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Sing Sing Prison Acquires a New Story and Preps for Museum Opening

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Archival image of the Powerhouse Photos courtesy of Sing Sing Museum

In 1929, the New York Yankees played an exhibition game in an unusual location. It wasn’t a major league stadium or even a famous park. And Babe Ruth, Lou Gehrig and their teammates weren’t playing a team known for its athletic prowess.

That game on September 5th was between the Yankees and the Ossining Orioles. The venue? Sing Sing Prison.The Orioles were the best team in the Mutual Welfare League, a.k.a. a prison team.

The Yankees toured the prison before playing in their iconic pinstripes. One man who was incarcerated at Sing Sing was too ill to watch the game, so Ruth autographed his cell wall. Apparently, the Yankees signed a number of baseballs and handed them out. One ball from that momentous game, signed by Ruth and Gehrig, was acquired by Sing Sing Prison Museum just before this past New Year at an auction in Seattle.

The baseball signed by Babe Ruth and Lou Gehrig during a game between the Yankees and the inmates. The ball was recently acquired for the museum.
Photo Credit: MBA Auctions

Brent Glass is the Interim Director of the museum which will open in part in late 2020. He says that ball, which will be on exhibit along with its history, is significant to the museum because it connects several prison stories.

The ball will “help us tell the story of one approach…to try to encourage men who are incarcerated to partake in recreation, and to become integrated in society when they leave.”

It also helps tell the stories of Sing Sing in popular culture.

Glass says Warden Lewis E. Lawes, who was in charge of Sing Sing at the time of the game, implemented a progressive theory about the importance of rehabilitating the men under his watch in part by making life more interesting for them and giving them recreational and athletic opportunities. He was also connected to Hollywood; Lawes had written several screenplays including, “Over the Wall,” about a man incarcerated at Sing Sing of course.

Over the prison walls is where three Ruth homeruns landed that day in 1929. The Orioles wore hand-me-down NY Giants uniforms to face their professional opponents, but that didn’t help. No surprise– the game was a rout. The Yankees won 17-3. And they gave the men of Sing Sing a great show.

A rendering of the powerhouse
Photos courtesy of Sing Sing Museum

A New Cultural Institution

When we think about Westchester’s many cultural institutions, Sing Sing Prison does not come to mind. It doesn’t make any Hudson Valley must-see lists, yet. But that will change in this next decade, with the creation of the Sing Sing Prison Museum, opening in full in 2025. The museum’s founders are on a mission to make the museum one of Westchester’s great cultural tourism destinations.

You might go for the history, or you might go to gain a greater understanding of America’s prison complex. You might be interested in the more macabre aspects of the fabled penitentiary. Or you might go for the baseball.

The Sing Sing museum will be devoted to telling stories like the Yankees game, as well as the full story of the institution and its evolution. It will highlight stories of its brutal past and most infamous prisoners like Ethel and Julius Rosenberg, and those of the ordinary men incarcerated there, as well as their families, and the rehabilitation work occurring there in the 21st century. And the museum’s installations will be designed to encourage visitors to examine the greater social justice issues of the prison system.

“That’s one of our major goals for the museum is to challenge people to reimagine the criminal justice system and to take action to create a more just society,” says Glass.

Glass, who is also Director Emeritus of Smithsonian’s National Museum of American History, says all stakeholders will be included in the creation of the museum. “We want to tell the story of how incarceration has affected everyone at Sing Sing. We want to talk to the men who are incarcerated. What stories do they think are important to tell? We want to talk to people who have been victims of crimes. We don’t want to leave their stories out.” And he says the museum will include the stories of the people who have worked there over the years.

Why build a museum at Sing Sing now? Glass says, “Every chapter in criminal justice history has a few pages written at Sing Sing.” Unlike a popular museum like Alcatraz, Sing Sing is still operating. And he adds that its proximity to New York City and historic sites in the Hudson Valley makes it a perfect location. It will also bring tourism and millions of tourist dollars to Ossining. The museum founders estimate that 260 jobs in the museum and the wider community will be created, as well as 100 construction jobs.

The Sing Sing Prison Museum will open a preview center in 2020 at the Powerhouse on the prison campus. The Powerhouse provided electricity to the prison from the 1930’s to the 1960’s and will be repurposed with the construction of exhibition spaces, classrooms and a theater, as well as space for re-entry programs to help released prisoners acclimate to society.

When the full museum opens in 2025, Glass says visitors will be able to enter the historic cellblock. “We would break into the prison in effect through a secure corridor that would connect the Powerhouse to the historic cellblock which is about 100 yards south of the Powerhouse. The historic cellblock, built in 1825, would be the centerpiece of the visitor experience because it is an extraordinary ruin that nobody gets to see at this point.”

Sing Sing has a notorious past–including 614 executions in the 20th century–but it is working to bring a sense of humanity to its prisoners through a variety of arts and educational programs. Rehabilitation Through the Arts provides year-round theater workshops and performance to the prisoners of Sing Sing. They also run workshops in dance, visual arts, music and creative writing. Hudson Link for Higher Education provides college educational opportunities to prisoners through private funding. The correctional facility has a garden and a professional master gardener, Douglass DeCandia, who works with the prisoners. There are also programs for the families of prisoners.

