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Family, Grit, Excellence: No Question!

Army West Point Softball is building on success and a firm belief that success comes when everyone is doing their best.

By Kim McDermott ’87, WPAOG staff

Photo above: The Army West Point Softball team just prior to doubleheader against Colgate on April 26, 2021

Army West Point Softball head coach Cheryl Milligan developed a love for softball at an early age. Having grown up in a baseball family, she says she can still remember her first softball practice and the feeling of the ball in the glove—she fell in love with it. She admits she was that kid who “specialized early,” but just never wanted to do anything else. She gave soccer, diving, and even gymnastics a try, but says no other sport seemed as right, so she played softball all year round. As a four-year student-athlete at Tufts University, she played in every inning of her career. She then remained at Tufts as an assistant and then head coach before coming to West Point.

Experience at an institution like Tufts, which also has such a high focus on academics, made the transition to West Point easy in some ways. She says, “I’ve seen a place where I know players are going off to be engineers or NASA scientists, but that doesn’t mean [the game] isn’t important—so getting them to embrace that can actually help.” At Tufts, Milligan took over from her old coach, whom she played for and coached with, so she was very familiar with the existing ethos. Having to establish her own team culture within the larger West Point culture has been more of a challenge. She knows that emphasizing to her players, “to be a better leader and person, commit to a cause, all those things sports teach you,” will ultimately be the key. And with that comes winning—not at all costs—but being willing to put in time and sacrifice to be successful is a big part of playing softball at the college level.

Cadet Madelyn Gilmore ’22 says: “I think playing softball helps with the challenges of being a cadet and the development into a future officer due to the pure nature of the game…you are constantly failing. West Point is a place where failing can come into play more times than we would like whether that be academically or physically. West Point will find the one thing you struggle at, and it will shove it in your face every day. Those that succeed here are the ones that look at those weaknesses and embrace them; they decide every day to somehow learn from it and find a way to grow.”

The story of Army West Point Softball is a simple one: the coaches want the women on the team to be better in all pillars of their leader development. Of course, they want to win games, too, but the coaches realize that the game is only one aspect of the cadet experience. In fact, Milligan says, “Anything less than trying to do what we can to make them the best humans is a disservice.”

Cadet Alicyn Grete ’23 recognized this during her first visit to West Point. She says: “I knew I wanted to come whether I could play softball or not. I loved how everyone at West Point seemed so committed to my individual success, from the cadets to the instructors to the people at the Center for Enhanced Performance. I was also drawn to the medical career path West Point provides and the amazing opportunities for research.”

Photo left: CDT Jolie Duong’22 (Pitcher/Utility) stealing base

Milligan recognizes why her players are at West Point. Unlike some programs, softball is not a sport with a future for them: their immediate future is firmly in the military. So, her coaching philosophy is all about helping the women understand and celebrate their roles on the team so they can learn and succeed. She likens it to branches on a tree. Imagine sitting in the trunk of a tree and you want to say, “I’d like my branch to go toward being the starting shortstop. That’s great—but right now I need you to be the best backup second baseman you can be.” Her aim is to find that sweet spot between allowing the tree to grow and blossom, while still allowing the team to get what it needs.

As a relatively new head coach, Milligan is still learning a great deal about the team and what they can do. A large part of this has been creating a common language. With only about two hours for practice on any given day, there is not a lot of time to spend discussing things. “We have lots of vocabulary lessons,” she says, so calling out a simple phrase can keep things moving, and everyone is clear. She believes the team is starting to understand this concept and the tone she is trying to set.

By her own admission, Milligan is a quiet coach. Gilmore says, “Her demeanor is a calm one, but I never doubt for a second that there is a constant fire of wanting to win and succeed on the ball field.” Milligan has high expectations for her players. She says, “You shouldn’t be doing something if you aren’t ready to go all in.” The team is extremely young, with less than a handful of juniors and seniors, so there is a lot of room for growth. Army West Point is a very talented team but still learning how to win. Milligan says, “It will be important to beat those teams with more confidence than us.” She adds, “That confidence will come in embracing our culture and what we bring to the table.”

