He could win her if he wanted to.

It would be easy, knowing her as he did, and knowing what he did about her.
So not long after, Lynde ventured to invite her, with Lord, McKibben, Mr.and Mrs.Rhees Grier, and a young girl friend of Mrs.Grier who was rather attractive, a Miss Chrystobel Lanman, to a theater and supper party.

The programme was to hear a reigning farce at Hooley's, then to sup at the Richelieu, and finally to visit a certain exclusive gambling-parlor which then flourished on the South Side--the resort of actors, society gamblers, and the like--where roulette, trente-et-quarante, baccarat, and the honest game of poker, to say nothing of various other games of chance, could be played amid exceedingly recherche surroundings.
The party was gay, especially after the adjournment to the Richelieu, where special dishes of chicken, lobster, and a bucket of champagne were served.

Later at the Alcott Club, as the gambling resort was known, Aileen, according to Lynde, was to be taught to play baccarat, poker, and any other game that she wished.

"You follow my advice, Mrs.
Cowperwood," he observed, cheerfully, at dinner--being host, he had put her between himself and McKibben--"and I'll show you how to get your money back anyhow.