Jack -

You were part of the newsies

Davey - 

You go to school

Racetrack -

You train horses at the tracks

Spot -

You work in the cotton mills

Crutchie -

You have an apprenticeship with a doctor

Mush -

You're a seamstress

Blink -

You have an apprenticeship with a teacher

Skittery -

You're a maid for pulitzer 

Bumlets -

You're Medda's assistance