Three Legacy-Minded Lessons from The Sandlot

Jul 15
6 min

It’s summertime, which means my kids are bored. They are bored with me, bored with each other, and bored with all the various summer camps we’ve spent half of our life savings on to keep them entertained. 

So, the other night, I suggested we watch an old movie. I’d make popcorn and we’d watch The Sandlot. My son immediately announced that the movie looked boring. “You’re killing me, Smalls,” I told him and then turned up the volume to drown out his moans. 

As I knew they would, ten minutes in, my kids were invested. I’d planned to work on the couch beside them, but I also found myself glued to the TV. It’s been a decade since I last watched The Sandlot on a hot summer evening. Still, here I was, laughing along with my kids when Squints kisses the pretty lifeguard, cringing during the scene at the amusement park when they try chewing tobacco and things get out of hand, and, admittedly, blinking away nostalgia when Benny hits a home run (managing to overlook that it’s for the Dodgers!). 

The Sandlot is over 30 years old, and it’s a classic. As I put my kids to bed that night, listening to them recount their favorite parts, I found myself musing about the lessons The Sandlot teaches us about leaving and living meaningful legacies. 

1. Community Matters

One thing I love about The Sandlot is its simple, yet beautiful, illustration of inclusion. The main character is not only new to the neighborhood but also navigating an undefined relationship with his stepdad. As a kid, I watched this movie for the hilarious one-liners. As an adult, I see it with fresh eyes, appreciating the nuance of the relationships. Smalls finds baseball because he’s looking for community—a place to belong. He’s not particularly interested in the sport at first but rather sees a group of boys communing around this common interest and wants to be a part of it. 

In our work around legacy building, we’ve seen time and time again that clients thrive in retirement when they have a strong community. This is unsurprising given the wealth of research within the field of positive psychology about how a strong community is foundational to living happy, fulfilled lives. We all want to be a part of something—whether a faith community, hobbyist group, book club, or part of the game. Belonging to a community gives us a sense of purpose, a meaningful way to spend time. And once we’re a part of a community, we gain the opportunity to invite others in. 

These days, when I watch older movies with my kids, I sometimes need to pause the movie to explain a taboo subject or talk through a portrayal that shouldn't be imitated in real life. But with The Sandlot, my kids saw someone using their position of power and authority to express kindness to an outsider, and I am 100% here for that lesson.

2. Time and Intention Bring Clarity

If you’ve seen the movie, you may remember the scene near the end when James Earl Jones’s character, Mr. Mertle, meets the main character and his newfound friend, Benny, after a wild chase by Mertle’s bulldog – The Beast. The Beast is fond of baseballs, and, to Smalls’ great misfortune, has chewed up a baseball signed by Babe Ruth that belongs to Smalls’ stepdad. When Mr. Mertle finds out, he tells Smalls he is “dead where you stand” before inviting the two boys into his home for a chat (obviously – we did pause here to discuss not going into strangers’ homes, but I digress). 

As it turns out, Mr. Mertle himself was a former baseball player who gave up playing after an injury left him blind. His home is full of old baseball paraphernalia, including a baseball signed not only by the Babe himself, but by Murderers’ Row – some of the best players in the history of the game from the 1927 Yankees. He offers this baseball to Smalls in return for the boys coming back to talk baseball with him. Smalls then offers Mr. Mertle's ball to his stepdad in replacement of the signed ball that he took. 

What struck me about the scene was the value and foresight Mr. Mertle had gained over time. A baseball signed by all those players would be (and is) incredibly valuable, and Mr. Mertle hands it off like it’s no big deal, probably because to him, it isn’t. What matters to him is having someone to talk to, to share his stories with, and to be in community. 

Over the years, I’ve been fortunate to witness similar responses from people nearing the end of their lives, thanks to my mother, who has a special heart for spending time with seniors. On occasion, I’ve joined her to hear the seniors’ stories, and every time I’m reminded of how little matters in the long run – most of them don’t want to talk about their career successes, their account balances, the awards they won, or the grades they received. They want to discuss “the good times” with the people they loved. It’s a valuable reminder that often the things that last, and are worth investing in, are the intangibles. When it comes to legacy planning, our job as financial advisors is to key in to your intangibles and make the most of your pursuit to build those lasting memories.

3. Spend Time Doing What You Love

Of course, in the end, The Sandlot is a movie about baseball, or maybe more accurately, the love of baseball. 

My brother played baseball when we were younger, and I spent my summers behind the dugout. My family has always loved the sport, even now, when our team is the worst team in the history of baseball (go Colorado Rockies!). We still watch because we love the game.

In the movie's final moments, Benny, grown up and now a professional player for the Boys in Blue, hits a home run to win the game. Smalls, who became a broadcaster, announces the whole thing with the joy of someone who loves the magic of the game. As the credits rolled, I texted my parents and brother that we were watching The Sandlot, and it made me teary – to which I could hear my dad saying, “There’s no crying in baseball” (we watched ALL the baseball movies growing up). In that moment, I felt a deep sense of appreciation for this common thing that my family enjoys. 

Part of living and leaving our legacies is the opportunity to invite others into the things that we love. Every summer, my family tromps out to Coors Field to watch a game together and tell stories about my grandma screaming at the radio that the ump had it wrong - long before my children were even born. It’s how we invite them into our legacy, recognizing that in as much as we hope to share with them the things we love, we also want to make space for them to invite us into the things that bring them joy. It is in those shared spaces that core, lasting memories are made, and why legacy planning is so essential – it asks us to consider what things bring us joy and how best we can share them. 

As we find ourselves deep in the throes of summer, I hope you find a reprieve from the heat and take a moment to consider some of the core memories you have from the summers of your childhood. Maybe you have fond memories of fireworks on the Fourth, or long days at the pool. Perhaps you remember learning to ride a bike or camping under the stars. I hope you get a chance to share those memories and maybe even invite your loved ones to make new ones, doing something special that you love. 

If you’d like to learn more about the ins and outs of legacy planning and how our process can help you take your wealth further, we’d love to chat.

Hannah Boundy, CFA®, CFP®

Founding/Managing Partner
With a background in both investing and operations, Hannah co-manages Sherwood's portfolios with Matthew Davis. She works with the rest of the team to align clients' investments with the rest of their legacy plan. She also runs Sherwood's back office, ensuring the entire team has everything they need to serve our clients well.
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