Henry Louis Gates presents legendary Chicago attorney James Montgomery with his roots

James D. Montgomery, the city of Chicago’s first Black corporation counsel, was presented Tuesday with his ancestral roots by Henry Louis Gates Jr., host of PBS’ “Finding Your Roots.”

As a 94th birthday present, Gates gifted Montgomery his “Book of Life,” a detailed account of Montgomery’s lineage on both sides of his family back to his third great-grandparents. The work was prepared by American Ancestors, a family history nonprofit based in Boston.

“There was more than I knew,” Montgomery said. “You know, I’ve learned that these people were industrious and landowners. And that gives me a sense of self-esteem and pride.”

The reveal was hosted Tuesday by Trinity United Church of Christ, where Montgomery is a charter member.

Montgomery was born in Louise, Mississippi, and thought that was as far as his roots went. But he learned that his ancestors have origins on plantations in Maryland, Virginia, and South Carolina.

Using an 1844 probate record document, it was determined Montgomery’s paternal third great-grandmother, Rosetta Guster, who was born in1807, his paternal second great-grandmother, Luvinia Guster, who was born in 1825, and three other relatives were recorded as property of George Fisher in Yazoo County, Mississippi. The record detailed what was to happen to his property after his death, which in this case, Montgomery's ancestors were guaranteed to Burwell Boykin, a prosperous slave owner with plantations across the South.

Gates surmised that the agreement between Fisher and Boykin could stem from a few possibilities.

“Fisher may have owed Boykin a debt, and they were property, and your ancestors were used to repay that debt,” Gates said. “It’s also possible that Boykin had loaned or leased your ancestors to Fisher.”

Gates went on to ask Montgomery how it felt to know that his flesh and blood were "passed around between two white slave owners, like farm animals, or farm equipment?”

Without hesitation, Montgomery responded: “Angry.”

The “Finding Your Roots” host took Montgomery through the same process he’s done with celebrities on television. Asking them questions about their skills and talents to possibly trace those same skills and talents back to their ancestors.

After coming to Chicago in 1937, Montgomery enrolled in Fuller Elementary and then went on to Phillips High School. Montgomery said his white guidance counselor attempted to dissuade him from going to college, suggesting that it would be too difficult. He went on to earn his undergraduate and law degrees from the University of Illinois Urbana-Champaign. Highlights of his law career include: becoming the first African American to serve as the city’s top lawyer, under Mayor Harold Washington; filing a class-action lawsuit against the Chicago Board Education, in 1961, claiming that the board deliberately created segregated schools; and serving as the attorney of record for Fred Hampton, the activist and leader of the Illinois chapter of the national Black Panther Party.

Gates said that Montgomery could trace the origins of his successful career to the entrepreneurial spirit of his ancestors. In Montgomery’s “Book of Life,” Gates included loan agreements between his ancestors and the Lintonia Building and Loan Association, where his maternal second great-grandparents, Alex and Patsy Oliver, took out a $600 loan and $200 worth of supplies, and put up 50 acres of their land as collateral.

“That Alex and Patsy, by 1899, already owned land, let me tell you this: This would have been, that was huge,” Gates said. “That was very rare for Black people to own land, particularly in Mississippi.”

Montgomery said his family still owns that land of 200 acres, and that once a year, he and his family members get between $10 and $50 for leasing the land.

This was only a partial ancestral reveal due to time constraints. Montgomery will have to take a DNA test to determine his genealogy that will detail the percentage of his sub-Saharan African Black, European, white and Native American ancestry. Tuesday’s presentation will not be part of the PBS “Finding Your Roots” show, but can be seen on Trinity’s Facebook page and YouTube channel.