[3] Rosewell began his political career as a young man, working in the 24th Ward of Chicago as a precinct captain.
[1][3] He worked in the private sector as a vice president in the public funds division of Continental Illinois.
[2][3] During his time with the bank,[4] he won election to the Illinois Constitutional Convention as a delegate from the 18th legislative district.
It had been alleged that he had understated debts from a failed clothing venture of his in order to qualify to receive loans from banks which also held substantial deposits from the county government.
[1] In the autumn of 1998, he resigned after pleading guilty to charges of having put two state legislators (Bruce Farley and Miguel Santiago) in ghost jobs in the treasurer's office, which gave thousands of dollars in salary and benefits in exchange for little or no work.
[1] After his death, a federal judge vacated his conviction, saying that Rosewell had been mentally unfit when he signed his plea agreement.