Greg Gutfeld, the sharp-witted host of Gutfeld! and co-host of The Five on Fox News, is known for his biting humor and unapologetic takes on politics and culture. But on a warm June morning in 2025, the man who thrives in the spotlight found himself undone by a simple, colorful piece of construction paper. His five-year-old daughter, Lily, had created a Father’s Day gift at her Manhattan kindergarten—a hand-drawn picture that brought the typically unflappable Gutfeld to the edge of tears. This is the story of a father, a daughter, and a crayon masterpiece that revealed a softer side of one of television’s most polarizing figures.

A New Chapter: Lily’s Kindergarten Adventure

Lily Gutfeld, the only child of Greg and his wife, Elena Moussa, started kindergarten in September 2024 at a private school in Manhattan. For Greg, a self-described “late bloomer” who became a father at 54, Lily’s transition to school was both exciting and bittersweet. “I’m used to arguing with adults on TV,” he quipped on The Five shortly after the school year began. “But nothing prepares you for your kid waving goodbye at the classroom door.”

Lily, with her mother’s dark hair and her father’s mischievous grin, quickly settled into her new routine. Her teacher, Ms. Clara Thompson, was a veteran educator known for fostering creativity and community in her classroom. As Father’s Day approached, Ms. Thompson planned a special event: each student would create a piece of artwork to honor their dad, to be presented at a small class celebration. The project was kept a secret from parents, adding an element of surprise that would prove especially meaningful for Greg.

The Kindergarten Canvas: Lily’s Labor of Love

In the weeks leading up to Father’s Day, Ms. Thompson guided her students through the art project. The children were given construction paper, crayons, markers, and stickers, with the instruction to draw something that reminded them of their fathers. For Lily, the task was both exciting and daunting. At home, she often watched her dad on TV, his quick wit and animated gestures filling the screen. But she also knew the quieter Greg—the one who read her bedtime stories, made silly faces at breakfast, and danced with her to old rock songs in their living room.

Lily’s drawing took shape over several days. Ms. Thompson noticed the little girl’s focus, her tongue poking out as she carefully selected colors. “Lily wanted it to be perfect,” Ms. Thompson later recalled. “She kept saying, ‘This is for Daddy, and he’s gonna love it.’” The drawing depicted a stick-figure Greg, identifiable by his signature glasses and spiky hair, standing next to a smaller stick-figure Lily. They were holding hands under a bright yellow sun, with a rainbow arching overhead. In the background, Lily added a crude but recognizable sketch of a TV set, a nod to her father’s career. At the bottom, in wobbly letters, she wrote, “I ❤️ DADDY.”

The classroom buzzed with creativity as the other children worked on their own drawings. Some depicted their dads fishing, playing soccer, or fixing cars. One boy drew his father as a superhero, complete with a cape. Ms. Thompson encouraged the students to share stories about their dads, creating a space where Lily proudly described Greg’s funny voices and how he always tucked her in with a kiss. “She was so proud of him,” Ms. Thompson said. “You could see how much she wanted to make him smile.”

Father’s Day at School: A Surprise Unveiled

The Father’s Day celebration was scheduled for the Friday before the holiday, June 13, 2025. Parents were invited to the classroom for a brief event, though they were told only that the children had prepared “something special.” Greg, juggling his demanding schedule at Fox News, initially worried he might have to miss it. But Elena insisted, knowing how much it meant to Lily. “You’re not skipping this one, Gutfeld,” she teased, her Russian accent softening the command.

On the morning of the event, Greg arrived at the school in his usual casual attire—jeans, a black T-shirt, and sneakers—his eyes hidden behind sunglasses. He joined a dozen other fathers in the colorful classroom, where construction paper decorations and alphabet posters lined the walls. The children, dressed in their best outfits, sat cross-legged on a rug, barely containing their excitement. Lily, in a blue dress with a bow in her hair, kept stealing glances at her dad, her grin betraying the secret she’d been keeping for weeks.

