Several years ago — around 2010 but I’m not sure precisely which year — Stan Smith was making an appearance at the USTA bookstore on the U.S. Open grounds. (It used to be where I believe there’s now a Polo Ralph Lauren shop.)

I was there as a fan and wandered in with my son when Smith was wrapping up. I approached and told him I admired him, or something along those lines, which was certainly true. Then I asked him a question, which I’ve regretted ever since. First, some background on why I asked what I asked, so that if you think I’m an asshole you’ll at least know the backstory.

I’m a career journalist, most of it covering finance and economics (though a couple of years ago I shifted to something of an offshoot — Washington policy analysis). Non-professionally, I’m a tennis fanatic, and have been so since the early 1970s. (I was born in 1963.)

I’ve always been drawn to what I think of as turning-point matches, moments that change a player’s career. It seems there are fewer of them than there used to be, which is probably worthy of an essay itself. Players have more lives nowadays. So when Djokovic hits that slapshot forehand return and comes back to beat Federer in the 2011 U.S. Open semifinals, you have to think that’s it for Fed. He’ll never win another Slam. But he wins Wimbledon the next year. And then he suffers a few more heartbreaking losses to Djokovic in Slam finals in 2014 and 2015, but defies logic and returns to win two Slams in 2017.

One match that fascinates me, in part because it seems to have been forgotten by the tennis cognoscenti, is the 1993 French Open final between Jim Courier and Sergi Bruguera. If you’re not old enough to remember or weren’t a tennis fan at the time, it’s hard to describe just how surprising Bruguera’s victory was. Courier had won the previous two French Opens. (Before Nadal, that was a pretty big deal.) He was playing with an aura back then. Though Pete Sampras had taken over the No. 1 ranking, at the time most people considered that a head-scratching technical glitch. Courier had won that year’s Australian Open, his second in a row, and was considered virtually unbeatable on clay. More important, he was far and away the best big-match player in men’s tennis. Super clutch.

It wasn’t just that Courier lost that final to Bruguera. He lost in five sets, after having won the fourth. You could maybe get your head around Courier losing if he had a miserable day and got wiped off the court in straights. But the notion of him losing a close match after regaining the momentum seemed implausible. On fumes, Courier reached the final of Wimbledon a few weeks later, losing to Sampras. Courier was 22 at the time. Though he had a very nice career for several more years, including as a Davis Cup stalwart, he never made another Slam final. He was never again the great player he was before the Bruguera match. I don’t know what happened. I can’t get into Courier’s head. But it was a hugely consequential match that may have changed the course of men’s tennis for the rest of the 1990s. If Courier wins that match, maybe he wins Wimbledon. Maybe he stays atop the men’s game. Maybe Sampras and Andre Agassi don’t hog as many of the big trophies of the mid- to late 1990s. Maybe Courier wins a couple more French Opens.

My interest in matches like that helps explain why, when I saw Stan Smith that day, I made the mistake of asking him about a match that probably marked the end of him as a great player.

I’ve long been intrigued by two matches Smith played. One is his victory against Ion Tiriac in the 1972 Davis Cup final in Bucharest. It was marred by a hostile crowd and blatant cheating by local linespeople. Smith showed amazing poise while all hell was breaking loose around him. I don’t recall the match; I’ve only read about it.

The other was Smith’s 1974 Wimbledon semifinal loss to Ken Rosewall. I was 10 at the time. I remember reading about it later in my local paper, The Washington Post. (My recollection is that back then the Wimbledon semifinals weren’t even on television in the U.S.) Smith was the quasi-defending champ that year. He had won Wimbledon in 1972. In 1973, most of the top players, including Smith, boycotted Wimbledon.

Against Rosewall in 1974, Smith was up two sets to love and 5-3 in the third. He served for it at 5-4, and then had a match point in the tiebreak (which was played at 8-8 in those days). Smith lost that tiebreak, and the following two sets.

Rosewall ended up getting waxed by Jimmy Connors in the final. The same thing might have happened to Smith if he had managed to beat Rosewall. Or maybe not; we’ll never know. Smith was 27, not ancient for tennis but not young. He continued as a regular on the circuit for about another decade. But aside from making the quarters of the U.S. Open a couple of months later, he never again got farther than the round of 16 of any Slam. Put simply, he had a great career (later overshadowed by his shoe fame). However, he was never the same player after that match.

