Novak, the Late Bloomer

Prologue

I remember the summer of 2001 well: I spent most of that summer going to tennis camp, playing tennis tournaments and bouncing around my new home. My family had just immigrated to the US in late May, and I was starting to think about what it would be like to go to 8th grade in the fall.

We had a “TV room” of sorts and my folks bought a 42 inch plasma TV. That was a big deal; I’ve never had a flat screen before. Eventually, the cable got hooked up and I was mesmerized: I couldn’t believe that there were so many different ESPN channels! I discovered ESPN Classic, which was showing SportsCentury all day long and I became obsessed with it. Something about watching sports in that faded color palette seemed more authentic to me. I’ve never come across the host Chris Fowler before, but he would of course go on to become an anchor commentator for Grand Slams on ESPN for the next 20 years.

Come late June, ESPN started broadcasting Wimbledon and I was glued to the TV. Pete Sampras was seeded #1 and had won seven out of the last eight Wimbledons. In the fourth round, he was facing 19 year old Roger Federer. I’ve never seen Federer play before and only tuned into the match late in the 5th set, which Federer ended up winning 7-5.

I don’t know if sports stats were made to be looked at retrospectively…but it always fascinates me that while we often look back at generational shifts in sports, it’s almost impossible to notice them in real time. It’s not just that Sampras never won another Wimbledon after that match. Sampras would never win another match at Wimbledon. And his all-time record of seven Wimbledon titles, would end up being broken 16 years later by none other than Federer. Sports can be brutal (beautiful?).

Like many other tennis fans, I took note of Federer’s smooth, complete game. It wasn’t just the serve and volley, which was still the norm on grass back then. But the full variety of shots, ranging from powerful forehands to backhand slices that would skid off the court.

Soon enough, Federer became my favorite tennis player. Indeed by 2005-2006, Federer was dominating tennis unlike anyone who has come before. Across those two seasons, he amassed a staggering 173-9 win-loss record (95%). His 92 wins in 2006 are a record that remains to this day (Djokovic achieved 82 in 2015 and Nadal peaked at 79 in 2005).

My appreciation for Federer’s craft began to grow as his career progressed in the late 2000’s and then deep into the 2010’s. Soon enough he was beating the next generation (Dimitrov, Berdych) and then…the generation after that (Raonic, Nishikori). He was timeless.

And of course being my stubborn young self, I could not switch over to Djokovic or Nadal. They don’t play the game like Federer! They’ll never catch his Grand Slam records!

But just like Sampras’s Wimbledon record, eventually my devotion was broken as well. Or perhaps it happened piece by piece. For a while now, I’ve wanted to share that story.

Five Years Later

In spring 2006, I was a senior in high school who had finally been accepted to college. I remember that period vividly. For the first time, I began feeling initial inklings of comfort in my new home. I had officially been in the United States for five years. My passion for tennis had persisted; indeed my most proud achievement at the time was being elected as a captain of our high school tennis team.

That May, I of course watched the French Open on TV. Nadal was defending his first title and a player by the name of Novak Djokovic was beginning to make some noise.

I missed the Nadal vs. Djokovic quarterfinal but I remember turning on the TV and seeing the Djokovic press conference after his 4-6, 4-6 loss (he had retired at the start of the third set). The 19 year old Djokovic, who was ranked #63 at the time, had a peculiar reaction to the loss:

I think I was in control because I think everything was depending on me.

I realized today that I don’t need to play anything special. Everybody thinks Nadal, for sure he is best on this surface, but he is not unbeatable, that’s for sure.

I think I could win today.

Given 99% of athlete press conferences are filled with generic non-sequiturs consisting of, “This is a tough loss”, “I wasn’t at my best today” and “You gotta give him credit”, this was at least refreshing.

I am fairly certain that the young Djokovic was not yet media trained and thus shared his raw, unfiltered thoughts. Which means that despite not having won anything in tennis yet, his brain processed a one-way loss to a top ranked player as “everything was depending on me”.

Two years later, Djokovic’s “I’m in control” self narrative largely rang meaningless. He was beginning to be known for his mid-match retirements. He retired in the semis of Wimbledon in both 2007 and 2008. At the 2008 US Open, when Andy Roddick was asked about his upcoming match against Djokovic, he suggested that Djokovic likely has, “A back and hip injury, cramps, bird flu, common cold and SARS”. (…oh the good old days when we thought “SARS” was the scariest thing out there…)

Djokovic went on to win the match but the “quitter” aura around Djokovic persisted. A few months later, Djokovic was facing Roddick again, this time at the Australian Open, and retired while behind in the fourth set. While Roddick’s commentary was more subdued, Roger Federer did not hold back:

He’s not a guy who’s never given up before… it’s disappointing. I’ve only done it once in my career… Andy totally deserved to win that match

I’m almost in favor of saying, you know what, if you’re not fit enough, just get out of here. If Novak were up two sets to love I don’t think he would have retired 4-0 down in the fourth

So there we had it. Novak Djokovic: a guy who sometimes gives up.

