"You don't belong here," the male midshipmen might say. A few seemed to take particular glee in pulling her down as she attempted the Herndon Climb, which culminates plebe year.
Cheslack was one of 295 female plebes, a record 24 percent of the entering Class of 2016. She and her classmates arrived Thursday expecting the toughest summer of their young lives. But they spoke matter-of-factly about the increasing gender equity of the brigade. That casual acceptance felt like victory for the women of earlier classes.
"It's a good reflection on the times," said Kurtz, now a Florida attorney and a reserve captain in the Navy supply corps.
The record number, up from 19 percent last year, is a natural result of long-term efforts to diversify the brigade, said Lt. Rachel Walker, an academy admissions officer. "I don't expect that it will stop there," she said.
There seemed little distinction between the male and female plebes as they waited apprehensively outside Alumni Hall.
"Honestly, it's not a big deal in this day and age," said 2012 academy graduate Jameson Marshall, on hand to assist with induction day.
In a few hours, the plebes would all wear the same white New Balance running shoes, share the same struggles to achieve a rigid salute and hear the same barked admonitions from upperclassmen. Women would be spared the head shavings imposed on male classmates, but that seemed the only break.
"I've heard not to worry about it, because they don't treat you any differently," said Ashley Paek, a soccer player and aspiring physician from Leesburg, Va.
When she expressed interest in the academy, her dad, a postal worker, said, "Oh my God. You're a girl, you can't go."
But once Paek's parents learned that the academy charges no tuition and has a significant percentage of female students, they changed their tune.
Paek was chatting with classmate Cynthia Nestor of Silver Spring. "It's amazing," Nestor said when asked about the progress of women at the academy. "It shows how much we're doing."
"It's everywhere," Paek added. "Women are stepping up."
Nestor said she warmed to the idea of the Navy when she saw a hospital ship delivering supplies and care in Haiti after the 2010 earthquake. She seemed unconcerned about the coming rigors of plebe summer.
"At the high school where I went, everybody treated everything as a joke, and I hated it," she said. "But this is about as serious as you get."
Some troubling aspects of life remain for women at the academy.
The Department of Defense reported 22 sexual assaults there in 2010-2011, twice as many as the previous year and up from five in 2006-2007. More than 16 percent of female midshipmen said they had experienced unwanted sexual contact in a 2009-2010 survey by the Defense Manpower Data Center. Academy officials have said they're not sure if assaults are actually up or if programs that encourage reporting of offenses are simply working better.
Regardless, this year's female plebes said they would deal with similar issues at any university.