Seeking Equity in Sports

Story by Marisa Donelan | Illustration by Caroline Tomlinson

Olivia Greenaway ’22 fell in love with the game of squash in middle school after following her older sister into the sport. By the time she reached Milton’s Upper School, she was the only freshman to make it to the varsity team — and the only Black girl in the program — struggling both off and on the court.

“Even though I had always felt different from my teammates, by the time sophomore year approached, my inferiority complex was at an alltime high,” she told a group of Independent School League (ISL) athletes, coaches, and diversity, equity, inclusion, and justice (DEIJ) directors in November. “There was no amount of encouragement from friends or family that would alleviate the sense of anxiety that I had built up around my skill level.”

Greenaway, who is now in her first year at Columbia University, was delivering the closing address at the first-ever ISL Changemakers Conference, held at Milton. Her advocacy as a Milton student for social change in athletics was one of the catalysts for the conference, which welcomed select groups of students and adults from 15 ISL schools. Programs throughout the day included workshops on racially conscious leadership skills, equitable leadership, tools for interrupting biased language and behavior, and how privilege shows up in sports.

Activist, filmmaker, and former college athlete Byron Hurt was the conference’s morning keynote speaker. Athletes have a built-in level of status in the United States, and their behavior can set the social tone for a whole school, he noted.

“Because you are a leader, you have the potential to shape the direction of this country, to shape the direction of your school based on your status and your influence as athletes,” he said. “Why do you have some extraordinary opportunity for influence, wherever you are? Whether we like it or not, whether we agree with it or not, whether we understand it or not, athletes have a very high profile in this country. And it’s really up to you to decide how to use your status.”

Invented in England in the 19th century, squash has earned a reputation as a game of the white, male elite. Its unique court requires dedicated facilities and expensive equipment, and there are few free, public programs for new players to learn, Greenaway noted. In the United States, squash is disproportionately offered in private schools, which Greenaway explained are predominantly white and often enroll students from wealthier families. In her first years as an Upper School player, Greenaway felt isolated as one of the youngest players and othered by her racial identity. She overheard comments from teammates mocking Black visiting speakers and was asked to demonstrate a “Crip walk” (a move associated with a notorious Los Angeles street gang).

After a particularly rough patch during her sophomore year, Greenaway talked with her father about quitting the team. He encouraged her to keep at it. She raised her concerns with her coaches, who comforted her and called a meeting with the team to discuss its dynamics. Things felt more welcoming after that, until, while watching a match, she felt something delicately touching her hair: The mom of a white teammate was petting her box braids.

The COVID-19 pandemic interrupted ISL sports for most of the 2020–2021 academic year, which meant that Greenaway’s junior squash season was canceled. Before returning senior year as a co-captain, she established the school’s Diversity in Athletics Student Board to start the conversation about inequity in sports at Milton and beyond. Working with faculty member Molly Swain and others, Greenaway suggested expanding the conversation beyond Milton.

In the meantime, Milton hired Melissa Lawlor as the firstever Upper School director of equity in the newly established Department of Equity, Inclusion, and Justice. Lawlor, a former college athlete, had organized a similar conference in her previous job in New Hampshire. Milton’s Athletic Director Lamar Reddicks is the DEI commissioner for the ISL, Lawlor noted, so Milton made sense as the inaugural host for the event.

“The feedback was amazing,” Lawlor said after the event. “Universally, the kids wrote in how much they had craved conversation across the league. They loved this concept of coming together as one team to tackle issues of racial inequity.”

Lawlor recalls being one of only three athletes of color on one of her college teams. Although her white teammates were kind and caring, she felt that she didn’t have the power to speak out about things that made her feel isolated.

“Half the battle is getting kids to realize that they have that kind of power as athletes and what they can do with that kind of power,” she says. “Do they just sit on it and perpetuate the status quo? Or are they going to be the ones to put their social capital on the line? Because that’s real allyship if you are willing to put something on the line for someone else who might not feel comfortable using their voice.”

In the fall of 2021, the Diversity in Athletics Student Board was up and running at Milton, Greenaway says. They had four areas they wanted to investigate: equitable access to sports for students whose families couldn’t afford expensive equipment and private training; interscholastic conversations about sports equity; the allocation of athletic funds to various sports teams; and diverse representation for underrepresented student-athletes.

“These social biases are not unique to Milton they are reflective of a problem that permeates all educational institutions,” she says. “We need to have uncomfortable conversations that inspire athletes and coaches to take long, hard, introspective looks at the shadow aspects of our schools.”

When her senior squash season came around, Greenaway and co-captain Rhea Anand ’22 were the leaders of a more racially diverse team, which captured the ISL title and ended up ranking 12th nationally. Greenaway herself felt more confident, which was reflected in wins on the court. “Having more athletes of color join the team reminded me that I, too, belonged, and was worthy of succeeding,” she says. Today, she belongs to a women’s league at StreetSquash in Harlem, a nonprofit program that provides urban youth with athletic opportunities, academic enrichment, community service, and leadership development.

Seeing the Changemakers Conference come to fruition so quickly after the idea sprouted was wonderful, says Greenaway, who credits current and former Milton faculty like Lawlor, Reddicks, and Swain, along with Vanessa Cohen Gibbons, Chris Kane, and Heather Flewelling for supporting the efforts that led to the event. “I hope that all the attendees left the conference feeling inspired and ready to spark change in their communities.”

This article first appeared in Milton Magazine. Reprinted with permission.