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Mailbag: Reflecting on Maria Sharapova's Career and Legacy

• Readers Jennifer and Zachary Lerner for the win:

• Last week’s podcast: Jamie Lisanti and I discuss Maria Sharapova:

• Next up: agent Max Eisenbud

• Lots of questions—and statements—about Sharapova. So let’s start here. On the morning she announced her retirement, Lisanti and I chatted about Sharapova. So, again, I can direct you above for starters. But with a few additional days to reflect…

When Sharapova announced her exit from tennis last week, there was one word in heavy rotation: complicated. It was used to describe Sharapova’s legacy, her mark on the sport and, by extension, Sharapova herself. Some of her career summations were awfully harsh, not just on social media but within the tennis media tent. Here’s Stuart Fraser and here’s the great Pete Bodo.

The relative silence among Sharapova’s peers was also deafening. When Caroline Wozniacki called it a career a few weeks ago in Melbourne, there was a multi-day, multi-media, multi-generational love-in. When Sharapova—a more accomplished player by any measure—announced the end of her career, even the WTA’s in-house response came across as dutiful and measured.

Rather than deem Sharapova good/bad or take binary sides— you know, the way social media demands we dwell on the complex—here was a player whose “brand profile” was clear. Instead, she was filled with contradictions and inconsistencies. As I wrote last week, she presented as regal and imperious and elegant; but she was a street-fighter on the court. By her own admission, she was not graceful or artistic; she won, often by simply outfighting and outflanking the opponent.

In many ways, Sharapova was polished and businesslike. “Buttoned up” was a term I often used. She was, in many respects, a consummate pro. And yet the handling of her positive doping test marked some of the most clumsy and amateur public relations I’ve ever seen in sports, never mind tennis.

As for the doping, again, it’s complicated. Meldonium was legal a few weeks before her positive test. Yet because something is technically legal doesn’t make it ethical. That Sharapova didn’t disclose on forms a substance that she had been taking for a decade… that’s a damning omission never fully addressed. Then again, she admitted to longtime use; unlike other athletes in a similar position. And she paid a steep tennis price, a steeper reputational price; and spent more than a year suspended. At what point do we believe that a debt has been discharged?

More complexity: Sharapova could be charming and witty and self-effacing. She could also be frosty in the extreme. At a time when the WTA locker room became more hospitable and a sense of collegiality, even friendship, passed among players, she remained at a remove. One story among many: Sharapova once practiced with a player ranked in the top five at the time. The player on the other side of the net turned her ankle during the session. Sharapova was unhappy when one of the members of her team tended to the injured colleague.

Sharapova prided herself on being a rational “businesswoman”— the kind of cold operator who would come from a family with a purported history of diabetes and, yet, launch her own line of candy. Yet she could also be quirky and superstitious. Comedian Chelsea Handler tells the story that, intending to go once, she returned day after day to the 2012 Olympic tennis event because Sharapova deemed her a lucky charm. (Sharapova would reach the gold medal match and then, characteristically, get trounced by Serena.)

It all left an unmistakable sense that she was heavily prominent, but not well-known. Intimate but distant.

Here’s what wasn’t complicated: Sharapova’s achievements, which remain the top-line of her bio. Five Majors, each of them at least once. Dozens of titles. A stint at No. 1. Olympic medals. Almost $40 million in prize money. We are talking about one of the towering figures of the last quarter-century.

That being the case, this too, is uncomplicated: it wasn’t supposed to end this way. Some residual taint from a doping ban. Results that plummeted upon her return. Four straight losses in Majors. A ranking outside the top 350. For a player so adept at curating an image and a brand, it’s a pity such an accomplished and relevant player couldn’t have authored a happier ending.


Hi, Jon: So you nailed it about Sharapova announcing her retirement this year. You indicated there would be a second one. Care to name that person?

—L. Pereira, British Columbia, Canada

• Carla Suarez Navarro? Wozniacki? The Bryans? (Already that’s a hell of a Hall of Fame ballot, a few years hence.) I’m not sure I had someone specific in mind. But anyone outside the 18-34 demographic is, inevitably, a candidate.

I've never been a fan and still regard that endless, awful and unnecessary shrieking as a form of cheating, but your essay did leave me with respect for her work ethic and intelligence.

—Lucy M.

• Thanks, but all credit goes to the Tennis Channel production team. Here’s the piece:

To mix sensory metaphors, I have a blind spot for grunting. I could name 100 attributes—good, bad and indifferent— for Sharapova that would occur to me before listing her soundtrack. But I realize I am in the minority. Upon her retirement, I was fully prepared for all the references to her doping conviction. I was astounded by how often people mentioned “grunting” in the top line of her career obituary.

Hi Jon, I have been a longtime reader and an avid follower of your mailbag. Happy to see that it’s back to normal. I live in Dubai- UAE which is the sports capital of the Middle East. We are blessed with a plethora of sports events, personalities (who come for the winter break to get suntan bliss) and of course even sports conferences. For all the famous guys who have been here, please we need to make a special mention of Novak Djokovic. We were fortunate to see both Stefanos and Novak play and meet and greet fans. What stood out was the patience, the willingness and people-friendly nature of Novak. He really does deserve all the accolades and good will. Indeed a tremendous ambassador for the sport. Firmly in the Novak camp now.

—Vijay Kavasseri

• Duly noted.

Hi Jon: Vaguely GOAT-related hypothetical questions for you today. If they had all turned professional and peaked at the same time, what are the chances that Thomas Muster or Guga Kuerten would beat Nadal in Paris, Sampras/Becker/Edberg beat Federer at Wimbledon or Agassi/Sampras beat Djokovic in Australia/New York? Intuitively I’d think that Sampras beating Federer at Wimbledon is the most likely (although Federer did obviously win their match up there) but has there really ever been a player who could have realistically beaten a prime Nadal in Paris?

