Softball Newcomer Realizes Future Potential At CHS

Softball Newcomer Realizes Future Potential At CHS


Cheshire High School senior Trinadey Santiago found herself at a crossroads in November of last year. Transferring from Danbury to Cheshire as a junior, she had to leave behind her childhood home for the chance to realize her potential in the classroom and on the softball field.

“At first, it was really hard because I had grown up with so many people in Danbury,” reflected Santiago. “I’m not the best at moving into new friend groups, but I put myself out there and I’m glad that I did.”

While the coronavirus pandemic prevented Santiago from making her Rams softball debut this year, she has already achieved two goals that she set for herself. In signing a Division II scholarship from American International College (Massachusetts) this fall, Santiago has earned the opportunity to keep playing her favorite sport and also become the first person in her family to attend college.

“It is really important to me,” said Santiago. “I can’t thank my family enough for their support. By being able to come to Cheshire, I’ve worked hard to earn the grades I need to get into college.”

Since many colleges closed their doors to visitors this year, Santiago initially struggled with her recruiting process, but then she remembered meeting Head Coach Shalise Tolentino prior to the pandemic. She toured AIC on Sept. 12 and then committed during her second visit on Oct. 17.

“I really liked the chemistry when I watched the team practice,” recalled Santiago, who started playing softball at age 7. “It was good to see the girls connect well.”

She was also drawn to the campus at AIC.

“It was busy like Danbury, but also had the feel of Cheshire where everybody knows everyone,” explained Santiago. “Both of those places have made me who I am today.”

Growing up, Santiago tried out gymnastics, soccer, and softball. She recalls planning to quit softball until joining the Danbury Crush program at age 9.

“A lot of my teammates were older than I was, so it was a big deal to still make the team,” stated Santiago.

In playing for the Crush, she started to like the freedom she had in softball.

“You play with others, but can also work on your own time,” said Santiago. “Softball has always been an escape for me. I can relax and feel comfortable.”

She feels that the sport has allowed her to spend more time with her dad Mike, who has coached on her travel teams.

“It has made our relationship a lot stronger because we have connected through softball,” Santiago reflected. “He is always there to help and understand me.”

Santiago started out playing mostly shortstop, but moved to catcher and third base right before her freshman year at Danbury High School. She has also played at first base.

“I like catching more than the others,” said Santiago. “You are involved in every play.”

At Danbury, Santiago shined as an underclassman, earning All-Fairfield Country Interscholastic Athletic Conference Honorable Mention and Second Team honors.

“I grew up with a lot of my teammates, so we were very close, but I didn’t feel like I could play to my full potential at Danbury,” explained Santiago.

In coming to Cheshire for her junior year, she felt comfortable working with the Rams softball program.

“It has shown me what it means to be part of a team,” stated Santiago. “They care about your feelings and you have so many other people that you can count on.”

CHS Head Coach Kristine Drust feels that having a supportive and judgment-free atmosphere has allowed her softball program to stay strong for years.

“Our environment is great for anyone new who is willing to be part of something bigger than themselves,” said Drust.

Santiago credits Drust for helping her develop on and off the field.

“She has made me realize a lot of things about myself as a person and a player,” explained Santiago. “She has taught me about accountability and how I should expect that from others.”

Santiago was excited to play for CHS this year, but when the coronavirus hit the U.S. back in the spring, the Connecticut Interscholastic Athletic Conference chose to cancel the 2020 season.

“It really stunk because junior year is big for recruiting,” reflected Santiago. “Not being able to play was tough because I wanted to show why I came here and what I can do.”

Despite not playing games, the Rams came up with activities like Zoom calls to keep the team together.

“I feel that we worked through the situation the best way possible,” said Santiago. “I’m glad that we didn’t put everything to the side.”

When pandemic restrictions were scaled back in the summer, Santiago was happy to return to the diamond with the Cheshire Wildcats.

“I had felt like I was trapped in quarantine, so it was so good to be back with everyone,” recalled Santiago. “Working with the girls made me feel comfortable.”

With the opportunity to play for her dad and friend Craig Sears, she decided to change programs to the Connecticut Impact Fastpitch Organization in August.

“I play with a lot of amazing girls from different (high school) conferences,” Santiago said. “Even though we don’t come from the same area, we get along really well.”

“She has an unreal work ethic and true passion for the game,” stated Drust, of Santiago. “When those two things meet up, your game grows quickly.”

After she moved to Cheshire with her dad, Santiago’s mother Candice and brother Quentin have come to join them this year.

“It feels good to know that I’ve found a home, and so have they,” stated Santiago. “It shows that the Cheshire (softball) program and community cares for others.”

Santiago is happy to be among a group of Cheshire seniors going on to play softball in college. Bri Pearson (Adelphi University-New York), Danielle Floyd (Johnson & Wales University-Rhode Island), Gracie Hemstock (Western New England University-Massachusetts), and Ella Watson (Fairfield University) will also play on the next level.

Since Adelphi and AIC both compete in the Northeast-10 Conference, Pearson and Santiago will move from teammates to opponents in college.

“I joke with her all the time that I’m watching her pitch really close now,” Santiago said.

A two-year starter, captain, and elite pitcher in the state, Pearson has played with Santiago for the last three years in travel softball.

“I’m glad that we have gotten closer,” said Santiago. “I understand her and she knows me, too.”

Santiago feels that the pitcher-catcher relationship is very important.

“If a coach can’t see something on the field and I know the pitcher, I can pick the right pitch and settle them down,” explained Santiago. “You need to have that kind of connection or you won’t reach your full potential together.”

Santiago hopes that health conditions allow CHS to play softball games in 2021. Prior to having last season canceled, Cheshire had won six straight division titles and captured the 2019 Southern Connecticut Conference crown.

The Rams had also made five consecutive state semifinal appearances.

Cheshire graduated quad-captains Lindsey Abramson, Ari Perlini, and Emma Watkinson, as well as Carina DeClement, from last year’s team.

“I’m so excited to play for them. I’m counting down the days until practice starts,” said Santiago. “I feel that we need to take the opportunity that our seniors didn’t get last year. We are not replacing them, but we are going to show what the program will do for them.”


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