Jordan Pettway: From D3 Basketball at Endicott Into a Sports Media Career
Listen to Jordan’s episode of the Student Athlete Sessions (Apple Podcasts)
Jordan Pettway grew up convinced he was going D1. He had the résumé: two state championship appearances, two All-State nods, honor roll, Notre Dame Fairfield — one of Connecticut's most respected programs. By every local metric, he was exactly as good as everyone was telling him he was.
Then he went to Putnam Science Academy for a post-grad year, walked into a gym with 24 kids who all played basketball, and watched 15 of them earn Division I offers.
"I had to elevate my game," he said. "What do you mean he's 6'5 and can play the same style of basketball as me? Like, I was confused."
That confusion turned into clarity. He landed at Endicott College, a D3 program outside Boston. And the path that followed — through a SLAM internship, a seat behind Pat Beverley's podcast cameras, and eventually a producer role at Barstool Sports — is one of the more unexpected post-playing career stories in D3 basketball.
Pettway recently joined the Student Athlete Sessions calling in from Queens, where he's been based for the last four years. The conversation covered recruiting realities, what D3 actually gave him, and how he built one of basketball media's more credible grassroots voices under the brand Shake Squad.
Jordan Pettway is a former Endicott Men’s Basketball Player.
The Prep School Wake-Up Call
Going into his junior year of high school, Pettway had to sit out AAU after shoulder surgery. With his main recruiting window gone, the post-grad year at Putnam wasn't a fallback — it was a strategy. A former teammate, Danny Upchurch, had done the same thing and gone D1 from there. Pettway figured he'd follow the path.
What he didn't fully account for was the room.
"We had like 24 kids there. We all played basketball. Everyone, every single person was good. We might have had 15 or 16 go D1."
At the time, AIC and Roger Williams were calling. Pettway wasn't listening. "I'm like a kid at the time. I'm like, no, I'm going D1, I'm going D1."
The prep year didn't produce a D1 offer, but it produced something more valuable: an honest look in the mirror. Pettway's advice for any high school player trying to calibrate their own level without access to that kind of environment is simple — start watching games.
"Back in 2016, you only saw the best player in the country on mixtapes, so you're like, alright, I don't have to be that. But now, you could go type in MAC games, you could watch highlights of what a low-major guard looks like, and then you could be like, whoa, he's actually really elite, too. You gotta start on the lower level. You gotta really humble yourself."
What Endicott Actually Gave Him
At Endicott, Pettway's career went like this: Sixth man as a freshman, starter by sophomore year, minutes dipped as a junior, and then COVID cut his senior season short. By his own admission, basketball didn't go exactly how he imagined.
"I kind of needed that little punch in the face — a humbling type of thing."
But zoom out, and the picture looks different. Three-time academic All-Conference. Highest GPA in his prep school class. Honor society. And crucially: three or four internships by graduation, including a stint at SLAM, while his D1 peers spent every summer on campus.
"At D3, you're home all summer, pretty much. I'm leaving school with 3 or 4 internships — especially in a media field where it's kind of hard to get into. People are seeing, oh, he has experience. That kind of set me up for my beginning jobs."
He was also getting something less quantifiable from the classroom. At Endicott, professors knew his name. They showed up to games. Coaches got automatic emails if a player was slacking. The accountability loop that so many D1 athletes escape through online classes and friendly advisors? Pettway was inside it.
"I remember at D3, if somebody was slacking on the team, their coach was getting an automatic email from the teacher. I always say, I'm glad I was in that. My teachers would be like, oh yeah, Jordan has a game tonight. It was more intimate."
He's since made peace with what D3 was and wasn't, even publicly. For a while, he downplayed it in professional settings, worried that covering D1 basketball while having played at the D3 level would undermine his credibility.
A trainer named Myrna Brady eventually called him on it.
"She was like, why do you always downplay that you played basketball? You played college basketball — not everyone gets to play minutes and play in championship games in college. And I was like, you're right, you're actually right."
Now he leans into it. Working in basketball media, he's found that most people around the sport have never touched a basketball. "I had a full advantage with that."
The Shake Squad Origin Story
Pettway's media career didn't start with a plan. It started with a hobby and a guy who needed help with his edits.
At Endicott, a former player named Drew Sawyer was training and building content for his page. He had a photographer but couldn't edit. Pettway could. So he started cutting video — first for Sawyer, then for other trainers, then just whenever he had a computer in front of him at an internship.
