The Long Game
Watch the Episode
Listen to the Episode
Episode Summary
Todd Merkow sits down with Linda Santo — sports media veteran, former colleague from the early days of regional sports television in Arizona, and the daughter of Ron Santo, the Chicago Cubs Hall of Famer — for a conversation that moves between the bleachers and the broadcast booth, between a childhood shaped by one of baseball's most beloved figures and a sports parenting journey that humbled her in ways she never expected.
Linda grew up in a household where baseball was everything — and also, paradoxically, where her father was largely absent from her own athletic life. Ron Santo was on the tail end of his playing career when Linda was born, and by the time she was old enough to play, he had moved into a real job in the off-season like most players of his era did before free agency changed the economics of the game. He was dad first, Hall of Famer second, and he rarely showed up at her games. Her brothers, six and ten years older, had more of the playing-days version of their father. Linda got the broadcaster — the Ron Santo who came back to the game through WGN Radio, who carried the weight of the Cubs on his sleeve every single broadcast, who made Harry Caray laugh and made Chicago fall in love with him all over again. She watched her father find his true passion in the booth, and she carries that image of him — emotional, authentic, completely himself — into everything she talks about on this episode.
Those coaches, those fathers — those are what we call frustrated athletes. These are the guys that didn't make it, and so here we go.
She played softball, figure skating, tennis, and soccer growing up, but never at a level that required the kind of commitment the current youth sports system demands. Her mom refused to drive her to the rink at 5am, and that was the end of figure skating. She laughs about it now, but she also wonders — genuinely — whether she could have gone somewhere with dance, which she loved and was good at, if anyone had pushed her toward it. Nobody did. The message in her house was: if you want to do it, great. If you don't, that's fine too. She's not sure that was entirely right either.
Fast forward to her own boys: Sam, the older one, who grew up with Ron Santo literally next door — sharing a wall, connected by a gate, with her father as the built-in babysitter while Linda worked — and Spencer, six years younger, who came up in a different era of youth baseball entirely. Sam was a natural. Switch-hitting from both sides in T-ball at three, equally strong left and right, throwing right but swinging left. Ron Santo saw it immediately and started working with him in the backyard. He sat in his folding chair at every Little League game — the same chair Linda still has — quietly watching, never coaching from the stands, occasionally pulling Sam aside at the fence to tell him to ignore whatever the dad-coach had just said about his hands. "Those coaches," he told Linda, "are what we call frustrated athletes." He was patient, present, and clear: just go up there and hit the ball. You're eleven. Have fun.
Ron Santo passed away in 2010, when Sam was almost twelve. The timing matters because what came next — the club baseball era, the showcase circuit, the pressure to be seen by college coaches before you've finished growing — arrived without his voice in the room. Linda had to navigate it alone, with his perspective as her only compass, and she found herself doing things she knew he would have questioned. Paying for extra hitting coaches. Investing in a club team that turned out to be a tiered organization where the A team traveled and the B team sat. Watching Sam get cut from his high school JV team as a freshman — not because he wasn't good, but because he was small, and the coaches were building a team to win, not a pipeline to develop. The kid who was cut alongside Sam is now 6'2". Sam is now 6'2". The coaches couldn't see it coming.
I still have PTSD from the whole experience. I just got myself in it.
Sam's story has a good ending. He found soccer — never played it before, tried out on a whim with some friends, made the team, and discovered that the absence of pressure let him play with joy again. He went back to baseball every year, eventually made the team as a senior, played on a squad that went to the state championship game, and graduated with two varsity letters. He knew going into college that his playing days were done, and he was okay with it. He plays softball now and jokes that he should have stuck with it.
Spencer's story is harder and more honest. Six years younger, coming up in the full club era, Spencer had the drive Sam didn't — the kid who was in the weight room at 5am, who ran through brick walls, who every coach wanted on their team because of his work ethic and hustle. But the skill was harder for him. The hand-eye coordination that came naturally to Sam had to be manufactured for Spencer, and the manufacturing — the hitting coaches, the club dues, the travel weekends, the batting cage in the backyard that came with the house she rented after her father died — never quite closed the gap. Spencer was an overthinker. He wrote "take a deep breath" and "this is just a game" and "have fun" on his batting gloves. Linda found them in the garage a week before this recording, cleaning out. She didn't know they were there. She read them and cried.
