BORN LEADER: Tyler Osborne tracks a shot during his career with the Princeton University men’s squash team. Osborne ’15, who helped the Tigers win the 2012 national title in his freshman season, is currently serving as a full-time assistant coach for both the Princeton men‘s and women’s squash programs. (Photo Courtesy of Princeton’s Office of Athletic Communications)

Tyler Osborne came to Princeton University in the fall of 2011 from Canada to join the Tiger men’s squash team as a prized recruit of legendary head coach Bob Callahan.

The Kingston, Ontario native quickly thrived in his new country, earning All-Ivy League and second-team All-American honors as a freshman, taking a key role in one of the greatest triumphs in program history, posting a victory over Trinity’s Miled Zarazua to help Princeton edge the Bantams 5-4 in the College Squash Association (CSA) championship match and end their 13-year reign at the top of the men’s college game.

After earning multiple All-Ivy and All-America honors over the rest of his college career, Osborne wasn’t ready to leave Princeton. Shortly after graduating in 2015, he was named as the full-time assistant for both the Tiger men’s and women’s programs, a position that became possible due to the contributions to The Robert W. Callahan ’77 Head Coach of Men’s Squash endowment, established after the coach’s untimely death earlier that year when he succumbed to brain cancer.

Osborne jumped at the chance to stick around at his alma mater and stay involved in squash.

“I had helped out with the Princeton summer camps three of my four summers,” said Osborne.

“I had been helping out with the Princeton junior program throughout my college life here. I love squash and I always thought it would be a hardship if I couldn’t continue in some fashion with squash. Having an opportunity to still be involved with it was something I was super excited about and then to have it be Princeton just makes it all more sweeter, trying to give back to the the university that gave me so much and so many memories. It was an opportunity I couldn’t pass up.

For Osborne, the historic 5-4 win over Trinity in February 2012 before an overflow crowd at Jadwin Gym remains the indelible memory of his Princeton career.

“The most amazing thing was the sheer number of people who were involved in that day,” recalled Osborne, who posted a career record of 57-10 playing in the top third of the Tiger lineup.

“The crowd was spectacular. I think for me, one of the main reasons I was able to get through that match was just the amount of support I had off the court rooting for me. I was never in an environment before that where you could feel so many people that wanted the same thing that you wanted and that gives you that extra motivation. As the match goes on, it would really be a letdown if I wasn’t able to pull this one out.”

Earning the title for Callahan made it extra special. “Bob has had a tremendous influence on me and every other Princeton squash alum as well as those in the squash community who are associated with Princeton,” said Osborne.

“Bob made us do the work. Just being able to give back and to win that title more for him and all of the hard work he put in to recruit us and to challenge us, is something special and definitely a memory that is going to be with me for the rest of my life.”

Osborne, though, hit a crossroad early in his freshman campaign, taking a brief hiatus from the team that fall as he struggled with the transition to college squash.

“I just needed to take some time to reset because mentally it became draining more than anything else,” said Osborne.

“Sure enough, you take a short break and you realize then I really love this sport. We had fun coming down and having that two hours every day, doing something that deep down I must really enjoy. It wasn’t a very long break, just a few days.”

Gaining that perspective has helped Osborne in his current role as he splits his time, working for women’s head coach Gail Ramsay and men’s head coach Sean Wilkinson.

“That is definitely the one thing I was able to bring to this program, that insider intel of what actually goes on; which days can we do harder practices, which days can we do lighter,” said Osborne, noting that initially he did have to establish a distance from players that were his friends during his playing days.

“They tend to know a lot about the academic side of it but the social side of it doesn’t come up with the coaches. I have good insight into saying that this weekend is probably not a good weekend to do anything because of the things going on campus outside of the academic and athletic world.”

Over the last year, Osborne has gained a lot of insight into the game and teaching from coaching with Ramsay and Wilkinson along with longtime volunteer assistant Neil Pomphrey.

