Yesterday’s announcement that J.C. Penney filed for bankruptcy did not affect many Westporters. The chain’s closest locations are in Trumbull and Danbury, and it’s been fading from public consciousness for years.
But there is (of course) a local connection.

J.C. Penney
When the founder of what was then a retailing behemoth died in 1971, age 95, the New York Times obituary noted that into his 90s he commuted 3 days a week from Connecticut to the store’s 6th Avenue headquarters in New York.
He lived for many years on Beachside Avenue, just south of the entrance to Greens Farms Academy.
The Times added this anecdote:
His conviction that merchants should exert themselves to serve their customers reached an inadvertent extreme a few years ago. A new resident of Westport, Conn., needed some paint in a hurry and looked up J. C. Penney in the phone book.
When a man answered the call, the potential customer asked, “Does the Penney Company sell paint?” The man re plied, “I believe we do, but let me confirm it.” He was heard dialing and then speaking on another phone. Returning to the inquirer, he said, “Yes, we do.”
What the caller did not know until later was that he had not been speaking to someone at J. C. Penney store, but to James Cash Penney, the founder, then in his late 83’s, who was also a Westport resident.
(For the full obituary of J.C. Penney, click here.)
When I worked for Mr. Lewis Gordon on the FT Bedford estate located on Frost Point on Beachside Ave. I was edging the driveway and saw Mr Gordon talking to a white haired gentleman across the street. I wandered over to ask a question but realized they were in deep conversation about something so I backed off. It was JC Penny himself!
I knew the Penney company in the 80s as my company printed their catalogs and I was part of the sales team. J C Penney was an American retail success story. James Cash Penney having joined and later bought out the partners of the original company – named the Golden Rule Stores – before changing the name but still operating under the Golden Rule. Alas, companies change and, with their move from NYC to Dallas in ’90, that was the beginning of the company losing its way. I recommend the book “Celebration of Fools: An Inside Look at the Rise and Fall of JCPenney” written in ’04 by Bill Hare (his brother Jeff is a Westporter). Bill Hare was Penney’s executive speech writer and his detailed knowledge of everything and everyone makes for a page-turner of a read.
J.C.Penney, the store, was originally a 5 and 10 (sometimes called a 5 and dime), along with F.W.Woolworth and H.L.Green. There was one of each of these in Norwalk in the 30s and 40s. Another was S.S.Kresge, later to become K Mart. There was a 5 and 10 in Westport on Main St. before Klein’s moved to that location.
Fascinating story! I also remember a 5 & 10 in the Compo plaza (am I mistaken?) that also held Finast (grocery)on the east corner, Morris’ Luncheonette (yummy hotdogs/franks & there was a Morris!), Silver’s, Franklin Simon on the west corner & I think Sam Goody (before it moved to Playhouse Square?) among others. PS – parking @ Finast was no fun!
My father was an attorney for JCPenney for almost 30 years. He did his Westport-NYC commute as well!
My mom and I met
Him and his wife on Compo Beach when I was two. He convinced my mom I should model. My
one real claim to fame was my
picture In Children’s Vogue when I was three.
His house on Beachside Avenue was designed by local architect Charles Cutler, Barlow Cutler Wotton’s father.
I grew up in Kemmerer Wyoming where the original golden rule store was started and still has (had) a J.C. Penney. Now inline in Westport. I am like a way less rich and famous J.C. Penney.
Every time I think I must have heard about all the famous people who have lived in Westport, or live here now, one more name pops up. So J.C. Penney goes on the list now. Hilarious story about him answering the question about paint, He was old line retailer down to his marrow, and that breed would spare no effort to avoid losing a sale.