As for me, I was a diehard Federer fan, so the assessment made complete sense.

The Big…2

By the end of 2010, I had experienced my first stretch in the “real world”. After graduating from college that summer, I joined the analyst program at one of the investment banks in NYC. My world was rocked and the days were blending. Every night I had the same dream: I am inside of a giant, endless spreadsheet, jumping from cell to cell.

I hadn’t watched tennis on TV in months but I would religiously check scores on my Blackberry and of course watch highlights at work. At the time, I worked on a large trading floor with rows of desks and computer screens. It was at this time that I discovered Grantland: as I walked around the floor, I would see Grantland permanently open across many screens.

In the tennis world, Nadal was beginning to make meaningful inroads, but Federer was still largely dominating the “greatest of all time” conversation. This is how things looked at the end of 2010:Federer was a week from breaking Sampras’s all time record of weeks at #1 (286)…which Federer surpassed in 2012, eventually hitting 310…which Djokovic surpassed in 2021.

Djokovic had won one Slam, back in 2008. He was ranked #3 in the world and had won some big matches but ultimately, out of his 43 matches against Federer and Nadal, he had won 10. Was he going to be a one slam wonder like Roddick? Two like Safin? Maybe three like Murray?

A Chocolate Square

A lot has been written about Djokovic’s groundbreaking 2011 season. Perhaps the greatest tennis season of all time. 70-6 win loss record. Three Slams. 10-1 combined against Federer and Nadal. And there was a 41The full win streak was technically at 43, but the first two wins occurred in late 2010. consecutive match win streak tucked in there as well.

But for me, the true pivot took place at the 2012 Australian Open, where Djokovic won the longest grand slam final in history, at almost 6 hours.

Djokovic beat Nadal not by overpowering him or by breaking his rhythm with some type of a defined game plan. He decided to beat Nadal at his own game. He decided to outlast him. Nadal was eager to get back to winning slams and was training with a renewed zeal going into 2012. In the documentary, he describes how during that time, his practice sessions were more painful than the matches themselves. He repeatedly uses the word “suffering” to refer to those practices. His coach Toni did not allow him to drink water for the first hour of each hitting session because it “was good for him to learn how to suffer”.

Over the years their matches have evolved, but in that all-time final, Djokovic simply outsuffered Nadal.

And the suffering was oh so real. This was the first time Djokovic and Nadal played a 5th set. After winning the 4th set in a tiebreaker, Nadal dropped to his knees and celebrated as if he won the match:

Watch on YouTube ↗

Surely in the brutal Australian heat, after 5 hours of tennis, Nadal had to be the favorite based on pure physicality? In the 5th, Nadal took the lead, serving at 4-2, 30-15. The points grew longer and longer. After yet another seemingly never ending point, where Djokovic threw the kitchen sink at Nadal and still managed to lose the point, Djokovic lay on his back exhausted:

Watch on YouTube ↗

(One of the most iconic tennis points of all time)

A few games later, he was holding the trophy.

That summer, I was visiting my parents at Cape Cod and my mom gifted me Djokovic’s new book, Serve to Win. What caught my attention was his description of the aftermath of that Australian Open win:

After I won, I sat in the locker room in Melbourne. I wanted one thing: to taste chocolate. I hadn’t tasted it since the summer of 2010. Miljan brought me a candy bar. I broke off one square — one tiny square — and popped it into my mouth, let it melt on my tongue. That was all I would allow myself. That is what it has taken to get to number one.

Allow myself. It wasn’t his team or his coach. It was what he granted his own self.

Three years earlier, he was being called out by Federer for being unfit. Now he was celebrating winning the longest Grand Slam final of all time with a tiny chocolate square.This reminded me of an old article I read about Tom Brady in the WSJ. In it, John Stallworth, a wide receiver, remembers one of his first workouts with Brady:Brady threw a perfect pass, one that the receiver simply had to cradle to catch. Stallworth dropped it. Disappointed, he ran back towards Brady, who profusely apologized.“He was pissed off at himself, he figured out he was an inch or two off” said Stallworth. “That’s when I realized: ‘Wow, this dude is crazy.’”

