This annotated week in baseball history: May 1-7, 1994

On May 6, 1994, Anthony Young won a game he started for the first time in more than two years. How does this dubious feat link him with Ike Pearson and Dolly Gray, to say nothing of Spud Chandler and Jon Lester? Read on to find out.

Perhaps because I was in New York, or perhaps because stories about low-level human suffering stand out, even though I was very young at the time, I remember hearing about Anthony Young. From May 6, 1992 through July 24, 1993, Young failed to win a single decision. In total, that left him 0-27 during the period. His failures as a starter went even longer, and it was not until May 6, 1994—almost 25 months after his last win as a starter—that he managed one.

Somewhat more improbably, Young was actually a fairly serviceable pitcher for most of the streak, albeit one suffering from horrible luck. In July and August of 1992, Young served as the Mets’ closer, going 0-1 (of course) but recording 11 saves with a 0.88 ERA. In 1993, he went 0-8 as a starter, but posted a perfectly respectable 3.52 ERA in that role.

(At Mets blog Amazin’ Avenue, they write that Young now coaches youth baseball in Houston “and in his leisure time hangs out under ladders with his collection of black cats.”)

Similar to the well-worn cliché that “you have to be a pretty good pitcher to lose 20 games,” it can therefore be said that you have to be a pretty good pitcher to lose 27 straight decisions.

Incredibly, despite his rotten luck when it came to finding a win, Young does not represent the all-time nadir—minimum 50 decisions—in winning percentage. In fact, he isn’t even the second-place man. The second-lowest winning percentage ever belongs to the memorably named Dolly Gray.

Pitching for the “First in War, First in Peace, Last in the American League-era” Washington Senators, Gray went a collective 15-51 over three seasons. That comes out to a .227 winning percentage, which is not altogether out of line with his career 75 ERA+.

In Gray’s (limited) defense, although his record was poor, had he not been stuck on such a truly terrible trio of teams—they went a collective 172-285 (.376) during his time there—it is unlikely his winning percentage would be so awful.

Of course, had he not been competing with the likes of Bob Groom (150 career losses) and Dixie Walker (career ERA+ of 83) to be one of the stooges behind Walter Johnson in Washington’s rotation, he might not have reached the needed 50 decisions.

Luckily for Gray, there is a player below even him in winning percentage. The unfortunate holder of that record is Ike Pearson, who pitched, on and off, in the majors from 1939 through 1948.

He pitched most of his career for the astonishingly awful Philadelphia Phillies of the early 1940s, a time that saw the Phillies perform so badly they attempted to rename themselves the Blue Jays in the hopes of making everyone forget about how awful they had been in the years prior. (It didn’t work.)

During his time in Philly, Pearson posted seasons of 2-13, 3-14 and 1-6. His best season in Shibe Park came in 1941, and he was still only 4-14! Of course, despite his all-time-worst winning percentage, Gray is not the pitcher most associated with losing when it comes to the Phillies of that era.

That distinction belongs Hugh Mulcahy, known as “Losing Pitcher” for his frequent accompaniment in the box score. This tells us you quite a lot about the Phillies of those years, who never lost fewer than 103 games while Pearson played there.

Of course, for every yin there must be a yang. (At least I think so. My Eastern philosophy is a little weak these days.) For all the not-so-great pitchers laboring on terrible teams with bad luck, there must be fine pitchers, on first-rate teams, with good luck. So it only seems fitting to look at those men—minimum 50 decisions—who have the highest winning percentages.

The man ranked third all-time in winning percentage is a Hall of Famer, Whitey Ford. There can be no doubt Ford benefited from the Yankee teams he played for, as his 22 World Series starts reflect. But The Chairman of the Board was no one’s idea of a slouch riding his team’s coattails. During his 16-year career, he led the league, at different times, in ERA, ERA+, complete games, shutouts and WHIP.

In second place is a man who—as I put the finishing touches on this column on Tuesday night—could see his winning percentage rise or fall, that being Boston’s Jon Lester. As of this writing, Lester’s winning percentage stands at .711. Like Ford, he has benefited from the work of his teammates—the Red Sox’s worst full season during his tenure was 86-76, and Lester went 7-2 that year.

Of course, he still has much of his career to go, but already having conquered lymphoma and pitching with the Red Sox might behind him, it seems likely Lester will be contending for the top spots on the winning percentage list for years to come.

Just ahead of Lester is another Yankee, Spud Chandler. Like Ford, Chandler saw strong Casey Stengel teams as the benefactor of his winning percentage. But also like Ford, Chandler earned his spot on the back of seasons like 1943, when he went 20-4 and led the league in wins, ERA, complete games, shutouts, WHIP and ERA+. For his efforts that season, Chandler won the American League MVP; he would go 2-0 with a 0.50 ERA in the Yankees’ 4-1 World Series victory over the St. Louis Cardinals for good measure.

The list of those pitchers with high winning percentages is largely full of names you would expect: Pedro Martinez and Christy Mathewson are in the top 25, as are active hurlers like Tim Lincecum and Josh Johnson. On the losing side are less notable names, ones that seem like they might be made up: Happy Townsend, Jim Walkup, Beany Jacobson. Yes, really, Beany.

But by virtue of reaching the 50-decision mark (and sometimes many more) these men established themselves as a cut above the truly terrible pitcher. Theirs is not a career any major leaguer would set out to have, but in baseball (as in life) someone has to be on the losing side.