- The Underdog Newsletter
- Posts
- He Was One “No” From Quitting
He Was One “No” From Quitting
He was benched in college, cut in the pros, and worked 5 jobs at a time on his way to the big leagues.
This week, I asked a big media influencer what he thought of The Underdog Newsletter.
Here's what he said:
"It's a tough niche...but if you care about it, you can keep grinding. Good luck!"
I used to look up to this guy. So yeah, that stung.
But instead of sulking, I’m using it as fuel. Let's prove him wrong and send this thing to the moon!
Here’s how you can help:
Think of one friend who’d love this newsletter
Send them your unique referral link – just copy and paste this 👉 https://newsletter.jokermag.com/subscribe?ref=PLACEHOLDER
When they sign up, you’ll win a Reader Takeover – meaning you get to pick a story idea for a future edition!
If everyone brings just one friend, we’ll double our audience, prove that guy wrong, and have a pipeline full of incredible stories for years to come.
Let’s do this. Thank you for being part of the movement 🤝
In today's edition...
He was benched in college, cut in the pros, and worked 5 jobs at once while grinding through indy ball.
On Thursday night, he got his first big league hit.
Let’s dive in 👇
UNDERDOG TRIVIA 🤔
Today's question was inspired by a subscriber. Thanks, Alex!
Which city has retired the same number for their NFL, MLB & NHL teams? |
Tap your pick to reveal the answer in a new tab – or scroll down to Extra Innings below!
This 29-Year-Old MLB Rookie Worked 5 Jobs on His Way to the Yankees
No time to read now? Click here to save it for later 🐶
He was “one more no” away from giving up on his dream for good.
The bills were piling up, and baseball wasn't paying them.
“When I was making $400 every two weeks in indy ball, playing overseas, playing winter ball, having all those odd jobs just to provide for my family – there was a time I was going to hang it all up.”
“The easy thing to do is just give up…but I didn’t.”
J.C. Escarra’s mother was only 12 years old when she left Cuba in the Mariel boatlift – a mass emigration where over 125,000 Cuban refugees crossed the perilous Florida Straits to come to the U.S.
His father left Cuba around the same time, and the two met later on as adults in the States.
Growing up in the Miami area, J.C. excelled on the baseball field.
He attended Mater Academy, a charter school with notable alumni like NFL running back Zack Moss and World Series champion Albert Almora.
J.C. planned to follow in Almora’s footsteps.
“He was a year older,” Escarra said.
“I saw everything he went through with USA Baseball, a first-round draft pick. So that was pretty cool.”
Despite batting .450 his senior year, J.C. had to wait until the 32nd round of the 2013 MLB Draft for his phone to ring.
The New York Mets took him with the 956th overall pick, but he decided to play college ball at FIU instead.
In his first three college seasons, the catcher hit 5 homers, but his batting average never crept above .271.
“There were a lot of times I was counted out, I was the underdog…I got benched in college, not playing for weeks at a time.”
Then, only 13 games into his junior season, a shoulder injury required season-ending surgery.
The big league dream was further away than ever.
But Escarra pressed on.
“I have fought a lot…I am a fighter, as my parents – who came from Cuba – raised me.”
He came back stronger than ever as a senior. In 53 games, he batted .305 with 10 doubles and 15 home runs.
That summer, the Baltimore Orioles drafted him in the 15th round (458th overall).
After the organization moved him from catcher to first base, he got off to a promising start, slashing .315/.395/.479 in A-ball in 2018.
But two years later, the pandemic wiped out the entire minor league season.
When he returned to action in 2021, he split time between the Double-A Bowie Baysox and Triple-A Norfolk Tides. But with each promotion, his production slipped.
In 95 total games that season, he hit just .223. Not exactly the numbers you want from a first baseman.
“Baltimore knew I was a catcher, but they didn’t give me the opportunity to catch, and even in those final days, I knew that reaper was coming,” J.C. said.
He hadn’t worn catcher’s gear in five years.
“I just wanted them to watch me throw five balls to second base from back there. I did – I threw five balls down to second base, but they never gave me the opportunity.”
The Orioles released him in April of 2022.
Pro baseball is littered with stories like this.
Only 17.6% of drafted players ever make it to the big leagues. The odds are stacked against you from the start.
The day after his release, J.C. found a lifeline with an independent league team called the Kansas City Monarchs.
His dream wasn’t dead, but the $400 bi-weekly paychecks weren’t going to cut it.
“I was going through a hard time,” Escarra said.
“I had just gotten released, just got married, just bought an apartment, so I had to put my big-boy pants on and try to provide for my family.”

His back was against the wall.
“I had to make money somehow, and no one was going to take away my home from me. I knew I had to make those payments, so I was doing anything it took.”
Between his time with the Monarchs, then the Puerto Rican Winter League, J.C. started driving for Uber to fill the income gap.
“It didn’t end up paying much. I don’t know how guys do it,” he told MLB.com.
“I was wasting money, a lot of gas. People don’t tip. [The passengers] were happy with the rides, and I never got a complaint – [there were] a lot of old ladies that don’t drive, going to doctor’s appointments and stuff like that.”
