THE ASHER ARCHIVES
A Grand Goodbye
January 22, 2050
By Asher Raines
Why do we do the things we do? Is it worth trying to be great?
What happens when we don’t reach our goals? Are they even our goals? What should those goals really be?
There are some events that force you to step back and examine questions so fundamental to our lives, even if we typically never think about them. When Evelyn Bailey announced her retirement from professional tennis last month, it came as a shock.
It wasn’t long ago that the 25-year-old was considered by many to be the future of American tennis. Her dynamic run to the 2042 US Open Women’s singles title just weeks after turning 18 inspired the nation and understandably drew comparisons to all-time greats including Serena Williams and Chris Evert.
The almost impossibly lofty expectations for the young star were never fulfilled — Bailey would never reach another major final — but she nonetheless achieved a successful career, capturing six singles titles and peaking at #5 in the WTA rankings in 2044.
Before her retirement, she remained inside the WTA’s top 50, a strong competitor with a seemingly lengthy career still ahead, although likely not as a serious Grand Slam contender. There was no major injury or circumstance that caused her to step away from the game. The situation was difficult for many to understand.
Throughout her career, I had the opportunity to speak with Bailey several times, including for a profile several years ago. As a reporter, you always want to be careful using words like “friend,” but we’re certainly friendly, and the news caught me off-guard as much as anyone else.
After the dust had settled, I asked Bailey for an interview, to which she agreed. But as we were making arrangements, it happened again.
A grandmaster by the age of 13, Malik Clemons’ meteoric rise in the chess world began two years later when he won the first of back-to-back U.S. Junior Chess Championships in 2045 and 2046.
Clemons crossed the 2700 FIDE rating threshold in 2047, becoming the highest-rated Black player of all-time, and followed it up with a titanic 2048, winning the U.S. Chess Championship and finishing third in the Chess World Cup, the latter earning him a spot in the 2049 Candidates Tournament, where the winner would earn the right to challenge Arturs Balciunas for the World Chess Championship.
Bobby Fischer remains the only American-born player to win the World Chess Championship. With Fischer’s 1972 victory over Boris Spassky now approaching 80 years old, Clemons captured the hope of American chess fans as the strongest homegrown talent of his generation.
However, he failed to win a single game at the Candidates Tournament, finishing in last place of the 10 competitors with a score of 5.5/18. Clemons dropped each of his first three matches, quickly falling out of contention and stifling national interest in the event.
He was only 19, but the performance drew heavy criticism and led to a run of poor form that lasted the next several tournaments. Clemons recovered towards the end of the year but unexpectedly announced an indefinite hiatus from the game on Dec. 28, citing burnout and mental health struggles.
This type of decision is relatively unprecedented for a player of his age and caliber — one of the top juniors in the world with a legitimate chance of becoming a future World Champion — and it came on the heels of a similar situation within pro tennis.
Two elite competitors once seen as America’s future in their respective sports, both leaving the pro scene in a span of just days. Is it merely a coincidence or a sign of something more?
NOTE: In this story, Evelyn will be in italics and Malik will be in bold. For color-coded conversations (which may improve readibility), you can read this version.
I met Evelyn Bailey at her home in Orlando, Florida. She plans to split time between Orlando and her hometown suburban Chicago, but in January, it’s an easy choice.
AR: How have these past few weeks been?
EB: It’s been nice! I was with my family over the holidays, which was great and really helpful while everything was in the news, and so it’s only been the last couple of weeks that I’m settling into this new life.
What do you think has been the biggest change for you so far?
All of the free time. It’s been such a huge adjustment, and I’m still learning kind of what to do with myself. I know that sounds stupid, but when you’re a professional athlete, or I guess any other kind of competitive field, you live it every single day.
I don’t remember the last time I went a day without training or traveling or competing — and that’s going back to when I was a kid. And don’t get me wrong — I’ve loved it. It just becomes your entire life.
Is it hard to imagine a life without tennis?
Yeah. Again, just because of how it’s been my identity forever. And I know I’m never going to have a fully “normal” life since I’m still someone people know. Hopefully, that will allow me to have some opportunities to pursue things I’m interested in and support causes I care about, but it’s definitely going to be quieter.
Like, I’m gonna need to make friends now, and…how do you even do that as an adult? Especially since I don’t have an office or workplace right now.
Even when I was younger, it’s not like I knew tons of people and was always going to parties. I was homeschooled.