Knowing all that, when I saw Smith I went into hard-hitting journalist mode and asked him about the Rosewall loss. I don’t recall exactly what I said. I might have just asked what happened. I could see his face fall, and after a few vague remarks he said, “You just ruined my day.” I felt terrible, as I should have.

Let me be clear: It was a total shithead move on my part. I wasn’t intending to make Smith feel bad; I just hadn’t thought it through. The question could be appropriate if I were on the job as a journalist and writing a big profile on Smith. In that case, if he had agreed to an actual interview and I was doing a story on his life, pretty much anything could be fair game. But I wasn’t there as a journalist. I was a fan, sucker-punching him with a question about what might have been the most painful loss of his career.

I’m sorry, Stan Smith. I didn’t mean harm. If I ever meet you again, I won’t repeat my apology, because I don’t want to even bring up the topic. But I’d love to ask you about that Tiriac match.

The first time I saw Monica Seles she wasn’t playing tennis.

It was March 1988, and 14-year-old Seles, wearing a high school letter jacket, was sitting in the stands of the stadium court of the Key Biscayne tournament (then called the Lipton International Players Championships) watching a late-night battle between Andre Agassi and Aaron Krickstein.

Earlier in the tournament Seles had lost a second-rounder to No. 3 seed Gabriela Sabatini, 7-6, 6-3, creating a buzz on the grounds about how well this unknown girl had played in only her second pro tournament against an established star (Sabatini herself was only 17 at the time). For Agassi-Krickstein, Seles was watching with some friends on a chilly evening as her Bollettieri academy pal Agassi blew a two-sets-to-love lead and a match point in the fourth before retiring after one game of the fifth set. (Yes, they played best-of-five at that tournament for all rounds in those days.)

Two years later — she didn’t play the tournament in 1989 — I was sitting courtside (I had a press credential and the press seats were damn good back then) when 16-year-old Seles won the tournament with a devastating display in the final over the since-forgotten Austrian Judith Wiesner. It would be only a slight exaggeration to say the collective mouth of the press corps was wide open in astonishment for most of the match. No one had ever seen a woman crush the ball off of both sides the way Seles did. People looked at each other with a recognition that what we were watching was a fundamentally different sport, at least for the women’s game, than what we had seen before. It was so cool. There was the distinct feeling we were watching something big as it was just getting started. Think the Beatles playing a Liverpool club in 1961.

When Seles played the tournament you sometimes saw her parents around the grounds. I never met them, but they would go to her matches and applaud the opponent’s shots. Not merely to be polite. You could see the excitement on their faces, like: Wow, did you see that shot Wiesner just hit? Their thinking seemed to be that a really cool thing about being Monica Seles’ parents was that you get credentials to watch great tennis up close. They were so genuine.

Why am I explaining this? Partly as a lead-in to a few upcoming essays on biases in tennis. All fans and journalists have their biases. Not political or ideological, but personal biases. They’re usually innocent enough. For journalists, the biases can come from personal interaction with the players, both negative and positive. My Seles bias stems from watching her in person when she was breaking through, and from viewing her parents as the antithesis of the stereotypical tennis parents. From then on I always rooted for her. Steffi Graf was an all-time great, and best I can tell, an exemplary person. But I always wanted Seles to win.

Even taking my bias into account, I feel comfortable asserting that no event changed the course of tennis history more than Seles’ stabbing on April 30, 1993. This topic should be a separate essay, but the numbers around Seles’ career up to that point are mind-boggling. She was 19 at the time, No. 1 in the world, and had already won eight Slams. She had just won the Australian Open — for the third consecutive year — and she was about to go for her fourth straight French Open. Those are some crazy stats.

After her comeback, she won one more Slam. Obviously, we can’t know how many more she would have won if she hadn’t been stabbed, traumatized and missed two-plus years. Maybe she would’ve gotten bored and trailed off. But certainly there’s no indication that would have happened. Mary Carillo recently described Seles as the player she would choose if she had to pick one woman to play a match for her life. It’s certainly not unreasonable to think that if it weren’t for the stabbing, Serena Williams today would be chasing after Seles’ Slam record, not Margaret Court’s. Even if you take into account only what Seles accomplished as a teen-ager, she’s probably one of the six or so greatest women players of all time. I might be biased, but that’s fair.