Journalism and Judaism: Kassy Akiva Speaks with The Commentator

Growing up in Chicopee, Mass., a struggling former mill town, Kassy Akiva (formerly Dillon) never gave much thought to Judaism — let alone imagined she would one day become an Orthodox Jew herself.

“We celebrated Christmas and Easter, but only as a cultural thing — like any typical American family,” Akiva, a reporter and video journalist for The Daily Wire, said in a conversation with The Commentator in early March. “There were maybe one or two Jewish people at my school, but nobody knew they were Jewish.”

Akiva, who converted to Judaism in April 2023, was previously a reporter for Fox News Digital and an editor at Jewish News Syndicate before joining Ben Shapiro’s conservative media company. Few would guess that she was raised by a single mother in a small Massachusetts town where approximately 15.2% of residents live below the poverty line.

“It was a rough place,” Akiva said of Chicopee. “A lot of people I was really good friends with in high school are now addicted to drugs or had very young teen pregnancies. When I was in school, one of my classmates got shot at a party and died.”

By the age of 16, her mother’s struggles with mental health and addiction forced Akiva to grow up quickly. She moved in with her older sister, balancing high school with a nearly full-time job working 25 to 30 hours a week at a daycare. “I was paying rent, buying my own food and had a car,” Akiva recalled. “I was pretty much an adult already — but I didn’t know anything else. It was just normal.”

Akiva soon became the first in her family to attend college directly after high school, enrolling at Mount Holyoke College in 2014 to study history and politics. As one of the lone conservative students on campus, Akiva quickly realized her politics set her apart from the rest of the predominantly left-leaning student body — a realization that would eventually drive her to enter journalism.

“I was still forming my beliefs at that point,” she said. “So, when I got to Mount Holyoke and they were asking my pronouns, I was very confused. During orientation, they were talking about ‘down with the patriarchy’ and cutting off a girl’s ponytail on stage, and I was like, ‘What did I do? Why am I here?’”

“It wasn’t college itself that was a culture shock — it was Mount Holyoke,” she added. “I knew things about politics and current events. But I didn’t understand that colleges weren’t friendly places for people who believed the things I believed.”

It was also this politically charged environment that sparked Akiva’s curiosity about a tiny Middle Eastern country she had previously known little about. During her freshman year, she enrolled in a course on the Middle East taught by a professor she described as openly hostile toward Israel. “He was assigning papers that were essentially textbook antisemitism,” Akiva said. “They didn’t present the other side at all. I was confused and started wondering, ‘Where is he getting this from?’”

Around the same time, Akiva received a phone call from a friend visiting Jerusalem who had just been attacked by an Arab. 

“He called me from the hospital and told me he had been stabbed with a broken bottle because he was Jewish,” she said. “I basically told him, ‘You’re crazy. Nazis don’t exist anymore.’ I had no idea what was happening in Israel.”

Just a few weeks later, three Israeli boys — Eyal, Gilad and Naftali — were kidnapped and murdered by Arab terrorists in the West Bank. “That’s when I started paying attention,” Akiva said. 

In the summer of 2016, Akiva signed up for a bipartisan, non-Jewish trip to Israel with young Republicans and Democrats from across the United States. On that trip, which she said she spent most of “partying and making friends across the [political] aisle” she was spontaneously baptized at the Jordan River. However, the memory that sticks out to her most from that summer was the Friday night she spent at the Kotel.

“It was packed,” she said. “People dancing, singing. It was overwhelming. One of the Christian girls on my trip told me later that I said, ‘I’m going to convert.’”

“I don’t even remember saying it,” Akiva said. “But she wrote it in her journal.”

A year later, Akiva studied abroad at the University of Haifa, where she fell in love with Shabbat. After returning to Mount Holyoke, she began studying under the guidance of a rabbi, reading Jewish books, eating at the kosher dining hall and lighting her first Shabbat candles in her dorm room. However, it would be years before she fully committed to Torah observance.

Her formal conversion process began in 2022. It was challenging, she said, slowed down by rigorous questioning from rabbis, frustrating delays and months spent immersed in Jewish studies at an Orthodox seminary in Israel.

“I’m annoying — I’m very Type-A, very persistent. You can’t tell me no,” Akiva laughed. “I showed up to my meetings with the beit din with folders full of papers. I documented every meal I ate and the families who hosted me. I kept lists of every book I read and every mitzvah I observed. I wanted to show them how sincere I was. But what they really wanted to see was growth — to make sure that from my first meeting to the last, I had learned a lot and had become humble.

“There were times when I got really frustrated. Rabbis would ghost me, not respond to emails for months and it drove me crazy.”

Finally, the day after Purim in 2023, Akiva received the news she had waited years for.

“They said, ‘All right, you’re ready,’ and I was shocked,” Akiva recalled. “I cried and began to question whether I was worthy,” she wrote in Commentary Magazine about the moment. “That’s how I knew I was ready.”

Today, Akiva, who chose the Hebrew name Devorah Ruth, is one of the few Orthodox Jewish women working in journalism. At The Daily Wire, her newfound faith has given her a deeper sense of purpose in her reporting.

“Me being Jewish has not changed my beat per se,” Akiva said. “But it’s made me more of an expert in it. I’m a more trustworthy person to cover Israel and antisemitism at The Daily Wire because a lot of people there aren’t Jewish and don’t understand the complexities.”

While being Orthodox in the media world has come with its share of logistical challenges, Akiva says she’s found ways to navigate them.

“Political journalism is brutal — some of the worst people you’ll ever meet are in this field,” she said. “But people are respectful to my face. I don’t know what they say behind my back, though. I’m sure people think it’s weird that I wear a wig.

“The hardest part is when I’m working on long assignments and my crew goes out for food,” she added. “When I’m on a shoot and there’s no kosher food, I’ll sit there with Diet Coke while my crew eats. Then I go home and eat cereal. When I was covering the U.S.-Mexico border in Texas, I didn’t eat hot food for five days because there was no kosher food anywhere. That was miserable.”

When asked if she recommends journalism as a career for an Orthodox individual, Akiva warned of the risks involved and the antisemitism that comes with that particular kind of publicity.

“I literally just got a message from somebody calling me the K-word,” Akiva said casually towards the end of the conversation. “If you’re a Jewish journalist covering Israel and antisemitism, it’s dangerous. My inbox is full of people being really hateful … If you want to be public like I am, you have to be really careful.” 

For those determined to make it in the field despite her warnings, Akiva’s advice was to focus on building as many connections as possible at an early age. 

“The only reason I got hired by The Daily Wire when I was 19 and in college was because I reached out to them,” she said. “I was already trying to report and made that connection.” 

“Another mistake students make is trying to be commentators before being journalists,” she added. “People don’t want to hear all the thoughts of a college student. They want to see that you can report first. Go into a breaking news internship and learn how to write a real story before trying to be a thinker.”

When asked what is next for her, Akiva replied that she is happy where she is. “I don’t want to be an editor,” she said. “I don’t want to do a podcast. I like being a reporter.” 

“Right now, my focus is growing in Judaism and my family — that’s my priority.”

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Photo Caption: Kassy Akiva reporting for The Daily Wire.

Photo Credit: Kassy Akiva