Winfield Holden Jackson

MONMOUTH – Winfield “Win” Jackson passed away on May 25, 2024, at his Monmouth home one week after his 78th birthday.

Win was born in Lisbon and spent his early years in East Bridgewater, Mass. His family moved to Monmouth in 1956 and Win began his 5th grade year there. Monmouth’s smaller environment provided Win a lot of opportunities starting with Little League baseball and later other school sports that were all great outlets for his competitive spirit. He graduated from Monmouth Academy in 1964.

An important choice Win made with the encouragement of his grandmother was to attend Antioch College in Yellow Springs, Ohio. Antioch was a five-year college with a strong Co-Op program. During his five years at Antioch, he had some exceptional experiences that made him more than ready for the world of work.

Win’s early work years were in the field of higher education and his first job was as a member of the Co-Op department at Wilberforce University in Ohio. Later he was hired to establish a Co-Op program at Central State University (CSU). During his tenure at CSU he initiated, in partnership with Model Cities of Dayton, Ohio, a college program that addressed the needs of non-traditional students in the Dayton area. That program continues, has expanded, and is known as CSU-Dayton.

Win’s years in higher education also included a stint for several years at the Academy for Educational Development where he was a consultant in finance to a variety of colleges and universities. During this time, he and a colleague were assigned to assist Saint Thomas University with financial issues that had arisen while trying to start a law school for Spanish speaking individuals. They hoped to attract students who would serve the nearby Hispanic neighborhoods that badly needed representation by people who could speak Spanish. Working with the trustees of the college they were able to get the college financially back on track including a path forward for the law school. That school thrives today known as the Benjamin L. Crump School of Law at St. Thomas University.

The culmination of Win’s work life was at Alternative Manufacturing in Winthrop. He was Initially hired in 1992 as a consultant during its early years of manufacturing circuit boards. Later, in May of 1993, Win was hired in the role of President and Chief Executive Officer and held that position until his retirement in May of 2010. He was an important force in growing the company and expanding their customer base. He was always proud that AMI, due to their out of state customer base, was importing money into Maine and proud of the workforce that was the foundation of their success.

For all Win’s work adventures, he was in his heart a family man and homebody. Home was his refuge and he designed the family home in Monmouth where they have lived for 35 years.

Win and his wife Heidi met when they were in the 5th grade, were married for 57 years and deeply appreciated the good life they shared together. In 1982 they were blessed by the birth of their daughter Emily, and she never lost her place as the apple of his eye. More recently, he happily welcomed the additions of his son-in-law, Jeremy Johnson, and grandson, Henry.

Win was a gregarious person and enjoyed interacting with people. He was passionate about politics, the Red Sox, and good food. He also enjoyed playing golf at Cobbossee Colony in Monmouth where he was a caddy in his youth. Though he was compromised by an illness in his last year, he increased his reading on subjects of interest, sharing what he learned with others.

Win was predeceased by his parents Holden and Dorothy Jackson.

He is survived by his immediate family members mentioned previously; his sister, Debby Smiley, brother-in-law, Dean Smiley, nephew, Aaron Smiley, his wife Martha; brother-in-law, Mert Dearnley, his wife Dede; brother-in-law, Fred Dearnley, his wife Stacey Hodges, a niece and several nephews.

The last months of Win’s life were made better by the assistance of the nurses and aides from Hospice.

Any donations in his memory can be sent to Hospice as follows:

Andwell Health Partners

(their new name)

15 Strawberry Ave.

Lewiston, ME 04240