Ms. Thompson welcomed the parents and explained the project. “Our kids have worked hard to create something from the heart,” she said. “These drawings are their way of saying thank you for all you do.” One by one, the children stood and presented their artwork, some shyly, others with theatrical flair. When Lily’s turn came, she clutched her drawing and walked to Greg, who was seated on a tiny chair that looked comically small beneath him.

“Daddy, this is for you,” Lily said, her voice loud with pride. She handed him the folded construction paper, her eyes wide with anticipation. Greg unfolded it, and for a moment, the room seemed to fade away. His trademark smirk softened as he took in the vibrant colors, the stick figures, the rainbow, and the TV set. When he read “I ❤️ DADDY,” his throat tightened. He blinked rapidly, later admitting he was “fighting like hell not to lose it in front of everyone.”

A Father’s Heart: Greg’s Emotional Response

Greg, known for his quick comebacks and irreverent humor, was uncharacteristically quiet as he studied the drawing. He pulled Lily onto his lap, wrapping her in a hug. “This is the best thing I’ve ever gotten, kiddo,” he said, his voice low but steady. The other parents smiled, some dabbing their own eyes as they watched the exchange. For a man who thrives on public debate, this private moment with his daughter was a rare glimpse into his softer side.

Later, Greg would describe the experience as “a punch to the gut—in a good way.” On Gutfeld! the following week, he shared the story with his audience, holding up a framed copy of Lily’s drawing. “Look at this masterpiece,” he said, his usual sarcasm replaced by genuine warmth. “My kid’s already a better artist than half the people on cable news.” The audience laughed, but the emotion in his voice was unmistakable. He went on to talk about fatherhood, admitting, “You think you’re tough, but then your five-year-old hands you something like this, and you’re a puddle.”

The drawing resonated with Greg because it captured the duality of his life—his public persona as a TV personality and his private role as a dad. The TV set in the background was Lily’s way of acknowledging his career, but the hand-holding figures and rainbow showed what mattered most to her: their bond. For Greg, who often jokes about his “grumpy old man” tendencies, the drawing was a reminder of the joy and responsibility of fatherhood.

A Family Moment in the Spotlight

Elena, who attended the event with Greg, was equally moved by Lily’s gift. A former Russian model and photo editor, Elena has largely stayed out of the public eye, focusing on raising Lily and running her fashion business. But she couldn’t resist snapping a photo of Greg and Lily with the drawing, which she later shared on her private Instagram with the caption, “My two favorite artists.” The image, which showed Greg’s rare vulnerability, was a stark contrast to his on-screen persona.

The Father’s Day celebration didn’t end in the classroom. That weekend, Greg and Elena took Lily to their home in Long Island, where they celebrated with a backyard barbecue. Greg hung Lily’s drawing in his home office, next to his collection of vinyl records and vintage posters. “It’s my new favorite piece of art,” he told friends, only half-joking. For Lily, the highlight was her dad’s reaction. “He said he loved it, Mommy!” she told Elena, beaming.

The Bigger Picture: Fatherhood and Perspective

For Greg, the drawing was more than a gift; it was a milestone in his journey as a father. At 60, he’s older than many parents of kindergarteners, a fact he often pokes fun at on his show. But fatherhood has given him a new lens through which to view the world. In interviews, he’s spoken about how Lily has softened his edges, even as he remains a lightning rod for controversy. His political commentary, often polarizing, takes a backseat when he talks about his daughter, revealing a man who cherishes the small moments over the loud ones.

The kindergarten event also highlighted the power of simple gestures. Ms. Thompson’s decision to create a Father’s Day project gave Lily and her classmates a way to express love and gratitude, fostering bonds that will last far beyond the school year. For the Gutfeld family, the drawing is a keepsake—a tangible reminder of a day when a five-year-old’s crayons outshone the brightest studio lights.

A Lasting Memory

As Father’s Day 2025 faded into memory, Greg returned to his hectic schedule, trading the classroom for the Fox News studio. But Lily’s drawing remained a touchstone, a symbol of the love that grounds him. In a world of hot takes and headlines, it was a quiet moment of connection that left the famously outspoken Gutfeld speechless. For a man who makes his living with words, the silence said it all.