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  • Published: 04/03/2020

Courtney Cawley Gray’s interest in planning events began at a young age. She has gone from creating party favors and decorating prom to planning huge events as sales director at the Chicago White Sox ballpark.

Courtney Cawley Gray admits luck was on her side September 24, 2016. Months prior, Gray, a director of sales at Levy, one of the nation’s foremost hospitality players, had booked a wedding on that date at one of U.S. Cellular Field’s private rooms—amid a nearly twelve-hour music festival. Coordinating a wedding at the Chicago White Sox’s stadium during the ballpark’s first concert in thirteen years posed a monumental challenge.

Mixing an intimate affair loaded with high expectations with the influx of 47,000 concertgoers complicated Gray’s promises to her clients.
But the detail-oriented Gray was up to the task. From creating special parking passes for wedding guests to setting a defined photo schedule, she worked alongside park operations staff, engineers, security personnel and other White Sox partners to execute a memorable affair for the couple, punctuated by an onstage shout-out from music superstar Alicia Keys.

“The planning gods were with us that day,” Gray said.

The Waterford, Michigan, native claims a long-standing fascination with the events business. Her mother owned a bridal store, which naturally thrust a precocious Gray into conversations about service, hospitality and event planning, while Gray spent her
high school years creating party favors and decorating cakes at a local bakery before decorating her senior prom.

While attending MSU, Gray worked at the MSU Bakery and then the University Club of MSU, where her role in banquets and events provided rich insights into coordinating front-of-the-house and back-of-the-house operations. Those respective efforts deepened Gray’s interest in the events business and propelled her into a pair of key internships, one at the Aspen Institute and a summer 2004 tour with Levy at the White Sox ballpark. Levy was so impressed with Gray’s initiative and flair that the Chicago-based firm created a White Sox sales position for her upon her graduation.

“It pays to be with an organization that recognizes hard work,” Gray said.

Her first year with Levy proved a wild one as the White Sox stormed to a World Series title.

“Baptism by fire,” Gray called the 2005 baseball season. “We were hosting events for 1,200 people or more each night because there was so much energy around the winning team.”

Fifteen years later, Gray now steers sales for Levy’s White Sox operation, overseeing budgets, forecasting and client events at distinct event spaces scattered around the 40,615-seat ballpark, now called Guaranteed Rate Field. From corporate gatherings to bar mitzvahs,
Gray customizes events to ensure client satisfaction.

“Every day is different, and that means a lot of excitement,” Gray said from her office overlooking the diamond.

Gray has also used her penchant for event planning—and her Levy connections—to enliven Chicagoland’s MSU community. She chaired Spartyball, an annual green-tie gala hosted by the MSU Alumni Club of Metro Chicago to fund MSU scholarships for Illinois students, for five years and continues to support the event’s production, including hosting this year’s event at the team’s field. “To combine my passion for events and MSU was a real special opportunity,” Gray said.

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