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Alumni Profile: Ernest Crosby ’72

Photo: Ernest Crosby ’72 and his wife, Monta

Ernest Crosby ’72’s story is one of perseverance. The only child of a single mother, Crosby grew up in the Jane Addams Homes on Chicago’s West Side. The environment in the projects was dangerous, he says, people to “stay clear of”; boarding school provided a place to reset.

“It was the first time I felt I could relax, to focus on my studies,” he says. 

Crosby entered Lake Forest Academy for his senior year of high school, having spent two years at Lane Tech in Chicago and one year at Saint John’s Prep in Collegeville, Minn. He enrolled at LFA through the ABC program (A Better Chance). It was thanks to a local high school teacher, Pete Miscinski, who also worked part-time at the Chicago Boys Club in Crosby’s neighborhood, that he learned about ABC. Pete helped him fill out the forms and get signed up for the admissions test.

“He was an awesome person; [My boarding school experience] would not have happened without him.”

While he looked forward to the opportunity to go away for school, first Saint John’s and then LFA, his mother and grandmother worried. This wasn’t something they had had exposure to; what would the environment be like? Ultimately, his mother did not stand in the way of what she knew was a good opportunity. 

“She let me do it,” he says. 

At the Academy, Crosby played football and basketball and did well academically, enjoying his courses in English and history the most. He made friends, primarily other African-American students, he says, and enjoyed being part of the boarding school community, having a room of his own in the dorm. His chief focus was on his education; he aspired to be a doctor or a lawyer. He remains grateful for the unfailing support of his mother, who affirmed his abilities. 

“Unlike most other parents in the projects, she never placed any limitations on me. She never said I can’t do that because I’m poor, or Black,” he recalls. “She always said, ‘Yeah, I can see you doing that—I know you can do it!’” 

From LFA, Crosby matriculated at Carleton College, where he graduated with a bachelor’s degree in economics. He began working in the sales industry for companies such as Honeywell and Campbell Soup.  He also spent time in the U.S. military. His work took him from Minnesota to Hawaii, California, and eventually back to Illinois, where he entered law school at Loyola University. Married and with two daughters of his own by this point in his life, Crosby and his family moved in with his mother, who had relocated from the city to the western suburbs, and attended law school at night while working a full, 40-hour week in the insurance industry.  By the time he graduated law school in 1993, he felt burned out and mentally exhausted. 

Time for a change, Crosby and his family moved South to Atlanta, closer to his wife’s relatives in Alabama. Crosby continued to work in the insurance industry until he eventually took—and passed—the bar exam and started practicing personal injury law. 

Before leaving Chicago, he drove his wife to the LFA campus and told her about his experience there. “You graduated from here?” she asked, impressed. This inspired his wife to recommend boarding school to their daughters when the time arose. 

“We never gave her a choice,” Crosby says, laughing, about sending his eldest daughter away to school. She attended Northfield Mount Hermon School in Massachusetts and later graduated from Mount Holyoke College; his younger daughter attended Rabun Gap-Nacoochee boarding school in Georgia, graduated from Denison University, and earned a master’s degree at the University of Southern California. 

Crosby considers himself fortunate. He received an excellent education and had opportunities in life. He sent two daughters to independent school and college and provided for his family. Widowed and later remarried, he had the support of his first wife to start law school in his 30s, and the encouragement from his second wife to eventually take the bar exam, 10 years after graduating law school. A sense of guilt, too, sometimes accompanies this gratitude: Why did I get these opportunities and not others? 

He revisits that time in his life when he shuttled between Lake Forest and Chicago’s West Side, those moments when he made “mental adjustments” between the life he was living in the northern suburbs – “the mansions, the tremendous wealth” – and the poverty in the neighborhood he grew up in. He remembers how he regulated the way he talked, how he interacted with people when he toggled between his life at LFA and his home in the city.

Despite the challenges he faced, he remains grateful for the education he received at LFA and the pathway it set him on toward college, law school, and his career.  

“On the surface there appears to be a lot of unfairness in life,” he says. “However, as a person who believes in God, I believe we always do what we are supposed to do. Things have a way of getting you to where you are supposed to be; they balance out. God does not make any mistakes.”

Crosby lives in Atlanta, Ga., where he is a practicing attorney.