How 840 Emails Led to An All-Pro NFL Career

Plus: the man bringing the knuckleball back to MLB, how $3 and a Blockbuster video rental led to a pro football career, and more.

Welcome back to the newsletter that loves underdog stories more than Orlando Arcia loves poking the bear.

If you’re a Braves fan, I’m sorry. We Philly fans can’t help ourselves.

Different order of events today, and I’ve got fun news for you at the end of this email.

I’ll give you a hint: it’s a brand-new referral reward (and pretty easy to get).

Today’s edition includes the story of an undersized kid who blasted out almost a thousand emails to get a shot at his dream.

Here's what else is coming:

  • A storybook moment in Foxborough

  • The man bringing the knuckleball back to MLB

  • How $3 and a Blockbuster video rental led to a pro football career

Let’s dive in.

POWERED BY: Down To Football

Struggling in your fantasy league? Stop wasting time binging podcasts and skimming articles.

Just join Down To Football. It’s free and only a 5-minute read 👇

Want to sponsor The Underdog Newsletter? Here’s how.

Underdog Trivia Question

What was the first college sporting event in American history?

  • A) Harvard vs. Yale boat race

  • B) Princeton vs. Columbia shot put

  • C) Brown vs. Dartmouth lacrosse

  • D) St. John’s vs. William & Mary basketball

The answer is at the end of this email! Look for the ⭐ emoji.

(Shoutout to subscriber Bryan G. for this week’s trivia question!)

Top underdog stories

🥊 Francis Ngannou is set to fight Tyson Fury later this month. The Predator’s journey has been jaw-dropping. Here’s how he overcame poverty and homelessness to become one of the best stories in combat sports. [Joker Mag]

⚾️ “In Italy, baseball is not really popular.” Meet pitching prospect Alessandro Ercolani, the first player from San Marino – the world’s 5th smallest country – to ever sign an MLB contract. [MLB.com]

🏈 Joe Horn was down to his last $3. Then he rented a video from Blockbuster that unlocked his path to the NFL. Here's his story plus more tales behind the best CFL players to make it to the NFL. [Joker Mag]

Feel-good post

The backstory: Foster Moreau was diagnosed with Hodgkin’s lymphoma in March 2023.

In Week 5, during the NFL’s Crucial Catch month, he scored his first career TD since returning to the field.

How Kalif Raymond Emailed His Way To An All-Pro NFL Career

Pop!

He knew it was broken the second he heard the sound.

“I looked down, [and] it’s turned to the right.”

There he was — Kalif Raymond – a 5’7” senior wide receiver with no college offers.

And now, just a few games into his last year of high school football – a broken ankle.

But to understand what happened next, you need to know where it all started.

As a 6-year-old, Kalif Raymond asked his mom to sign him up for football. She refused.

So that small “ask” turned into two years of begging.

Finally, thanks to some nudging from his stepdad, Kalif’s mother relented.

“I had a diving catch my first or second game of little league,” Raymond said on a podcast.

“But I could catch, because every time I caught the ball, I fell down.”

But the little 8-year-old kept at it. And he turned into a pretty good player by the time high school rolled around.

In that moment his senior year, the window on his football career was closing fast.

That’s when he looked up to the stands and spotted his best friend’s dad, Lawrence Nelson. A man who helped him navigate countless challenges.

“He’s been my biggest mentor up until this moment,” Raymond said. “[He] taught me everything I know.”

Instead of doing it all for him, Mr. Nelson taught Kalif how to do it himself.

“He gave me the greatest gift that I think I could’ve gotten from him.”

After the season-ending injury, Nelson laid out a step-by-step plan:

  • Go to ESPN dot com

  • Gather a list of every single college football program in the nation – from D3 to D1

  • Go through every single staff directory, and find every coach’s email address

  • Email every single coach with your name and highlight tape

“I ended up conjuring up about 840 emails,” Kalif said.

“And then, out of that I probably got…maybe 10 to 15 responses. Out of that, only maybe two or three were like legitimate ‘we want you here’, and Holy Cross was one of them.”

