The top image is my great grandfather John Cummings(also known as 'Commings' in Ireland) citizenship papers. This copy was requested by his wife Catherine in 1920. John and Catherine Cummings were parents to Catherine, Charles, Mary and Cecelia (also known as Celia and Claire).
I am not sure who the man in the second photo is. He is definately a Cummings (or Cummings related) My town's local historian (Henry Cooke-Randolph, MA) designs period costumes for movies and such and I am hoping he will be able to tell me more about the hat in this photo. I am wondering if the man was a trolley conductor or something like that.
Once I find out what he did, I should be able to determine who he was.

Update:
My Mother's cousin informs me that this is my Mother's Grandfather who came to Boston from Ireland, married and had a few children and then abandoned his family to return to Ireland. He was a streetcar conductor, hence, the hat.
Have I mentioned lately how much I love the internet? : )