This Hudson Valley Family Has Major League Baseball in Their Blood

When two of your sons are picked up in the Major League Baseball draft on the same day, life is suddenly a whole different ball game.

When Caden Dana was 10 years old and getting ready for his Montgomery elementary school’s annual field day, his mother Amanda made what might seem like a counterintuitive request: she asked him to lose.

“He was all set to compete in four different events, and I told him to think about holding back a bit so that another kid could get a win,” she recalls with a laugh. Though his mom often referred to him as her “Gentle Giant,” and he cared deeply for his friends, Caden was bigger than his classmates and so athletically gifted that he had a sizable natural advantage. “It just felt like the right thing, to give other kids a chance.” Caden agreed.

Caden Dana
Caden Dana. Courtesy of the Tri-City Dust Devils.

He was the fourth child born to parents Fred and Amanda Dana, both lifelong athletes. When his older brothers Cullen and Casey were nine and seven, they were already playing travel baseball for a 9U (nine and under) team called the Montgomery Generals because they didn’t want to wait to be old enough to age into local rec leagues. “At three, Caden was the team’s bat boy and he loved it.”

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Casey Dana
Casey Dana. Courtesy of the Tri-City Dust Devils.

In other words, Caden watched everything his brothers (and older sister Kyleigh) did, and then he did it, too. “He started swimming at age two and rode a bike without training wheels at three,” says Amanda. “Really it was just abundantly clear all along that the four of them were drawn to sports and had very strong competitive instincts.”

Kyleigh, age 12, with her first game ball.
Kyleigh, age 12, with her first game ball. Courtesy of Amanda Dana.

When the eldest son, Cullen, was going into 9th grade, he got an invite to a football camp at Don Bosco Prep in Ramsey, New Jersey. After his first day, the head coach called to strongly encourage the Danas to enroll Cullen so he could be the starting quarterback for the Don Bosco freshman team. “We had to make a quick decision and it turned out to be the right one,” says Amanda. All three boys ended up at Don Bosco Prep to plug into the amazing athletic program and prepare to head into NCAA Division 1 college programs at Seton Hall University (Cullen), University of Connecticut (Casey), and University of Kentucky (Caden).

Casey, Amanda, Kyleigh, and Caden after a game.
Casey, Amanda, Kyleigh, and Caden after a game. Courtesy of Amanda Dana.

Fast forward to a typically hot summer day a little over a year ago—July 19, 2022, to be exact. That’s when Amanda saw her second- and third-born sons’ dreams come true in a way few mothers ever will.

The Major League Baseball’s (MLB) annual draft was underway. Caden, a right-handed pitcher who led his high school team to the Non-Public A state championship and No. 1 spot in the statewide rankings, was drafted by the Los Angeles Angels on the third day, in the 11th round. Mindbogglingly, he was not the first, but the second Dana son to be drafted by MLB. Four years prior, in 2018, Cullen had been drafted by the San Diego Padres.

The Dana siblings, Casey, Caden, Kyleigh, and Cullen.
The Dana siblings, Casey, Caden, Kyleigh, and Cullen. Courtesy of Amanda Dana.

Not long after, Casey was drafted in the 16th round. By the Angels, no less. And just like that, both brothers were on their way to the majors. Together. “It was just the most amazing time for them,” says Amanda. “For all of us, of course, but especially for them.” It was the culmination of over two decades of fierce determination, plenty of hard work, and the commitment of the entire family.

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Describing herself as “a loyal fan,” Amanda freely admits that their family life literally revolved around sports from very early on. The Dana kids, at varying times, played baseball, football, softball, and volleyball. “At times it could get a little crazy,” she says. “There were days when I had four kids playing on four different fields. It was like, ‘What do we do here?’” The answer was for her and Fred (they have since amicably divorced) to divide and conquer.

Amanda and Caden at the 2022 non-public A State Championship.
Amanda and Caden at the 2022 non-public A State Championship. Courtesy of Amanda Dana.

