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Gretchen Tucker Underwood

Academic administrator Gretchen Tucker Underwood was born on October 11, 1943 in Boston, Massachusetts to Judge Herbert Tucker and Mary Tucker. After graduating from Jamaica Plain High School in 1961, Tucker Underwood attended Howard University before transferring to Southern Connecticut State University, where she received her B.S. degree in education in 1968. In 1972, Tucker Underwood went on to receive her M.A. degree in educational administration and a certificate of advance graduate study from Boston State College.

After teaching social studies for three years at Wilbur Cross High School in New Haven, Connecticut, Tucker Underwood was hired as a teacher at Brookline High School in Brookline, Massachusetts in 1970. She later became the school’s Metropolitan Council for Educational Opportunity (METCO) coordinator. By 1996, Tucker Underwood was promoted to dean of students of Brookline High School. In the 1990s, she was also the first African American elected as a town meeting member while living in Wellesley, Massachusetts. Tucker Underwood served Brookline High School as the dean of students until her retirement in 2007, after thirty-seven years with the school. In 2008, Tucker Underwood moved to Oak Bluffs, Massachusetts; and, in 2014, she ran for Dukes County Commissioner as a democratic write-in candidate, and was elected to one of the seven seats. Tucker Underwood was re-elected to the seat in both 2016 and 2018. In 2019, she was appointed chair of the commission.

Tucker Underwood chairs the annual celebration commemorating an artist, educator, and writer from Martha’s Vineyard, Della Hardman. She was a member of Delta Sigma Theta Sorority, an advisory council member for Martha’s Vineyard Youth Leadership Initiative, and has served on the boards of the Big Sister Association and Martha’s Vineyard chapter of the NAACP. From 1996 to 2000, Tucker Underwood served as president of the Boston Coalition of 100 Black Women. In 2019, she was honored by the Massachusetts Commission on the Status of Women at the sixteenth annual Unsung Heroines of Massachusetts program, held in the Massachusetts State House.

Tucker Underwood resides with her mother in Martha’s Vineyard, Massachusetts. She has one adult daughter, Gretchen Mercer, and two grandsons, Brandon and Jason Mercer.

Gretchen Tucker Underwood was interviewed by The HistoryMakers on August 19, 2019.

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Boston Latin Academy

The Cambridge School of Weston

Southern Connecticut State University

Boston State College

Jamaica Plain High School

William Lloyd Garrison Elementary School

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Favorite Season




Favorite Vacation Destination

Any place warm and sandy.

Favorite Quote

Every shut eye ain't sleep.

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Speakers Bureau Region City

Martha's Vineyard



Favorite Food

Anything anybody else cooks.

Short Description

Academic administrator Gretchen Tucker Underwood (1943- ) worked at Brookline High School in Massachusetts for thirty-seven years as a teacher and dean of students before serving Dukes County, Massachusetts as county commissioner for three terms.


Wilbur Cross High School

Brookline High School

Dukes' County

Favorite Color

It changes by the season.