For the past ten years, attorney Jonathan Wetmore and his wife Amanda have quietly turned gratitude into action through Santa’s Helpers Toy Drive—a tradition rooted in faith, generosity, and a deep belief in paying it forward. What began as a simple desire to help one family experience the joy of Christmas has grown into a community-wide effort supporting dozens of children and families each year through the Boys & Girls Club of the Lower Naugatuck Valley.
Guided by Jon’s connection to the Club, the power of small acts of kindness, and the unwavering support of friends, family, and colleagues, Jonathan has seen firsthand how giving can ripple far beyond the holidays. In the reflections below, Jonathan shares the heart behind the tradition, the stories that have stayed with him, and why he believes being a “giver” isn’t just something we do—it’s who we’re meant to be.
Origins & Inspiration
Q: What inspired you to start Santa’s Helpers Toy Drive ten years ago? We do our best to always be grateful for all of the blessings in our lives and believe that giving back and helping others is incredibly important.
A: We had a 1 year old daughter at the time and felt incredibly fortunate to provide a nice Christmas for her. We wanted to help another family have that same experience.
Q: Why was supporting the Boys & Girls Club of the Lower Naugatuck Valley especially meaningful to you?
A: I served on the Board of Directors for the Club for a period of time but ultimately had to step away because I did not have the time that the Club deserved to devote to the position. I believe strongly in the Club’s mission and have heard many stories of the wonderful children and their families who attend the Club who could use a helping hand. The Club is such an incredible resource for the children and their families.
The Heart Behind the Tradition
Q: Over a decade, what has kept you motivated year after year?
A: The letters we receive from many of the families expressing gratitude about how much of a difference the gifts and the gift card makes in their lives. That’s what it is about- putting a smile on a child’s face and lending a helping hand to parents who could use some help.
Q: How has this tradition shaped your holiday season?
A: It has definitely made it busy! We started with helping just one family and it has now grown to 50 children and 38 families. We have 3 young kids of our own so we try to balance enjoying our own family time during the holiday season with the time it takes to complete the toy drive. We have a really great system now and a lot of people who help in many aspects of the Toy Drive. We get more efficient each year but it definitely takes a village.
Q: Do you have a favorite memory from one of the early years of the toy drive?
A: The wrapping party is always my favorite. Our friends show up every year and we spend hours hanging out and wrapping gifts. It is great to get everyone together and spend time with one another.
Gift wise- My friend, Dan Martin, plays the guitar and I always said to him how I wanted to learn how to play. He showed up at my house one day with a guitar and said ‘let’s be about it instead of talking about it’ and he gave me a lesson. I did not stick with it and put the guitar in the corner.
Fast forward a couple of year later, as party of the Toy Drive, a child wanted a guitar which did not come in in time. I wrapped up the guitar that Dan gave to me and delivered it to the families house on Christmas Eve. Knowing Dan, he would want me to ‘pay it forward’. The child’s actual guitar was delivered the day after Christmas. The family gave me Dan’s guitar back and we gave the child the correct guitar. I picked up the guitar again and take a lesson once a week, which I probably would not have ever done if Dan never gave me that guitar and I did not have an opportunity to pay it forward and give it to a child who needed it. That’s the magic of being a ‘giver’.
The Process & the Team
Q: How do you organize your annual gift buying and wrapping marathon?
A: It has definitely changed over the years. Early on we helped about 10 kids or so. Our friends, Chris and Emily Chapman, would help us shop. We would all take a day off of work and go to the mall. As it got bigger we would have to order everything online, which my staff at my law office helps with. In the early years the gifts for the kids would come mixed together in one box so we would have to sort each gift and figure out which gift went where, which was a challenge. Now we are able to order the gifts so all of a particular child’s gifts essentially arrive in one box with the child’s name on it, which # they are in our list and which club (Shelton or Ansonia) the child attends. We still need to check each box to make sure everything arrives but this certainly makes it easier.
Our friend and Boys & Girls Club Board Member, Rich Carroll, helps us move the gifts from my office to our house and organize the gifts before the wrapping party.
Once our friends come over, we have a great system on how to wrap them, double check to make sure everything is where it should be and ultimately get the gifts to the Club.