If we’re being generous, that’s a 1.7% response rate. But it didn’t matter, because the work paid off.

Kalif Raymond – the undersized senior with a broken ankle – had an offer to play college football.

It wasn’t until he stepped foot on campus at Holy Cross that it all sank in.

“I was like, ‘Oh, I’m about to play college ball!’”

He played in 10 games his freshman year, mostly as a return specialist, and was named first-team All-Patriot League.

It was a preview of things to come.

He always knew he was going to try for the next level.

“When I attack something, my ultimate goal is to achieve the highest level I can. I’ve put in so much time and effort, why not shoot for the NFL?”

But it wasn’t always a certainty.

As Kalif watched his friends get jobs on Wall Street and enter the workforce, doubt crept into his mind.

“I’m at Holy Cross, DI-AA, it’s not for sure…I need to have a backup plan just in case.”

Going into his senior year, he called the Holy Cross Alumni Association, saying:

“I need a job, but I don’t need a job…I need something I can put on my resume, but I can’t spend a lot of time because I have to invest my time into football.”

The man on the other side of the phone understood, giving him that internship and backup plan he was looking for.

While it landed on his resume, he never needed it.

The whole puzzle came together during his senior season. And everything Kalif knew he could be finally showed on the field.

In 11 games, he posted 74 receptions for 978 yards and 9 touchdowns – concluding with his name etched in the school record books.

After being projected as a 7th-round pick, he went undrafted in 2016.

He ultimately signed with the Denver Broncos as a UDFA before bouncing around to four different teams in his first three NFL seasons.

After a 2017 season that saw him record his first career catch, he started a new training regimen.

“I literally was doing like five or six workouts a day.”

The routine was intense:

  • Run a mile in the morning

  • Meditate and stretch

  • 9 AM workout

  • 11 AM footwork drills

  • 12 to 2 PM on the JUGS machine

  • Late-night workout at 24 Hour Fitness

“I did that every day for the whole summer,” he said. “I came back in such a positive mood…that definitely changed my life a little bit.”

Fast forward to today: the 5’8″ undrafted receiver has found a home with the Detroit Lions.

He was a second-team All-Pro in 2022. And before this season, he signed a contract extension that will keep him in Detroit through 2025.

“There is no substitute for hard work…the person you want to become has to mean more to you than the person you are now.”

“No matter how great you are, the next great one is already sitting there waiting to take your place.”

⭐ Trivia Answer:

A) Harvard vs. Yale boat race – two oars from the 1852 regatta were auctioned off for an estimated $3,000,000 to $5,000,000!

Wanna send in a trivia question or fun fact for the next edition? Reply to this email.

Thanks for reading! 🤝 

If you enjoyed this edition, send me a quick reply and let me know which part you liked most.

Or, just vote on the quick 5-second poll below:

How would you rate this edition of the newsletter?

And do you like the new order of sections? (long-form story at the bottom)

Login or Subscribe to participate in polls.

Your feedback helps me make this the best newsletter it can be.

Til next time,
Tyler

Tyler O'Shea headshot

P.S. I’ve got a brand-new referral reward for you! To unlock it, all you need to do is refer one friend to join the newsletter. Here’s your unique referral link 👇

Extra Innings…

  • Rest in Peace Tim Wakefield 🙏 a man who defied all the odds and inspired thousands of people along the way.

  • In the spirit of the legendary knuckleballer, another man is bringing the famous pitch back to MLB.

  • Non-sports news: a kind-hearted homeless man helped a first grader with special needs who wandered off a mile away from her school.

  • Fun find: Christmas is right around the corner, and I found the perfect gift for the BBQ lovin’ baseball fan in your life.*

  • If you made it down here: I appreciate you! I wouldn’t be doing this if it weren’t for people like you. Thank you for sending positive feedback and sharing these stories with your friends & family. It truly means the world.

*This is an affiliate link, which means if you buy something through it I will earn a small commission at no additional cost to you.

Reply

or to participate.