During her days at Darien High School, Cassidy Schiff was one of the most prolific multi-sport athletes in Blue Wave history.

In her four years starting on the ice for the Wave, Darien won three FCIAC girls ice hockey titles and took the CHSGHA state championship in 2016 and 2017. Schiff was an All-FCIAC and All-State player as a senior co-captain and her overtime goal won the 2017 state crown.

A knack for winning carried over to softball where Schiff was a four-year starter for the Wave. A two-time All FCIAC Second Team selection, Schiff was co-captain of Darien’s 2017 FCIAC Championship team.

With that kind of pedigree, one would assume the road to collegiate athletics would be a given. That said, for Schiff, the road to the NCAA had its fair share of twists and turns as she did not commit to either sport and matriculated at Trinity College last fall without a roster spot.

“I knew I loved Trinity academically and that it was a good fit for me,” Schiff said. “But I didn’t know if the numbers would work in my favor. So when I started in the fall I was trying to figure out how the timing and juggling would work out between school and sports and what would be the best fit for me.”

Schiff started attending softball workouts the second week she arrived at Trinity and developed a strong bond with the team, helped in no small part by an old FCIAC rival and summer travel teammate, Gillian Birk. The former Staples High School star had already made the team and encouraged Schiff to try out as a walk-on.

“Those were my first friends on campus,” Schiff said. “My social group was going to be softball from the beginning. Everyone else was running around campus like Bantams with their heads cut off, not knowing who their friends were so that part was easy for me.”

Motivated by her new social dynamic, Schiff decided to make softball her priority and kept hockey on the back burner by joining the club hockey team. Trinity head coach Caitlin Hitchcock was familiar with her from the travel circuit, but Schiff took nothing for granted until she had cemented her spot.

“It was a roller coaster,” Schiff said. “There were so many months leading up to it. From September to February, there are no coaches around. The girls are just doing team bonding and all the freshmen are just trying to get integrated. Once the 6 A.M. tryouts started in February it was like a switch turned on and everyone was in high gear. It was a little scary at first but then as things kind of worked out, I knew I was meant to be there.”

Schiff ultimately earned a spot on the team, something that came as no surprise to her former high school coach.

“A coach always wants to see their players go on to play at the next level if they’re capable of doing that,” Wave softball coach Nick DeMaio said. “I was confident that if Cassidy played up to her capability she would not only make the team but that her coach would realize that this kid is a real asset.”

That realization did not happen overnight. Schiff spent a good deal of the season on the bench, used primarily as a pinch runner with only two at bats under her belt over the first 22 games heading into an April 17 doubleheader at Wesleyan.

That’s when everything changed.

Inserted at second base in game two of the twin bill, Schiff made the most of her opportunity, going 3-for-3 against the Cardinals. The next day she scored two runs in a start against Western Connecticut. Later that week Schiff started two of three games against Colby, going 4-for-7 with six runs and four RBI to help lead the Bantams to a sweep.

“I just kept pushing myself,” Schiff said. “I knew that when I was on the bench every time our coached looked down, there were all these really good players so I knew that I had to make the most of what I was given.”

By the time the NESCAC playoffs rolled around, Schiff had earned a starting job at third base, the one position that had not been solidified in the regular season.

Schiff finished the year with a .391 average and 16 runs scored. Five of her nine hits went for extra bases as Trinity won 10 of the 15 games Schiff appeared in — again proving that her track record as a winner was no fluke.

“Girls from our program have gone on to be very successful and I think Cassidy is going to be one of them,” DeMaio said. “I think she takes the approach of relaxing and doing the best that she can. She made the most of it and things have turned out really well for her.”

“I think that all my high school coaches prepared me very well,” Schiff said. “We had been successful and had championship teams, but those coaches knew what it was going to take. It was very rewarding being able to come back not only having made the team but having the whole story of working my way onto the team. If you had told me I’d be starting by the end of the year, I would have said, ‘no way.’”