Tag Archives: “Tuskegee Airmen”

Ted Diamond’s Legacy

Kerstin Rao retired in 2021, after 2 decades as a teacher in Bedford Middle School’s gifted program.

Among her many wonderful experiences was the chance to meet World War II Army Air Corps combat navigator Ted Diamond. He died on Tuesday, at 105.

The longtime Westporter — who (among many other accomplishments) served 3 terms as 2nd Selectman — made quite a mark on Kerstin’s students.

And on her. She writes:

When I read on “06880” that Ted Diamond had passed, I found my heart filled with gratitude for the brief times I got to know him during his Veterans Day visits, when I taught at Bedford Middle School.

For at least 2 decades, possibly longer, Bedford’s 8th grade social studies teachers have organized visits by local veterans each November. The impact of these visits is often profound. Students would come into my classes the rest of the week bringing up points the veterans had talked about, wondering what they would have done if they were in the same situation, and curious about ways to serve the country.

Kerstin Rao and Ted Diamond.

My classroom was usually the gathering place as veterans arrived. The PTA would put together a breakfast, and the vets used that morning time to catch up with longtime friends. There was plenty of talk of grandchildren, ailments, and some razzing between the branches of service. However, I also observed how the older vets were genuinely curious to hear from the younger service members about their experiences.

Whenever I could, I brought my sketch journal. I quietly sat in the back of different classrooms as the vets shared their stories. Some years I made drawings of the men and women as they spoke, jotting down the insights that moved my heart. I’m glad I captured a sketch of Ted and some of his thoughts in my journal.

In 2016, Ted told how some men in his unit held deep racial biases. But when they were pinned down and the Tuskegee Airmen saved their lives, those biases were obliterated.

Kerstin Rao’s 2016 journal includes a sketch of Ted Diamond, and some of the important ideas he shared with Bedford Middle School 8th graders.

In 2017, he brought a photo of his unit. He pointed to a few faces, saying this one was from Michigan, this one was from Colorado. He said he could have brought photos of his wing shot off, or the engine of the plane across the way on fire, but to him, this was the single most important picture. He wanted the students to understand that no matter where we are from, we are one country, working together.

A photo Ted Diamond (top row, 2nd from right) shared with the students.

Ted Diamond stood out to me because every year, without fail, his stories focused on our shared humanity. He had a graciousness and gentle humor that made his listeners lean in. He took us into the moment during pivotal times of his World War II battle experiences. He always left us with the message that we have far more in common than we realize, and this is where the true promise of our country resides.

In my lifetime, I’ve never witnessed such bitter division in America as we have lived through these past few years. Nationally and locally, I am troubled to notice a greater willingness to violate the rights of others, speak in inflamed rhetoric without a willingness to listen, and openly expressed innuendo that violence could be inevitable.

Violence is not inevitable.

Discord is not inevitable.

When we pause a moment, we realize that we dishonor the legacy of our veterans if we allow our country to erode from within. I heard this expressed by several veterans over the years. If Ted has left us a call to action, it is this: Each of us has a choice. We could pull further apart, or we could strengthen our country by working together. We can choose integrity, understanding, and connection which becomes a service to our country.

For this message which guides my own path forward, I am truly grateful. Thank you, Ted.


Ted Diamond’s family is still preparing his obituary. But they sent along a few photos. Here is a century-plus, of a well-lived life.

Ted Diamond is the youngest child in this photo.

Ted Diamond, as a World War II Army Air Corps combat navigator.

Ted and Carol Diamond’s wedding. They were married for 75 years.

Ted and Carol Diamond, and their 2 sons.

Carol and Ted Diamond.

Ted Diamond, looking pensive.

Ted Diamond, with his great-grandson Peter.

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Trey Ellis Tells Tuskegee Airmen’s Tale

Trey Ellis had done a lot of things in his life.

He’s written movies, books and TV shows. He’s been a political pundit, a social critic and a Huffington Post contributor. He’s won a Peabody, been nominated for an Emmy and shortlisted for a PEN Award.

Trey Ellis

Trey Ellis

He teaches at Columbia University, was a non-resident fellow at Harvard, and taught or lectured at Yale, NYU, the University of New Mexico, and in Brazil and France.

But until a decade ago, the Westport resident had never written a play.

That’s when the Lincoln Center Institute commissioned a work by Ellis about the Tuskegee Airmen. He’d already earned honors for a 1995 HBO film on the African American pilots who overcame fierce racism to become one of World War II’s finest US fighter groups. They never lost a bomber.

Ellis and Ricardo Khan turned the movie into an hour-long play, called “Fly.” Originally aimed at students, a longer version was staged a few years later at the Vineyard Theater in Massachusetts, then the Crossroads Theater in New Jersey — one of America’s leading black companies.