Fred owns and runs Dana Distributors, a successful beverage distribution company, and is part of an executive team managing the Blue Sky Sports Complex in the town of Wallkill. Amanda is the director of tourism for Orange County, the executive director of the Orange County Film Office, and president of Hudson Valley Tourism. They constantly scoured the kids’ sports schedules and compared them against their own work obligations. Amanda says that she had to learn to work, as she puts it, “extremely efficiently,” because the goal was to always (or almost always) have a parent there. “We did a ton of driving, and there were times when Fred and I literally drove past one another on opposite sides of the same road, heading to different games.”

Cullen and Casey on the Don Bosco Prep football team.
Cullen and Casey on the Don Bosco Prep football team. Courtesy of Amanda Dana.

They were out there watching and cheering in snow, hail, and extreme temperatures. Life was hectic, but they felt the tough logistics were worth it. “To us, it was normal. And we believe team sports are a phenomenal way to build friendships and lay the foundation for solid character and resilience,” she says. As athletes, they learned to crave success and do what it takes to win. Doing what it takes includes countless rigorous practices, consistently eating right, getting plenty of sleep, and sometimes missing parties or other fun social events. Athleticism at their level means a 360-degree commitment, Amanda points out. “And it really was our family lifestyle. I mean, we turned tournaments into vacations.”

The Dana brothers.
The Dana brothers. Courtesy of Amanda Dana.

But she believes they also had genetics on their side. Both parents were accomplished athletes in college, he as a baseball player and she in both track and field and volleyball. “Because of his college experience, Fred knew so much about what it takes to make a play for Major League Baseball, and he shared that information with the boys, explaining the many ins and outs to help maximize their chances of getting picked up in the draft. Amanda gives her ex-husband “a huge amount of credit” for the kids’ success.

Bat boy Caden, age 3.
Bat boy Caden, age 3. Courtesy of Amanda Dana.

Of course, MLB contracts were the dream. “When people asked my sons what they wanted to be when they grew up, they didn’t want to be doctors or lawyers. They wanted to be pro baseball players,” says Amanda. But sports also, as she puts it, “rounded them out as good humans.” They developed strong work ethics and learned how to play through pain and cope with difficulties and disappointments, like strikeouts in key innings and important games that ended in the loss column. “The boys kept their eyes on the target and learned over time to handle hard times and commit themselves to doing better,” she says. “They also figured out that a sense of humor can help, which is a terrific life skill.”

Baby Cullen with Fred.
Baby Cullen with Fred. Courtesy of Amanda Dana.

Sports rounded them out as good humans. They learned how to play through pain and cope with difficulties and disappointments.

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In the end, at least for now, the sport that had long held the family together has taken two of the boys away for a sizable part of the year. The Dana brothers live together in Washington state and play for the High-A affiliate of the Los Angeles Angels organization, the Tri-City Dust Devils. The team plays in Gesa Stadium in Pasco, one of three cities (along with Kennewick and Richland) that make up the state’s Tri-Cities metro area. Caden, 19, is a pitcher, and Casey, 24, is an outfielder. At press time, they were due home in mid-September for a month or so during off season, but will then head down to Jupiter, Florida, to settle in for winter training.

Casey, Amanda, and Caden.
Casey, Amanda, and Caden. Courtesy of Amanda Dana.

Of course, Amanda misses her boys when they’re away working, but this was always the goal. “They were the ones that kept at it, we just supported them as best we could,” says Amanda. “Now they’re living their dream.”

Casey, 10, Caden, 5 and Cullen,12.
Casey, 10, Caden, 5 and Cullen,12. Courtesy of Amanda Dana.

Meanwhile, her other two kids are still local, and Amanda is grateful for that. Unfortunately, Cullen experienced a career-ending injury (a torn labrum) and was released by the Padres’ farm team in March 2022. “He has recovered beautifully, he just can’t be a Major League Baseball pitcher anymore,” she says. Daughter Kyleigh graduated from the University of Tampa this past May. Both work in the family business and still love sports. Cullen, 26, is an avid golfer, as is Kyleigh, 22. “She still plays volleyball and pickleball, too,” says Amanda. “I just played pickleball with her last night, she’s really good.”

By The Numbers
The Dana brothers’ major league stats:

Related: Where to Play Pickleball in the Hudson Valley

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