Dyson ran a real estate agency in Minneapolis in Hennepin County in the late 1850s. He represented Washington County in Minnesota’s Democratic Convention in 1859.

He lived in Hill Top, Charles County, Maryland. In 1855 he inherited eleven slaves from his late father, and they were valued collectively at over $4,000. [see appraisement and distribution of property of Bennett Dyson, Probate Court, Charles County, Maryland, 1856.] In April 1858 he offered a slave for sale in Maryland after having established a business office in Minnesota.

Adam: a “Negro Man” worth $275 in 1855.

Catharine: a “Negro Girl” worth $300 in 1855.

Emmaa “Negro Girl” worth $400 in 1855.

George: a “Negro Man” worth $800 in 1855.

Harry: a “Negro Man” worth $150 in 1855.

Harrya “Negro Boy” worth $150 in 1855.

Johna “Negro Man” worth $750 in 1855.

Kita “Negro Woman” worth $650 in 1855.

Neda “Negro Boy” worth $300 in 1855.

Roberta “Negro Boy” worth $125 in 1855.

Winnya “Negro Woman” worth $150 in 1855.

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