Dover-Foxcroft – Jefferson “Skip” Leon Prestridge Jr., 82, passed away January 13, 2026, at Massachusetts General Hospital in Boston with family by his side.

Born November 1, 1943, in Brewer, Maine, he was the eldest son of Effie Mae (McGray) and Jefferson Leon Prestridge Sr. In 1961, he earned his high school diploma from RHAM High School in Hebron, Connecticut.

Jefferson went by the nickname “Skipper” or “Skip” by friends and family. Aptly named and following in his father’s footsteps, Jefferson served honorably in the U.S. Navy from 1962 - 1968. During that time, he attended the United States Naval Academy (USNA, Class of 1968) and served aboard the USS Kittiwake (ASR-13) during the Cuban Blockade. Upon leaving the Navy, he started a family and earned a Master’s Degree in Education. A dedicated educator for 36 years (1969 – 2005), he served his communities as a teacher for children with special needs, and as a ninth grade English teacher and football coach, eventually moving into administrative roles. As Principal at the Charleston Mountain View Correctional Facility, he built a therapeutic education program for youth that became a model nationwide. He particularly enjoyed recalling representing the teacher’s union in Hamden in the 1970s, telling the story of picketing with his family to ensure that the teachers’ voices could be heard.

Throughout his life, he expressed unwavering pride and passion for learning and teaching. He taught his children how to change the oil, replace a flat tire, do a layup, build a bookcase, tighten bolts without over torqueing, and what a triple play is. He also instilled in them a love of reading, poetry, and literature, including how to properly recite a poem.

Jefferson decided that in retirement he needed something to keep him busy, so he built a “camp” up at the lake—a two-story, two-bath cabin for everyone in the family to enjoy. He could be spotted landscaping his yard and that of the Dover-Foxcroft Library with his dog by his side.

Jefferson was a loving husband and father. He was extremely supportive of all of the women in his life, encouraging them in their education and careers, and offering advice, support, and mentoring.

Jefferson is survived by his wife, Lori (Perrigo) Prestridge; daughters, Dr. Katherine Prestridge and her husband, Ben Sims, Kristen Murphy and her husband, Brenden, their mother Marcia (Trotta) Prestridge, and Catherine Carpenter; stepchildren, Major Stephanie Hasenfus and her husband, Lieutenant Colonel Alex Brubaker, and Nikolaus Hasenfus; sister, Nina Zahacefski and her husband, Ronald; and several nieces, nephews, and grandchildren. He was predeceased by his parents and his brother, Tommy Prestridge.

A graveside memorial service with military honors will be held 1 p.m. Friday, May 22, 2026, at the Puddledock Cemetery in Charleston, Maine (169 Puddledock Road, Charleston). Arrangements are in the care of the Lary Funeral Home. Messages of condolence and memories may be expressed at www.laryfuneralhome.com. Jefferson loved a good story, so if you have one, don’t hold back. The family would love to hear it. In lieu of flowers, donations may be made to adoptaclassroom.org in his honor.

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Jefferson In His Own Words

Excerpt from Last Will and Testament, dated 19 February 2010.

“I was a Navy officer during time of war and was a master mason of Brainerd Lodge in New London, CT. Served aboard the USS Kittiwake, ASR-13 during the Cuban Blockade. Born in Brewer, ME in 1943. Attended United States Naval Academy 1964-1968. BS, MS, Sixth Year from Southern Connecticut State University. My dad was a submariner during WWII and Korean War and mother worked in the aircraft factory at Pratt and Whitney in Connecticut. I am a grateful son and proud of my parents and heritage. The Prestridge family descends from Thomas Prestridge who was an indentured servant at the end of the 17th Century, emigrant from England to Virginia. Have been a sailor, teacher and school administrator, a descendant of farmers for 300 years of the McGray and Prestridge lines. At times I have erred, been lost and adrift, but have always been blessed with many kindnesses and forgiveness from teachers, neighbors, friends and especially wonderful family for which I am grateful.”

Excerpt from Personal Writings, 2025.

“I’m a student of Thomas Jefferson, Horace Mann, John Dewey and even a bit of Barry Goldwater to name a few. I read the Old and New Testaments in the King James Version because I love the beauty of its lyricism. I like the great discoveries and ideas our ancestors have left for us in poetry, literature, mathematics, and science. I believe in a balanced budget. I own several guns and enjoy shooting them although I would not kill an animal except to provide food for my family. I believe in the nuclear family, single moms and the other families of choice or necessity that exist today. People should work for a living the way my family has as farmers for 320 years in this country. Criminals should be prosecuted with equal justice. Negotiate from strength and never abandon your allies. I support voting and fair elections. I defend our institutions that protect our health and social structure, and insure our national security. I believe in the 14th Amendment that protects our property rights; as well as the entire Constitution, civil rights, and civil discourse without insults and threats. We need a strong military independent from politics. I have proudly saluted the flag at the Naval Academy, West Point, on Navy men-of-war, Fourth of July parades and around the world. I will always salute, but understand why an Olympic champion makes a fist, an athlete takes a knee or a citizen protests with a BLM banner for equal justice. We need a modern professional police force for our communities. Rich people should pay their share of taxes and nobody should be above the law. Old white men should not make my daughters’ health care decisions for them. Women and essential workers must have equal rights and economic access. Maintain a WALL of separation between church and state. “Render unto God what is God’s.”Americans should have fair access to health care and education that gives them practical skills and teaches them respect for all people no matter their race, religion, or ethnicity. I’m a student of Thomas Jefferson, Horace Mann, John Dewey.”

