The Little Company’s founder was Captain Obadiah Little. He was a Maine-man and second son of Judge S. P. Little. His family connections had secured him a place at the Military Academy at West Point where he finished at the middle of his class, and one place ahead of his friend and roommate Thomas Jefferson Mason the son of a Virginia planter.
In their final year Obadiah made the acquaintance T. J.’s younger sister, Sarah. The two struck it off well, and they were wed soon after his commissioning. Again family connections came into play, and he was posted near her family home at Fortress Monroe.
Events in the West soon intervened however, and Lieutenant Little was sent Illinois as part of an expedition against the Black Hawks. He was a capable officer, and one who fostered loyalty in his men. It was in Illinois that he contracted the gut sickness, however, and nearly died. On his recovery, he was deemed unfit for regular service, but was offered a commission as Captain in the Madison County Militia, a position he readily accepted.
Sarah joined him in Illinois, and was accompanied by George Mason, a slave of about seventeen years of age. Obadiah was no abolitionist, but he was a man beholding to the law. As such he had his wife transfer George to a forty year indenture, as was the Illinois way.
They were happy together, and set up on sixty acres which was put to corn. It wasn’t a big farm, but it was easy enough for him and George to handle. He had his Militia pay as well, and could be looked to for some occasional lawyering as well.
Two years on, his beloved Sarah died in childbirth, and left Obadiah in no fit state to do much of anything. He resolved that there was nothing in civilisation worth staying for, so resigned his post, and headed West. He freed George of his indenture, but found that he was not so easy to get rid of. Nor was his corporal “Stubby Greene,” so together they formed the Little Company, and headed for the Oregon Trail.
See also: The Little Company: Stubby