Michelle Cobb Retires after 20 Years at GDS

Michelle Cobb approached her decision to leave GDS with the same intensity that defined her as both an artist and an educator. She did not want to quietly transition to her next chapter with a vacation; she wanted a challenge worthy of the note on her easel: I have yet to create my greatest work.

While Michelle was a practicing artist throughout her 20 years at GDS, the weekends and summers she carved out for her own work were no longer enough. At the end of the 2024–25 school year, she retired from her roles as Chair of the Studio Art Department and High School art teacher to devote her full energy to her craft. Her first stop: a 2025 summer residency at New York’s School of Visual Arts, where she applied her plein air techniques—traditionally practiced in the open air of the countryside—to urban environments.

“I couldn’t believe that I was accepted into this program at my age,” said Michelle, 70. “But I think participating in art residencies around the world during the last 15 summers and having my own studio practice gave me an edge. I was up and running without any hesitation almost immediately after the residency started.”

This dual identity as teacher and working artist was Michelle’s superpower, many of her colleagues and mentees said. By maintaining a rigorous personal practice, she served as a living blueprint for her students. She didn't just teach a curriculum; she modeled the discipline of a professional. This created a rare credibility in the studio, where her own artistic evolution fueled her ability to lead others through theirs.

“She didn’t expect anything from anyone else that she wasn’t expecting from herself,” said former HS art teacher Nick Ryan, who worked closely with Michelle. “Within a year or two of her taking over, the body of student work had jumped 10-fold in quality.”

The Art of Seeing

The artistic drive was there from the beginning. At age four, Michelle covered a wall in her grandmother’s Nashville home with a sprawling mural, certain that praise would follow. “But I got in a lot of trouble,” she said, laughing. By age 10, she declared her intentions to her parents: she was going to be an artist. Her father (a surgeon) and her mother (a psychologist) worried about that choice, citing the lack of opportunities for Black female artists at the time. But her father eventually gave his blessing with a single condition: that she strive to be the best. “That set my standard for life,” she said.

Guided by both passion and pragmatism, Michelle merged her creative ambitions with professional security. After earning degrees from Skidmore College and George Washington University, she launched a career at Time-Life Books. At age 28, she became the youngest—and first Black—promotion art director at Sports Illustrated in New York City. She developed campaigns for the Olympics, the U.S. Open, the Kentucky Derby, and other high-profile sporting events. “But no matter how successful I became, I didn’t feel like a ‘real artist,’ so that constantly gnawed at me,” she said.

Seeking a new direction, she moved to Delaware to lead communications for Sanford School. But it was a chance encounter in Wilmington that truly shifted her trajectory. While wandering through the Delaware Art Museum, Michelle found herself transfixed by the work of Edward Loper, Sr.—the celebrated Black painter known for his vibrant plein air palette.

When Michelle realized that Loper was teaching a class for far more advanced painters, she pleaded with him to let her in until he finally relented. But the victory was short-lived. After several lessons, Michelle pressed Loper on why he was not providing her with much feedback. His response was biting: “Because you weren’t listening. You’re not here to learn. You just want to replicate pretty photographs.”

Shattered, she packed up her supplies and left. But after six months of persistence and reflection on both her own goals and Loper’s teaching, Loper allowed Michelle to return.

The reconciliation marked the start of a 16-year mentorship that informed Michelle’s artistic vision and teaching style. Under his tutelage, she internalized the practice of seeing color and working from observation, principles she would later instill in students when she joined GDS in 2005.

Throughout her tenure at the School, Michelle evolved her craft by completing a circuit of international summer residencies—from the sun-drenched landscapes of Umbria, Tuscany, and El Bruc, Spain, to the Rhône Valley and Aix-en-Provence in France, as well as Martha’s Vineyard and across West Africa in Ghana, Togo, Nigeria, and Benin.

DEVELOPING ART WARRIORS

At GDS, Michelle brought a new level of rigor to the studio, epitomized by her insistence on using oil paints—a complex, slow-drying medium that carries prestige but demands careful handling and technical discipline.

“It was an indication that she wanted us to give students a professional art studio experience,” said Nick, then-head of the Studio Art Department. “She was highly structured about evaluating the work at every stage, setting clear objectives, and being very specific in her critiques.”

Among Michelle’s many signature contributions was the annual Identity Art Show, inspired by her work as an AP Studio Art Reader—where she continues to evaluate portfolios for the College Board. Equally vital was the plein air course she created, which emphasized direct observation, a key component of her teaching. For that course, she took students to the park behind GDS and taught them to apply swatches of color side-by-side, never blending or relying on photographs.

