about
Troy Daring, Jr.
Founder & Director, Head Coach
After a labrum tear ended his playing career, Troy Daring Jr.—a former Canadian National Champion, Canadian Futures Showcase (formerly Tournament 12) alum, and NJCAA/NCAA student-athlete—channeled his passion for the game into coaching and development. A 2019 recipient of the NCAA Troy Berry Award for Leadership, Character & Integrity, and a former collegiate coach, Troy founded the Ontario Winter Baseball League (OWBL) in Fall 2021 to support and inspire the next generation of players.
In 2023, the OWBL evolved into a branch of DARING ◆ DIAMOND SPORT DEVELOPMENT, allowing Troy to further his commitment to player development and meaningful mentorship. Through this platform, he continues to create impactful opportunities for amateur athletes.
Troy’s coaching résumé includes experience at the Canadian collegiate level, guest coaching at NJCAA and NCAA programs, the Toronto Blue Jays Academy, and the Ontario Blue Jays. He holds a BA in Psychology and an MBA from Wayne State University, Michigan’s third-largest university.
With firsthand knowledge of what it takes to succeed at the next level, DARING ◆ DIAMOND SPORT DEVELOPMENT is dedicated to equipping young players with the experience, instruction, and insight needed to elevate their game.
Chris naylor
Assistant Coach, Player Growth Consultant
With over 20 years of coaching experience, Chris remains a dedicated mentor in the baseball community, committed to helping athletes grow, succeed, and deepen their love for the game.
He has coached elite programs including the Mississauga North Tigers, Northern Dirtbags Elite, and the Ontario Blue Jays—developing talent both on and off the field. Under his leadership, teams have secured multiple Provincial and USA Championships, along with the prestigious 2015 National Championship title.
Chris’s coaching philosophy is rooted in discipline, enthusiasm, knowledge, and positivity. He fosters a structured yet supportive environment where players thrive through hard work, respect, and passion for the game.
Baseball is deeply personal for Chris—he has coached his three sons from t-ball to travel ball, all of whom were first-round MLB draft picks and have gone on to successful professional careers. This journey stands as his proudest achievement as both a father and a coach.
Chris is passionate about guiding the next generation of athletes, ensuring they are prepared for the challenges and opportunities the game presents.
testimonials
The program is incredibly well organized. Troy has found the balance between demanding development and fun. It’s an experience unlike any of the other many, many….many development programs I have sent my boys to. He creates unique experiences that the boys don’t have exposure to with their regular OBA club teams. So impressive!
Tom Edwards
Assistant Coach, Oakville A’s 11U AAA
Troy is an AMAZING coach who can pull the best out of each and every kid on that field. The program [OWBL] also teaches the kids how to approach every play like a pro from the way they move to the way they think through a play. I wish more programs provided such necessary skills for winter development.
Toni Atell
Mother of Carter Kikuchi, Leaside Leafs 13U AAA
Matthew had his best season yet… He has made both AAA teams he tried out for and he was offered spots on two CPBL teams. I believe that your OWBL contributed to that and as a parent, I truly appreciate you taking the time for youth baseball to get some game reps in over the offseason and the coaching you provide the players.
Peter Budziak
Director of Events, Vaughan Vikings
We have seen great improvement in our son’s batting and pitching skills with Troy’s coaching over the past several months, which also helped to build confidence in him. Troy exudes positive energy and coaches in a very constructive manner – he carefully identifies issues in mechanics and corrects them on the spot in a tone that’s encouraging. My son and his teammates also really loved the cool drills that Troy designed for the team training which made the indoor baseball season fun and effective.
Jasmine Pan
Mother of Lawrence Gould, Mississauga Majors 11U AA
My son attributes his improved approach at the plate to the drills Troy meticulously ran him through. Whenever he feels the need for a mental refresher, he revisits those drills, firmly believing they have played a significant role in his growth. Troy accomplished something that no other coach, instructor, or even myself has been able to do: he instilled unwavering confidence in my son, enabling him to become the best player he can be.
Todd Riverso
Director of Coaching & Player Development, Halton Hill’s Minor Baseball Association
I wanted to share something with you that Keelan told me on the ride home (he had me in tears). He was full of stories you told him… but one really sat with him. He told me a story about a prospect you had that asked their mom to leave when she walked in the room. He said that this didn’t sit well with you and Keelan agreed. He said ‘Mom, that’s why I always say thank you to you and Dad, even when you tell me that I don’t need to”. Troy, what you do for these kids is immeasurable… sure, you teach them to be amazing baseball players, but, more importantly you show them how to be amazing humans. THANK YOU for having such a profound effect on our son. You really are one of a kind.
Jenn Mitchell
Mother of Keelan Mitchell, Oakville A’s 14U AA
