At 5:14 on a June morning in 2015, John McEnroe woke up in Paris in a sweat, briefly confused about where he was and whether he had missed a match. The anxiety of that moment is something he captured in the prologue of his 2017 memoir, But Seriously, noting how little thirty years do to smooth over the biggest what-ifs of one’s life. Once jolted into reality, he realized it was all done and dusted; he had lost the 1984 French Open final to Ivan Lendl all over again in his dream. It still wakes him once, usually twice, during every French Open he works as a commentator. Now 67, he has put the regret on record again, as he finally makes one long-overdue announcement, per Tennis 365.

“Do I have regrets? Yes. I could have won more tennis matches,” he said in a recent interview with Tennis365. “I should have won the French Open, I should have played the Australian Open more often. But I’m still talking to you now all these years later, so that suggests I left some kind of mark.”

McEnroe skipped the French Open on six occasions during his career, while the Australian Open was still dealing with its remote location, fluctuating dates, and comparatively low prize money, and many top players routinely stayed away. McEnroe himself made only five Australian Open appearances during his career. His best run in Melbourne came on his debut in 1983, when the second seed reached the semifinals before losing to eventual champion Mats Wilander. He returned only four more times, reaching the quarterfinals in 1985, 1989 and 1992. That left his seven singles majors concentrated entirely at the other two Grand Slams: three Wimbledon titles and four US Open titles.

The French Open, though, became the more glaring omission in an otherwise extraordinary résumé. The tournament was played on slow red clay, a surface that naturally reduced some of the advantages of McEnroe’s serve-and-volley game. The red clay was hence not his favorite surface, and the hot sun and two weeks of best-of-five-set matches made Roland-Garros particularly demanding for him.

McEnroe had never progressed beyond the quarterfinals in his first four appearances in Paris, but that changed in 1984, as he suddenly looked almost unbeatable on the clay, dropping just one set through his first six matches before beating longtime rival Jimmy Connors in straight sets in the semifinals.

He then took a two-set lead over Lendl in the final before the match slipped away in five sets, in the only French Open final of his career. McEnroe later said he was playing his best tennis in that match. “It was a match I should have won, and it turned into the worst loss of my career,” he wrote in his memoir. Before that, he had already named that final the biggest disappointment of his career, and admitted that in his first six years on tour he “didn’t take the French Open very seriously”

The stakes, too, looked much deeper once all was done. McEnroe went on to win Wimbledon and the US Open that year. Had he beaten Lendl in Paris, he would have won the first three Grand Slam tournaments of the year and been in position for what was then a calendar Grand Slam, since the Australian Open was played in December at the time. He eventually recorded an 82-3 season, the best single-season win rate of the Open era. McEnroe has since wondered aloud whether he should have played two more Australian Opens and two fewer Davis Cup ties, and said it could have meant more majors.

“I was the best tennis player in the world and that isn’t enough for you, so that’s tough. There’s nowhere else to go with that,” McEnroe added in the interview.

The what-ifs extend beyond the Grand Slam calendar, as he kept running after regrets to get over them, and eventually burned out.

After the 1985 season, McEnroe reached a point where he needed to step away from tennis altogether — taking a six-month sabbatical in 1986 and a seven-month break following the 1987 US Open — fantasizing about what life might look like without the sport. Yet retirement was never quite what he wanted. When he announced his indefinite leave, he was already telling people he expected to return, insisting there were still “a few more fights” left before he and Jimmy Connors called it quits.

When McEnroe eventually came back, though, he admitted that the desire to compete had not fully returned and that he still had to find the player he had once been. The pattern followed him for the rest of his career: even in 1987, while saying he expected to stop playing within two years, he was simultaneously talking about returning to his 1984 level and becoming No. 1 again. His exit in 1992 was similarly reluctant. After losing to Goran Ivanisevic at the Grand Slam Cup, McEnroe said he would probably no longer play tournaments but resisted making an official retirement announcement.

In practical terms, that marked the end of his full-time singles career, but not quite the end of his playing days. After sitting out 1993, McEnroe accepted a wildcard into the 1994 Rotterdam Open, making a brief return to singles before losing to Magnus Gustafsson, 6–2, 7–6(5), in the first round. That Rotterdam defeat was ultimately his final ATP Tour singles match. Even then, he continued to return to the professional circuit in other forms, most notably in doubles, reinforcing how difficult it was for McEnroe to break away from tennis.

Amidst all that internal chaos, his marriage to actress Tatum O’Neal, which had begun in 1986, was falling apart. He said he had told her that if he did not win another major, he would stop playing and look after their children so she could pursue acting. The marriage ended anyway, and he said it threw him into disarray.

So now, in 2026, years later, he is finally taking the opportunity to announce his retirement in clear words: “In fact, I never officially announced my retirement from tennis. So I’m here to do that today! I was so emotionally distraught and caught up in everything around my personal life that I never really said I was done with tennis.”

He added that wondering about “coulda-woulda-shoulda” will not help him now, that he hopes to be a slightly better person and father each year, and that he was not that father while his children were growing up, but wants to be now. In 2022, when the documentary McEnroe came out, he told Tennis365 he could look in the mirror and see improvement over the years. He also said that more focus would probably have won him more matches, though he would likely have been “more boring”.

Hence, fittingly, he ended his delayed retirement announcement saying that “it’s tough when it ends for any athlete. You always think you can win one more.”

And yet, for all the titles McEnroe believes he left behind, the years after his playing career have hardly been empty. He found another voice in tennis, becoming a familiar presence behind the microphone for ESPN, the BBC, CBS and other networks, turning the same candor that once got him into trouble on court into a second career as one of the sport’s most recognizable commentators.

He found another outlet in art, opening a gallery in New York in 1994, and another in music, playing guitar and performing with his own bands. He even became a familiar face beyond tennis, appearing in films and television shows before taking on the unexpected role of a narrator for the Netflix show Never Have I Ever.

But perhaps his most lasting second act has been built around giving younger players opportunities. In 2010, he helped establish the John McEnroe Tennis Academy and founded the Johnny Mac Tennis Project, which provides under-resourced New York children with tennis, education, and mentorship. The project now reports having reached more than 20,500 students and awarded $11.8 million in scholarships.