He wrote 'take a deep breath' and 'this is just a game' and 'have fun' on his batting gloves. If you're looking at your batting glove to say 'have fun' — oh my gosh.
Spencer got cut freshman year too. Came back, made JV sophomore year, won most improved, became a leader. Got in his head again junior and senior year. Stopped growing at 5'9". The system that had been telling him he could get to D1 quietly stopped telling him that. He's in college now, happy, succeeding, still loves the game. Linda has PTSD from the whole experience — her word, not a clinical diagnosis, but the feeling is real. She got swallowed up by it. She sat in the stands with parents who were convinced their kids were going to the majors. She felt the stomach knots. She asked Spencer what he was thinking after bad at-bats when she knew she shouldn't. She got caught up in it despite knowing better, despite having Ron Santo's voice in her head the whole time saying: this is too much. This is not how it should be.
All that matters is what you have in your heart.
Her advice is simple and comes from a place of genuine reckoning: let them make more decisions for themselves. Ask them. Sit them down and ask them if they're having fun, if they want to keep going, what they actually want. She pushed a little too much — not dysfunctionally, not in a way her boys would blame her for, but more than she needed to. She wishes she'd played more sports with them and less of the system. And she closes with the one thing her father told her that she carries everywhere: all that matters is what you have in your heart.
Top 5 Takeaways
The frustrated athlete in the stands is a real phenomenon — and it's not always who you think. Ron Santo, one of the greatest third basemen in Cubs history, sat quietly in a folding chair at Little League games and said nothing. The dads adjusting eleven-year-olds' hand positions were the ones who couldn't let it go. Linda's father had a name for them: frustrated athletes. Parents who never made it, or whose pipe dreams never materialized, and who are now trying to manufacture through their kids what they couldn't achieve themselves. The antidote isn't absence — it's presence without agenda. Show up. Sit down. Let them play.
The late bloomer problem is real and the system punishes it. Sam was cut from his high school JV team as a freshman because he was small. The kid cut alongside him is now 6'2". Sam is now 6'2". The coaches were making a decision about a fifteen-year-old's body that his body hadn't finished making yet. Parents of late bloomers need to hear this: the system is not designed to wait for your kid. JV is supposed to be a development squad. In practice, it's often a miniature varsity tryout. If your kid gets cut, it is not a verdict on their ceiling.
Multi-sport athletes find their way back. Sam found soccer when baseball cut him. The absence of pressure — the novelty of a sport where nobody knew his grandfather, where nothing was expected — let him play with joy again. He came back to baseball on his own terms, made the team as a senior, went to the state championship. The sport he almost quit became the sport he finished with. Parents who force early specialization are often foreclosing exactly this kind of recovery arc. The kid who plays two sports has somewhere to go when one of them gets hard.
The overthinking problem is a mental health problem. Spencer wrote reminders on his batting gloves. He kept his stats on a notepad in his room. He was in the weight room at 5am. He ran through brick walls. And he still couldn't get out of his own head at the plate. Linda eventually found herself looking for sports psychologists, then realizing — as Todd notes — that what Spencer probably needed was a therapist, not a sports psychologist. The distinction matters. A sports psychologist helps you perform better. A therapist helps you understand why you're suffering. When a kid is writing 'have fun' on his batting gloves, the performance problem is downstream of something deeper.
If you're good, they will find you. Ron Santo said it. Linda says it. Todd says it. The scouts, the coaches, the college programs — they are looking. They are not missing good players. What they are missing is players who burned out at fourteen because their parents were running a self-promotion campaign on social media and paying for showcase tournaments every weekend. The system creates the illusion that visibility is the bottleneck. For most kids, it isn't. Development is the bottleneck. And development requires rest, multi-sport play, and the freedom to fail without it meaning something about their future.
Ask your kid. Linda's single biggest regret is not sitting her boys down more often and asking them directly: do you want to keep doing this? How much? At what cost? She made assumptions. She pushed because she thought they wanted to be pushed. She got caught up in the system because the system is designed to make you feel like opting out is abandonment. The simplest intervention available to any sports parent is a direct conversation with their kid — not after a bad game, not in the car on the way home, but in a quiet moment with no agenda. What do you want? Are you having fun? What would you do if you could do anything?
This episode is free because of supporters like you.
Help us reach more families — so more kids have happy moments and fewer harmful ones.
