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Pinstripe Alley Top 100 Yankees: #77 Ray Caldwell

The fun-loving, peculiar righty had a whirlwind tenure with a crumbling Yankees organization.

Ray Caldwell
George Grantham Bain/Library of Congress (public domain)

Name: Raymond Benjamin Caldwell
Position: Starting pitcher
Born: April 26, 1888 (Corydon, PA)
Died: August 17, 1967 (Salamanca, NY)
Yankee Years: 1910-18
Primary number: N/A
Yankee statistics: 96-99, 3.00 ERA, 2.95 FIP, 248 G, 196 GS, 1,718 IP, 803 K, 150 CG, 17 SHO, 99 ERA-, 98 FIP-, 29.0 rWAR, 19.2 fWAR


Ray Caldwell was an exceptionally talented man with a proclivity for chaos. His baseball career was marred by a lack of punctuality and extreme unpredictability, but he made his mark on a forgotten era of Yankee history anyway.

Dissent in Highlander-Land

Caldwell grew up with divorced parents, uncommon at the time. His spindly six-foot-two frame earned him the nickname “Slim.” Remarkably, Ray didn’t pick up a baseball until age 20. Two years later, he was pitching for the New York Highlanders.

Caldwell’s express path to a major-league mound took him through several minor-league stops, starting with semi-pro teams in Western Pennsylvania, where he immediately drew interest from MLB scouts observing the lower-level circuit. He impressed manager Duke Servatius of the Class C Ohio-Pennsylvania League’s McKeesport Tubers in an All-Star exhibition, so he joined them in 1910. Soon after, scouting director Arthur Irwin of the New York Americans took a liking to Caldwell and offered him $1,500 to join the team in September of 1910 (the equivalent of $46,000 today). Not too shabby for a guy who’d been in organized baseball for under three full seasons.

The Americans/Highlanders/Yankees were in the midst of a bitter managerial Game of Thrones maneuver when Caldwell entered the fray. Manager George Stallings, modestly successful, was forced out by first baseman Hal Chase in a coup that ended with Chase holding the managerial spot in addition to being the star player. According to baseball historian Bill James, Stallings actually pioneered the long-standing and still-ubiquitous practice of platoon advantages, changing his lineup to mostly righties when facing a left-handed starting pitcher. He had the team playing well coming off an awful 1909, but Chase got his way* to the detriment of the team in the long run.

*Stallings got the last laugh, as he moved on to the Boston Braves and skippered them to a shocking World Series victory in 1914.

Caldwell arrived in the fresh aftermath of the change with a few games left in 1910. The ascending rookie was thrown into the fire and held his own in his first MLB action with a 3.72 ERA in six games, mostly in relief. He ended the season on a strong note and earned his first victory by spinning a complete game against the Red Sox in the season’s final game, putting Highlanders fans on notice of his immense potential. New York finished in a distant second to the powerhouse Philadelphia Athletics that year, and 1911’s monumental task was bridging that gap. Under the dysfunctional leadership of the Shakespearean-nicknamed “Prince Hal” and the shadowy presence of gambling burgeoning on the team, that didn’t happen, and the Highlanders finished with a .500 record.

In a difficult first full season at the highest level, Caldwell found a way, as he always did, to prosper through the chaos. He stayed healthy and posted 256 innings in 1911 as the number two behind the ace Russ Ford, maintaining a 3.35 ERA and racking up 5.4 WAR on his way to establishing himself as a long-term presence for the Highlanders.

Ray Caldwell, N.Y. A.L

When 1912 rolled around, Chase quit, replaced by Harry Wolverton, and things did not go well. The Highlanders went 50-102. Wolverton himself played in 35 games, of which the team lost 32. Ray had a down year hampered by injury and ineffectiveness. He received his first slap on the wrist of many as a member of the team in the form of a fine for missing a road trip to Boston.

After this disaster, it was clear something had to change in the leadership once again. The organization officially became known as the Yankees, scrapping the Highlanders moniker when they moved to the Polo Grounds from Hilltop Park. Suddenly, the two teams competing for New Yorkers’ support were roommates. Future Hall of Famer Frank Chance was hired to bring a stable managerial presence to the newly minted Yankees, and the move paid off. 1913 saw attendance numbers spike back up after cratering in the 102-loss season. All of these aesthetic improvements couldn’t do anything for the lousy on-field product, and the Yankees started 2-15, finishing with a 57-94 record.

