His mother, Angelique McGulpin (Bead-Way-Way or Mecopemequa) was a daughter of Maketoquit (Black Cloud), the chief of a large band of Grand River Ottawa.
When his parents divorced, his older brother Francis remained with Maketoquit's band, while his younger sister Sophia was adopted by fur trader Magdelaine Laframboise, a close friend of the family.
In 1834, as founder John Jacob Astor prepared to retire, the company was reorganized as a partnership with Ramsay Crooks as president and senior partner.
[2] Furthermore, Bailly had an ongoing feud with Indian agent Lawrence Taliaferro, which had culminated in a series of incidents involving confiscated whisky, lawsuits, and a threatened duel between the two men.
Bailly refused to give up his business until his contract expired the following summer, but agreed to take Sibley with him to the mouth of the Minnesota River and introduce him to "the people, the country, and the far-flung operations of the Dakota trade.