OTIS — The O’Brien family is approaching the second anniversary of the night their 20-year-old son, Jack, was killed in a snowmobile accident. Since then, they have mourned and cried, but they have also honored his memory by raising nearly $250,000, donating much of it to help everyone from children to the elderly.

“It’s funny because he was so humble. He’d be embarrassed because all the attention is on him, and he was not that type of person,” said Jack’s mother, Star O’Brien.

“It’s taken us almost two years to get to the point where you smile more than you cry, and that’s what he would want. He wouldn’t want us sitting every day, crying and not living our lives,” she continued.

The idea to honor Jack came in the days following his death in the western Adirondacks in New York. The family established the Smile Like Jack Memorial Fund, aptly named for a young man who exuded happiness.

“When we lost him and started digging around for some pictures, we couldn’t find any where he wasn’t smiling. Whether you were mad at him, arguing with him, telling him what to do, he always smiled,” said Mike O’Brien, Jack’s father.

Giving and recovering

In the last two years, Smile Like Jack has raised nearly a quarter of a million dollars, giving $150,000 back to the community by funding scholarships, donating money to the Otis Senior Center and helping fund the local food pantry. The fund also paid for a local veteran’s seeing eye dog and recently gave $10,000 to St. Mary’s High School in Westfield to help the school buy a 12-passenger van.

Raising and donating money to the community has helped the O’Briens grieve and recover from the death of their son.

“We know he’d be proud of us for doing this. It helps because we’re doing good for kids, young adults and senior citizens. We’re doing something that he would be proud of to keep his name going,” said Jack’s mother.

Star O’Brien remembers the exact moment — 10 minutes before midnight — when she got an emergency call from a family friend who had been snowmobiling with Jack. The friend called to say her son was missing. Mike O’Brien jumped in his truck and began the nearly four-hour trip to where Jack was last seen.

On the ride to New York, Mike O’Brien received a call from police, who confirmed his worst fears.

“He told me the news I didn’t want to hear, but I already knew — Jack was no longer with us. I called Star at 2 o’clock in the morning to tell her we no longer have a son,” recalled Mike O’Brien.

News of Jack’s death quickly spread around town, and by the time Mike O’Brien got home, there were more than 100 people at the house to support the family. Hundreds more came in the following weeks. The community grieved the loss of a young man everyone knew.

“We got messages when he passed away from people we didn’t even know that said he pulled us out of a snowbank when we got stuck, or helped us change a flat tire. He just had a great heart,” said his mother.

Always a saver

Mike O’Brien said his son earned the nickname “Deposit Jack” because he saved so much of the money he earned, beginning with a landscaping business he founded when he was 13 years old. He mowed lawns and cleaned up yards, but since he was too young to drive, his mother brought him to jobs and meetings with customers.

In exchange, Jack paid for her manicures and pedicures.

“He was always out hustling and making money,” said his father.

Jack O’Brien followed in his father’s footsteps, graduating from high school and joining the family’s construction business. Not long after he left school, he built himself a $700,000 home, with help from his dad, uncles and friends.

The 20-year-old loved football and was an avid outdoorsman. His other passions were hunting and fishing, along with riding almost anything that moved including trucks, snowmobiles, jet skis and dirt bikes.

The O’Briens, along with their family and friends, raise money for the memorial fund by hosting a 5K and 10K race that attracted hundreds of runners. The annual event in early July has become the biggest gathering of the year in Otis.

The fund also partners with Whitetails Unlimited, a wildlife organization, to run a banquet that raises money and helps fill the nonprofit’s coffers. They hope to raise even more money by adding a golf tournament to its roster of fundraising activities.

The family also sells merchandise on its website, SmileLikeJack.com.

Jack O’Brien was the “ringleader” of a group of friends that met all of the time at his family’s home. His parents had to buy groceries in bulk to feed them all. Since Jack’s passing, the friends don’t meet quite so often.

When Jack died, his sister Erin put plans to go to college on hold, but she is now attending the University of Alabama, inspired by a brother who loved and encouraged her to do great things.

“In some sense, Jack’s guided her to be where she is now in her life. He’s guiding a lot of people into doing things that they normally wouldn’t do. Things they wouldn’t try,” said his mother.

Smile Like Jack’s mission is to give people the chance to “live their legacy just as Jack would — working immensely hard in the trades and living life to the fullest in the great outdoors.”

For more about the foundation, visit SmileLikeJack.com.