First of all, let's just get this off the table now: He broke up with Sarah for differences unforeseen by him at the time of the movie's end, but yes, they were split, and thank God.
Cowboy was a newsie until about a year after the strike, when he finally got to go to Santa Fe. While he was there, Jack met a lovely lady whom he married and loved for the rest of his very long life. They settled down in Illinois, where he got to live his dream of being a cowboy as he started his own successful ranch.
Jack became the father of four children, including Velma Kelly, who would co-headline with a certain Roxie Hart on the Chicago stage after killing her sister and Jack's other daughter, Veronica. (And all that jazz!)
Spot Conlon:
Unlike Jack, Spot stayed in the newsie business for a good long while, for about five more years. When he finally stopped selling papes, he still stayed in Brooklyn, developing a semi-successful newsstand.
Spot didn't think about marriage too much when he was younger, so he married rather late in life. After Spot was married, he decided to go into the crime solving business. Spot became one of New York's most famous gumshoes ever. He continued to hunt down Brooklyn baddies for the rest of his life. He's so stubborn that he may very well still be alive for all I know!
Racetrack Higgins:
Race continued his life of gambling for pretty much the rest of his life, though he was very prosperous, gaining a ton of cash over the years. So much, in fact, that it led him into a little trouble with the law.
Later, after he'd settled down, Race only had one son: Harry "The Horse" Higgins. Harry the Horse became a prominent gangster and gambler in New York, following in the footsteps of his old man. However, it backfired on Race when, in his older years, Harry turned him in to the authorities to collect the reward: $5,000. (Anyone who's seen "Guys and Dolls" knows what I'm talking about!)
Les Jacobs:
I always imagined that Les became a great actor with shows all over the world and when he got older (when he decided it was time for him to retire) he bought Irving Hall! --submitted by FrenchyGoil
