Post-Mortem: Maria Sharapova


Below is an unpublished reaction to Maria Sharapova’s loss to Serena Williams at the 2019 U.S. Open. With the recent news of Sharapova’s retirement, I’ve decided to publish my analysis the pair’s “rivalry” below:

Cause of death? Serena Williams.

From the first toss, I, too, was engulfed in the excitement that buzzed within Arthur Ashe Stadium and across TV sets all over the world. The Serena-Maria rivalry is one of the few that has been able to captivate the attention of the avid tennis fan and the uninitiated spectator alike.

However, when Sharapova’s final backhand sailed long, sealing a routine 6-1, 6-1 win for Williams and extending her masterful record against the Russian to 20-2, I felt foolish for briefly believing that we might actually have a match on our hands.

Both of these icons are at the tail ends of their careers. While Serena remains a contender to win Grand Slam trophy No. 24 and cementing herself as the Greatest of All Time, the light at the end of the tunnel grows dim for Sharapova, who is projected to fall out of the Top 100 at the end of the US Open fortnight.

How did Maria fall from her lofty position atop the tennis world? Yes, there have been injuries. And yes, there was the suspension. But, most importantly there has been the inability (or refusal) to adapt her game to the changing tennis landscape.

The birth & death of Maria Sharapova can be traced in her fifteen-year rivalry with the ubiquitous Serena Williams.


Sharapova Serena Williams Wimbledon 2004 Final

A star was born when the rangy, teenaged Maria Sharapova won Wimbledon in 2004, a victory that came at the expense of Serena. Fighting with a dog-toothed ferocity and punctuating shots into the corners with a shriek, Sharapova fought her way to a 6-1, 6-4 dismantling of Wiliams, which, at the time, was the worst Grand Slam loss of her career.

While the Williams Sisters transformed the finesse-dominated sport with their powerful baseline games, Sharapova’s flatter groundstrokes seemed to pack a just little more punch.


Sharapova Serena Williams 2005 Australian Open Semifinals

Heading into their 2005 Australian Open semifinal match Sharapova was in the ascendancy.

She backed up her Wimbledon triumph with a win over (an albeit injured) Williams at the 2004 WTA Finals. It appeared the young Russian was destined to claim the No. 1 ranking.

Imbued with confidence, Maria brought her typical A-game to Margaret Court Arena. Firing bombs into the corners of the court, Sharapova claimed the first set 6-2. However, a string of errors at 5-6 in the second set gave Serena her first break of the match and the second set.

In the third, Maria rebounded, serving for the match twice and thrice holding match point to lead their head-to-head 3-1. However, this is when Serena flipped the script.

Realizing that Sharapova’s power was greater than hers, Serena relied on her B-game assets (i.e. her superior footwork, topspin, and variety) in order to tear Sharapova apart.

Ultimately, Serena would triumph 8-6 in the third, on her way to lifting the 2005 Australian Open trophy. The rest is history.


Sharapova Serena Miami Final 2013

In 2013, the record stood 11-2 in Serena’s favor.

However, many of those losses occurred during a period in which Sharapova was returning from shoulder reconstruction surgery.  A glimmer of hope shone when Sharapova briefly returned to World No. 1 in 2012 after claiming the title at Roland Garros.

Facing off in the 2013 Miami Open final, Sharapova lead 6-3, 3-0 against a flat-footed Serena.

I was sitting in the nosebleeds for that final. A young tennis fan at the time, I thought that this would be the day that Sharapova would finally reign supreme.

When she held for 3-0 in the second set, I recall overhearing a woman behind me say, “Serena will pull out of this. I’ve seen her do this too many times before to count her out.”

Upon hearing this, I remember thinking to myself, “How stupid. She’s down 3-0!” However, after Serena reeled off the next twelve games in a row, it was I who was the fool.

Never count Serena out. Lesson learned.


Sharapova Serena 2013 Roland Garros Final

Despite the disappointing loss, many pundits felt that Sharapova was closer than ever to beating her rival once again.

Many pointed to her improved performance on clay, a surface that was undoubtedly Serena’s weakest, as a potential arena for the Russian to emerge victoriously.

Only a couple months later, this prediction was put to the test when Sharapova and Serena faced off in the Roland Garros final.

The contest was close, but the outcome was the no different than before. Maria lost in straight sets, swallowing a 4-6, 4-6 to the younger Williams.

