Getting to Know Your Westwood Neighbor: Jim Reilly, Army Veteran

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Jim Reilly is an Army veteran who resides in Westwood with his wife and three children.

Editor’s note: As Veterans Day approaches, Westwood Minute continues its coverage this week that highlights veterans who have served and sacrificed for our country.

I first interviewed Mr. Jim Reilly in May of this year, intending to commemorate Memorial Day with a feature on a veteran. Before moving to Westwood two winters ago, Mr. Reilly had achieved the rank of captain while serving in the U.S. Army. But I revised my publication plans based on his comments.

“I’m always uncomfortable when people wish me a Happy Memorial Day. Memorial Day is to remember those who gave the ultimate sacrifice in service to the country,” says Mr. Jim Reilly. Mr. Reilly notes that he wears a memorial bracelet in remembrance of a good friend who was killed in Afghanistan.

“My West Point class still has the most members who have died in the global war on terror since 9/11,” he says. “When someone wishes me Happy Memorial Day, you are talking about me in November.”

Veterans Day is this Thursday, November 11, 2021 and it's prime time to introduce the community to a neighbor who has honorably served.


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Mr. Reilly served in the military for ten years, from 2004 to 2014, with four deployments to Iraq of 12 to 15 months each. He is a 2004 West Point graduate, having been recruited as an athlete to that school by the lacrosse coach. 

Image by West Point - The U.S. Military Academy from Flickr

The military presented the combined draw of not having to rely on his parents to pay for school and the opportunity to join a brotherhood of teammates and classmates, he says. West Point and the military provided a general team atmosphere that he enjoyed and in which he thrived.

Upon graduation from West Point, Mr. Reilly was commissioned as a second lieutenant. His first duty station was Fort Riley, Kansas, where he served as an officer of the armored calvary. It was no surprise to him when he was deployed from there to Iraq, with 9/11 still fresh in the nation’s memory.

In Iraq, he joined a tank platoon unit of 15 other men. What struck him about Iraq was how hot, dry, and poor the country was, and by contrast, how well Americans live in the United States.

“Even the poorest people in the United States are better off than the majority in Iraq,” he observes.

The mission of his unit in Iraq was to provide security along the main supply route - the highway between Iraqi cities, from Kuwait to Baghdad and from Baghdad to Mosul. Tanks would patrol up and down, ensuring that military supplies and food could be transported. There were occasional small arms fire, and snipers were the biggest threat. He and his unit also needed to be wary of improvised explosive devices (IEDs) and other types of roadside bombs.

Image by Expert Infantry from Flickr

At the time Mr. Reilly arrived in Iraq, conflict surrounded the country’s first democratic election. There was “a lot of violent turmoil” he says, as Al Qaeda attempted to disrupt democracy from taking hold.

Mr. Reilly recalls the first time he experienced his tank being hit by a roadside bomb. He said, “You freak out. You keep driving. You’re shaking and there’s dust. Debris gets into your eyes. It feels like five minutes to get your bearings, but it’s probably ten seconds. You check to see that everyone is okay. Check the tank. But you’ve practiced this scenario before. You fall back on your training.”

And then, incredibly, “It becomes sort of normal after a while. It happened about once a week that the platoon would get hit by a roadside bomb,” he says.

Thankfully, Mr. Reilly never experienced any deaths under his command. There were bangs, bruises and concussions from roadside bombs. A good friend was shot by a sniper. He and his unit secured the area, returned fire to neutralize the threat, and got his friend first aid. His friend has recovered and is still serving in the military.

Mr. Reilly came back home in 2011 and was stationed at Fort Hood in Texas until 2014. He met his future wife Colby, then a student at Baylor University in Waco. Because he didn’t envision himself raising a family with the frequent, extended absences required by a military career, he left the armed services for civilian life. He worked for an oil and gas pipeline company for two years. He and his wife welcomed their first child, Livinia.

In 2016, the family moved to Massachusetts to be closer to family. Mr. Reilly is originally from Connecticut and his wife’s family is from the nearby towns of Dedham and Medfield. He worked at CVS Health in Woonsocket, Rhode Island, and they welcomed another daughter, Shea. He applied to law school.

In 2019, Mr. Reilly started classes at Suffolk Law in Boston on a dual JD and MBA degree program. While he is hitting the books now and looking ahead to graduation in May 2022, Mr. Reilly has also been building experience as an IBM intern and privacy analyst. He provides advice on breaches of security. It’s a mix of law and business which he enjoys. Down the road, he doesn’t view himself as a litigator, but could pursue something related to business law.

Suffolk Law School sidewalk by Mistermuckle from Flickr

Given an opportunity to reflect on life after the military, Mr. Reilly notes that he appreciated the opportunity to live in Iraq, a country that is not as fortunate as ours. It has given him a perspective that enables him to have less to complain about on a day-to-day basis, he says. 

Mr. Reilly notes that in some ways, being in the military was the best job in the world, with team camaraderie and a focus on accomplishing the given mission. At other times, it was the worst, he says, as he remembers the risks and the times he has seen someone get hurt.

As to his new life with his expanding family in Westwood (a third daughter, Allie, was born this July), he says, “We haven’t taken full advantage of the community due to the pandemic, but love the neighborhood and the community. We’re looking forward to getting more involved as much as we can.”

Thanks to Mr. Jim Reilly for being interviewed for this article.



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