For his part, Caldwell pitched just 164 innings but recorded a 2.41 ERA in another promising season. In an interesting bit of trivia, he started the inaugural game at Ebbets Field on April 5, 1913 against the Brooklyn Dodgers. By the end of 1913, Caldwell was a bona fide difference maker and a solid number two starter.

1914 was perhaps his magnum opus with the Yankees — he had a career-best 1.94 ERA in 213 innings, but the team languished in mediocrity again. Caldwell was consistently great against the most fearsome lineups and asserted himself as the staff ace. He drew many comparisons to Walter Johnson, the seminal right-handed pitcher of his day.

Ownership quarreled with Caldwell, fining and disciplining him several times. His manager Chance was somewhat puritanical for Ray’s taste and didn’t approve of his penchant for disappearing. As Caldwell’s success on the field came together, he partook more in nightlife escapades, and baseball became an afterthought. Many publications of the time hinted vaguely at his manic behavior and substance abuse, and he butted heads with many. At midsummer, he’d tallied 84 strikeouts, and about $900 in fines from Chance. Midway through the year, Chance threw up his hands and gave way to budding star shortstop Roger Peckinpaugh as player-manager.

The Yankees seemed even less appealing once Caldwell got an offer from another league for more money. He took action, following his former rotation-mate Ford to the upstart Buffalo Buffeds of the new Federal League and skipping out on the final two months of the Yankees’ season. In the offseason Caldwell negotiated a three-year deal worth $8,000 per year with the Yankees, at which point he was sued by Buffalo for breaching his deal with them. The Federal League folded, though, and Caldwell was back with the Yankees, no-harm no-foul.

The team was on its fifth year of disarray, and was eventually sold to Col. Jacob Ruppert and Cap. Tillinghast L’Hommedieu Huston prior to the 1915 season. Under new ownership, Caldwell was paid commensurately and motivated — he performed well in the first year of his deal with a career-high 305 innings of 2.89 ERA ball. He also had his best offensive season as a left-handed hitter and meshed well with new manager “Wild” Bill Donovan, probably for the same reasons Donovan earned that nickname. The team, though, finished in fifth place once again.

Where’d Ray go?

As the Yankees’ 1916 Opening Day starter, Caldwell matched up with Walter Johnson and the Senators in a prime matchup of generationally talented pitchers from different eras. Caldwell lost that one, but the pitchers dueled later that year and the game went to the Yankees. He suffered a shattered kneecap in July as the weight of expectation mounted, and his performance lagged.

In early August, as comparisons to the iconic Johnson were reaching a fever pitch, Caldwell went AWOL when the Yankees needed their ace most for the pennant race. His manager and friend Donovan even reached his limit of tolerance, calling his desertion “foolishness” and issuing his first fine as skipper to Caldwell on this occasion. He eventually was charged his salary for the two months missed. The team finally climbed back to a winning record, finishing 80-74 in 1916, but the last two months without Caldwell were disastrous.

Rumors of his whereabouts during this time range from treatment for alcohol abuse to a covert identity pitching in Panama. The fact that he allegedly came back with a striking tan didn’t help the latter perception. This abandonment was enough to turn the owners against him — each game he missed, their faith in him looked more and more misplaced. Caldwell showed a propensity in his career for infuriating his superiors at every turn. At this point, he was up to three managers and two owners who publicly admonished him.

A brief redemption tour began in 1917 in which Caldwell expressed contrition publicly. He pitched well the first half of the season, but once again his attention and priorities strayed drastically once the season reached its most critical portion. The fines started rolling in as he partied with the team’s young stars. He was getting older and was essentially a league-average pitcher in 1917 and 1918.

His next great escape came to dodge the draft in 1918. MLB shut down early in compliance with the draft for World War I, and Caldwell didn’t need to be told twice. He bolted to work at a shipyard in Hoboken, considered his mandatory war-effort job, avoiding being drafted for combat. The only problem was that he, as always, didn’t tell the team of his whereabouts.

