Chamber Chat with Rob Greenstein

By Lori Sachare

At 7 a.m. on a rainy Monday, Chappaqua’s Rob Greenstein darted into Starbucks with the energy of someone who just consumed a Venti espresso–and that was before he got his coffee. He had been up since 4:30 a.m. and already had exercised in his home gym and completed some work for his self-owned law firm.

As fiercely organized as he is motivated, Greenstein runs his personal injury practice, coaches his sons’ baseball teams, and has managed to launch the Chappaqua/Millwood Chamber of Commerce, (along with co-founder Christine Yeres, managing editor of, which boasted over 100 members as of August.

Rob and Cindy Greenstein with their kids Mason, Jessie & Daniel.

Greenstein originally became involved in New Castle issues when he wrote frequent letters to the editor of on an issue he was passionate about: the Chappaqua Crossing project. He later realized that since he had developed name recognition, he could parlay that into another passion of his–helping the Town of New Castle and its merchants– and decided to run for a position on the Town Board.

It was a desire for life in a small town that in 2003 brought Greenstein and his wife of 14 years, Cindy, to Chappaqua from Manhattan. “We love small towns. We go to small towns on vacation,” he noted. Since then, his 8-year daughter Jessie, her twin brother Mason and their 10-year-old brother Daniel have benefited from the fine schools that were one of the reasons for the Greensteins’ move, and Cindy has served as chair of the Westorchard PTA.

Although he enjoys country living, Greenstein saw room for improvement. “This town has potential, but it’s not what it could be,” he commented. He believed the Town Board was on the right track in planning improvements, and decided to run so that he could help. Although he lost the election, he still wanted to assist local merchants.

“We needed a Chamber of Commerce,” he said. And in his get-it-done fashion, Greenstein went about creating a volunteer board whose members, as of July, had no formal titles. The board works alongside a paid administrator, Linda Degelsmith, to put forward the mission of the Chappaqua/Millwood Chamber of Commerce, which is “dedicated to fostering economic growth and to advancing the commercial well-being of the community through strong and vibrant business districts,” according to its website,

As a partner for 17 years in his own law firm (Greenstein & Milbauer, LLP), Greenstein said he understands small businesses. “We have rent to pay, we have a payroll,” he explained. He uses this knowledge to help the chamber with their directive of “connections, commerce and community service.” The chamber was officially introduced in June, and in the same month it arranged for merchants to sell food at the Gazebo concert sponsored by the Town of New Castle and Music In Chappaqua.

Greenstein is proud that the Chamber inaugurated A Taste of Chappaqua this past summer, where local businesses could showcase their food to the public. This fall, Greenstein would like to involve merchants with the Town of New Castle’s Ragamuffin Parade.

The Chappaqua/Millwood Chamber of Commerce is run by five provisional volunteer board members, who work with Linda Degelsmith, a paid administrator. Elections will be held at a later date.

The Gazebo was chosen for the logo of the Chappaqua/Millwood Chamber of Commerce, because Rob Greenstein feels it is a very special place. He would like the Chamber to facilitate the planning of many more fun events there for New Castle residents.

Will Greenstein run again for Town Board? “Maybe,” he responded. Stay tuned.

Lori Sachare is a freelance writer living in Chappaqua.

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