Bobby Caldwell’s Wife Opens Up About the Singer’s Torturous Final Years

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A bad reaction to a commonly prescribed antibiotic left him in pain “24 hours a day, seven days a week.”

Up until the onset of the pandemic, Bobby Caldwell, the singer-songwriter who died last month at the age of 71, was regularly performing. The crooner behind the 1978 hit “What You Won’t Do For Love” still toured across the United States and in Japan, where he enjoyed a devoted following. But in 2020, when the world stopped, the music did, too — at least for Caldwell. By that point, he was “living a tortured life,” his wife, Mary Caldwell, says. 

Pain that coursed from his limbs up into his spine hounded him day and night, and in his final years, he was unable to walk without help. His decline was swift, Mary recalls. One day, he was still the vibrant embodiment of “blue-eyed soul” whose songs are still being sampled in music today. The next, he’d lost all feeling in his fingertips and could barely strum a guitar. What happened? The performer had been “floxed,” a term used to describe the brutal array of side effects caused by fluoroquinolone antibiotics. 

The Food and Drug Administration has issued a series of advisories about these drugs and recommended they only be used for stubborn infections, but few Americans seem to be aware of the risks. Mary’s hope is that by providing an intimate view of the harm fluoroquinolones exacted on Bobby, others will exercise greater caution around these commonly prescribed antibiotics. 

“I wouldn’t want anyone else to suffer this kind of fate,” she tells us.


Bobby’s downhill slide began on January 13, 2017, when he awoke with a cold. He was preparing for a 20-show tour in Japan and was hoping to curtail his runny nose and cough when he visited an urgent-care clinic. He came home with a prescription for cough syrup and levofloxacin, according to Mary, 63, who worked as Bobby’s manager and eventually became his caretaker.

For the next seven days, he dutifully took the medication — until one morning, he wasn’t able to stand. He told Mary that his “Achilles were killing him,” she says. She inspected the long tendons at the back of his ankles and found them inflamed and tender. The next day they saw an orthopedist who scratched his head and asked Bobby if he’d recently jumped off a building. Absent that, he couldn’t see how Bobby had sustained this level of tissue trauma. “It was so bizarre,” Mary says.

They eventually learned later that both of his Achilles had ruptured, one of the odd symptoms the FDA warned consumers about back in 2008. The reaction isn’t thought to be common, but it happens often enough that Barbara Trautner, M.D., Ph.D., a clinician at the Houston V.A. Medical Center studying antibiotic use, has a regular refrain for patients who start feeling pain there: “Call me right away.”

Mary quickly suspected that the levofloxacin was to blame. She researched the drug online and found a long list of warnings that included nerve damage, dangerous blood-sugar fluctuations, and even aortic rupture. But at that point, “it was like the genie was out of the bottle,” she says.

“It was so abrupt. Up until that seventh pill, life was great. Then it literally was like the curtain came down. Everything changed for the worst.”


Over the next couple weeks, Bobby developed peripheral neuropathy, defined as damage to the complex web of nerves outside the brain or spinal cord that can lead to a loss of feeling in the extremities, digestive issues, and unrelenting pain. Initially, Bobby felt a burning sensation that was isolated to areas below his mid-calf. But this “white-light pain,” as he described it to Mary, began to spread and intensify, radiating up his back and making it unbearable for him to stand on his own. 

“He said it would feel like somebody was hammering from his heels straight up, constantly,” Mary says. 

He also lost feeling in his fingertips, making it harder and harder for him to play the guitar or piano. Bobby was an accomplished musician who had performed in bands since he was a teenager in Miami, but without his sense of touch, he was reduced to groping around the keyboard, just hoping he was striking right the key, he told Mary. 

At first, Bobby and his band were able to disguise his disability. The singer was once an energetic presence onstage, sometimes collapsing to his knees while belting out a note. But after he was floxed, he spent most of his set seated behind the keyboard. On that first tour in Japan, his long-time manager, Jack White (not to be confused with the frontman for The White Stripes), said they dimmed the lights at the start of each show to discreetly wheel him onto the stage. “I was trying everything I could possibly think of to make it less obvious,” White says.

Bobby would often make light of his condition, telling the audience that “he tripped or rolled off the couch wrong,” White says. But not being able to work the stage “took a toll on him mentally,” White says.

Bobby kept operating this way over the next three years, returning to Japan several more times and playing in shows across the U.S. After growing up in a show business family, entertaining was the only way of life he’d known, and he intended to do it for as long as he could, Mary says.

“He used to say, ‘Look at Tony Bennett,’ [the legendary vocalist who retired at 95]. He would have kept going and going and going,” Mary says. 

Bobby was preparing for another tour in 2020 when Covid-19 brought all live music to a halt. In some ways, it was a small mercy, Mary says, because Bobby didn’t have to throw in the towel — his hand was forced by a global pandemic. But in his final years, his suffering only engulfed him further. Doctors attempted to ease the pain, at one point even prescribing narcotics, but nothing seemed to work. 

He was robbed of even little pleasures, too. Bobby was always known as a dapper entertainer (a reputation that helped him book a gig as Sinatra in a Vegas revival show) who rotated through dozens of pairs of fine leather shoes while performing. But the neuropathy had essentially disfigured his feet, leaving them too swollen and painful for him to slip on his favorite Italian loafers. He slipped into a depression, and after his final show in February 2020, he stopped singing altogether, Mary says. Privately, he raged that what he thought was a harmless drug had turned his life into a mosaic of agony. 

“He was miserable,” Mary says. “He’d go from being sad — I did see him literally weep — to being angry about what happened to him.” 

In the months leading up to his death, Bobby was eating very little and had lost a lot of weight. Then on the morning of March 14, 2023, he emerged from the bedroom with his walker. Mary was happy to see him moving, but as they sat together in their home in Great Meadows, New Jersey, he began to slouch onto her. Bobby died in her arms.

“He was gone, after six years and two months of torment,” she says. 

In the days after his death, there was an outpouring of grief. Obituaries ran in The New York Times, The Washington Post, and Rolling Stone, all commemorating the soul singer who helped shape music across multiple genres throughout four decades on the stage. “What You Won’t Do For Love” has been covered by countless artists, from Boyz II Men to Michael Bolton. His tracks have been sampled by Tupac and Common, and even now they find their way into new music. But the artist never thought much about his massive sonic footprint, Mary says.

“He wasn’t really a self-absorbed guy,” she says. “Without a doubt, if Bobby had seen the press coverage when he passed away, he would absolutely not have believed it.”

Mary is grateful both that Bobby received the attention his tremendous talent deserves, but also that tucked into all these tributes there’s a mention of floxing. In mid-March, after Mary tweeted about her husband’s fluoroquinolone reaction, millions of people searched Google to learn more about these nasty side effects. She hopes that by sharing Bobby’s story, others could be spared. 

That advocacy includes warnings about which questions to ask your doctor anytime you’re prescribed antibiotics. Mary recommends inquiring about what the medication is, what side effects it causes, whether it’s been given a black box warning, and whether your physician would take the drug themselves.

“If listening to this story saves one person from a nightmare like this,” she says, it’ll be worth it.