Freddie Gillespie Accomplishes the Unfathomable Going from DIII to the NBA

Before I started covering the Toronto Raptors, ironically the day Rudy Gobert tested positive for COVID-19, I was a sports reporter in a small town in northwestern Wisconsin. 

Writing for a newspaper in small-town America typically means covering every local sporting event from amateur bowling to high school football and sometimes DIII basketball. No offense to the UW-Eau Claire Blugolds who had their best season in recent memory during my lone year in Eau Claire, but DIII basketball was among my least favourite sports to cover. To me, the problem with DIII hoops was it felt like the end of the road for the young men and women who choose to keep playing sports into college. It was a sports career on life support heading for an impending end. It wasn't a means to a free education like DI basketball as much as it was playing out the final years of a game before reality set in.

For better or for worse, I've always been a bit of a realist when it comes to playing basketball. It pains me when I hear young basketball players say their goal is to play in the NBA one day. I get it, set high goals and all that stuff, but the chances of making the NBA are so infinitesimally small that it seems entirely unrealistic to even shoot that high. But then you hear stories of players like Freddie Gillespie who somehow defy all the odds and make it out of DIII not just to play DI basketball but eventually and unfathomably to the NBA.

Why? How? How could someone in that situation, playing in those cavernous DIII gyms look at their situation and think with any sort of degree of sincerity that one day they could play in the NBA?

"Have you ever seen a mustard seed?" Gillespie asked me responding to my question about his belief in himself. "It’s like really small. So sometimes that’s all I had, I had this really small inkling and I thought if I just work off of that then maybe I can get there.

"Did I think this is what it would look like or was I crazy confident and boasting around about it? No, but I had a little bit of faith."

That faith, he said, came from his mother, Alberder, who instilled in him an unwavering belief in himself. Even when the odds looked impossible, she forced him to look at things differently, choosing to see the glass half full, he said, instead of half empty.

"If you can do that there's no limits to what you can accomplish," he recalled her saying.

On Wednesday, that dream became a reality for Gillespie as he signed a two-year contract to remain with the Raptors for the rest of this season and potentially next year if the team opts to guarantee his deal.

"Honestly man, I know people are like, oh yeah, you know, I grinned to get here and all the suffering – not all the suffering, but all the sacrifices – paid off. But honestly, at the end of the day it’s a privilege, you know what I mean" Gillespie said. "This is one of the most esteemed fraternities in the world. There are 450 players that get to do this, so to be able to be one of them at this moment and to be able to get this opportunity is amazing."

Gillespie's journey to the NBA is almost unfathomable. The world of high school basketball scouting has become so intense and so good these days that it's almost impossible for an NBA-level prospect to truly slip through the cracks and fall to the DIII level. For all 300+ DI basketball programs to miss on Gillespie and for him to still crack a roster at Baylor is a miracle in and of itself. But then, to make the most of his 10-day contract not once but twice and then to sign a full NBA contract, well that's a story I'm not sure I can fully comprehend.

He gives hope to hundreds of thousands of boys playing high school basketball across the continent who have been told they're not good enough. He, for better or for worse, is a physical representation of why you shouldn't give up on your dreams; why you should keep grinding every day because even the seemingly impossible is possible.

Truthfully, I don't know if that's a good thing. I hope that it's not false hope because his story and that of Miami's Duncan Robinson seems almost too impossible to be replicated. And yet, here they are. They worked their way out of those cold empty gyms and onto basketball's biggest stage. 

I guess they just have more faith than I do.