Inside the studio, CJ Greenhill Caldera ’10 remembers the “Ten Commandments-style list” that Michelle posted on the studio wall. Among them was a “don’t evaluate” mandate that called on students not to step back from the canvas—a habit Michelle said distracts from direct observation and invites self-doubt. Eager to impress, CJ tied her Doc Martens shoelaces to a stool to train herself to stay still and focused.

“We had drill sergeant Michelle—the no-smile, no-A+ Michelle who made us art warriors,” said CJ, now a curatorial assistant at the Hirshhorn Museum.

But along with the tough love exterior came unyielding support.

When CJ exhausted the School’s Advanced Placement offerings as a sophomore, Michelle curated a two-year independent study, set aside studio space for her, and even helped her price her work for the open market. By graduation, CJ said her portfolio was so formidable that Wellesley College lured her with the promise of private study under a prize-winning painter. “Michelle helped make this possible by giving me space to endlessly produce and be challenged,” CJ said.

As a collective thank you, several of Michelle’s students have donated more than 30 original pieces to the School at Michelle’s request–including CJ and Mai-Han Nguyen ’17. These works are part of a permanent art collection displayed throughout GDS.

For Mai-Han, Michelle’s impact extended into the home. Her immigrant parents supported her talent, but an arts career felt abstract and risky to them. As Mai-Han’s advisor, Michelle helped bridge that gap, warming them to the idea of art school. Today, Mai-Han is a Background Animation Artist for Nickelodeon. “It’s really because of Michelle that I’m living my dream,” she said. “She is my mentor, my friend, and my biggest inspiration.”

That sense of possibility took on a specific resonance for Jazzmin Cox-Caceres ’19, who found in Michelle a mirror for her own future. “Michelle taught me what life could look like as a Black artist and educator,” said Jazzmin, an Afro-Latina who recently taught history at GDS. This mentorship included practical training in everything from drafting artist statements to preparing digital files. Now an MFA candidate at Philadelphia’s Tyler School of Art, Jazzmin said, “Michelle helped me feel like I could be an artist in every sense of the word.”

“NOT FROM WHERE I’M STANDING”

While Michelle was busy helping students find their voices, she was just as intentional about listening to them. As she saw it, her teacher status did not grant her a monopoly on vision.

Marlo Thomas, Assistant Head of Equity and Inclusion, saw the power of Michelle's approach through her son, Montez McNeil ’20. While sketching a skeleton in art class, Montez was corrected by Michelle, who told him the angles and shadows were off. “Not from where I’m standing,” he replied.

Michelle didn't pull rank. Instead, she climbed onto a stool, looked at the model from his sightline, and immediately understood. "Oh my God, you're right," she said.

“That was a beautiful moment of adult modeling,” Marlo said. “My son felt valued and heard because Michelle was willing to ask herself: What does it mean to continue to be a learner?”

It was a disposition Michelle knew well. Even after moving to DC, she visited Loper, her mentor, every weekend in Delaware until his death in 2011 at age 95. Toward the end of his life, as Loper struggled with dementia, Michelle grew worried that her skills would diminish without his eye. As a test, she brought him a mixed batch of paintings: some created under his tutelage and others painted independently.

He could barely remember her name, yet his artistic eye remained sharp. He immediately separated the two groups. “I don’t know where you did that first batch, but they’re good," he told her. "The second batch? Not so good.”

It was the confirmation she had feared, and in time, the gift she needed. The bar Loper set for her in Delaware hasn’t budged.

Her artwork and designs now reside in notable collections, including Stanford University’s Black Graphic Design History Collections Initiative and the U.S. Supreme Court chambers of Justice Ketanji Brown Jackson. For four decades, she has taught painting, drawing, and graphic design at various institutions, including the University of Maryland, the Metropolitan Museum of Art, and the University of Delaware. She continues to teach painting online at Smithsonian Associates and she was granted a solo show at the Woman’s National Democratic Club in April 2026.

Still, Michelle treats these accolades as merely markers on a continuing journey. She remains her own toughest critic. “I’ve come to realize that I may never be satisfied,” Michelle said. “I don’t know what the standard is that’s going to make me feel like I’ve arrived. All I know is I want to keep evolving. I don’t want to get complacent.”

(Originally published in Georgetown Days magazine 2025-2026)