He was named after his paternal uncle Ya'akov (Yankel) Olin (his father's elder brother) who died in 1889 at the age of 32. He used the name Joseph (Joe) as he feared even late in life that he might be considered to be in Canada illegally. My Dad (Izzy Olin) told me that whenever anyone from the family would call him Jack that he would nervously say: "Shh, Joe, not Jack!"
I believe that he initially entered Canada legally through the Port of Quebec City aboard the SS Crefeld out of Bremen on June 25, 1913 but then went to Chicago and then may have reentered Canada illegally.