For more than two decades, Jimmy Kimmel has been a nightly presence in American households—a late-night host with a quick wit, a warm laugh, and a style of humor that often managed to feel both mischievous and comforting at the same time. But behind the effortless charm and the familiar desk, a storm has been gathering. Now, according to those closest to him, that storm may push him toward a decision fans have long feared: walking away from television altogether.

In early 2025, Kimmel experienced one of the most devastating losses of his life—the sudden passing of Cleto Escobedo III, his childhood friend and the longtime bandleader of Jimmy Kimmel Live. For 20 years, audiences had come to know Escobedo as the smiling musician behind Kimmel, the one who laughed at his jokes, played him into commercial breaks, and shared subtle on-screen chemistry that could only come from decades of true friendship. But the connection ran much deeper than that. Kimmel and Escobedo had been friends since 1979, long before fame, long before late-night television, long before either could have imagined the careers they would build side by side.

According to Globe, a source close to Kimmel described the depth of the grief that followed Cleto’s death—and how profoundly it affected the 58-year-old host. “Jimmy is spiraling,” the source said. “He’s known Cleto since he was just a kid and he never expected him to be gone this soon. It’s got Jimmy facing his own mortality and questioning everything. He’s in a very dark place.”

Those who have watched Kimmel navigate difficult moments on air—mass shootings, political upheaval, his own son’s medical struggles—know that he is not a man who hides his emotions easily. But when he delivered the monologue announcing Escobedo’s death, viewers saw a version of Kimmel that felt stripped bare.

“We’ve been on the air for almost 23 years, and I’ve had to do some hard monologues along the way,” he began, his voice thick with grief. “But this one is the hardest because late last night, early this morning, we lost someone very special who was much too young to go.”

He paused, visibly struggling. The studio, usually filled with laughter and applause, felt suspended in a somber silence.

“It’s just not fair,” Kimmel continued. “He was the nicest, most humble, kind, and always funny person… He was just a great older brother. No baggage, all love. There’s no one in my life I feel more comfortable with.”

To many, the monologue felt less like a statement from a television host and more like a eulogy from a man broken open. Shortly afterward, Kimmel took a week-long hiatus from the show—something he rarely does outside of vacations or special events.

But what fans didn’t know then, and what now appears clearer than ever, is that Kimmel was already standing at a crossroads before this loss. His grief didn’t create the crossroads—it simply illuminated it.

In an interview with the Los Angeles Times in 2024, months before Escobedo’s passing, Kimmel had hinted that his time in late-night might be drawing to a close. “I think this is my final contract,” he said, half-joking but clearly torn. “I hate to even say it, because everyone’s laughing at me now—each time I think that, and then it turns out to be not the case.”

Retirement had been hovering at the edges of his mind. He had spent 23 years shaping Jimmy Kimmel Live, transforming it from a chaotic new show fighting for ratings into one of the most enduring and influential programs in late-night television. But time, family, and personal loss have a way of shifting one’s priorities.

According to the source who spoke with Globe, the emotional blow of losing Escobedo may have accelerated the timeline. “Jimmy is tired and he’s grieving and he’s completely burned out. You can see just by looking at him that he’s barely holding it together,” the source said. “People in his life are begging him to step back from the show before the job eats him alive. They’re terrified that if he doesn’t make a change soon, the stress will destroy him. He’s never been this down.”

Those closest to Kimmel have expressed growing concern, urging him to take a longer break or even consider stepping away permanently. Running a nightly television show requires stamina—not just physical stamina, but creative stamina, emotional endurance, and the ability to absorb criticism, cultural shifts, and relentless public scrutiny. Even in the best of times, the host of a major late-night program carries the weight of constant performance. Doing so while grieving a lifelong friend is almost unimaginable.

What makes Kimmel’s situation especially poignant is that the show is more than a job to him. It was a dream he built with Escobedo at his side. They shared inside jokes, childhood memories, the rise from small-town kids in Las Vegas to nationally recognized entertainers. Their friendship began when they were barely teenagers—two boys trading jokes, talking about music, trying to figure out life. Losing someone who has known every version of you is a particular kind of heartbreak.

For Kimmel, the loss seems to have cracked open deeper questions. What does he want the rest of his life to look like? How much longer does he want to carry the nightly responsibility of hosting? And is the show the same without Cleto sitting a few feet away, grinning at him with that familiar mix of amusement and brotherly affection?

While Kimmel has not announced any formal plans to retire, those around him say that the grief has shaken him in a way nothing else has. Even if he chooses to remain on television beyond his current contract, many believe he desperately needs time—time to process, time to rest, time to heal without the relentless pressure of performing five nights a week.

Experts often remind us that grief is not linear. There is no schedule, no set of steps, no predictable shape. It appears in waves—some gentle, others crushing. And when grief intersects with burnout, the emotional toll doubles.

Kimmel has built a career on humor and heart, but even the strongest public figures are human behind the camera. Only he can decide what comes next. His future—whether in late-night television or away from it—depends on what he believes will bring him peace in the aftermath of a loss that deeply altered his world.

For now, all anyone can do is hope that he receives the emotional support he needs, that he allows himself the space to grieve fully, and that whatever choice he makes about his career is one that honors both his well-being and the memory of the friend he loved so much.

Fans may not be ready to imagine late-night TV without Jimmy Kimmel—but the decision ahead is his alone, and it is clear he is facing it with a heart still heavy, still healing, and still searching for the way forward.