—Dave, London

• Thanks, that’s a fun thought exercise. The usual qualifications apply for technology. (And, I would add, wealth. When Federer/Nadal/ Djokovic have net worths deep into nine figures, they have access to career-prolonging and career-enhancing services—entire teams, rehab specialists, private air travel—that differentiates them from their predecessors.)

Still, I would think that, in their primes, Federer beats Sampras six of 10 times on grass, based mostly on which player is having the best serving day. Nadal wins nine of 10 on clay. He’s just too physical for Muster—a fellow lefty by the way—or Guga. And Djokovic wins the majority of any 10 matches on hard courts. Some of this is recency effect, sure. And some of this is probably distorted by equipment. But consult YouTube and watch for markers like court positioning and weight of shot.

A historically ungenerous answer here, I realize: but I see the Big Three dominating in any era.

This snippet from one your answers caught my eye. "That the women’s field—with a best-of-three format more conducive to upsets." Chris/Martnia/Steffi/Serena won their Grand Slams without having the cushion of a five-set format to avoid upsets. While I'm a fan of five sets and think women should also play five sets (maybe in the second week), the fact that the above four almost never got upset in a best-of-three format is a testament to their greatness.


• Great point. And one we probably have not stressed sufficiently. The dominance of Chris/Martina/Steffi/Serena is all the more impressive, given the best-of-three format.

This is the example I always give: If you and Steph Curry were each given a half-court shot, it’s possible that you might get lucky and swish yours; and he might miss his, drawing the back iron or whatever. If you were each given 10 half-court shots, there’s no way you’re beating him. The bigger the sample size, the greater likelihood for a regression to the mean. (i.e. the “right” result will present itself.)

In tennis terms, beating a favored opponent in best-of-three is less impressive (and more likely) than beating them in best-of-five. And we see this with our own eyes, right? Jiri Vesely can beat Novak; A 36-year-old Tommy Haas can beat Federer; Kyrgios can beat Nadal in best-of-three. It’s a much different proposition in a longer match. By that extension, the dominance of the aforementioned women, who mostly (and in the case of Serena, only) played best-of-three is all the more noteworthy.

Dear Jon, a few years ago I called you out for referring to Anna Kournikova as a “pioneeress.” You penned a mea culpa in response, which I appreciated. Now I read a recent column that refers to Serena Williams as a “titaness.” All I can say is...really??? A devoted fan who loves your writings and insight, but who is a tad disappointed (again).

—Gwin Krouse, Allentown, Penn.

• I confess, I transgress with that excess.

Shots, Miscellany:

Someone raised this point and it is strange: the USTA still hasn’t filled its vacant U.S. Open tournament director position. If you meet qualifications and can work for $400,000 or so, please send your resume to White Plains, N.Y.

The United States Tennis Association (USTA) and Peter Burwash International (PBI) today announced a strategic partnership that brings together the national governing body for tennis in the United States with one of the leading tennis club and resort management companies. Through this relationship, both parties will combine resources with the aim to continue growing the sport of tennis, with particular focus on attracting younger players.

Today, Lilly Pulitzer, the iconic Palm Beach-inspired fashion brand, is announcing a partnership with the WTA (Women’s Tennis Association), the leading women’s sports league worldwide. Set to begin this month, the two brands are uniting for a youth empowerment initiative, aimed to inspire confidence and optimism in future generations as part of Lilly’s new “Be the Sunshine” campaign.

The ATP and FedEx Express today announced a sponsorship renewal that will see the shipping giant remain an ATP Platinum partner, while strengthening its sponsorship and becoming the new title sponsor of the ATP Rankings.

The United States Tennis Association (USTA) and Bermuda Tourism Authority today announced plans for a weekend full of tennis events and activities to take place on the island April 3-4. The first-ever “Courts & Shorts Weekend” in Bermuda is part of an ongoing celebration of the island’s place as an outstanding tennis destination for fans, players, enthusiasts and historians… Former world No. 1s Andy Roddick and Arantxa Sánchez, both former US Open singles champions, will play in Saturday’s exhibition at Coral Beach & Tennis Club, 4:00 p.m. – 6:00 p.m. (AST). This ticketed event will serve up fun, engaging matches with the featured players interacting with the crowd. Other participants include 1993 French Open doubles champion Luke Jensen, Chanda Rubin, former world No. 6 and winner of seven WTA singles titles, 2000 Wimbledon singles quarterfinalist and three-time ATP Tour singles titlist Jan-Michael Gambill, along with a number of young, rising tennis stars. VIP experience packages are available for fans, which include a Friday evening reception, preferred access to the exhibition matches and a post-exhibition reception. Please visit for more information on purchasing a VIP package and general admission tickets.

Matt had our reader riff to take us out:

Are U.S. tennis fans (and the broader tennis world) sleeping on Acapulco? The men's fields the past few years since changing to hard courts in 2014 are usually stacked. It's the only 500 in North America besides DC. It pairs a small WTA event with some big names and up-and-comers (Kenin finaled last year; future USO champs Stephens and Panetta won there). It seemingly has more opportunity to corral US/Canadian/Latin American players who don't want to travel to cash grab but deep draw events in the Middle East to prep for IW/Miami. Better yet, I love the classic siesta friendly scheduling. Matches don't start until 4 so you get plenty of beach time and a nap before the entertainment. And the event is clearly well attended and festive. Moreover, flights to Acapulco in February are much cheaper than small price gouging Palm Springs airport (hotels too). After shelling out a small fortune to Larry Ellison for my IW tickets this year I also might want to take my tennis dollars south of the border. Cheers, Matt