“With Sean being relatively new and Gail having been here for over 20 years, they have different ways of setting up their systems and their teams,” said Osborne.

“There are benefits to each program and so trying to learn each system and also learn what different players on the teams need and using that to build my coaching base gave me a solid year of learning from the two of them.”

Ramsay, for her part, believes that Osborne has made a valuable contribution to her program.

“For his age, he is mature and professional,” said Ramsay, who has been coaching the Tiger women since 1994 and has guided the program to five Howe Cup national titles.

“He brought that connection with the teams and the coaching staff, which could sometimes be disastrous, but in his case, the experiences were really positive and he did a great job.”

In her view, Osborne has also brought a unique competitive experience to his role.

“He hit the ground running; he coached some throughout college and he is self taught in his own game,” added Ramsay.

“Those type of people have a real insight in how to play and how to get people to do things. He did bring that element to the team.”

Wilkinson was excited to have Osborne remain around the men’s team.

“It was pretty much a no-brainer, Tyler has got a tremendous squash IQ,” said Wilkinson, who coached Osborne in his final two college seasons.

“You get a lot of great athletes that learn to play squash. Tyler is a great athlete who actually understands the sport at a much deeper level.”

In Wilkinson’s view, Osborne has displayed an even deeper understanding of the game over the last year.

“He has developed phenomenally well; he is in a situation where he gets to work with two head coaches that have slightly different styles of communication and certainly different takes on the game,” said Wilkinson.

“With his ability to learn and understand the game at a deep level, I think he has really come a long way. I don’t find myself holding his hand. He is the type of assistant coach that if I have to miss a day for whatever reason, I am not panicking. I don’t have to tell him what to do or leave a lesson plan for him. He really does do a tremendous job with all of our kids.”

Due to Osborne’s progress, Wilkinson believes that the young assistant has a bright future in coaching.

“I don’t think there is a coach in the country that wouldn’t want him working for his program; he is head coach material right now,” said Wilkinson, who succeeded Callahan as the Tiger men’s coach and is in his fourth season leading the program.

“I know from being in Tyler’s shoes a few years ago, being a young assistant coach with a lot of enthusiasm, you have to be patient to wait it out. That is unfortunately the way it is at the moment. If he is willing to be patient and hang on and wait for the right opportunity, someone is absolutely going to snap him up. He is the real deal.”

Osborne, for his part, is showing an enthusiasm to master the fine points of coaching.

“I am starting to develop a stronger voice and starting to have a better knowledge of each of the coaches, their systems, and the players,” said Osborne.

“Having seen the players from a coaching point of view for two years, I can figure out what certain players need and how I can best help them and the advice I can give them that I think will get them there. I also took the time last year to go through two levels of coaching development in Canada. Those clinics definitely helped to give me the tools I need to become a better coach and a more insightful coach to help the players as best as I can.”

Focusing on match tactics is a key component of Osborne’s effort to help his players.

“To me that is the one part of the game I have always had a pretty good understanding of and it is the one part that I feel like I can give back,” said Osborne.

“Whether it is watching and doing match reviews with the players, even in matches, I think it is something I have a good grasp of.”

While recruiting is seen as a necessary evil by many assistant coaches, Osborne is relishing that aspect of his job.

“It is neat hearing of people’s interest in Princeton and pursuing which players we think would make the best fit for the programs and which players we think would help us on and off the court,” said Osborne.

“It is like a puzzle, trying to put it together. There are so many tremendous players and athletes out there from all over the world that trying to find those that would best help Princeton makes it exciting.”

Osborne is excited to still have a place in the sport and is in no rush to leave Princeton.

“With the amount of fun I am having doing this job, it is tough to see myself not staying involved in some way in college squash,” said Osborne.

“This happens to be one of the jobs where if you are in it, you are in it for the long haul. A lot of the coaches across collegiate squash have been with their teams for years. The turnover rate isn’t that high. I am happy to bide my time and work for a little bit and see what becomes available.”