While only a couple months before, Maria appeared closer than ever to emerging victorious over Serena, after Roland Garros that day couldn’t appear further away.


Sharapova Serena US Open 2019

That brings us to today.

Many attribute Serena’s dominance over Sharapova to a fabled & unending quest for revenge upon the Russian for the aforementioned 2004 Wimbledon final. Heck, even Sharapova herself carries this belief, writing in her autobiography:

“But mostly, I think she hated me for hearing her cry [after the match]. Not long after the tournament, I heard that Serena told a friend – who then told me – ‘I will never lose to that little b…. again.’” – Sharapova in Unstoppable, My Life So Far

However, it’s far more complicated than that.

Serena’s mastery over the Russian lies in the versatility to her game. The American’s superior speed & footwork, mastery of topspin, and variety have allowed her to deconstruct the Sharapova game.

Furthermore, Maria’s inflexibility (both literal and figurative) over the years to adapt her game to counter these assets (or develop a B-game in general) is equally to blame for manufacturing the rivalry that never was.

In 2005, Serena flipped the script. However, the tennis world is still (and has been) waiting for Sharapova to respond.

Live by Serena. Die by Serena.

Maria Sharapova’s Top 10 Shadiest Moments

Maria Sharapova made a career by hitting the felt off the ball like no other. However, her uncanny ability to throw shade at her opponents certainly helped cement her status as a bonafide diva icon.

As the five-time Grand Slam champion and former World No. 1 hangs up her racquets, let’s count down the Russian’s most memorable verbal clashes.

Sharapova Dimitrov

10. Sharapova vs. Dimitrov

We will not be seeing any more of Maria Sharapova in 2020. However, both her & her ex-boyfriend Grigor Dimitrov have already delivered an exchange that will undoubtedly rank amongst 2020s more memorable off-court moments.

In 2013, news of Sharapova and baby-faced Dimitrov’s budding romance took the tennis world by storm. However, by Wimbledon 2015, the couple reportedly called it quits.

In her biography “Unstoppable: My Life So Far”, Sharapova writes:

I was supposed to be focused, getting prepared for my own matches, my own triumphs and defeats, on the largest stage of my career. I had been watching his match that day only because I’d lost early at those championships. So his good memory was my bad memory. What meant everything to him happened only because I had lost.

Fast-forward five years, Sharapova was approached by Dimitrov while taking a spin in the commentary booth at the Kooyong Classic (an Australian Open tune-up exhibition). As the Bulgarian ducked inside the booth, the Russian quickly questioned Dimitrov’s choice in attire:

“What’s this yellow thing going on?”

“You like it, huh?” he asked.

“Not really,” she chided.

“You used to like yellow on me, but that’s OK,” he replies. “People change, I get it.”

I think it goes without saying that the term “just friends” might not be the most appropriate term to describe the state of this duo’s current relationship.

Sharapova Radwanksa

9. Sharapova vs. Radwanska Pt. 1

Masha leads Aga in their H2H 13-2. Despite this lopsided record, the Pole has never shrunk back from criticizing her Russian rival — especially for her signature grunt shriek.

In response to Aga’s comments, characterizing Maria’s grunt as “really annoying”, Maria poses a simple question: “Isn’t she back in Poland already?”

Enough said.

Sharapova Serena 2013 Roland Garros Final

8.  Sharapova vs. Serena Williams

Sharapova initially rose to prominence with her underdog win over Williams in the 2004 Wimbledon final. However, since that signature win, Serena has owned the rivalry. While their on-court head-to-head should be considered anything but a rivalry, the pair’s intensity off-court certainly can.

Heading into Wimbledon 2013, Sharapova and Serena had re-ascended to the summit of the women’s game. They had just sparred in the 2013 Roland Garros final and looked fated to face-off at Wimbledon yet again–nearly ten years after Sharapova’s iconic win.

Before the first ball was struck, controversy sparked when comments from a Rolling Stone profile of the younger Williams seemed to target the Russian:

There are people who live, breathe and dress tennis. I mean, seriously, give it a rest.” Serena exits the car and the conversation moves on to a top-five player who is now in love. “She begins every interview with ‘I’m so happy. I’m so lucky’ – it’s so boring,” says Serena in a loud voice. “She’s still not going to be invited to the cool parties. And, hey, if she wants to be with the guy with a black heart, go for it.” (An educated guess is she’s talking about Sharapova, who is now dating Grigor Dimitrov, one of Serena’s rumored exes.)