Perhaps some of the families of early twentieth century prisoners might still have their signed baseballs from the 1929 game against the Yankees. Glass is hoping the museum might be able to acquire a few more. In the meantime, this one will be on view at Sing Sing’s new museum later this year, a wonderful testament to the idea that people who are incarcerated benefit from the occasional diversion and a reminder of what’s possible on the outside.

Six Tidbits About Sing Sing

  • The 1,200 cells in the historic cellblock built in 1825 were seven-feet long, six-and-a-half feet high, and three-feet, seven inches wide.
  • In the 19th century, some prisoners were subjected to punishments like the “shower bath,” similar to waterboarding.
  • David Berkowitz, aka “the Son of Sam,” was incarcerated at Sing Sing.
  • Some Hollywood movies filmed scenes at Sing Sing including “Breakfast at Tiffany’s.”
  • Julius and Ethel Rosenberg were executed at Sing Sing
  • Bruce Springsteen, Joan Baez, Harry Houdini and B.B. King have all performed at Sing Sing

The True Meaning of Friendship: Dr. Jeff Gilbert & Artist Michael Bailey

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(L-R): Michael Bailey and Dr. Jeff Gilbert
Photo courtesy of Dr. Jeff Gilbert

A Chappaqua neighbor famously coined the phrase, “It takes a village.” When Dr. Jeff Gilbert befriended Michael Bailey, a homeless artist, he proved her words true.

Gilbert was on his way back to his home in Chappaqua after the June 22nd Yankee game when he spotted a shoeless man sitting on Babe Ruth Plaza surrounded by pictures of baseball player Aaron Judge and football player Saquon Barkley. He stopped to purchase the five-dollar Judge print, and as he boarded the train, he regretted not buying the Saquon picture. He tracked down the artist via the artist’s website – artofzebra.com – listed on the print.

The artist, 60-year-old Bailey, has been down on his luck and living on the street after a bad marriage, difficult partnership, bout of depression, and subsequent drug problem. Bailey, an architect with an MBA from the University of Chicago, opened the Zebra Gallery in 1990. In 1995, he expanded the Zebra Gallery, establishing Zebra Art, Inc., an art publishing and distribution business. “I had a million-dollar business, and I lost everything. It was going very well for a while. Then, with my divorce, and my son being taken away from me, everything went bad,” says Bailey.

Bailey grew up with his mother and his sister, Helen, in Chicago. Helen, who now lives in California, still maintains Bailey’s site. Bailey’s son, who lives in Tampa, stores some of Bailey’s original artwork. But since 2007, Bailey has lived on the streets of Chicago, New York, Dallas, Cleveland, and various other cities to which he’s traveled, trying to promote his artwork. “I’m trying to show my work,” relays Bailey.

A Friendship Forms

Gilbert became more than another person whom Bailey met in his travels. They became fast friends when Gilbert gave Bailey a copy of his children’s book, Milton’s Moment. “That was a gesture of friendship,” according to Bailey, who refused to take money for the Saquon print Gilbert wanted to purchase.

“I felt like I knew Michael from somewhere as soon as I met him,” says Gilbert, who just “knew Michael was a good person.” Overwhelmed by Bailey’s story and kind nature, Gilbert invited Bailey to dinner and then to visit him up in Westchester. “We have so many resources available up here. Things that Michael could never access on his own,” notes Gilbert.

A Supportive Community

But Gilbert couldn’t change Bailey’s life on his own. So, he reached out to his wide circle of friends and to the Chappaqua, Briarcliff, Pleasantville, and Armonk communities via FaceBook to tell Bailey’s story.

Thanks to the power of positive social media and community support, Gilbert witnessed “so many members of our community mobilizing to make a difference in this man’s life.” Helena Terilli, Co-President of the food pantry at the Methodist Church in Pleasantville, bought Michael almost $300 of new clothes. And the community has contributed almost $5,000 to the gofundme.com page that Gilbert established for Bailey.

“I meet a lot of people in different cities,” noted Bailey, “but it was Jeff who changed my life.” For the first time since 2007, Bailey is no longer sleeping on the streets. While he does not have a home yet, he is staying in hotels as he travels the country to show his work.

Thanks to Gilbert’s efforts, Bailey’s artwork is also being exposed to a significantly wider audience. In June, he was invited to show and sell his work in Pleasantville at Yogolicious and The Village Bookstore.

The opportunity to connect to more people and to show and sell his work to people who didn’t know anything about him six months ago, is deeply meaningful and life-altering for Bailey, who sees art as his spiritual calling. “Art is my gift from God. When someone buys a piece of art from me, I tell them that I am sharing this gift.” Bailey generously shares this gift with others, often giving children free prints of their favorite athletes, superheroes, or musicians.

Late this summer, Bailey spent some time in Chicago, working on a painting of the New York Yankees’ veteran pitcher, CC Sabathia. He showcased it at the table that The Rotary Club of Chappaqua donated to him for Chappaqua’s Community Day on September 14th. Gilbert also arranged for Bailey to show his art at the Chappaqua art gallery, The Art Closet.

Future Plans for Bailey

After Community Day, Bailey spent a few days selling prints outside of Yankee Stadium before he hit the road once again. He then returned to sell his prints at the Chappaqua Children’s Book Festival on October 5th. In the coming months, Gilbert will continue to look for “creative ways to help Michael.” No doubt, he will continue to rely on his “village” for help.