Doing Well
by Doing Good

The Story of Arthur Winn

by Joshua M. Sklare,
Michael L. Cramer

Pages from Doing Well by Doing Good: The Story of Arthur Winn by Joshua M. Sklare and Michael L. Cramer

Arthur Winn’s road to success began rather modestly in Brookline, Massachusetts during the 1940s and ’50s. After losing his father at age 16, Arthur grew up quickly, learning that the only way to control his destiny was by working hard and thinking fast. While some people might describe him as the “best developer of affordable housing in America,” he sees himself a bit differently. In his mind, life must be about helping people, both as individuals and as communities. The desire for financial independence may have been his goal, but making a positive impact on society became the real end game. 

As a real estate developer and as a father and grandfather, Arthur has built a lasting legacy based on five simple words: Doing well by doing good.


The Winisky story and the Winn legacy began long before Joseph met Bea Connors on a Boston sidewalk. The tale began with Joseph’s parents in the year 1902, not in Beantown but in the small Baltic country of Lithuania. On July 3 — one day after American troops ceased fighting in the Philippines and one day before America celebrated its 126th birthday — Mordechai Winisky, son of Yerachmiel and Chana, married his young bride, Esther Pearlstein in Vilnius. Known by its Jewish inhabitants as Vilna, it was the largest city in Lithuania, then part of Czarist Russia. Vilna was known as the “Jerusalem of the North.”

Mordechai and Esther were not just from Lithuania, they were of Lithuania which meant that, like all other Jews from this region, they were referred to as “Litvaks.” What exactly was a Litvak? For one thing, it meant you were highly unlikely to be attracted to the mystical movement known as Hasidism that swept through parts of Eastern Europe during the 18th century. Litvaks were known for their sharp minds, dry wit, analytic reasoning skills, and keeping their emotional side, which attracted so many to Hasidism, in check. They were also known for their moral straightness and charitable nature. One can imagine that Arthur, the grandson of two Litvaks, might have acquired some of his out-of-the-box thinking and problem-solving prowess, not to mention his intellectual tenacity, from those Lithuanian roots. After all, Arthur once described himself in the follow way: “My son says I’m a perfectionist. I grind it into the ground and understand it better than anyone else in the world.” Sounds like a Litvak!

Mordechai Winisky had established himself as a shoemaker, a solid and indispensable profession. If you lived in Lithuania at the turn of the last century, you did not head for the Chestnut Hill Mall when you needed a new pair of shoes. You paid a visit to the local cobbler, who would craft the shoes from scratch. Such were the economic circumstances; there were hundreds of shoemakers in places like Vilna, all eking out a similar living. Like many others in Vilna at that time, Mordechai and Esther were recent arrivals. The Winisky family hailed from the small town of Bystrytsa, about 24 miles northwest of Vilna. The Pearlsteins came from a larger town, or shtetl, called Stoklishok. It’s nothing new in the modern era — either in Lithuania or America — when people leave small towns for the greater economic opportunities in the city.


Montefiore Press