Every sports movie has a permutation of that sped-up sequence, when the protagonist starts to find his groove leading up to the big fight. Similar to how Hillary Swank ran through her opponents early on in Million Dollar Baby. That’s what the next few years of Djokovic’s domination felt like.

Watch on YouTube ↗

Over the five year span from 2011 to 2015, Djokovic finished as #1 four times. The incredible momentum carried over into the 2016 French Open, where Djokovic finally completed his career Grand Slam.And also held all four Slams at once (Nole Slam).

Two Surgeries

In Rocky IV, the signature training montage juxtaposes the all natural granola Rocky in the Siberian (?) winter with the technology-native Ivan Drago (I guess everyone picks their own path to prepare for the Cold War ending fight):

Watch on YouTube ↗

What happened over the next few years in the tennis world kind of reminded me of that. The two greats navigated the brutal realities of sports and specifically, longevity.

Djokovic’s dominance began to slow at the end of 2016. Some commentators suggested Djokovic struggled with motivation. He was also dealing with a persistent elbow injury, which eventually led him to retire in his quarterfinal match at 2017 Wimbledon. After the retirement, Djokovic announced that he was shutting down the rest of his season:

“I am a hunter and my biggest goal is to find the winning spark on the court again.”

By early 2018, Djokovic was sitting outside of the top 10 and won one tournament in all of 2017.

My First Surgery: Djokovic Edition

I’ve always found this period of Djokovic’s career fascinating. And my perception of it has shifted meaningfully as I got older myself. Quick level set: by end of 2017, Djokovic’s career prize money sat at $110M (second to only Federer who was at $112M, after having won a monster 2017 season with $13M of tennis earnings). Djokovic was still 3rd in the Grandslam race but if he quit tennis at that moment, he would permanently be part of the “greatest ever” conversation due to his dominance in the 2010’s.

Djokovic was battling a nagging elbow surgery, which was beginning to point towards surgery. But surgery stood in complete contrast to his all-natural holistic approach to training. Djokovic’s hesitation to have his first ever surgery was clear in the comments he made over time:

There is a possibility that they will propose surgery, but I don’t think that is good. To go to be cut in surgery or to poison myself with pills — none of the solutions is good.(Wimbledon 2017)

I was trying to avoid getting on that table because I am not a fan of surgeries or medications. I am just trying to be as natural as possible, and I believe that our bodies are self-healing mechanisms(2018)

In early 2017 season, Djokovic played at his favorite slam - the Australian Open.Which he would go on to win a record 10 times. Djokovic lost in the fourth round to unseeded Hyeon Chung. And thus finally, in February 2018, eight months after he shut down his season to try to heal his elbow Djokovic had the elbow surgery. The first surgery of his career, at the age of 30.

Later that year, in November, in an interview filmed inside of a speeding SUV in Paris, Djokovic admitted the emotional toll of the surgery:

I just cried for two or three days. I cried after I had the surgery on my elbow. Every time I thought about what I did, I felt like I had failed myself

We often talk about athletes who ended up pushing themselves to the brink and ended up having a sort of a breakdown. Think Jennifer Capriatti with the shoplifting. Or even Nadal in the mid-2010’s, when he realized he needed to soften his training cadence and try to enjoy life at least somewhat.The Netflix Rafa documentary does a nice job showing this period, where Nadal ends up bringing Carlos Moya as a coach and realizes he needs to have joy off the court to achieve longevity.

But for Djokovic…what broke him was not the spartan self-imposed training & life regimen. It was a surgery. A surgery which turned out successful and allowed him to win many more Slams. Still, at the time, he saw failure.

Shortly after the surgery, Djokovic was beginning to play some tournaments. In his press conferences, he was talking about finally playing without pain for the first time in two years. In Indian Wells, he lost to a qualifier ranked 109. Then a week later in Miami, he lost to French journeyman Benoit Paire (ranked 47) in just over an hour. While his public comments after the loss were subdued, his wife Jelena, would later describe how after that loss, Djokovic told his team he was ready to quit:

He said to me that he’s quitting…He lost in Miami and that was a terrible loss and then he just gathered all of us inside, ‘You know what guys, I’m done.’ We cried and we were like ‘What are you doing?’

At that year’s French Open, Djokovic was seeded 20th and lost to a 72nd ranked Cecchinato in the quarters. In the press conference, Djokovic said something that stood in stark contrast to what he said after that very first loss to Nadal at the same tournament 12 years earlier:

I don’t know what I’m going to do

Three weeks later, he entered Wimbledon ranked outside of the top 20.