During her pre-tournament media day interview, Sharapova didn’t hold back:

Obviously I have a tremendous amount of respect for Serena and what she’s achieved on the court. You can never take anything away from that.

As for myself, or whether it was about somebody else, nothing personal, you know– if she wants to talk about something personal, maybe she should talk about her relationship and her boyfriend that was married and is getting a divorce and has kids. Talk about other things, but [don’t] draw attention to other things. She has so much in her life, many positives, and I think that’s what it should be about.”

Unfortunately, we never got to see the pair translate these tensions into a grudge match (both fell before the quarter-finals that year). However, given Sharapova’s measly 2-20 record versus the American, it’s probably better for the Russian that that encounter never came to pass.

Sharapova Radwanska WTA Finals

7. Sharapova vs. Radwanska Pt. 2

As aforementioned, Sharapova and Radwanska’s relationship can be described as testy-at-best. However, the Russian’s pulverization of the defensive-minded player can be seen as a metonymic example of Sharapova’s ability to pummel the rest of the tour into submission throughout her career (save Serena, of course).

At the 2012 WTA Finals, the pair played a grueling classic, with Sharapova emerging victorious by the score of 5-7, 7-5, 7-5. During the third set, after a point that required the former World No. 1 to hit not one, not two, but three overheads, she jeered at her rival: “Run! Run!”.

You can “run, run” all you want, but in the end, even fast feet aren’t enough to quell the mighty power of Sharapova.

Sharapova WADA violation

6. Sharapova vs. Retirement

In 2016, when Sharapova sent a mysterious invitation to tennis journalists to attend an unexpected press conference in downtown L.A., many speculated that the Russian superstar was set to announce her immediate retirement from the sport.

In the end, Sharapova shocked the world by disclosing her failed drugs test.

Whereas many other players who have failed drugs tests in the past (Marin Cilic, Richard Gasquet, Sara Errani, and Barbora Strycova to name a few) have retreated from the public eye, Sharapova instead chose to face the public directly.

While wrapping up proceedings, Sharapova affirmed her intentions: to fight the charges and return to the sport. In fact, she addressed the rumors about her retirement head-on:

I know many of you thought I would be retiring today and announcing my retirement. But, if I was ever going to announce my retirement, it probably would not be in a Downtown Los Angeles hotel with this fairly ugly carpet.

Leave it to the always design-savvy Sharapova knock the hotel carpet whilst in the midst of attempting to save her reputation.

Sharapova Wozniacki Australian Open

5. Sharapova vs. Wozniacki

When Sharapova was granted a wild card into the 2017 U.S. Open, her first Grand Slam match following her 2016 doping violation. many players felt the preferential treatment wasn’t deserved.

None were more displeased than two-time finalist, “sweet” Caroline Wozniacki. On a day in which the Dane bottomed out in the second round (to a player ranked outside the Top 100–no less), Wozniacki arrived at her press conference with guns blazing. Upset about having to play on Court 17, Woz slammed tournament organizers for placing “cheater” Sharapova on a stadium court for the second consecutive match.

When asked about Wozniacki’s comments in her presser, Sharapova retorted:

As you know, I don’t make the schedule. If they wanted to put me on a parking lot in Queens, I’d be more than happy to play there.

That’s not what matters to me. What matters to me is that I’m in the fourth round. I don’t know where she is.

I think we all know that if Sharapova were to play in a parking lot in Queens, that would be the hottest ticket in NYC that night– not a stadium ticket featuring Wozniacki.

Sharapova Ivanovic Brisbane Final 2015

4. Sharapova vs. Ivanovic

In 2014, Ana Ivanovic re-entered the women’s Top 10 and the Sharapova-Ivanovic rivalry was renewed. Meeting in the Cinncinatti semifinals, Ivanovic led 6-2, 5-2 before completely falling apart.

In the blink of an eye, Sharapova stole the second set and led by a break in the final. In the middle of the 4-3 game, Ivanovic took an unusual medical timeout, asking the physio to check on an irregular heartbeat.

When play resumed and Sharapova double-faulted the break away, she tapped her wrist and instructed the umpire:

“Check her blood pressure.”

Needless to say. the comment was heard around the world. Unfortunately, Ivanovic would have the last laugh, winning the match 7-5 in the third.

Sharapova Bouchard Handshake

3. Sharapova vs. Bouchard

When news broke about Sharapova’s failed drugs test, none were harsher on the Russian than Eugenie Bouchard.

