Riverside’s Associate General Counsel Back Home Again After Achieving Her Dream

October 10, 2022

Our Stories
African American Woman in a floral shirt smiling

Well before Shukita Massey became Associate General Counsel for Riverside, the region’s premier healthcare system played a significant role in her life.

For starters, she was born at Riverside Regional Medical Center, where her mother, Angela Whitaker, worked for 32 years. Whitaker didn’t deliver babies, though she spent the majority of her career as a unit secretary for the hospital’s Labor & Delivery department before retiring in July 2022.

Massey occasionally joined her mother at work — recalling the thrill of riding down the escalator as a youngster to shadowing her mom years later. Often after work, Mom and daughter would share TV time together, tuning into dramas “Matlock” and “Murder She Wrote.”

“I know it’s cliché, but I found those shows fascinating,” Massey said. “I realized very early that I wanted to be a lawyer.”

Her goal never seemed far-fetched, and Massey credits a program called An Achievable Dream for providing the resources she needed to thrive. Riverside’s Board and management led the effort behind the transformative program that targets children who may not otherwise have access to the same opportunities, exposure, tools and resources as their affluent peers.

Massey was part of the inaugural class as a third grader. She and her peers remained at their respective high schools but took part in afterschool and summer enrichment opportunities. Massey remained in the program until she graduated from Heritage High School in Newport News.

“The program started off as a summer program for approximately 100 kids and now it’s developed into schools across multiple jurisdictions,” she said. “It’s exciting to see how it’s grown over the last three decades.”

Today, An Achievable Dream operates five schools serving more than 2,000 students from Richmond to Virginia Beach. Riverside has been instrumental in that growth.

“The power of the program is the sponsors, and Riverside has definitely been there from the beginning,” Massey said. “I’m very proud to be able to be with Riverside knowing years ago they had a role in helping me get through school and succeed. Knowing there were teachers and counselors and community support for us, knowing we had people who were rooting for us, that was motivation for me. I knew I had to succeed because there were all these people cheering me on. I’ve always said An Achievable Dream played a pivotal role in getting me to where I am today.”

At 14, Massey volunteered at Riverside and was later hired as an admissions clerk, working there during college breaks and summers while attending Mary Baldwin University. She graduated with a business degree.

Accepted into the Marshall-Wythe School of Law at William & Mary, Massey spent a summer completing an externship in Riverside’s Legal Affairs office.

After earning her Juris Doctorate, she clerked for a judge before spending the next 12 years as a prosecutor in the Hampton and Norfolk Commonwealth’s Attorney offices. Her path changed again thanks to a call from Riverside.

“I had the opportunity to come back as Associate General Counsel,” said Massey, who began her current role of overseeing all litigation matters involving Riverside in June 2022. 

“It’s definitely rewarding when you’re able to assist a provider who is going through a challenging situation or needs some direction,” she said. “Assisting families through their most vulnerable times and coming to a resolution that everyone is in agreement with so everyone can move on to live productive lives is very rewarding.”

While she’s come full circle, Massey did marry along the way. She and her husband, Melvin, are parents to three boys: Jailen, 20; Jeremiah, 10; and Jaxson, 7.

Professionally, she’s enjoying a new challenge in a familiar environment.

“I very much like that it’s a friendly atmosphere, very conducive to collaboration and teamwork and getting the job done,” she said. “Riverside really caters to its customer, the patient. Everyone has that in mind always.”

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