After all those shenanigans, Caldwell finally became more trouble than he was worth, and his luck as a member of the Yankees had run out. He was shipped to the Red Sox before 1919 and face-planted to the tune of a 3.96 ERA, awful for the Deadball Era. Incomprehensibly, the Red Sox made Caldwell and a young Babe Ruth roommates on the road, and suffice it to say Ruth developed some bad habits from Caldwell. The veteran didn’t make it through the season, as the Red Sox released Caldwell on August 4th.

Cleveland was the next team to take a shot, and legendary manager Tris Speaker had an idea. Speaker told Caldwell to get drunk after pitching, take the next day off, and work hard on the other days. It was unorthodox, but with the help of the now-crafty veteran adding a spitball to his repertoire, Caldwell had a 1.71 ERA in 52.2 innings in a small role on Cleveland’s first World Series winner. It would be Caldwell’s only championship in a 12-year career.

Touched by Zeus

The most famous anecdote of Caldwell’s career is nothing short of poetically symbolic. He was literally struck by lightning in the ninth inning of a 1919 game for Cleveland, and stayed in to finish the game. He later had a beautiful account of his thoughts at that moment:

“My first thought was that I was through for all time, living as well as pitching. But when I looked up and saw I was still in the diamond and that fans were in the stands, just as they were before I was hit, I just had to laugh with joy. I never was so glad to be living in all my life, and wouldn’t it have been tough luck for me to be stricken just as I had won my first game for a club that was willing to give me a chance when other clubs thought me through. I tingled all over and just naturally sank to the ground. I guess it was almost a minute before I saw Spoke Speaker and the others running toward me and realized the trumpets were not sounding for me yet.” - Ray Caldwell

Major League Baseball fell into tatters after 1919 with the revelation of the Black Sox gambling conspiracy. He used the spitball to regain the effectiveness of yesteryear and climbed to the mountaintop in the 1920 season as a World Series champion with Cleveland. Finally, he’d found some sort of redemption.

1921 was the end of the road for the embattled Caldwell. A 4.86 ERA in 147 innings at age 33 brought to a close his whirlwind 12-year career. Caldwell had a zest for life as a baseball player, though, and played on numerous minor league teams in the South after 1921. He loved the game that he didn’t start on until later in life, and kept on trucking, officially retiring from all organized baseball at 45.

Ironically, Caldwell turned out to be one of the longest surviving Deadball Era players. He and his fourth wife landed in Buffalo, occasionally turning out for an Old-Timers’ Game or two, but mostly sticking to themselves. He pursued a career in his stepfather’s footsteps working as a telegraph operator for a railroad, something he had a real passion for. Caldwell had one son, James, but he was very close with the stepdaughters from his fourth wife, too.

Caldwell passed away of cancer at age 79 on August 17, 1967. It’s difficult to find emotionally honest accounts of Caldwell’s personal life and reasoning for seemingly erratic actions. He was a man of relatively few words to begin with, the kind of guy to finish a game after being struck by lightning and act like it was the most natural thing in the world. A lot of the primary sources describing Caldwell are a product of their time, limited by the antiquated view of addiction as a bad habit rather than a disease.

In an obituary, a reporter who covered Caldwell said simply “his irregular habits destroyed his effectiveness.” While rigid, sportswriting of the time did provide delightful descriptions of Caldwell’s game:

“Ray Caldwell teased the champs [Philadelphia Athletics] with a slow, hypnotic floater, which dipped over the plate so easily that spectators in the grand stand [sic] could read Ban Johnson‘s signature on the leather.”

As confounding as his story off the field was, his performance on it was elite when the stars aligned. The raucous, devil-may-care attitude of Roaring Twenties New York was still a few years out, but Caldwell ushered it in a little early. On the mound as well as off it, he made a habit of skirting rules. He even prolonged his career using a pitch that would be outlawed soon after. At the height of his success came his most complete unraveling, but that’s how it goes sometimes. Pressure can be a crippling force in anyone’s life.

In any case, Caldwell lived with gusto. His aversion to being tied down is an understandable and natural human instinct. Over the course of his career, he found a way to flash brilliance. And if a person flashes brilliance, they are brilliant, consistency and potential be damned. Caldwell is a Yankees legend, albeit one around when the team couldn’t put it together. He’s also a World Series champion. Congrats on a fully lived life, Slim.

Staff Rank: 76
Community Rank: N/A
Stats Rank: 55
2013 Rank: 55


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78. George Selkirk
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