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How Sending 840 Emails Led Kalif Raymond to an All-Pro NFL Career

“The person you want to become has to mean more to you than the person you are now.”

Chronicling the journey of Kalif Raymond, from undersized high schooler to Division 1-AA football at Holy Cross to NFL All-Pro
Credit-AP/Joker Mag


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.

“That kinda sets up the story for everything else…that moment right there was, I think, one of the biggest moments.”

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 At The Podium with Manuel Amezcua.

“But apparently that was the only way 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.

“I remember being on the field and I’m like, ‘Hey, y’all are gonna have to tape this ankle up because I don’t have [any] offers.’”

“They’re like, ‘it’s turned to the right, you ain’t going back out there.’”

A quote from NFL wide receiver Kalif Raymond: "When I attack something, my ultimate goal is to achieve the highest level I can."

That’s when he looked up to the stands and spotted his best friend’s dad, Lawrence Nelson.  The 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 everything 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.

In his next two seasons, Raymond was a steady contributor in the return game and started working his way onto the field as a wide receiver too – starting 5 times as a sophomore, then 9 games as a junior.

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

“The NFL has always been an aspiration for me,” he told the Worcester Telegram & Gazette in 2016.

“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 helped him, 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.

With his eyes on the next level, Raymond ran into another roadblock.

Holy Cross didn’t have a pro day.

A quote from NFL All-Pro Kalif Raymond: "The person you want to become has to mean more to you than the person you are now."

So he was forced to find another way to get in front of professional scouts.

“That’s a whole process.  You’ve gotta call a scout, the scout has to call the school, the school has to say, ‘Oh, you wanna see this guy? We’ll let him in,’ and then it’s not your pro day.”

After scrambling to piece things together, he found an opportunity at Harvard.

“I had kind of like a historic pro day as far as what not to do.”

The paperwork had the start time set an hour later than the actual start time.  For the first time in his life, Kalif Raymond wasn’t early to a workout.

He was the last guy to show up.

“It was a lot going on, but thanks to all the training…[I] ran a 4.3, and that’s all she wrote from there.”

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 the 2023 NFL season, he signed a contract extension that keeps 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.”

Here are a few more football stories you might like:

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Written By

Division III baseball alum (McDaniel College) and founder of Joker Mag. Sharing underdog stories to inspire the next generation.



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