That night he pawned his watch for all it would bring. This put him in funds again, but gave him pause. He decided to stop gambling and go to work. But the morning paper contained a tempting list of entries. It was Saturday, and a short day.
He went to the track as usual, and at the end of the third race was "broke." Then he met Murray Jameson. Both were surprised. Checkers told him his story, and borrowed ten dollars. Murray lost fifty more by playing Checkers' tips, against his own better judgment. Murray was "sore"—Checkers apologetic. This was his first experience as a tout. After that he picked up a precarious living, selling whatever articles of value he possessed, one after another, until he had left but the diamond star he had given Pert as a wedding gift, and a scanty wardrobe.
When necessity caused him to part with the star he forswore the races, and for two full weeks conscientiously sought for legitimate employment. But Chicago was filled with idle hands, which the closing of the Fair months before had left there stranded. Everything was overcrowded. Business was dead, and his search was unavailing. Then he took up "touting" as a profession. He rotated between the various "merry-go-rounds," which were open all seasons of the year. The tout's stock devices—the "bank-roll" game, the "phoney" ticket, the "jockey's cousin"—he worked with better success than most; but, as a rule, his method was simple. He sought the acquaintance of such as he thought might be "persuaded," and by showing confidence where they were doubtful, knowledge where their own was lacking, he usually managed to get some four or five men to make bets during the day. Those who won were grateful, and generally paid him well for his "information." The losers got an explanation of "how it was" and "a sure thing for the next."
One thing, however, must be said for Checkers. He never "touted" a horse unless he thought it had a best chance of winning. That is, if there were five horses in a race, and Checkers had five men "on his string," he never descended to the common practice of getting each one of the five to bet on a different horse, and thus "land a sure winner."
All five were certain to have the same chance, and to stand or fall upon Checkers' judgment.
Some weeks later it was that I first met him, at Washington Park, Derby Day. He told me afterward that the minute he saw me he knew me for a "mark" and tried to "get next."
Yet, for all, Checkers was not innately bad. He was weak, I 'll admit, and cruelly mistaken; but he had a simple, lovable nature, and a natural longing for higher things. A case in point: I learned by chance that he never missed a Sunday at church since the death of his wife. He had no predilection, and I espied him one day in my own sanctuary. When questioned about it he told me these facts, and confessed to the pleasure he found in going.
"I don't know," he said; "I always enjoy it. It's quiet and cool; everybody 's well dressed, and I like to sit there, close my eyes, think over my troubles, and listen to the music. And then, again"—here his voice grew soft—"I 've a feeling that it pleases Pert to know that I 'm there. She liked me to go to church, and I think she knows it now when I go; do n't you? I would n't take a great deal of money and think that she did n't know."
What Pert must have thought of his actions weekdays was perhaps a fair question; but it was one that I had the heart not to ask. And so it went on; my efforts to get him a position and reform him ending in nothing, as I have previously related.
After the big meeting closed Checkers reached his lowest ebb. It was during these days that he made my office a loafing place. I suppose that for six weeks I practically supported him, lending him two or three dollars at a time, to "square his room rent," "get out his overcoat," "pay a doctor's bill," "play a good thing," and heaven knows what not—each time assuring him that I positively would not succumb again, but regularly doing so. Still, I never begrudged it. A couple of hours with him was worth a few dollars at any time. I divided the expense between my amusement and charity accounts; and, in truth, when with him I never could tell whether pleasure or compassion had the upper hand with me. I have tried to set down with some succinctness the major part of his experiences as I heard them; but I fear they have greatly lost, in the telling, that delicious flavor of originality which Checkers' person, voice, and manner gave to them as I heard them piecemeal. Many of his sayings, when repeated afterward by Murray or me, scarcely caused a smile, while coming from him they had seemed to us excruciatingly funny. But I believe the secret was this—he never seemed to say anything with the primary idea of being funny. He always looked up with genuine surprise when his listeners laughed, and only joined them, when the mirth was infectious, by deepening a little the cynical curves at either corner of his expressive mouth.