Robert Lee Holland died peacefully on Sept. 5 with his wife Michele, daughter Rashida and son Kiar by his side. He was 88.

He was a Renaissance man whose life was a rich tapestry of roles: psychologist, teacher, veteran, entrepreneur, inventor, fisherman, carpenter, plumber, model, dancer, skater, percussionist, baker, cook, electrician, draftsman, political activist, bowler, floorer, jazz enthusiastic, farmer, son, father, husband, uncle, cousin and friend.

He was born March 13, 1935 in Hollywood, Fla., the youngest of Hazel and Albert Holland’s children. At 15 he joined the U.S. Army’s Harlem Hellfighters, showing early signs of resiliene and dedication. His academic pursuits, funded by the G.I. Bill, led to a master’s degree in psychology from Syracuse University and a doctoral program at Yeshiva University.

His professional path included significant roles in social services, vocational rehabilitation and as the first African-American school psychologist in the Smithtown, N.Y. school district. He was an innovator in student counseling and served as president of the State Association of School Psychologists.

His teaching roles extended to Stony Brook University, Suffolk Community College and mentoring at Empire State Independent Studies Program, an adult program that translated work experience towards college credit in the pursuit of their degrees. In addition, he was hired by the Suffolk County Police Dept to screen police applicants while maintaining his private practice.

Summers off from school afforded Bob the opportunity for a summer venture. He was inspired to invest in property on Martha’s Vineyard as other family members had done. He purchased a “handyman’s special” between Shearer Cottages and his brother Al in Oak Bluffs, and later acquired commercial property on Circuit avenue, where he opened Vineyard Vines Inc., which sold casual and dress jeans and accessories, and Holland House Bake Shop, where he sold his specialty breads and baked goods.

Despite no formal training in drafting but a fluid imagination, curiosity, determination and a vision, Bob conquered the task of drawing up plans for the renovation and expansion of the Holland House, to the amazement of the builders. He did the plumbing, flooring and many other tasks himself, and endured the myriad of frustrations and rewards involved with Martha’s Vineyard property ownership.

After the house was completed, he and his family moved from N.Y. to live on the Island full time for a few years. In 1997 the family moved to Orlando, Fla. but continued spending their summers on the island every year.

Bob’s life was rich with activism: he participated in the March on Washington. Locking arms with Dr. Martin Luther King Jr. during the March was one of his proudest memories, along with meeting Muhammad Ali and Dick Gregory. He also received recognition for his community service.

Besides the birth of his children, his proudest memories also included modeling for the Cottagers’ Fashion Show, being an extra in the movie Jaws and sponsoring the Oak Bluffs summer basketball team.

Bob leaves behind his wife Michele, son Kiar, daughter Rashida McGregor, son in law Brian McGregor, granddaughter Briana McGregor, daughter Sheryl Brown, son in law Todd Brown and granddaughter Heather Brown, along with a multitude of nieces, a nephew, cousins and friends to lovingly honor his life and memory. His spirit lives on in the lessons he taught and the love he shared.

He was predeceased by all of his siblings: Albert, Carrie, Lawrence and Jackson.

A celebration honoring his life and memory will be held Tuesday, Dec. 26 at CB Bistro in Orlando, Fla. from 5 to 9 p.m. To RSVP, contact Michele at 407-595-3749. A celebration on the Vineyard will be held on a date to be determined in 2024.