Excerpt from Personal Writings, 2024.

“TEACHERS ARE A CLASS

Teachers as a class (pun intended) have had immeasurable influence on my life. They inspired me to learn, to be open minded to ideas and to all people.

They Inspired me to be physically, mentally and morally strong. They inspired me to care about my country by studying history, battles, leaders, and legal case studies.

They taught me to use a microscope, slide rule, library, basketball and baseball; all opening up worldsof the seen and unseen. They taught me the physics of motion, energy and electricity along with the geometry and calculus to describe what I saw.

Our PE teachers got the boys and girls together and gave what some called "the parts lecture," otherwise many of us would have been clueless.

They gave me logic and reason and taught me to express my thoughts coherently and convincingly.

They taught me to work with others and to practice teamwork that shared victory with my mates, and likewise to own my share of responsibility no matter the outcome.

They insisted on objectivity and the scientific approach to consider empirical outcomes absent personal bias.

They encouraged me to pursue my true love for literature and language to higher levels.

They showed me how to draw and paint to see things inside myself through creativity.

When I came up short in the classroom, courts and playing fields, they took me aside and coached me with high expectations to do my best.

Anytime a whole class of people, police, politicians, firefighters, soldiers or nurses are lumped into one identity there will be flaws, blemishes and shortcomings; just so we find each of us as an individual has room to grow and improve.

Teachers generally have difficulty earning enough money to support their own families. They often work two jobs, tutor and sponsor student activities that consume their afternoons and evenings. This is especially true in Maine and rural communities. Yet they will buy lunch for a child, bring materials to school and contribute to charities.

There is more that I could add. I have seen teachers from positions I have held as a school custodian, aide, colleague, vice principal, principal, adjunct university instructor and superintendent of schools.

Teachers approach their work with serious intensity and compassion. The teacher knows that you must first establish a relationship of trust and caring for an environment of learning to exist. They are exhausted at the end of the day by hundreds of interactions with students who have many psychological/emotional needs. They get external pressures from parents, administrators and school boards. On top of that the political community demands instruction and testing in areas that get in the way of professionalism and productivity. Teachers have been scapegoated and blamed by politicians for everything from Sputnik to over eating, decline in values and drug abuse.

"Teachers' Union" is an oxymoron. I was President of a 600 member union. Within that there were three subgroups the indys "Federation" and the "Association." Teachers are very independent thinkers who will not be led and are further divided politically among Indys, Dems and Repubs.

The only thing that unites them is general consensus on what's good for kids.

American teachers mainstream all students: autistic, ODD, learning disabled, speech and language impaired and physically and mentally disabled among others.

I am grateful for the time they gave to this naive farm boy from Maine to show him the world, to become the first male in his family to go to college.

Teachers are unsung American heroes, my heroes, the soul of grace, the protectors and perpetuators of our society and our way of life.

TEACHERS ARE FIRST CLASS.”

Excerpt from Personal Writings, 2021.

“MEMORY LANE. Celebrated my 21st after the NAVY/ND game in 1964 at a pub in Philly with my first Manhattan.

Soon feeling quite feisty, my classmates and I, heading back to the bus, were halted by a 2/c Midshipman who demanded my name, which was not forthcoming from my saucy mouth. They delayed him while I scooted back to the bus and slouched in my seat with my cap over my face. He boarded the bus, questioned folks and wanted to know who I was.

“He’s been sleeping for an hour,” someone covered for me. He left steaming.

It gave real meaning to the words:NEVER BILGE A CLASSMATE. Go Navy”

Excerpt from Personal Writings, 2021.

“Age brings a new perspective on life and faith.

Kris Kristopherson was visiting a friend and sitting in the church when the words of “Why Me Lord” came to him. He expresses his gratitude for the fortunes in life and declares his contrition for his excesses and errors. He asks Jesus to take a chance on saving his soul.

I have only had glimmers of Radiance from time and plenty of time to reflect on my errors and omissions but haven’t gotten around to writing my final poem as the great Samurai Warriors model so well.

I’m getting along pretty well with the expiation part in my mellow years. For my epitaph and final song, I’m somewhere between Johnny Cash, KK, Van Morrison and Bruce Springsteen.

I just wrote some words for my classmate who passed this month borrowed from VM.

“Smell the sea and feel the sky,

Let your soul and spirit fly

Into the Mystic”

The big Mystery awaits ready or not.”