Eugenie was quick to call Maria a “cheater” and go so far as to say “a cheater should never be allowed to play the sport ever again”.

When Maria returned to tour in 2017, the young Canadian elaborated, “She’s not someone I can say I look up to anymore.”

However, tensions between the two were fraught years before Maria’s doping violation came to light. The similarities between the two players are uncanny. From their blonde hair to their supermodel looks to their flat, aggressive baseline games. In the words of Chris Evert, Bouchard is Sharapova’s “mini-me”.

In 2014, the young Canadian looked ready to surpass her older counterpart, leading Sharapova in their Roland Garros semifinal. However, Maria ultimately gritted out the match, winning the second set 7-5 before running away in the third.

By 2015, Sharapova had figured the young Canadian out, asserting mastery over Bouchard in a straight-sets drubbing in the Australian Open quarterfinals.

Needless to say, the two losses left Bouchard hungry for revenge.

Somehow, the draw gods heard her pleas and just a week after her dismissive comments rocked the tennis world, the two were projected to face-off in the Madrid Open second round. In response to Genie’s comments, Sharapova answered: “I’m above that.”

In the end, Bouchard emerged victorious over Sharapova, a jaw-dropping victory given that the Canadian had been in a slump since her breakthrough 2014.

However, Sharapova would have the last laugh. Without uttering so much as a word, Sharapova mocked the Canadian’s affluent upbringing with a simple Twitter-like heard around the world (see below).

Bouchard Insufferable Like

2.  Sharapova vs. Misogyny

Women face a host of unfair social expectations, and none carry the weight of those expectations more than the female athlete.

In a world that overemphasizes the worth of a woman’s physical appearance and undervalues characteristics such as her strength and intellect, Maria Sharapova shatters these expectations.

Exhuming both strength & beauty, Sharapova teamed up with Nike ahead of the 2006 US Open in order to silence the misogyny of some critics.

The ad follows a young Sharapova heading to her US Open match from the Waldorf-Astoria Hotel. The people she passes along the way each sing a line from the iconic West Side Story tune “I Feel Pretty”.

However, as the song climaxes, the match begins and Sharapova smacks down a return ace punctuated by her iconic grunt. Silence.

Sharapova Roland Garros

1. Sharapova vs. The French Crowd

In 2008, Sharapova was at the peak of her career. She recently won the Australian Open (in straight-sets) and rose to World No. 1. The only hole in the 21-year-old’s resume was a French Open title.

With an open draw, 2008 looked to be the year that the “cow on ice” would finally reign supreme on the terre-battue. However, in the fourth round, Maria found herself in a battle on Court Suzanne Lenglen with compatriot Dinara Safina and the French Crowd.

While Maria was fending off break point after break point, the unruly French crowd was shouting during points, applauding her double faults, and mocking her trademark grunt.

After saving another match point by firing a missle of a forehand onto the court’s tramline, Sharapova let out a shriek:

Allez up your fucking ass!

While Sharapova would lose that day, she would silence the Roland Garros crowd by winning Roland Garros not once, but twice.


The Legacy of Maria Sharapova: To Live & Die by Commitment

After nineteen years on tour, Maria Sharapova has decided to call it a career. While the news might not be completely unexpected, the announcement certainly sends tremors throughout the tennis world and beyond.

The Russian is undoubtedly an icon, With five Grand Slam singles titles, a career Grand Slam, an Olympic silver medal, and twenty-one weeks atop the WTA rankings, Sharapova’s career belongs in the Hall of Fame. Furthermore, off-court, she’s been able to translate tennis stardom into mainstream cultural relevance, reaching a level of ubiquity that few other players have been able to achieve.

From her meteoric rise through her sputtering downfall, the foremost trait that defines Sharapova has been her commitment.

Sharapova 2004 Wimbledon Trophy

When she swept aside Serena to win Wimbledon in 2004, the commitment was obvious. With the way the rangy teenager launched herself into each of her shots, sending flat bullets onto the court’s tramlines, Sharapova committed to each and every one of her groundstrokes.