Soon, he was shuffling through side gigs:
Tutoring
Delivering food
Coaching 8-year-old Little League
Measuring rooms for a local contractor
Substitute teaching high school classes
At one point, he was working five different jobs at a time.
“We were living paycheck to paycheck, but we were making it happen.”
When spring rolled around in 2023, he was on the outside looking in – 28 years old without any opportunities in affiliated baseball.
“My family would have been okay, and probably would have preferred it, if I stopped playing baseball and got a regular job.”
But he knew he owed it to himself to take one more shot.
“I felt something in my heart that if I gave up baseball at that time and that moment, that I would regret it for the rest of my life.”
He went back to indy ball, this time with the Gastonia Honey Hunters of the Atlantic League.
That year, he tried something unconventional: taking less batting practice.
“Usually I try to over-hit. In the past I’ve hit too much,” he said early that season.
“So this year, I actually changed it a little bit and I’m hitting less. I guess that is helping me mental wise at the plate – thinking less, thinking less about my swing and just seeing the ball and hitting it.”
It worked.
J.C. had his best year of pro ball, slashing .348/.423/.707 while leading the league in home runs (15) and doubles (14).
By mid-June, his contract was purchased by the Toros de Tijuana in the Mexican League.
He kept the momentum rolling in the Puerto Rican Winter League, Mexican Pacific Winter League, and the Caribbean Series in Miami.
By then, MLB scouts were paying attention.
In January of 2024, the Yankees offered him a minor league contract.
“Things can really change overnight no matter what you are going through,” J.C. said.
“I thought that I was done with this game, this game that I have played for 25 years, and now I feel the highest that I have ever been. Things are looking great, I feel great, I am playing great, and I feel like it is up from here.”
Despite being on the older side for Double-A, the 29-year-old played well enough to earn a call-up to Triple-A before the end of 2024.
He kept grinding in the Dominican Winter League in the offseason, winning the batting title with his league-best .363 average.
The work paid off when the Yankees invited him to their big league Spring Training in 2025.
With the backup catcher spot wide open, Escarra knew the opportunity was there.
After all those sleepless nights, wondering if his playing days were over, he finally had a chance to prove he belonged in Major League Baseball.
And he delivered.
Escarra finished the spring batting .302, clubbing 3 homers, and impressing the Yankee pitching staff with his work behind the plate.
But when manager Aaron Boone called him into his office in late March, J.C. wasn’t sure what to expect.
“If it was gonna be good news, I expected there to be more people in the room, but when I saw just him, I got a little nervous.”

Boone started the conversation by saying, “This is difficult to have to do,” and Escarra’s heart sank.
Then, suddenly, he paused mid-sentence and said, “Nah, you’re going to the big leagues.”
J.C. erupted.
“You’ve earned the right to be here and be that guy,” the manager said. “Pack up for The Show.”
“See you in the Bronx!” the new big leaguer replied.
Moments later, he FaceTimed his mom.
“We’re going to New York,” he said. His mother yelled with joy.
“The dream came true. We did it.”
The clip went viral, and for good reason.
“That’s what I want, is just for my story to be an inspiration to everyone out there,” Escarra said.
“I just happen to play baseball, but they could use it for whatever they do, whatever goals they have, so I just want to inspire.”
On Opening Day, J.C. pulled out his phone, opened a familiar app, and called for a ride.
“Two years ago, I was Ubering,” he said from the back of the Uber, “and now I’m a New York Yankee in the major leagues.”
A few days later, in front of 43,382 fans at Yankee Stadium, J.C. ripped his first major league hit – a double down the right field line.
“We were all excited. We’re all pulling for that guy; we know his story,” said Yankees captain Aaron Judge.
“But besides that, just the type of person he is, to battle through that type of adversity. He’s come in here every single day with a smile on his face, trying to make guys better, trying to push guys all the way in Spring Training.”
For Escarra, his story is bigger than baseball.
“It’s just a testimony that these things can happen,” he said.
“And it doesn’t have to be making it to the big leagues, it could be getting that dream job or starting that business. Any dream you have inside of you, any goal you have set…it could happen because I was just another guy. Nothing makes me special.”
🐶
Today’s article was written by yours truly.
If you enjoyed it, check out these two other hand-picked stories:
Add this to your reading list:
There’s a reason The Underdog Mentality is selling like hotcakes.
One reader said that the book “left me motivated to push past obstacles and helps provide a fresh take on life's situations.”
Another declared, “I actually enjoyed it even more than I thought I would.”
Other readers say that Chapter 1 alone is enough reason to pull out your wallet and grab this book today.
Thanks for reading!
If you love this newsletter, don’t forget to share your referral link with a friend so you can pick our next story!
Til next time,
Tyler
Extra Innings…
🌟 Trivia Answer: D) New York – #1 was retired by the Yankees (Billy Martin), Giants (Ray Flaherty), and Rangers (Ed Giacomin).
🔥 Ryan Gusto notched his first MLB strikeout last week. He’s come a long way from getting cut three times in high school.
💰 Neil Pane wonders if either of these two MLB orphan squads can write their own Cinderella story.
Reply