After Rube Waddell’s death on April 1, 1914, he was eulogized by Christy Mathewson in his nationally syndicated column. Mathewson compared Waddell to one of his own former teammates with the Giants:
“He was a man, who, like ‘Bugs’ Raymond, wasted a wonderful natural gift. If both these players had taken care of themselves they might still be stars of the big leagues.”
Rube
Mathewson said a teammate had recently told him a story about Rube’s time with the Louisville Colonels:
“Waddell was always notably careless with money, and he never kept track of how much he had or how much was coming to him…Mr. (Harry) Pulliam…hit on a scheme in 1899 to make ‘Rube’ save money.
‘”Rube,’ he said to Waddell at the beginning of the season, ‘I am going to give you $2 to spend every day, and then we will pay you the balance of what we owe you at the end of the season so that you won’t be broke all winter. The club will take care of all your living expenses.”
After Waddell agreed to the deal:
“So after every game that year Mr. Pulliam gave Waddell his $2. He was never a high salaried player in his palmist days, and I believe the figures written into the best contract he ever had did not amount to more than $3,500, which would not be much for a star of his ability in these times.”
Mathewson said at the end of the season Pulliam had $150 left for Waddell:
“’Now, be careful of that money,’ advised Mr. Pulliam, ‘because it has got to last you for a long time.’
“’Sure,’ said Rube.
“By the first of November Mr. Pulliam heard from Rube, and the report said he was broke. Waddell received a response of $25, which lasted him for a couple of weeks, and he had to repeat his request for money. This occurred several times and then Mr. Pulliam sent him $100 for Christmas. Rube was back for more by the first of February.”
Rube Waddell
When Waddell reported to the Colonels that spring, Mathewson said, Pulliam “figured it up,” and he had still held back $1100 from Waddell’s 1899 salary:
“He sent $1000 to Waddell’s father…Then he handed the $100 to Rube.
“’That was still coming to you from last season’s work,’ said Mr. Pulliam. Waddell pocketed the money without complaint. If he had drawn his salary twice a month during the season as the rest of the players did, the improvident Waddell would not have had a cent left by the close of the 1899 campaign.”
Baseball History Daily 
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