What followed was one of the most incredible mid-season turnarounds in sports:

Djokovic won Wimbledon. Then he won the US Open. And then he finished 2018 ranked the #1 tennis player in the world.Tennis rankings are calculated on a Last 12 Months basis, so to be ranked #20 in the world in July and finish the year #1 requires an immense second half push.

My First Surgery: Federer Edition

During this time, Federer also underwent his first ever surgery, at the age of 34. I wouldn’t quite call his approach the Ivan Drago carefree “if he dies, he dies” philosophy, but it was surely more businesslike than Djokovic’s.

After losing to Djokovic in the semis at the 2016 Australian Open, Federer tore his meniscus while bathing his two daughters. He immediately had the surgery and continued with his season.

At the time, Federer had won 17 Slams and was considered one of the greatest ever. Indeed, it was unheard of in modern tennis to win majors at 35.The last time that was done was in early 1970’s when Ken Rosewall won 1971-72 Australian Open at the ages of 36-37. Andre Agassi had laid the blueprint for late career dominance and played his last farewell match at the age of 36. His last slam victory came at the age of 32 (Sampras won his final slam at 31).

So the blueprint for post 35 dominance did not exist. Especially after a torn meniscus, an injury that is notorious for ending careers.

After this loss in the semis of the 2016 Wimbledon, Federer shut down the rest of his season stating that he needs more extensive rehabilitation following the knee surgery.Is it insane that on a not fully rehabbed meniscus…Federer reached the semis of Wimbledon where he lost in 5 sets to Raonic?

Entering 2017, Federer had not won a slam since 2012, had not played a match in over 6 months and dropped to #17 in the world. The general feeling among the press was that Federer would likely not win another slam and his tally would remain at 17.

At his first tournament, the 2017 Australian Open, Federer started off sluggish by beating a qualifier in four sets. I remember watching the post match commentary where the consensus was that Federer is far from top form and therefore was not a contender.

But by the third round things began to shift. Federer dispatched world #10 Berdych in 3 straight sets. In the next match, he defeated 5th seed Nishikori in 5 sets. In the semis, he faced his rival #4 seed Wawrinka. Once again, Federer won in 5 sets.

Suddenly, we were back to another Federer vs. Nadal final. Federer was nearing 36. Coming off two five set matches. Playing against the most physical player of all time in the Australia heat. His record against Nadal had slipped to 11-23. More notably, going into the match, Federer lost to Nadal the last 6 times they played at Slams. Indeed, the only slam where Federer had beaten Nadal was Wimbledon (back in 2006 and 2007!).

I expected Nadal to win the match in maybe three or four sets. When Federer found himself down a break in the 5th set (1-3), it felt like it’s time for DJ Khaled to pop out of somewhere and give us a high quality, “Another one!”

I remember a class reading of the final scene of Romeo & Juliet in 9th grade English, where Romeo believes Juliet is dead but we as the readers, know she’s simply sleeping. Don’t drink that poison! She’s gonna wake up! “That’s called Dramatic Irony”, Mr. Styles explained to us.

Since then I’ve often thought that tennis scoring and the momentum swings it enables may be best described as Dramatic Irony. Because at 3-1 in the 5th set, could Nadal have predicted that he won’t win another game?

After the match Federer described his inner monologue at that moment:

I was talking to myself, saying like, ‘Just relax, man. The comeback is so great already. Let it fly off your racquet and just see what happens’

Federer pulled off the improbable. And Djokovic? He lost in the 2nd round of the same tournament. He was just heading into his 2017 slump. Meanwhile, Federer went on to compile a 4-0 record against Nadal in 2017, win 2017 Wimbledon and then defend his title at the 2018 Australian Open! Shortly after, in February 2018, Federer became the oldest ever #1 ranked player in the world, at 36 years of age.

I mean he has to be the greatest of all time, right?

Snap Back to Reality (aka Wimbledon)

All that brings us to 2019 Wimbledon. Going in, many were saying that this is likely Federer’s last opportunity to win a slam. He was a few weeks shy of 38 years old, playing on his home turf. Because of the small time difference with London, I was able to watch his matches live at work from my Boston office.

In the semifinal against Nadal, I remember calling over my coworkers into my office when the back & forth in the final game of the match began. Federer was serving for it, but of course Nadal saved 4 match points before Federer finally won the semi, which turned out to be the last match he played against Nadal.When all was said & done, the Federer vs. Nadal H2H at Slams looked like this:French Open: Nadal 6-0
Australian Open: Nadal 3-1 (Federer won that sole 2017 final)
Wimbledon: Federer 3-1

The final against Djokovic turned out to be the longest final in Wimbledon history (seems like Djokovic has a knack for getting himself into these “longest of all time” finals).