Do you regret that at all?
No, and I would never criticize my parents or my coaches or anything like that. But it’s not the easiest lifestyle, right? There are a lot of things I missed. I never had a prom. And on some level, who cares? It probably wouldn’t have been the greatest night of my life, but there are experiences I wish I would’ve had.
Now, it all worked out for me. I was pretty successful. But not everyone is going to be a professional tennis player.
And yet, so many people spend their whole lives training, trying to get college scholarships or whatever. That’s awesome, too. It just creates such a competitive environment where you’re scared of not doing every little thing to give yourself an advantage because if you don’t, someone else will.
No, absolutely. The entire culture around youth sports in this country is crazy. There are so many parts to it, also. The early specialization, all of the travel, it’s incredibly expensive. And the stakes feel so high, even down to the parents yelling at umpires at t-ball games.
I mean, at the end of the day, we’re talking about kids.
Yeah, and everything with trying to grow a brand on social media, too. There are 10-year-olds with managers. It makes no sense.
But also like, what are you going to do about it? Maybe some lines get crossed, but everyone’s only trying to do the best for their kids. It’s so hard to make it.
The real shame is that I do think you kind of have to take it that seriously if you want to be a professional. It can’t just be something you like to do.
I don’t know. It’s complicated.
MC: Man, it was scary. That was the lowest point of my life. It took weeks to start feeling like myself again.
Malik Clemons traveled to Berlin last April with hopes of earning a spot in the World Chess Championship. Instead, he returned to Dallas humiliated.
It’s evident how much the event still bothers him. I don’t want to make him relive it again, but I have to ask.
I wake up every day feeling invincible. That’s how it’s always been. You gotta understand that I’m a crusher. Any challenge you put in front of me, I’m gonna take it down. That’s the mindset.
So having to sit in front of that board feeling helpless after getting embarrassed over and over — it was like going through hell.
What are some of the thoughts that were going through your head at the time?
Well, first off, I was questioning my preparation. When you reach that level of chess, everyone’s played a million games against each other, so a lot of it becomes studying your opponents’ recent games, anticipating what they might throw at you, and using engines to explore lines and variations that might catch them off-guard a bit.
But beyond that, I think there was a ton of pressure. It’s not every day that chess is talked about in the media, and I knew how big of a moment it was for chess in the U.S. and especially, you know, for people who look like me.
I wasn’t only playing for myself. And so after I lost the first few games, I really felt like I had to make something happen, just to give people some positivity and maybe some momentum for myself. But when it’s the best players in the world, that’s never a position you want to be in.
Do you think all of the noise impacted your play?
Probably. I mean, who knows? It doesn’t matter. My performance was not acceptable.
I would argue that participating in the Candidates at age 19 is an unbelievable accomplishment by itself.
Maybe, but what’s the point of playing if you’re not going to win? The fact that I qualified is proof that I deserved to be there, and I did not play like I deserved to be there.
People my age or even younger have competed in the Candidates many times. No one’s going to look back and remember how young I was. If they remember anything, it’ll be how I was outclassed.
It’s clearly taken a toll on you. Even if it was important, isn’t it still just one tournament in your very accomplished career?
But there isn’t the same attention directed towards all those other tournaments. And honestly, you should be judged by how you perform in the biggest moments.
No one’s paying attention to the other stuff I’ve done. What the average person knows is that I was supposed to be something for them, and I failed at that.
Random people aren’t messaging me when I play well in other tournaments. But I got tons of hate messages all over social media, in my DMs during the Candidates. And I know I’m not supposed to let that all bother me, but guess what, it does. Because even if those people suck, I sucked too. They’re not wrong.
That doesn’t make those kinds of messages okay.
Yeah, but that stuff comes with the territory.
This next phase of your life comes with a lot of freedom — you could really decide to do any number of things.
For sure! I’m finding that super exciting right now.
Do you have an idea of what your next career move is?
Well, I hope it’s a bunch of different things. What I’ve found over the last several years, and I’m sure it’s even more this way for other jobs, is that life is just so busy. On top of your work, there are always appointments and errands and things you should look into, and people you should talk to.
There isn’t enough time to do everything while also having hobbies and a social life. And then sometimes you’re just tired and you want to take a nap or watch a movie without feeling lazy.
Yeah — that’s adulthood in a nutshell!