Q: Your group has grown into a small team of “elves”—what roles do your friends play in bringing this to life?
A: We could NOT do this without our friends and family. We started this Toy Drive and they have all stepped up to support us each and every year. Our friends and family donate their time and energy and help in all aspects- whether it is donating, spreading the word, wrapping, organizing the gifts, carrying boxes and delivering the gifts. During Covid, they all stepped up and actually ordered gifts, wrapped them and dropped them off at our house so we could keep the Toy Drive alive. They are always there and help us see it through, no matter the circumstance. We are very fortunate to have an amazing ‘village’ and are incredibly grateful for all of their support.
Impact & Connection
Q: How has partnering with the Club influenced your understanding of the community?
A: It certainly puts things into perspective. You see an hear stories of people who are amazing people who just need a helping hand. Seeing the amazing work that the entire staff of the Club does is incredible as well. They have an amazing impact on the lives of the kids at the Club.
Q: Is there a particular story or message from a Club family that has stayed with you?
A: Yes definitely. Each year we get lists from the families and the Club does a great job having the kids make Christmas lists as well. One family had 3 young boys- I believe ages 7-13. The parents each worked multiple jobs. Despite trying all three boys did not make Christmas lists. The counselor kept encouraging them to do it when the youngest boy said, “I’ve never received anything on Christmas so I know Santa is not real and I don’t want to make my parents feel bad because I know they can’t afford any gifts”. What struck me was how mature this young man was but also how sad that he never got to experience the innocence and wonder that most children get to receive. Also how difficult that must be on the parents who were incredibly hard working, good people doing their best to make ends meet.
The boys were huge fans of the Mets and had never been to a game. We got the entire family front row seats to a game with access to the field before the game as well as gift certificates for food, etc.. to purchase at the game. A board member arranged for a round trip limo ride to bring them to and from the game. That was by far the largest gift we ever gave.
Q: What does it feel like knowing your efforts brighten the holidays for dozens of children each year?
A: It is gratifying. You never truly know the impact that you have on someone and you hope that it is a change for good in some small way.
Tony Robbins- who is probably the worlds #1 motivational speaker, an entrepreneur and billionaire- often tells a story who he grew up in a very poor home. They often had nothing to eat. On Thanksgiving, they were not able to dinner. A man who heard that they were down on their luck knocked on their door and dropped off an entire Thanksgiving meal. As a young boy, what he took from that experience was that if a stranger cared about him, then he should care about strangers. When Tony turned 18 years old he decided to pay it forward and feed one family on Thanksgiving even though he did not have the means to do so. The next year he fed two families and so on. He has now fed over 1 billion people through his charity. That started because a stranger cared about him and his family. We hope that our Toy Drive has a small positive impact on the children and their families that will ripple around the world.
Looking Ahead
Q: After ten years, what do you hope for the future of Santa’s Helpers Toy Drive?
A: That it continues on and one day our children and their friends and cousins will carry on the tradition.
Q: Is there anything you’d love the community to know about getting involved or supporting local kids?
A: It is one of the best things that you can do. It does not have to be a massive toy drive. A simple donation or a helping hand is enough. Giving -whether it be financially, your talents or your time- will change you for the better. I’m religious and believe in a higher power. Some call it energy or karma. Whatever you want to call it, it doesn’t matter. What I can guarantee you is that the more you give, the more you will receive. Whatever you give, just seems to come back to you. You never need to worry about giving too much. Just give your time, talents and treasurers without any expectation and what comes back to you will be greater than you could ever imagine. Donating, helping, and giving will change you as a person. Giving and helping others is what we are on this rock for. It is what matters in the end. Be a giver…
Personal Reflections
Q: What would you tell someone who is considering starting their own giving tradition?
A: It is well worth it and just do it. Just start. You’ll figure out the details. Start small and let it grow organically. Encourage your friends and family to participate. You are doing a wonderful thing for the community but also starting a tradition with your loved ones that will give back to you as a person.
Q: How has this decade-long journey enriched your lives?
A: It grounds you and makes you appreciate the important things that you are blessed with such as friends, family and an amazing community. That’s really what matters. Shelton and the Valley are an incredible community. We both grew up in Shelton and it never ceases to amaze us how supportive the community is.