Cy Young, Walter Johnson, Don Larson, Robin Roberts, Steve Carlton, Phil Niekro, Denny McLain and Red Ruffing (among others). Here is a hint. The only pitcher to manage this feat in the new century is Mike Maroth of the 2003 Detroit Tigers.
What these pitchers have in common is a twenty-game losing season. Six of the above twenty-game losers have been enshrined in the baseball Hall of Fame, Johnson, Young, Carlton, Roberts, Ruffing and Niekro.
Maybe this dishonor is not as shameful as it seems. There have been more twenty-game winners than losers. In many cases, a pitcher has to be intrinsically good enough to be dispatched to the mound over and over again during a long losing campaign. In fact, some twenty-loss seasons were actually winning seasons. In 1979, Phil Niekro finished the year 21-20 for the Atlanta Braves who only won 69 times as a team. Wilbur Wood went 24-20 with the 1973 White Sox.
But Niekro and Wood aren't off the hook. Each of them had a second twenty-game losing season in which they lost more than they won.
Who lost the most games in a season? Going back to the year 1900, the honor belongs to Vic Willis of the 1905 Boston Beaneaters with a record of 12-29. If the name sounds vaguely familiar, that may be due to another distinction awarded to Mr. Willis. He was voted into the Hall of Fame by the Veterans Committee in 1995, based on his eight twenty-win campaigns.
One has to dive into the rich pool of nineteenth century hurlers to find a thirty-game loser. The last player to do so was Coldwater Jim Hughey with a sparkling record of 4-30 for the 1899 Cleveland Spiders. Thirty-plus game losers were fairly common in the late 1800's due to number of games pitched each season by individual players. During the 1870's and 1880's, many pitchers started sixty games or more.
Who was the biggest loser in baseball history? The envelope, please. The winner is John Coleman of the 1883 Philadelphia Quakers (Phillies). The Phillies managed in their first year of existence to set a record that has not been bested (or worsted?) since. Mr. Coleman pitched in 65 games and lost 48 of them. His record was 12-48. What's worse is that Coleman was Philadelphia's best pitcher, starting all but 32 of his teams contests.
A special award goes to Tricky Nichols who went 4-29 for New Haven in 1875. Try to imagine his record had he not been tricky.