Which is crazy! Imagine giving people the time to actually explore the world a little bit, think through some things, develop some opinions, and evaluate their own life. That’s what I’ve been doing lately and it’s just so refreshing. It’s such a shame that it feels like such a huge privilege.
But yeah — I guess to answer your question, I think about it in two parts — things I want for myself and ways I want to help others.
I’ve gotten to do some commercials in the past and thought that was super fun, so I know I want to explore more acting opportunities. I would also love to try broadcasting, and then I mean this isn’t really a job, but when I was a little girl, I was always painting and making art, so I want to get back into that.
I also want to use my platform to advocate for gender equality and help provide resources for girls to participate in youth sports and to also work within the sports industry. That’s very important to me.
And that’s so awesome to hear. I love how thoughtful you are in how you’re approaching everything as well. You’re obviously still young but you seem very aware of your goals and ambitions and aren’t afraid to go for them.
I think that’s something that will resonate with a lot of people, and I think a lot of people will be supporting you.
Well, thank you, I really appreciate that. It’s kind of wild to me that having a career is kind of seen as being this one thing that you do for decades. Obviously, if that idea works for someone, then that’s great, but I just know how people have such diverse interests — we shouldn’t have to limit ourselves.
And then for me, I also think about how I can have an impact beyond being a tennis player. Not many people are in the kind of position I am, and since sports have given me so much, I want to make sure I can give back and bring positive change to the ecosystem.
When most people look to switch careers at age 25, it’s viewed as a quarter-life crisis. But there isn’t a sense of crisis around you at all. You kind of seem to have it mostly figured out.
Haha, I don’t know if I’d go that far, but I do feel very content right now, and I’m definitely looking forward to the future.
Maybe Evelyn doesn’t have it all figured out, but I think I’d still pay for half her clarity.
I’ve been in this business for almost a decade now and I’m still not exactly sure what I’m doing. The title says reporter, but this is not reporting.
I’m hijacking a story about two other people to talk about myself. My thoughts and opinions are all over everything I write. That’s not journalism, but it must be part of the appeal. After all, there’s some reason you’re here.
What does that make me? Some guy who loves to hear himself speak? A wannabe Thompson or Plimpton who’s not nearly as important as he thinks he is?
I don’t know. You’ve got to be able to speak earnestly, and you’ve got to be able to criticize the things you love.
So much of the sports media seems to lack a spine — there’s the entertainment side, which is filled with hot-take artists fighting to be the most boisterous for the sake of clickbait virality and talking heads who are pompous and abrasive in the name of “telling it like it is.”
The “news” side is a 24-hour P.R. machine where the default state is to view every event as an exciting success and every change as a positive. Being too critical risks losing access.
I wonder a lot about my place in this field and where I can have the most impact. A lamentable aspect of the news cycle is how each story has such a short shelf life. So much is done just so there can be something that day. Words disappear into the ether almost as fast as they’re written.
Nearly everything I write is sports, and the vast majority of that is tailored specifically to an American audience. It’s certainly not all about being known, but I do question whether some of my ideas could have a broader impact if the packaging was different.
It all comes back to this idea of having diverse interests. I love sports, but there are times when I don’t want to have to worry about following events or stories, and there are times when I question my belief in the goodness of sports that lies at the core of our fandom.
Those are the times for doing something else.
I wish everything could be put on pause.
Explain that.
Yeah, so like, for my own sake, I need to stop competing and get off the internet for a while. Just kind of reset. But by doing that, I’m missing a lot. There’s gonna be stuff in the chess community and stuff in the world that I’m not gonna see. It’s FOMO, for real, to not be a part of the conversation.
And then when I do get back to competing, it’ll take some time to get back into that rhythm. The rest of the world doesn’t stop because I do. I wish it would, though.
So you do think you’ll return to chess tournaments?
For sure. I want to be the world champion. I know I can be the world champion. That hasn’t changed — now just isn’t the right time. But that’s the whole reason I do this.
What is this the right time for, then?
I’m actually going to be enrolling in college this fall to study computer science. I’m still waiting back from some applications to make the final choice of where, but I am excited about it.
Wow, good for you. What all went into making that decision?
It’s weird, man, because on the one hand, I’m one of the top chess players in the world, but on the other hand, I do want to feel like a normal person my age. I want to have that college experience. I want to make friends and go to parties and do all that learning of becoming a real adult.
Have you felt…I guess…isolated over the past couple of years?