In the next two ensuing seasons, under the scrutiny of the spotlight, the young Russian struggled to replicate Grand Slam success. While critics lambasted the ‘one-dimensional’ nature of her game, which could easily unwind with streams of double faults and unforced errors, Sharapova never shrunk from her aggressive nature. From the staredown she gave her opponents at the baseline as she readied her serve to the shriek that she delivered as she pummeled the felt off the ball, Sharapova was a baseliner who came to pulverize.

sharapova wimbledon

In 2008, while at the peak of her career, Sharapova succumbed to a shoulder injury that required reconstructive surgery to fix. She returned the following season, however, it took her over two years to return to the game’s elite. Her serve never regained its potency. And, without that weapon to reliably start points on the front-foot, the Russian found it increasingly more difficult to navigate her service.

Nonetheless, she grinded away. She bottomed out early at many big tournaments. And, she suffered countless humiliating losses. Eventually, she found her stride and in 2012 she hoisted a Grand Slam trophy once again–at Roland Garros of all places. The commitment paid off.

As it stands, Maria Sharapova is the only player to win a major title after undergoing a shoulder reconstruction– a feat that she’s accomplished not once–but twice.

While the final chapter of her career will always be tarnished by the meldonium controversy, it perhaps highlights Sharapova’s unparalleled commitment more than any other. When the Russian invited the tennis media to an L.A. hotel (with a “fairly ugly carpet”), to reveal the failed drugs test, she displayed a commitment to her actions. Not once during the ensuing six-month series of tribunals did she deny using the substance. Instead, she committed to her argument: she had been taking the drug legally for the past decade and was not aware of the change in the drug’s legal status. Furthermore, this period demonstrates Sharapova’s commitment to come back.

Unfortunately, while she returned to the tour in 2017, the results never returned with her. Suffering numerous aches and ailments, her body did not want to cooperate. Nonetheless, for the better part of three years, she trained while waiting out these nagging injuries (undergoing at least two minor surgeries in the process).

Sharapova Retirement

Maria Sharapova’s legacy is a complicated one. However, if it weren’t for her undying commitment, we would have never been able to experience her meteoric highs and miserable lows. Whatever she sets her sights on next, her unwavering commitment will take her there and beyond.

WTA Retirement Watch 2020

As the decade pulls away in the rearview mirror, the prospect of retirement looms ahead for many of the recent decade’s greats.

Just recently, the tennis world digested the news of the immediate retirement of Dominika Cibulkova, former world No. 4, 2016 WTA Finals Champion and 2014 Australian Open runner-up. It is impossible for any die-hard tennis fan not to miss the peppy Slovakian, with her tennis ball-sniffing prowess and tendency to create knock-down, drag-out classics (if there is one match you have to watch it is her 2016 Wimbledon fourth round versus ‘The Magician’ herself, Agnieska Radwanska).

However, Dominika certainly isn’t alone in her contemplation of retirement. In fact, on the ATP Tour, many of her male contemporaries, such as David Ferrer & Tomas Berdych, have also called it quits. With the upcoming 2020 Summer Olympics in Tokyo looming around the corner, many of these players may find it to be the perfect time to hang up their racquets.

Check out below for my list of the Top 10 players likely to retire by the close of 2020.

(NOTE: for the purposes of this list, only players formerly ranked in the Top 10 are in consideration):


10. Sam Stosur

Being a former World No. 1 in doubles, a three-time double Grand Slam winner, and a singles Grand Slam champion, Sam Stosur’s CV arguably earns her a place in the tennis Hall of Fame. In fact, her triumph over Serena Williams in the 2011 US Open Final ranks amongst one of the biggest Grand Slam final upsets in history.

However, the Australian’s best days appear to be over. A wrist injury in 2017 saw her ranking dip and she currently ranks World No. 92. In 2018, to start the year, she hoisted her home Slam’s trophy in Melbourne by winning the doubles title alongside Zhang Shuai. However, her year was punctuated by losing a dramatic Fed Cup rubber to France.

It is questionable whether she’ll be able to qualify for the Olympics, given how long her singles ranking has fallen and the fact that only the Top 10 ranked doubles players gain direct entry into the event (and Sam currently sits at World No. 15 in that discipline).

She’s recently hired a new coach, former doubles partner Rennae Stubbs. However, I expect the 2020 season to be treated as a victory lap for the Aussie veteran.


9. Sara Errani

The former World No. 5 & 2012 French Open Finalist’s reputation took a permanent hit when the ITF announced that the Italian failed a doping testing in February of 2017. Given her string of poor results leading up to the failed test, the controversy may not have made headlines if she had not attributed the failed result to “accidentally” ingesting her mother’s cancer meds while eating homemade tortellini…

While she petitioned to reduce her sentence, her own federation petitioned for it to be extended. Ever since she’s been struggling to regain Top 100 form (heck, she’s even been struggling to get her serve in the court).