In the 5th set, Federer was up 8-7, 15-15 on his serve. Two aces later, Federer was up 40-15. Two match points. Two points to win his ninth Wimbledon title. But again…Dramatic Irony.

Tennis is such a unique sport in that there are no “easy” shots. The slightest misstep or arm tweak and the ball sails out. There are no easy lay-ups or dunks. And even the top players routinely miss “easy” short in big moments. Think back to this year’s French Open final: Flavio Cobolli completely missed an overhead on Zverev’s matchpoint:

Watch on YouTube ↗

And overheads are supposed to be “easy”. Whereas just getting the return in play against one of the best grass court players of all time requires absolutely perfect timing, all while navigating the pressure of a matchpoint.

I wonder if at that moment Federer was thinking back to the 2010 and 2011 semifinals that he lost to Djokovic at the US Open. In both of those, he also had two consecutive match points at 40-15. In 2010, the match points were on Djokovic’s serve. But a year later, Federer was up 40-15 on his own serve. The way Djokovic saved that first match point has become an iconic clip…he unleashed a “go for broke” forehand return. Federer did not even budge.

Watch on YouTube ↗

Djokovic’s facial expression prior to the point, the shot itself and his reaction after is the Stuff of Legends

After the match, Federer, who had built his career around being composed and polished, would famously call out Djokovic for that reckless return:

“Confidence? Are you kidding me? I mean, please. Some players grow up and play like that — being down 5-2 in the third, and they all just start slapping shots. I never played that way. I believe hard work’s going to pay off… For me, this is very hard to understand. How can you play a shot like that on match point? It’s not a guy who believes much anymore in winning… To lose to someone like that, it’s very disappointing, because you feel like he was mentally out of it already. Just gets the lucky shot at the end, and off you go.”

When asked about Federer’s comments, Djokovic replied casually, “Yeah, I tend to do that on match points. It kinda works.”So at 8-7, 40-15, was Federer expecting Djokovic to slap the ball again? To be “out of it” and no longer believe in winning? Or was he thinking that already twice he had lost to Djokovic in slams after being up 2 matchpoints?

Forty eight minutes later, when Djokovic won the match 13-12 in the 5th set, Federer had managed to lead in virtually every statistical category:

It’s somewhat common, in close tennis matches, that the winner ends up actually winning a handful of points fewer than the loser. But we’re usually talking about 4-5 points. Federer won 14 extra points! He hit FORTY extra winners, while making only ten more unforced errors.

Djokovic put on his vintage clutch performance when it mattered. He won all three tie breaks and…the two match points he needed to save.

Epilogue

That 2019 Wimbledon marked a shift.

Federer never reached another Slam final. Shortly after he would start dealing with a torn meniscus on his right knee this time and undergo three surgeries across 2020-2021. He played his last professional match in 2021 at Wimbledon at the age of 40, ranked #6 in the world.Federer technically played one more “professional” match 14 months later at the exhibition-esque Laver Cup. He was unranked by then.

Nadal had a late career resurgence and won an incredible four more slams. He retired in late 2024 at the age of 38, ranked outside of top 150.

Djokovic went on to win eight more slams. As of June 2026, Djokovic is 39 and is currently ranked #7.

That 2019 Wimbledon final also marked a shift in my view of the “greatest ever”. I still loved watching Federer. But it became impossible to deny that Novak Djokovic has been able to achieve something otherworldly. For me personally, the reason for the shift is captured in this table:

The post-2011 run eventually enabled Djokovic to set another record: most weeks as the #1 ranked player of all time (428), eclipsing Federer and Nadal by 118 and 219 weeks respectively

There is no question that all of the Big 3 possessed incredible talent and work ethic. Federer and Nadal were each able to ascend to the top off of their initial push. Federer with his silky beautiful strokes. Nadal with his incredible raw physicality.

Djokovic did not have a super power of his own. His innate talent also allowed him to have incredible success and get to #3 in the world. But he had to do something else, on his volition, at the age of 23, to position himself for the post-2011 dominance. He built the super power in the second leg of his career. What he said after that first loss to Nadal turned out to have lasting truth to it:

I was in control because everything was depending on me

And that’s what I’ve found the most inspiring.

Novak Djokovic is my favorite tennis player of all time.

June 2026