Yeah. It’s been a lot of studying, a lot of travel. Um, it’s just strange to be on a completely different routine and lifestyle than any of the people you grew up with. There are very few people who understand what this life is like.
There are definitely lots of sacrifices that you have to make. And you’re right that I can understand that conceptually but I’ve never really lived that life. I sometimes wonder about that, though.
Because so many people aspire to be great, those sacrifices that are necessary to be great are always viewed through a positive lens. But as you’re saying, it’s not that simple.
Sure, but if I don’t make those sacrifices, you don’t know who I am. We wouldn’t be doing this right now. Like, if you have a goal, does it matter what you have to do to accomplish it?
You’re the one on an indefinite hiatus. You tell me.
I think this is what I have to do, but I understand your point. There have to be some ways to find balance or to feel like a real person.
We’re not machines. Humans will never beat machines in chess, so that’s not something worth striving for.
How are your relationships with other top chess pros? Is there a camaraderie between you all, or is it too competitive?
It depends on the person, I’d say, but for the most part, everyone is friendly. There are a few people I’m closer to, but there is some comfort in seeing the same people all of the time.
Again though, we all know each other so well as chess players that there’s also something funny that happens when someone has a move or an idea that fits so well with who they are that it almost makes you laugh.
So much of it comes down to the anticipation, huh? And being able to put yourself in someone else’s head?
Haha. It makes it even more satisfying when you beat them.
Competition lies at the heart of sports. But if we’re allowed to step back for a moment, why are we trying to win, anyway?
Maybe this will sound dumb. It doesn’t seem compatible with my line of work at all, but I can’t help thinking about it from time to time.
For an individual or team to win a game or competition, their opposition has to lose. On a concrete level, success in sports is conditional on the failure of others. For this idea to serve as the basis for an entire system feels less than ideal.
If there is such a joy in winning, it’s strange to devote enormous resources in an attempt to make others not experience that joy.
Do we want to be better than other people as a means of making us feel good? Or do we need that success to validate the effort we’ve spent training?
Is it society itself that has taught us to only value those who win? What would that say about our society if we cannot all be winners? Any system where people who don’t win are failures both ignores the role luck plays in success and sets everyone up for failure since inevitably, everyone will eventually lose.
The hedonic treadmill is the human tendency to revert to a baseline level of happiness shortly after experiencing positive or negative events. This suggests that on a psychological level, winning does not lead to long-term happiness. And if that’s the case, our values are misaligned.
Perhaps the real issue is simply the seriousness with which we treat everything and how high a value we place on winning. If we were kinder to ourselves and others with regard to winning and losing, and placed as much emphasis on effort as results, wouldn’t that lead to a healthier system for all?
I think we have to, since competition is unavoidable, lying at the heart of sports as it does so many things in life.
…
… It is unavoidable, right?
Could there be such a thing as a cooperative sport, one that isn’t a zero-sum game?
There is obviously the idea in sports that can be done individually (track and field, swimming, cycling, etc.) of competing against oneself for personal bests. However, any formal competition still pits athletes against each other.
But is there a way for all participants to contribute towards a common goal? It certainly exists in many board games and non-”game” pursuits. People work together to achieve things all the time. Could this serve as a framework for a sport? Would there still be spectator appeal?
Rocket launches are appointment viewing…
10, 20, 30 years from now, how do you think you’ll reflect on your tennis career?
I think I’ll be really pleased with it. I got to travel the world doing what I love, I pushed myself, I achieved great things, and I was able to leave on my own terms. That’s pretty rare.
Does it bother you that some people will think you didn’t live up to expectations or call you a “bust” since you weren’t the generational, face-of-the-sport type of figure many thought you could be?
You know, I did feel that a lot in the couple of years after I won the US Open. It was like I needed to win another Slam or at least make a final to prove that I deserved the first one. There was major imposter syndrome back then. It doesn’t help when the best-case scenario for your career becomes what people expect out of you.
But as I got further into my early and now mid-twenties, I became more at peace with it all.
It’s like, I did everything I could, right? And I know that, and I’m happy with that. So, is it really about being the best ever, or just being the best you can be?
There is something very funny about how quickly people will turn on you when they realize you aren’t exactly what they wanted you to be.
Yeah — it makes you remember that at the end of the day, you’re a product to them.
Professional athletes wouldn’t be in the position they are if no one cared about the sports they played. So your life becomes this thing that other people consume for entertainment.
