they were bad; it just means nobody stood out as a dominant "ace." In 2025, we saw Aroldis Chapman and Edwin Díaz dominate the "Reliever of the Year" categories, but they weren't even in the conversation for the Cy Young. That's just how the game is played now.
The All-Time Legends
If we're talking about the GOATs of this award, you have to start with Roger Clemens. He has seven. Seven! He won them with the Red Sox, Blue Jays, Yankees, and Astros. It’s a record that might never be touched.
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Then you have the "Big Unit," Randy Johnson. Between 1999 and 2002, he won four in a row. He was a 6-foot-10 lefty throwing 100 mph with a slider that made professional hitters look like they’d never held a bat before.
Pitchers with the most Cy Young Awards
- Roger Clemens: 7 (1986, 1987, 1991, 1997, 1998, 2001, 2004)
- Randy Johnson: 5 (1995, 1999, 2000, 2001, 2002)
- Steve Carlton: 4 (1972, 1977, 1980, 1982)
- Greg Maddux: 4 (1992, 1993, 1994, 1995)
- Clayton Kershaw: 3 (2011, 2013, 2014)
- Max Scherzer: 3 (2013, 2016, 2017)
Sandy Koufax also has three, and he did it back when there was only one award for both leagues. Think about that. He wasn't just the best in the National League; he was the best in the world.
The "Year of the Pitcher" and Rule Changes
In 1968, Bob Gibson posted a 1.12 ERA. It was so dominant that MLB actually lowered the pitcher's mound the next year because hitters were completely helpless. Gibson won the NL Cy Young that year, obviously.
Another weird quirk? Until 1967, there was only one winner. Period. Commissioner Ford Frick thought one was enough, but once he retired, they split it into the American League and National League.
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In 1969, we even had a tie! Denny McLain and Mike Cuellar both got 10 votes. After that, they changed the system to a "weighted" ballot. Now, writers pick a top five, which is why we don't see ties anymore.
What to Look for Next
If you're trying to predict the next wave of Cy Young award winners, stop looking at the win-loss column. It's almost irrelevant now.
Look at Strikeout-to-Walk ratio (K/BB). Look at WHIP (Walks + Hits per Innings Pitched). In 2025, Tarik Skubal’s WHIP was a ridiculous 0.89. That is how you win awards in the modern era. You basically have to be perfect.
To really understand the elite level of these pitchers, you should check out the advanced splits on sites like Baseball-Reference or FanGraphs. Focus on "ERA+"—it compares a pitcher to the rest of the league while accounting for their home ballpark. A 150 ERA+ means the pitcher was 50% better than the average. Pedro Martinez’s 2000 season had an ERA+ of 291. That might be the single greatest pitching season in the history of the sport.
Keep an eye on young guys like Paul Skenes and Yoshinobu Yamamoto. The game is getting faster, and the "stuff" these guys are throwing is harder than anything Cy Young himself could have imagined.
Track the "Pitching Triple Crown" (leading the league in Wins, Strikeouts, and ERA) during the mid-season. While "Wins" are fading in importance for the award, a Triple Crown winner almost always secures the trophy, as Skubal did in 2024.