Subscribe to Baseball History Comes Alive

Free Bonus for Subscribing:

Gary’s Handy Dandy World Series Reference Guide

Today Mike Janacek returns with the interesting story of Ray Caldwell’s very unusual contract terms, given to him by his manager, that well-known “Doctor” of psychology, the great Hall of Famer, Tris Speaker. As weird as it sounds, it seems to have worked! I think you’ll enjoy Mike’s amusing essay. -GL

Another Edition of

“From the Lighter Side…”

Ray Caldwell’s Unusual Contract

And that’s putting it mildly!

“Caldwell could be as great as Matty or Walter Johnson, but instead of choosing their careers, he is evidently going to be another Rube Waddell.” -Sportswriter Grantland Rice

When I came across this story, I was amazed. It has to be considered one of the most bizarre events in major league history. Ray Caldwell toiled for 12 seasons in the big leagues (1910-1921) for the New York Highlanders (later becoming the Yankees), Boston Red Sox, and Cleveland Indians. Over his career, he went 134-120 (.528), with a 3.22 ERA, 184 complete games, 21 shutouts, and 1006 strikeouts. He was considered one of the elite pitchers of his era. Only his drinking and off-field behavior stood in the way of his greatness. Ray was one of seventeen spitball pitchers grandfathered out and permitted to continue throwing the spitter after it was outlawed in 1920.

In 1910, Ray began his professional career with the McKeesport Tubers in the Ohio-Pennsylvania League, recording 18 wins before signing with the New York Highlanders in September. In his rookie season with the Highlanders, 1911, Ray went 14-14, with a 3.35 ERA. Interestingly, he also played 11 games in the outfield and was even used as a pinch hitter on several occasions. He also recorded a respectable batting average of .272. In his best year, 1914, with the newly named Yankees, Caldwell went 17-9 with a 1.94 ERA, leading a team that won only 70 games and lost 84, finishing in seventh place in the eight-team American League. Despite his outstanding year, his drinking problems and poor attitude resulted in several run-ins with his manager, Frank Chance.

By 1918, his numerous injuries and persistent alcohol problems contributed to his failing to complete the season. He left the Yankees in August to join a ship-building firm to avoid military service after being drafted. As the Yankees had not given him his release, they decided to rid themselves of their troublesome pitcher and traded him to the Red Sox. With the Red Sox in 1919, Caldwell roomed with Babe Ruth, and the pair developed a propensity for outbreaks of misbehavior. The Red Sox cut Caldwell in August.

A few weeks later, seeing that the talented but troubled pitcher was available, Indians manager Tris Speaker presented him with an unusual contract in an attempt to control his behavior. The contract stated that on game days when Caldwell was to pitch, he would go out and get drunk afterward. Caldwell was perplexed, looking at the contract terms:

“You left out one word, Tris. Where it says I’ve got to get drunk after every game, the word “not” has been left out. It should read that I’m not to get drunk.”

Speaker smiled. “No, it says that you are to get drunk!“

Speaker then explained the precise regimen on which he was placing Caldwell, adding that he expected Caldwell to abide by it every week. The manager was truly ahead of the times. The gist of Ray Caldwell’s rather unconventional contract (consisting of what in later years would be termed “reverse psychology”) can be summarized as follows:

“Pitch, drink, sleep, run, BP…

Rinse, and repeat”

Caldwell would pitch on his scheduled day and then, following his stint on the mound, he’d perform his so-called “mandated drinking duties.” Ray would then be allowed to skip coming to the ballpark the next day to sleep off his hangover.

But two days later, Speaker would expect him at the ballpark bright and early to run as many wind sprints as the skipper thought Caldwell needed. And then three days after every start, Caldwell was to throw batting practice. 

Historians believe Speaker, a true innovator as both a player and manager, thought Caldwell’s talent was worth the unusual risk and that by giving him a “free pass day” of unrestrained drinking, Caldwell might be able to stay on track for the other three days of a pitching cycle.

After reading the terms of the unusual contract proposal, Caldwell simply shrugged his shoulders and reportedly responded with a sly smile: “Okay, I’ll sign!”

I guess we can conclude that “Dr.” Tris Speaker’s reverse psychology was a success, as Ray Caldwell posted a 20-10 record with a 3.86 ERA for the 1920 Indians, helping them win the American League pennant and World Series championship over the Brooklyn Robins.

Ray Caldwell also has the distinction of being the only player to survive a lightning strike during a game in which he was pitching – and finishing the game! So stay tuned…that’s a story for another day!

Mike Janacek

(1) Lewis, Franklin, ”The Cleveland Indians.” G.P. Putnam’s Sons, January 1, 1949.

Opening quote by Frankland Rice found on the SABR biography of Ray Caldwell, written by Steve Steinberg, which was also a source for this essay

We’d love to hear what you think about this or any other related baseball history topic…please leave comments below.

Subscribe to Baseball History Comes Alive. FREE BONUS for subscribing: Gary’s Handy Dandy World Series Reference Guide.  

Visit the Baseball History Comes Alive Home Page