We know very little about the first child of Michael and Bridget. His name was James M. Donlin, also known as "Jim". He was born November 10, 1862.^[32] He may not have used the "Donlin" spelling, as his father was illiterate and that particular spelling may not have been established by the time Jim left home (1877-78).

Jim is known to have left home at age 15. He turned 15 in November, 1877, months after his mother Bridget died. It may be that his departure was precipitated somehow by his father's remarriage on Christmas Eve 1877.

Mike Donlin received word that his eldest son Jim had died in Stillwater, Minnesota immediately after Mike and the family had constructed their first barn at their homestead in Spring Township, Hand County, SD, and were preparing for a dance. Mike is reported to have said "bury him where he died."^[33] In light of this, it is plausible that Mike and Jim parted on bad terms. Given the reported location of Jim's death, it appears likely that he died in prison. Hence, Mike may have said what he did out of a sudden shock or disappointment, rather than a long-standing feud. That said, Mike and Jim might have had significant differences to have stayed apart for so long.

We paid the Washington County Historical Society to perform a record search for a James Donlin in the Stillwater area for the decades preceding 1910. Though the researcher had a variety of records at his disposal, and stated that death records of prisoners would have been generated, still he found nothing. In light of this outcome, it seems doubtful that we'll ever find evidence of the place and time of Jim Donlin's death.