While Errani may have been the tour’s most consistent Italian from 2012-2013, her compatriots Francesca Schiavoni,  Flavia Pennetta, and Roberta Vinci have since surpassed her accomplishments (and retired themselves). I expect the Italian to hang up her racquet and join their ranks in the coming months.

Carla Suarez

8. Carla Suarez Navarro

It feels like Carla has been on tour forever. Turning pro in 2003 (at the age of 14), many pundits made comparisons to another Spanish teen phenom–Rafael Nadal. While her career never quite rivaled Rafa’s, she did enjoy success in her own right.

In 2016, the Spaniard was on a tear, notching nine Top-10 wins during the first five months of the season, reaching the finals of Miami & Rome in the process (losing to Serena Williams & Maria Sharapova in those finals, no less). The run of form buoyed her ranking to World No. 6 & the trophy in Dubai the following year.

Her seven (yes, seven) Grand Slam quarterfinal appearances are nothing to laugh at. However, her form has taken a slide after suffering a wrist injury in 2018. The technique on her one-handed backhand (which is a work of art), depends on the ability to flick her wrist, and as such, she hasn’t been able to produce the angles that her game depends on.

While she still ranks amongst the world’s Top 40, I expect the Spaniard to call it a career after 2020.

(NOTE: On December 3rd, 2019, Carla announced that 2020 will be her final season.)


7. Andrea Petkovic

Andrea Petkovic is certainly the player I would miss most if she chose to bid adieu to the tour.

The German’s story matches her unique personality. After a dazzling 2011, in which she reached three (yes, three) Grand Slam quarter-finals, she suffered a gruesome on-court knee injury, tearing her ACL. Returning to tour nearly two years later, she reaggravated the injury in her comeback faceoff versus Viktoria Azarenka.

It wasn’t until 2014 that Petko returned, briefly reentering the Top 10 in 2015 and reaching the French Open semifinals. However, since, she’s hovered around World No. 60.

Andrea is one of the most intelligent players on tour. She studied political science in university & consistently talks about her love of writers like Ernest Hemingway in her press conferences. In fact, she recently won a journalism award for her contributions to Racquet Magazine.

All in all, I expect the German to always be a consistent presence in the tennis community, however, due to her uncooperative body, her playing days may be numbered. Hopefully, we’ll get to see the Petko dance at least one last time!

(NOTE: On December 11th, 2019, Andrea announced that she has no plans to return, however, a recurring injury will likely force her to miss the 2020 Australian Open.)


6. Svetlana Kuznetsova

In 2019, the Russian reminded us why to never count her out. In Cinncinatti, she sliced and diced her way through the likes of Anastasia Sevastova, Sloane Stephens, Karolina Pliskova, and World No. 1 Ash Barty before losing a tight final to Madison Keys,

However, despite the run of form, the Russian failed to carry momentum into any other tournaments to close out the year.

Svetlana is an interesting character. She first tasted the highest glory that the sport can offer by winning the US Open as a teenager in 2004. She would eventually rise to World No. 2 and once again taste Grand Slam success by winning Roland Garros in 2009. However, her results in the past decade have not nearly touched those heights.

When she reached the semifinals of the 2016 WTA Finals (after a bizarre match in which she gave herself an on-court haircut), she explained the source of her energy to continue to fight, even after all these years: her heart.

However, given her recurring wrist & knee injuries, you have to wonder how much more heart the Russian has left to give through 2020.


5. Caroline Wozniacki

The Dane has long-rued the moniker of “Slamless No. 1”. However, after overcoming a hobbled Simona Halep in the 2018 Australian Open final, her days of answering the question, “When are you going to win a Slam?” are finally over.

Since hoising the biggest trophy of her career, she has failed to replicate that success. She’s reached only eight quarterfinals in thirty tournament appearances between 2018 & 2019. At the end of 2018, she revealed her diagnosis and battle with autoimmune disease rheumatoid arthritis. While she claims to have managed the condition, she played a truncated season this year (compared to the jam-packed schedule she typically plays).