Recent circumstances have not made it easy for the team to demonstrate its potential. Last year, due to COVID-19, the entire schedule was disrupted. At one point in the 2021 season when they would normally have had 30 games in the books, they had only 13. There were also no tournaments this past season, preventing the team from gaining experience competing against multiple teams in one event. Milligan says the frequent COVID testing and schedule changes created “lots of adventure,” and she knows that the post-COVID environment will bring more surprises and allow her to continue learning more about West Point.

Milligan cites three values that describe the chemistry or dynamic of her team: family, grit, and excellence. “We’re new coaches, but we’re working to be that first phone call when something big happens,” she says. Like family, the members of the team have each other’s backs—on and off the field. “We may fight and not all get along, or someone won’t say the right thing, but we’ll be easy to forgive and forget,” says Milligan. The grit factor is all about remembering the gratitude. Milligan tells her players it does not matter how bad their day was: they need to appreciate how fortunate they are to be “standing here at a great academic institution, getting a great education—and you get to play the game you love.” And of course, excellence is defined as striving for greatness in all their pillars, not just on the field. Milligan says that her players must use all 24 hours in the day to their best advantage in all these areas.

The team’s mantra is “No Question!” Grete says, “Someone will ask ‘Can you get a hit here?’ or ‘Can you make this play?’ or ‘You got me?’ and they answer, ‘No Question!’” Gilmore chooses to look at “No Question!” as another way to represent and show her teammates unconditional love. “No matter how much we may fight and bicker like sisters, at the end of the day we will pick one another up without any hesitation.” Grete says: “Softball has also helped me learn how to deal with conflict on a team. When we spend 3-5 hours a day together every day, we are likely to run into conflict sooner or later. Learning to deal with this in a loving and mature way will be an invaluable skill as a future officer.”

Photo right: CDT Ellie Caldwell ’24 (Catcher/ Infield) playing infield

Many coaches find it difficult to choose a favorite or proudest moment for their team. Milligan is no different and says there are so many: the wins, an undefeated season, watching a player earn an award for excelling in other areas such as academics. And, especially at a place like West Point, she feels graduation is “pretty amazing.” To see the players walking away—bonded for life— and to know they may have never met and become friends if not for softball, “you realize you’re affecting lives, for more than just the four years.”

Milligan had no connections to the military prior to West Point, other than her husband was a pitching coach for the Army West Point Baseball Team. She had left a coaching position at Tufts to reunite her family as her son was beginning school fulltime. While she was working from home, with her son in kindergarten, she sought out opportunities—one of them being a vacancy when an assistant coach at West Point left. Milligan was asked to fill the void. In June 2019, she was named the head coach.

Like the other Army West Point head coaches, Milligan understands the value that her alumni players bring to the team.

While COVID has affected her plans to include more alumni-focused events, it remains part of her vision. She recalls a time when the team had the opportunity to talk with Lieutenant Colonel Anne C. McClain ’02, who was aboard the International Space Station. When a player asked what McClain pulled from her West Point experience that prepared her so well for the mission, McClain indicated it was the teamwork, perseverance, and time management learned as a cadet-athlete that prepared her, and that she draws on it every day. Milligan says it is great for her softball players— soldiers, West Point cadets—to see women doing great things in the military and serving as role models. She looks forward to future engagements with the alumni players who have no doubt gone on to great things in all endeavors, and who can inspire her players.

She is still figuring it out, but Milligan is well on the way to creating one of the strongest Army Softball programs yet. While it is still early in her tenure, she foresees the toughest adjustment will be “learning how we use our day.” She realizes that cadets are busy, but they need to know it is worthwhile to spend the time to improve and develop. She says, “The time can even be seen as a break, but it should be a working break. Everyone needs to give their all.”

Grete knows that the players can balance their strengths and weaknesses and help each other to reach individual and team goals. And Gilmore says: “I love the idea that I would be challenged every single day to either grow with the tough times or be defeated by them. I can confirm that that challenge is present every day here at the academy, but every day I grow, and I am truly thankful for that. And the Army Softball team helps those challenges get a bit easier, which is an amazing blessing to me.”


Printed in West Point magazine, Summer 2021, all rights reserved.