Rube Waddell’s constant moving led to many contracts but very few raises. Even while his popularity with fans had greatly increased ticket sales, and soap and cigars were being named after him, he earned little money and saved none. His top reported pay, according to Baseball Library, was a meager $2,800.

Manager Connie Mack claimed that Waddell preferred winning games to earning money, but regardless of how he felt about money, Waddell spent whatever he did earn as fast as he could, and he almost always spent it on alcohol.

As noted in Philly Sports History, Mack tried different tactics to curtail his star’s drinking, including doling his salary out in $1 increments. He also entrusted Waddell’s travel per diem to team trainer Frank Newhouse. According to The Society for American Baseball Research, Mack instructed Newhouse to accompany Waddell everywhere and do what he could to control his spending on drink.

Often, however, Waddell outsmarted his handlers. Sometimes he would devise money-making ruses, then use the cash to buy alcohol. He would go on benders, missing games, and returning to the clubhouse in bad shape. This cycle of abuse repeated itself season after season, and with each new trade, Waddell’s value as a player decreased. At one point, according to The New York Times, Waddell was so in arrears on his debts, he spent time in jail. By the end of his life, he was penniless.

For several seasons in Philadelphia, Osee “Schreck” Schrecongost was Rube Waddell’s devoted catcher and his roommate. As noted by Sporting Life (via The Society for American Baseball Research), Schrecongost’s “most notable trait was that he was the only catcher who could make Waddell pitch his best.”

Schrecongost was almost as wild as Waddell, and their mutual fondness for alcohol made them particularly compatible. Even their public spats had a genial quality. In “My Thirty Years in Baseball,” manager John J. McGraw recalled how Schreck demanded a clause in his contract forbidding Waddell from eating crackers in their shared double bed: “I didn’t mind the flat crackers so much. But for a whole week last year I woke up with elephants’ tusks and cowhorns stickin’ ‘tween my ribs.”

Unfortunately, as with Waddell, Schreck’s alcoholism affected his performance and enraged Philadelphia manager Connie Mack. Schreck remained a season with the Athletics after Waddell’s 1908 trade, but his poor alcohol-impaired play eventually compelled Mack to release him as well.

After 1907, Waddell and Schreck never again played together, and both men’s careers went into decline. Waddell had lost not only his most patient and skilled catcher but his closest friend as well. Schreck died a mere three months after Waddell in 1914. He was quoted on his deathbed saying, “The Rube is gone and I am all in. I might as well join him.”

No one was quicker to throw a punch or wade into a melee than Rube Waddell. His record of fisticuffs was the stuff of legends. His fights led to brief stints in jail and sometimes to suspensions and fines.

Two confirmed altercations had serious consequences for Waddell. As reported in Baseball History Daily, during a 1903 game in Philadelphia, Waddell, after enduring several innings of heckling, waded into the stands and attacked a spectator. Although the fan, a known “ticket speculator,” was himself arrested, the American League president suspended Waddell for five days.

The second fight took place in February 1905 and involved both of his in-laws, with whom he was living in Boston, separate from his then-wife May Wynne Skinner. According to The Society for American Baseball Research, a drunken Waddell was preparing to move out when his father-in-law asked for board money. Enraged at the request, Waddell attacked his father-in-law with a flat iron, and when his mother-in-law tried to intervene, he hit her with a chair.

Waddell fled the scene, and an arrest warrant was issued. Through some probable string-pulling by Connie Mack, Waddell avoided jail, and charges were dropped. However, the special treatment Waddell received fueled his teammates’ growing resentment of him, and the resulting bad press further stained his reputation.

For much of his career, Rube Waddell indulged in goofy cockiness and pranks, on and off the field. As noted in Baseball Library, one of Waddell’s favorite bits of showmanship was to send his teammates off the field during exhibition games and then strike out the side. Rules prohibited him from doing the stunt during Major League games, which required nine defensive players on the field at all times. But in one league game in Detroit, he found a way around the regulation. He ordered the outfielders to go to the edge of the grass and sit, and then he whiffed the side.

According to The Society of American Baseball Research, in another display of brashness, Waddell did cartwheels from the mound after defeating the great Cy Young in a grueling 20-inning outing. He later bartered the “winning” ball for drinks at bars around the country.

Just before the 1905 World Series, however, his signature confidence began to disappear. Although known for battling through rough patches and completing a record number of games, Waddell left a September match after two unremarkable innings. Not only was his departure from the field unusual, so was his choosing to sit quietly with fans in the bleachers instead of retreating to the dugout. It was a move that baffled the press and unnerved his coach and teammates.

The unexplained change in behavior seemed to be a harbinger of bad times to come.

As with everything else in his life, the details of Rube Waddell’s final years are convoluted. After being traded to the St. Louis Browns in 1908, he continued to pitch reasonably well and draw crowds for two more seasons. However, in 1910, with his love life in tatters and his drinking and temper out of control, his career in the majors ended.

He wound up in the minors in late 1910, bouncing from team to team. According to Philly Sports History, in 1912, while he was living in Kentucky, a local dam collapsed, causing flooding throughout the region. Waddell, of course, raced to help, rescuing trapped people and standing for hours in cold water stacking sandbags at the levees.

The protracted effort, while heroic, apparently caused Waddell to contract pneumonia. In his weakened state, he also developed tuberculosis, or the “white death.” As noted in his biography in The Society for American Baseball History, after struggling through most of the season, he was forced to quit pitching in November 1913. Supported financially by Connie Mack and others, the broke and weak Waddell then found care at a sanitarium in San Antonio.

Weighing a mere 130 pounds, the once strapping Waddell died a few months later, on April Fool’s Day, 1914. He was only 37. In eulogy, Mack described Waddell as the greatest pitcher in the game, a kind sinner to whom he and baseball would always owe much.