While she may be experiencing difficulties on-court, off-court she appears to be in good spirits. She recently married retired NBA star, David Lee. Considering the humiliating manner to which her former-fiancé Rory McIlroy called off their wedding not-to-be, I’m sure she couldn’t be happier. In fact, many of her on-court contemporaries, like Daniela Hantuchova, have alluded to the fact that her happiness off-court may be eating at her devotion to the sport, especially given all that she’s achieved.

(NOTE: On December 6th, 2019, Caro announced that the 2020 Australian Open will be her final professional tournament.)

US Open Tennis

4. Venus Williams

At the age of 40, Venus Williams could become the oldest player to compete in Olympic singles (since the sport was reintroduced in 1988). However, at the moment, Venus is far behind in the race to claim one of the four singles qualifying spots on the U.S. team. Currently, her sister Serena, Madison Keys, Sofia Kenin, Alison Riske, and Coco Gauff rank above the seven-time Grand Slam singles champion.

While there is one wildcard that the Olympic committee may grant to a former Gold Medalist or Grand Slam champion, that wildcard looks like a highly competitive prize with 2016 champion Monica Puig, Maria Sharapova, Viktoria Azarenka and Williams all vying to make the cut.

Queen V is a trailblazer true and true, but, after years of setting her sights on Tokyo, you have to question where the future Hall of Famer finds the motivation to continue to fight heading into her forties.


3. Maria Sharapova

Speaking of Sharapova, the Russian is still on a quest for redemption, after her brief 2016 ITF suspension due to a failed drugs test. While her competitive flair remains intact, she has yet to generate any kind of momentum since returning to tour in 2017.

Her first-round losses at Wimbledon & the US Open were nothing short of humiliating (particularly her 6-1, 6-1 drubbing by “nemesis” Serena Williams). In fact, she ended her season ranked World No. 131, her lowest ranking since 2002.

It certainly doesn’t help that she has basically been in rehab for the majority of her return, attending to recurring shoulder, forearm, and hip injuries.

The game has evolved since Sharapova hit her peak–requiring a blend of strength, spin, and athleticism to reach the top. Sharapova possesses only one of those assets, and, combined with an uncooperating body, it appears her days are numbered.


2. Viktoria Azarenka

I cannot think of a player with worse luck than Viktoria Azarenka.

Winning the Australian Open in 2012 amidst a 26-match win-streak, Vika emerged as the de facto World No. 1 and the decade’s only true rival to the GOAT, Serena Williams.

However, her reign at the top was cut short due to an aggravated Achilles injury. It took her a few years to regain confidence in her movement (and an endless series of unfortunate first-round draws didn’t help either).

When she achieved the Sunshine Double in 2016, blasting Serena Williams off-court in the Miami final no less, it appeared that the Belarussian had reascended. However, her pregnancy, which she announced shortly thereafter, forced her away from competition yet again.

Unfortunately, due to a highly-publicized custody battle, Vika didn’t return to court until 2018. And, since her return, she has yet to win a title or make a deep run at a Grand Slam.

This year, she enlisted the help of Wim Fissette, who coached her to the Sunshine Double in 2016. In fact, the Belgian is responsible for career-best seasons from many players, including Simona Halep, Kim Clijsters, Angelique Kerber, Johana Konta, and Sabine Lisicki.  However, it appears that he has left Vika’s camp and is now working with Naomi Osaka.

After a first-round loss in Melbourne this year, Vika broke down in tears, admitting, “I’ve been through a lot of things in my life, and sometimes I wonder why I go through them.” She continues, “But I think they’re going to make me stronger. I want to believe that. And, I’m going to work hard for it.”

We all have to hope that 2020 starts to show the fruits of the former World No. 1’s labor, because few deserve it more.


1. Angelique Kerber

It might seem premature to list the 2018 Wimbledon Champion as a prime candidate for retirement. However, while the German has realized her greatest achievements in recent years, they have all occurred after the age of 28. Angelique holds the unique distinction of being the oldest woman to ascend to World No. 1 for the first time.

The German reached the Indian Wells final to lead 2019, her season was undone by Bianca Andreescu and an ankle injury that she succumbed to during practice in Madrid. She ended the year ranked World No. 20.

It is no secret that Angelique is one of the more popular players on tour. However, many of her closest friends that she rose through the ranks with, including Ana Ivanovic, Aga Radwanska, and Caroline Wozniacki, have already called it a career.

While recently, the German has made it a habit of excelling in  even-numbered-years, you have to wonder if the German might contemplate calling it quits if she faces another difficult year.