It’s since moved on to Ford’s Theatre in Washington — where several of the real Tuskegee Airmen saw it — and the Pasadena Playhouse.

Ellis is very proud of “Fly.” The other day — quoting Martin Luther King — he noted that while the arc of the moral universe is long, it bends toward justice. However, the playwright added, recent racial strife in America has made stories like the Airmen’s more relevant and important than ever.

Fly - Trey Ellis

Now “Fly” — which the New York Times called “a superior piece of theatrical synergy” — is coming to the New Victory Theater on 42nd Street. It runs March 11-27.

Ellis will be there. So will his family — including his son Chet (the name of one of the show’s main characters), and Chet’s friends.

But there’s one more place Ellis would like to see it produced: the Westport Country Playhouse.

“I go to as many productions there as I can,” the playwright says. “I would love to bring this to my adopted hometown.”

Trey Ellis’ Long, Literary Road To Westport

Trey Ellis is an American Book Award-winning novelist, Emmy-nominated screenwriter and Columbia University professor.

Trey Ellis

His books, articles and blog posts — on fatherhood, politics, the black middle class, race relations, pop culture and much more — make him a familiar face on TV and radio shows, and in the pages of newspapers and magazines, as varied as “All Things Considered,” the New York Times, Playboy, Salon and the Huffington Post.

He wrote the screenplay for the HBO film “The Tuskegee Airmen”;  completed a screenplay for Morgan Freeman, and adapted a novel for Whoopi Goldberg, Danny Glover and Spike Lee.

He’s lived in Italy, France and Japan. He speaks Italian, French, Spanish and Portuguese.

He surfs, snowboards, and does advanced yoga.

And, since September, Trey Ellis has been a Westporter.

Growing up in Hamden, Trey “jumped over Fairfield County” on his forays into New York City. But he says he “always liked the idea of Westport.” When he remarried 2 years ago, his blended family drew him here.

Amanda Lynne Freeman

He wanted room — and good schools — for his own 2 children, and their newest son. His wife, Amanda Lynne Freeman — who writes about parenting and relationships — is getting her Ph.D. in sociology at Boston College. And teaching at John Jay in New York.

Westport was a natural fit.

The fit became even more natural when — looking at rentals — Amanda mentioned to one homeowner that she was reading The Three Weissmans of Westport.

“My daughter wrote it!” replied Shirley Schine. (Trey then learned that her daughter, Cathleen Schine, now lives in Venice, California — where he also spent several happy years.)

So here he is. It’s been a wonderful move, Trey says.

“I like the peace and quiet. It’s amazing to look up at a red-tailed hawk, dodge deer, see a hedgehog — and then be at Columbia in less than an hour.”

He calls Westport “clean, progressive and artistic. There are great schools, and very pleasant people. I’m a booster of Westport.”

That may be because, when he and his wife were searching for rentals, they met so many Westport boosters.

“Everyone seemed to have moved here from the city. They all went so far out of their way to help us. It was almost like they’d gotten a hidden memo, to do whatever they could for us.”

Trey Ellis several years ago, with his daughter Ava and son Chet.

Trey is black. His wife is white. Their child is Chinese. Though the specifics of their family are unusual, he says, “people here are open to everything. We’ve met Brazilians, Indians, you name it. There are a lot of international people, and a lot of people who have lived abroad.”

He worried how quickly his children would adapt. The answer: very quickly.

His 8th grade daughter and 5th grade son have gotten involved in school plays, soccer, dance and tennis. His kindergartener has plenty of play dates.

“There’s a lot of color in the schools,” Trey says. “It’s not necessarily black — but there is an international influence there too.”

And — just like New York — there are many blended families.

Though he has a seemingly endless number of projects — a new play premieres at Ford’s Theater in September, and he’s finishing another movie — he’s already looking ahead.

Among Trey Ellis' works are the books "Bedtime Stories: Adventures in the Land of Single Fatherhood" and "Platitudes: The New Black Aesthetic," and the screenplay for "Tuskegee Airmen."

“The book I want to write is ‘My Gay Dad,'” Trey says. His father came out when Trey was 21, and died soon afterward of AIDS.

The book would combine familiar themes — masculinity, fatherhood, the black experience — with a son’s memories. “He taught me about sweetness and softness,” Trey says with pride.

Though he loves Westport, and his family easily adapted to life here, Trey misses some elements of urban life.

“New York is magical at night,” he says. “And museums — it’s hard to find time to get there. I thought I’d have time to do all that. I’m still looking for the perfect balance. My life revolves around the train schedule now.”

He laughs. “I’ve become the guy who races through Grand Central.”

Still, he’s having a great time. He works on the train. He works in the quiet hours in Westport. His family is happy.

And for Christmas, they got him a kayak and paddleboard.