With the labor combined with the weather of Pontiac proving harmful to his health, he returned to Detroit where he began working for the general trader Oliver Newberry.
[4] Dole arrived at the settlement, as it was at the time—having a population of fewer than two hundred people—in 1831, the same year that Cook County, Illinois was established,[3][5] settling at Wolf Point.
That year Newberry would send beef and hides produced by Dole to eastern US markets, Chicago's first such shipment.
It used man-powered blocks and tackles to lift stacks of grain to its upper floor, where they were emptied into chutes into ship holds.
The company would continue to expand in the years after Dole's death, being a leading player in the city's grain market.
[5][13] Five days later, Dole was elected to the town's inaugural board of Trustees along with Madore B. Beaubien, E. S. Kimberly, John Miller, and Thomas Jefferson Vance Owen.
[15] Dole was the director of the first state bank of Illinois and helped to organize the Chicago Board of Trade.
[1] Dole was the unsuccessful Whig nominee in the March 1844 Chicago mayoral election, losing very narrowly.
The election result was voided by the Chicago Common Council, which claimed that there had been electoral fraud by the Democratic Party.
[19] Dole was an early and active member of the free Kansas movement, and became the treasurer of a national committee for the cause.
[4][9] Near the end of his life, Dole lost the significant sum of $80,000 by investing in a real estate deal that a friend had assured him would be a guaranteed success for him, greatly diminishing his personal financial wealth.