Baseball and Billionaires: When Sports Mimic Life & How We Can Better Connect Around Them

Entry points that help us find common ground and perspective

The first time I saw my mom cry was in 1998, sitting on the carpet in front of the 15” TV in our living room. She had rosary beads in one hand and was wiping her eyes with the other as we watched what would ultimately be a 4-0 sweep of our beloved San Diego Padres by the New York Yankees. I was too young to understand anything meaningful about the game of baseball or how truly historic that Yankees team was; they would go on to win 125 games with over five future Hall of Famers, including Derek Jeter and Mariano Rivera.

What I did understand was that the Padres were the good guys I watched at Qualcomm Stadium and who showed up at my brother’s little league games, while the Yankees were the big, ritzy bad guys from New York City. Between that and my mother’s tears, my tiny 6-year-old brain comprehended that this was something resembling David vs. Goliath, but there would be no slaying of the giant this time, and I was really, really sad.

Fast forward to 2025, and the LA Dodgers just won their second consecutive World Series. It was an absolutely electric 7-game series that will possibly go down as one of the best in history. The Dodgers came out on top—the team with the highest payroll in baseball—who also happens to be the team my husband and I have adopted since moving to LA. It’s a team our friends and family root for, helping us connect to our new home, with a killer stadium and hot dogs. A good team that, until pretty recently, felt easy to cheer for because winning is fun and baseball rocks.

Sports Matter

I’m a huge sports fan, and loving sports has helped me in ways I can’t fully quantify. From finding footing in new cities to connecting with new colleagues, friends, partners, and parents—specifically men with whom I have little else in common—sports have been central to my existence for as long as I can remember. It’s a universal entry point for small talk, killing time, or, in a recent conversation I had, a way to share political views in a place that felt safe and organic.

I was catching up with a colleague who is a massive Milwaukee Brewers fan, born and raised in rural Wisconsin, after the Dodgers swept them in the Championship Series (NLCS) to head to the World Series. On paper, my colleague and I couldn’t be more different, and not just in our sports fandom. He’s 28 years old with two dogs and three kids under three. He’s the first in his family to work a corporate job after his lifelong dream of being a police officer was dashed by an injury three months after he graduated from the academy. He loves to hunt and fish and proudly refers to himself as a redneck - a badge of honor. Since 2016, he’s voted Trump every time he’s been on a ballot and can confidently say he’s never voted for a Democrat in an election. His whole life he’s felt like the underdog, overlooked by the ruling elite as a poor, white, hardworking American who has been the lifeblood of this country, just like his parents and grandparents before him.

He sees his own story in the Brewers. He loves that they’re the underdogs because it reflects his identity; it’s him and his gritty, tight-knit crew against the world. He never minded that everyone counted him or his team out because they were just going to keep quietly working harder than everyone else, proving them wrong in the process.

However, during this past NLCS, he felt like the odds were insurmountable. There was no amount of hard work or homegrown talent that could conquer the Goliath that was the LA Dodgers. The Brewers, who have one of the lowest payrolls in the MLB, not even half of LA’s $500 million dollar spend, crumbled almost immediately against the big, ritzy, bad guys from LA with seemingly unlimited money and resources. The Brewers crushed the regular season, legit had the best record across the entire MLB, only to lose four straight games against the richest, most powerful team in baseball. I had seen this movie before, 17 years ago when my Padres played the Yankees, and despite being on the other side this time it still felt like shit.

This discrepancy in spending is all possible because of MLB’s very lax salary cap, something that has come into discussion during LA’s insanely dominant postseason run. A conversation that has played out in real life, from Mamdani’s speeches to Theo Von podcasts to conversation with my colleague. When the system is being run by the rich elite to benefit only themselves, what does that mean for the rest of us? How do we fix it? Can we? Suddenly we weren’t talking about the Brewers and the Dodgers; we were talking about the haves and have-nots—and he’s truly someone who has never had.

Entry Points

In Unfortunately Not a Sound Bath (UNSAB), we talk a lot about finding entry points into difficult conversations and how to authentically connect once we’re there. So for over an hour, we just talked. Sports were the entry, but it became increasingly clear that baseball wasn’t the only place where my colleague felt it was the world vs. him. He’s worried about healthcare and the cost of living, despite both he and his wife working good, steady jobs. He feels like all our elected officials have completely lost sight of the needs of his community and others like it. He’s worried about America on the global stage, a country he loves so deeply but doesn’t recognize. A place where it feels like only the rich and powerful can succeed, where the billionaire owners of the LA Dodgers can keep buying the best players—despite already having so many—and continue to be rewarded for it under the facade of meritocracy.

We talked about our own circumstances, the obvious privileges and the much less visible disadvantages. We discussed our frustrations with politicians and the cruelty we’ve seen around ICE, as well as the violence we’ve witnessed on both sides of a protest, his as a policeman and mine as a protester.

Throughout our conversation we naturally aligned on so many things, the most important of which was defining the villain: the rich, powerful elite who concentrate wealth and power only among themselves and have an insatiable need for more. The billionaire team owners and donors who lobby for things like lower corporate tax rates while gutting social services that both our families have relied on in the past.

I didn’t set out to have this vulnerable dialogue about our fears for the people we love and those we don’t even know. Since being a part of UNSAB, I know better than to expect or try to witness an “a-ha” moment or prompt a life-altering revelation based on my well-structured argument about our political ecosystem. I just took the time to listen, ask questions, and connect with someone who thinks and feels very differently from me. I offered him the space to process, learn, reflect, and question what he believes on his own terms, but more importantly, I went into that space with the genuine intention to do the same.

Keep the Conversation Going

We ended our conversation with a commitment to keep this dialogue going as friends, colleagues, and people who believe that America isn’t just for the Goliaths.

To take this from the theoretical into the practical, shoutout to my fellow UNASB Haley for the ask, here’s a few questions I asked during the course of the conversation that kept us in our ~flow state~:

1. Would you be willing to sacrifice the current hands-off approach from the MLB for what you & I agree to be intervention to increase fairness/ level the playing field?

This transitioned us into talking about the role of government and things like Affirmative Action that had been branded as partisan issues, where he said “I had never thought about it that way”.

2. What are your thoughts on how to maintain the integrity of college sports? Right now the state of NIL feels deeply unfair to smaller programs, but going back to the old model of a concentrated elite profiting off of uncompensated athletes doesn’t feel right either.

Prior to me asking that question, we had both agreed that Name, Image, Likeness [NIL] has completely changed the landscape of college sports. This allowed us to talk about complications and differing viewpoints, not reduce it to an overly simple black or white issue. The gray area gave us the ability to disagree, ask questions, respond to each other, and find common ground.

3. Given it feels like it’s only liberty & justice for the deepest pockets right now, what’re some things you think would signal a shift back to those core ideals for all?

This allowed us to take the conversation from left & right to up & down. We were able to define a villain(s) and align ourselves against it.