At the peak of his playing career, Jevohn Shepherd would sometimes wake up in the middle of the night in a cold sweat. Despite everything going well, perhaps because everything was going well, worries about the future started to creep in.

“I was having so much fun, I was performing at such a high level and I was thinking, ‘Oh my gosh, what happens after this?’” Shepherd said.

What happens after this, following more than a decade playing professional basketball around the globe, is that Shepherd continues having fun and continues his hoop dream. Only this time, he does it as a broadcast analyst, working the play-by-play booth for the CEBL, and now, in his next step, as the newly appointed general manager of the Ottawa Blackjacks in the CEBL.

Speaking shortly after the announcement was made, Shepherd was excited, but also eager to get things moving. In a year where plans of all kinds have been shifted, put on hold or cancelled indefinitely, taking over as a general manager in a time of uncertainty is a challenge unique to 2020.

“It’s been upside down for the past week and couple of days, but the dust is finally settling and we’re getting back to some normalcy, which is cool,” Shepherd said. “It’s great news, but nothing actually starts until months from now.”

The nerves of wondering what’s next replaced with a calm that can only come by knowing you’re exactly where you want to be.

“It was amazing,” Shepherd said of getting the news. “It was a great feeling because I feel like I have a good connection with the Canadian basketball community. There’s some good rapport there.

“It was exciting because it was like, ‘This can be a job? Something I do everyday?’” Shepherd continued. “Talk and communicate with friends that I played with, that I played against? Coming up with a blueprint and a common goal? I have to thank the Ottawa Blackjacks for the opportunity.”

Professional athletes dedicate so much of their lives to accomplishing the goal of playing professionally, and then when they are able to do so, they know that the window will be much shorter than other “normal” jobs. Retiring in the mid-thirties is usually an indication of a long and enduring career. Knowing he was nearing the end of those days, Shepherd began to reach out to those in his circle who had finished their careers and successfully transitioned to something beyond basketball. Among those he contacted was former Senior Men’s National Team captain and teammate Jermaine Anderson. 

“Having a strong support system that truly loves you helps a lot,” Shepherd said. “Guys that have gone through it and are going through the process as well, you learn from them. That helps tremendously. Jermaine Anderson was a big help. I had a lot of mentors along the way as well. Things just start to unfold. You start to identify what you want to do after and begin to re-apply everything you’ve done to accomplish so much in basketball, except now you’re just going to channel it in another avenue.”

Like Shepherd, Anderson’s post-playing career led to the CEBL, where he was named general manager of the Hamilton Honey Badgers earlier this year.

Shepherd’s basketball roots run deep. His passion for the game began at an early age as he watched his uncle play at the park while he was growing up. Though too young to join in with the grown men playing, he would watch patiently, then eventually was rewarded with a chance to mostly just pass the ball until he became old enough himself to join in. While his earliest memories at the park are some of his fondest, he also credits the arrival of the Toronto Raptors franchise with helping that hoop love to flourish.

“The influence of Damon Stoudamire, Vince Carter, those guys are like mythical characters, but at the same time they’ve helped to develop that love through the influence they have” Shepherd said.  “There’s always the love for Michael Jordan, everybody loves Jordan, but the Toronto Raptors were our own. That gave us the identity as Canadian basketball players and that helped to start that basketball culture.”

After leaving home when he was 18 to attend the University of Michigan, Shepherd knew he would go wherever his basketball journey led him. He also knew eventually he would return home and give back to the basketball community that gave so much to him when he was younger.

“It means a lot to me because I've spent so many years away,” he said. “I left Toronto when I was 18 and now I’m 34.  There's been too many years in between and it means a lot. I wouldn’t do it anywhere else than here.”

After spending more than 12 years playing for Team Canada at various levels, getting to watch how basketball has exploded in Canada while he’s been away toiling at his own craft overseas has been incredibly gratifying for Shepherd. When he left for university, dreams of making it to the NBA were a long-shot for Canadian, while now it’s an expectation for Canada’s top young talent.

“It’s an amazing feeling of accomplishment because you now know you were a part of laying that foundation,” Shepherd said. “The next generation continued on the path you took and improved it and innovated,” Shepherd said. “I didn't accomplish the big goal of making the NBA, but if you look around we have a record number of Canadian born guys in the NBA. Whatever happened before them helped to lay the foundation. Their accomplishments are just as much mine and I celebrate them as well. To see Jamal Murray going off, to see Cory Joseph going into his 10th year, to see Tristan [Thompson] win a championship, to see Kelly [Olynykl] in the finals. All guys I've played with and against, seeing them as young kids into grown accomplished men [has been amazing].”

With the title of general manager in Ottawa, Shepherd will now be in charge of providing deserving opportunities for Canadian hoopers who would like to play professionally without having to leave the country.

“I think it’s just putting the pieces of the puzzle together,” he said. “It’s almost like a project and to see it unfold I'm very excited. When I get emails from the Ottawa Blackjacks staff, there’s so much support. I'm literally there to put the pieces of the puzzle together. The support system over there has been tremendous and I’m just excited to get to work.”

Much has changed with respect to basketball in Canada since Shepherd first left home to begin his own career. From the record number of Canadians in the NBA like he mentioned, to the aforementioned Toronto Raptors winning the franchise’s first NBA title in 2019, Shepherd is immensely proud of each step forward Canada has taken.

“The landscape and the culture has changed so much and it’s great to see,” he said. “There’s just so much more opportunity for the youth today. Canada Basketball does a really good job with their youth programs and their ID programs to really continue the successes we’ve had and that’s amazing as well. Everybody is giving back and everybody is benefitting. Especially, and most importantly, the younger generations.”

With former Canada Basketball teammate Anderson serving as a key voice and support system for Shepherd as he navigated his early post-playing days, Shepherd says bonds like this are common among former Canada Basketball teammates. While he singles out his experience with the Senior Men’s National Team at the 2010 FIBA World Championship in Turkey as a highlight in his professional career, he says the friendships and family he’s made along the way will always matter most. 

“The relationships, the camaraderie, there’s nothing that can substitute that or replace that,” Shepherd said. “That takes precedence. Those memories last forever. Those guys [are incredible.  I got messages from Jesse Young the other day, Andy Rautins, Rowan Barrett, Steve Nash.  We always share memories and it doesn’t go away. It’s a bond.”

Most recently, these bonds were on display when Ottawa announced Andy Rautins as the assistant general manager of the BlackJacks. Though their playing careers took different routes, both Shepherd and Rautins share a common goal that extends beyond the task at hand.

“We want to be the same mentorship for the next generation that’s going to be retiring in the next 10 years [that we had from those who retired before us], so they can have a smoother adjustment as well,” Shepherd said.

Witnessing the improvement of young players and the strides in youth development in Canada, Shepherd sometimes wishes he could fast forward into the future a few years to see what’s ahead.

“I’m excited to see where Canada is going,” he said. “Continuing to develop our talent,  I definitely will have to be a part of and look forward to being a part of and look forward to being a voice of the new school.”

With a new title, a new and exciting project in front of him, and basketball still firmly in the forefront, Shepherd is content. Extremely thankful for how things have worked themselves out, Shepherd says he knows it doesn't get better than getting to combine one's passion and purpose. “True happiness and true wealth is living in your passion,” he said.