Head of the Class

Meet Brig. Gen. Cindy Jebb, West Point’s first female dean

Rockland County native Brig. Gen. Cindy Jebb made history this summer when she became the first female dean of the academic board at the United States Military Academy of West Point, replacing Brig. Gen. Tim Trainor, who had held the position for six years. 

Jebb, who served as professor and head of the Department of Social Sciences before the appointment, was born and raised in New City, where she attended Clarkstown South High School, played varsity sports, and ordered pizza from the former Town Tavern. She graduated from the Academy in 1982 (she was one of only 64 graduating female cadets in that class), and has several post-graduate degrees, including a doctorate in political science. Among her accomplishments are serving as the Deputy Commander of the 704th Military Intelligence Brigade, conducting human security research in Africa, and completing study projects in Iraq and Afghanistan. She and her husband, Joel, met as undergrads at the USMA, and raised their three children in Cornwall. 

Hudson Valley magazine recently had the opportunity to attend Jebb’s first conference, meet the woman behind the uniform and learn more about her journey to the head of the United States’ most prestigious military academy.

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Where were you when President Obama nominated you for the position and how does it feel to be dean?
The superintendent announced it at the Athena’s Arena Conference, which marked 40 years of women at West Point; I was teaching a class. When I went back to my office, I saw that my cell phone had ‘exploded’…I feel humbled when I see the great people who came before me and to have this opportunity to build on their legacies. There are almost no words to express how honored I am to be here and to serve and work with these phenomenal staff, faculty, and cadets. 

I feel there’s a lot at stake going forward, so it means we need to continuously advance. There’s no room for complacency. That’s what motivates me and inspires all of us. What makes it exciting is that we’re all here for a common purpose, and that’s what unites us, and that is the defense of the Republic.


Was it difficult leaving Cornwall after becoming dean?
It was emotional when we walked through the house, and you just see all the empty spaces, because that’s where we raised our children. But now living on post, we feel very honored to live in such a historic home. We’re looking forward to sharing it with members of the community. [Moving] was bittersweet, but now we’re more on the sweet end.

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What do you like most about your job?
“What I like the most is working with people. We have phenomenal faculty and cadets. They’re inspiring, they’re energizing, and they’ve made a decision to commit to service.


What’s your favorite part of campus?
What’s really beautiful is the library. If there is one place I like to go and reflect, it’s there. If you go to the top floor, you get a beautiful view of West Point. In the afternoon it’s interesting because you can look down and see some of the cadets drilling, the baseball team playing, cadets maybe tossing a Frisbee, or running, and the parachutes coming down from the parachute team practicing. It’s all the activities going on right in front of you.


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How do you prepare the cadets for life after West Point?
The West Point academic program is a liberal arts education program. They have opportunities to major in over 37 majors, and this is all designed to teach how to think, not what to think. No one can sit here and imagine what kind of challenges our graduates are going to find themselves in, so we need to make sure that we’re providing the experience, curriculum, and mentorship to really develop that mental agility to be able to think through those kinds of challenges. It’s not only about being problem-solvers, but to be able to anticipate new kinds of problems, to know what problems not to solve, and to feel comfortable being part of a diverse team.

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