"If I had a computer in front of me for my internship, let me just edit some random basketball footage, play with stuff."
That scratched enough of an itch that when he graduated and moved to New York, he kept going. He landed behind the cameras at Pat Beverley's podcast — one of the earliest athlete-hosted shows in the current wave — and watched how on-camera talent operated up close.
"Being around Pat Bev, and Mikey at Overtime — they were never scared to say something, never scared to be on camera. How they were on camera was how they were off camera too. I was like 22, 23, and I was just like, I like that."
That observation eventually pushed him in front of the lens himself. He'd been reluctant — "I'm an editor, I'm an editor" — but he started talking over footage just to give his videos a face. The opinion side took on its own life.
"People started to trust my opinion. People reach out to me now asking, oh, what should I do with this, with that."
Now people walk into gyms and know him as Shake before they know his name. He's five years into building the brand, a producer and on-screen presence at Barstool Sports' Hooping and Hollerin', and still running Shake Squad Media's coverage of grassroots basketball independently — from AAU tournaments to high school gyms where kids are playing in front of double-digit crowds.
"I walk in the gym like, oh, Shake, Shake, what's up. People might not even know my real name, just off the company."
Being Early on the Right People
One of the underrated perks of covering grassroots basketball for long enough is that you compile a mental — and literal — archive of who you saw, when, and how good they looked.
Pettway was at Nike Peach Jam for the first video he ever posted. A 16U kid was blowing up on TikTok, and Pettway caught him on camera. The kid shared the video. Pettway's page got a boost. The kid's name was Jared McCain — now a rotation player for the Oklahoma City Thunder and one of the most recognizable young faces in the NBA.
"Now, to see his stardom — he's one of the most famous young players now. I have so many examples of that. I've kind of seen that from the jump."
The one he's most proud of spotting early: AJ Dybantsa, now a projected lottery pick. Pettway watched him dunk on someone in 8th grade.
"I never really used to talk about the grassroots stuff to my casual viewer friends. I'd be like, yo, one of your teams is gonna be relying on him one day."
The D3 Financial Reality
Jordan didn't sidestep the cost question. D3 tuition is real, and so are his student loans. But he's direct about how he thinks about the math.
He was a strong student coming out of high school — honor roll, high GPA — and that academic record opened aid doors that basketball couldn't.
"Get good grades. That's where your off-the-court stuff helps. Even if you're not a crazy basketball player, you get school scholarships from your grades. I do have student loans, but I'll do that 10 times over instead of going to a school that might not even have the major I wanted."
He also pushed back on the idea that cost is fixed or non-negotiable. He's seen athletes get D3 down to $5,000 a year by stacking academic scholarships, local awards, and institutional grants.
"There are so many different scholarships out there. You might not get a straight-on athletic scholarship, but there's other ways around things. It just depends on your situation."
His broader advice: Sit down with your family and your guidance counselor, do the research, and stop making the decision on sticker price alone.
On Where College Basketball Is Headed
Pettway has watched the landscape shift from inside the media industry. His read: the money is consolidating at the top, and everything below it is going to feel the trickle.
Hartford dropped to D3. St. Anselm moved from D2. The transfer portal has made low-major rosters more unstable than ever.
"The talent level of everywhere is gonna move up. A lot of schools will end up going D3. Even D3 players get a chance to move up — like, the talent will just rise everywhere, especially with the popularity of basketball."
He pointed to Aaron Nakruma — D3 at Worcester State, D1 at Tennessee State, now getting NBA call-ups — as proof that the path upward is real, if you keep playing.
What He'd Tell His 18-Year-Old Self
When asked the question every guest gets, Pettway didn't hesitate long.
"I would just tell them to chill out. It'll be okay. Just relax a little bit. I was kind of pressed with everything — I had to get a few shoulder surgeries, I was trying to play through everything. I would just tell them to relax, we'll be okay, soak it all in."
For someone who spent his teens convinced the D1 dream was right around the corner, there's a certain peace in how he says it. The path didn't go where 17-year-old Jordan thought it would.
It went somewhere better.
Jordan Pettway is a video and on-screen producer for Barstool Sports' Hooping and Hollerin'. Find him on Instagram and across platforms @ShakeHoops, on YouTube at Shake Squad Media, and on The Basketball List podcast. He and Drew Sawyer also run Thank You Basketball, a platform highlighting New England basketball talent. Listen to his full conversation on the D3direct Student Athlete Sessions podcast on Spotify, Apple Podcasts, or wherever you get your podcasts.