When that happens, a lot of athletes become fads. Oh, you’re the hot new thing. You’re not cool anymore. And it’s mostly based on whether you’re winning or not. That’s a weird relationship to have.
It must be pretty hard to divorce yourself from all the noise and just focus on doing the best you can.
Well again, I’m fine with it now. I feel like I got everything I needed from tennis. And that doesn’t mean I don’t love tennis — I think I’ll always play, and we need to feel like we can do things without needing to be the very best at them.
But on a professional level, I don’t know what more I had to gain.
At some point, there are diminishing returns. Only a few people win Slams each year, and even if I won another one, how much would that change my happiness or even the way people look at me?
I said to myself, hey, I can spend the next five or 10 years or whatever doing this, but it felt like that would just be putting off other things.
It really sounds like your goals changed and now they just don’t align with what people expected from you, or what you would’ve even expected from yourself. I remember the first time we spoke, back in ’45, you very much had those aspirations of wanting to go down as a legend in the sport.
Back then I couldn’t think about much besides tennis. I think when you’re young, you’re trying to figure out, hey, I’m really good at this thing, how far can I possibly take it?
And of course, everyone around you is doing whatever they can to help and keep pushing you because they want you to maximize your potential, and it’s fun for them to be a part of that journey, as well.
Sure, and it also takes time to maybe figure out everything you want out of life.
Yeah, you learn about yourself and life just by living. I mean, who’s the same person they were five years ago? I’ll probably be a lot different five years from now. That’s kind of the beauty of it.
I understand that being put into the public light has been difficult for you, but is there still some pleasure in knowing there are people who look up to you and that you’ve maybe inspired to take up chess?
If there are kids that want to play chess because of me, that’s very cool. But honestly, it’s something that I try not to think about as much because when you’re playing, that’s kind of a distraction. My performance has clearly suffered in the moments where people are looking for me to be something for them.
I’m…not super comfortable with being seen as a national face for chess or an ambassador or anything like that. I just want to play my best.
This is all about proving to yourself that you can be the best in the world. Would it be a failure if you never got there?
Disappointing for sure. I want to be proud of myself but it’s hard to feel proud when I lose. It feels too bad.
I want to ask what you might think is a weird question. You obviously believe you have the potential to be the world champion, but what obligation do you have to that potential?
What exactly does that mean?
So, I’ll give you an example. Let’s say there’s a world-famous director who is regarded as one of the all-time greats. But now let’s say he’s 80 years old. Does he have an obligation to continue making movies, to share as much of his talent with the world as possible? Or should he retire and spend the rest of his life not worrying about his creative output?
Well, it all depends on what he wants to do. If he still loves making movies, he should make movies. And if he wants to retire, he should be allowed to do so.
But there is nothing compelling him to continue working just because he has a natural talent, even if that means the world won’t get to see everything he’s capable of making?
No, that would be silly. There’s no point in worrying about a legacy since you won’t even be around to see it. And at some point, we’ll all be gone, so it doesn’t really matter what we do.
That’s such an interesting perspective to me because it seems to me like you’re in a similar type of situation. You have a special talent but at the same time it’s causing you hardship and there is a desire to have other experiences.
I see the parallels. I’m struggling at the moment to balance what I want to accomplish with what I need right now, but ultimately, my point remains the same. People should do whatever they want.
The more I contemplate Evelyn and Malik’s situations, the more typical they feel. We all go through phases of questioning the path we’re on in life. These look different as we age and perhaps the responsibilities we accumulate make it more difficult to alter that path, but the feeling doesn’t go away.
Maybe our collective surprise comes from a place of idolatry — that our sporting heroes or celebrity figures at large have reached a place so many of us want to go. It doesn’t make sense for them to question their path. Instead, they should continue down it as long as possible.
We are then forced to encounter the harsh truth that happiness is not something that becomes permanent upon reaching an achievement. That a promotion, house, car, etc. will not solve your problems.
That the ones looked up to and the ones looking up can be more similar than either realizes should please both parties. Success is a matter of perspective.
…
If there was a message you had to give to anyone reading this, what would it be?
I am trying. And I will come back stronger.
Do what makes you happy. You are enough.
Asher Raines Stories
An Overindulgence of Madness
Taysom Hill Plays Other Sports
The Loophole Owner
Asher’s Radio Interview (a follow-up to The Loophole Owner)
For All-Time’s Sake
A Grand Goodbye
