How well-placed is Novak Djokovic to surpass Roger Federer's Grand Slam record?

Not long ago, Novak Djokovic stood significantly behind Roger Federer and Rafael Nadal on the list of the most prolific champions ever at the major events, and slightly beneath Pete Sampras. 

With his 12 Grand Slam tournament titles, Djokovic was eight behind the Swiss Maestro, four back of the redoubtable Nadal, and he trailed Sampras by two. He had not taken a major since collecting his fourth in a row at the 2016 French Open. His mind was muddled. His elbow was ailing. 

He was simply not the essential Novak Djokovic we had marveled at for so long, not the same inexhaustible individual who had dominated tennis comprehensively from the start of 2015 into the middle of the following year, when he was victorious at five of six Grand Slam tournaments.

But since the middle of 2018, Djokovic has reinvented himself, surpassing all of his rivals, playing the game once more as only he can, leaving audiences gasping at his singular skills. 

And so the battle for all-time supremacy at the majors among the men has been altered decidedly. Federer remains at 20, Nadal has climbed to 18, while Djokovic has moved past the great Sampras into third place with 16 of these prestigious prizes. 

No longer is Federer safe at the top. Nadal is now in tenuous territory at No. 2 on the ladder. 

And Djokovic is so sharply focused on the goal of getting to No. 1 on the list—and he is playing such an inspiring and unassailable brand of tennis—that only a fool would dismiss his chances of eventually surpassing both Nadal and Federer.

Lifting his game up to that an unimaginable level has set Djokovic up for a stirring season ahead. The Djoker was his candid self when he said, "I am aware that making history of the sport that I truly love is something special. Of course it motivates me." 

"Playing the Grand Slams and the biggest ATP events is my utmost priority in this season and the seasons to come. How many seasons are to come? I don’t know. I’m trying not to think too much in advance." 

"I do want to definitely focus myself on continuing to improve my game and maintaining the overall well being that I have—mental, physical, emotional —so I would be able to compete at such a high level for the years to come, and have a shot at eventually getting close to Roger’s record. It’s still far."

Indeed it is. But, having thought a lot about this lately, after following the trajectory of Djokovic’s career closely, and examining his future alongside what might be ahead for Federer and Nadal, I believe Djokovic has a good chance to finish ahead of his two chief rivals. 

That will depend largely on exploiting every opportunity he has over the next couple of years, piling up the big titles one by one over that span, and making a concerted effort to reach at least 18 and perhaps as many as 20 by the end of the 2020 season. 

That would mean securing three to five of the next seven Grand Slam tournaments. I see no reason why he can’t get that done.

In 2020, therefore, Djokovic would be well positioned to close the gap even more with Federer - with the Serb upstaging Swiss at the Wimbledon this year. That might have been Federer’s last best chance to win a major. 

Djokovic could win at least two and possibly three of the four biggest tournaments in 2020. To be sure, we will find out by then if the enigmatic Alexander Zverev is ready at last to strongly contend for a major, and discover if others will come to the forefront. 

Stefanos Tsitsipas will make his presence known at the remaining majors this year after his surge to the semifinals at the Australian Open. But it might not be until 2020 or beyond that he is ready to win one of the premier titles. 

The likes of Daniil Medvedev, Karen Khachanov, Borna Coric and Denis Shapovalov could well be ready to threaten the game’s hierarchy by then, as will others.

But Djokovic will be awfully hard for any of them to beat when the stakes are highest. The way I look at it, he should win four or five more majors between now and the end of 2020. 

If he manages to capture four, he would be at 20, and as long as Federer does not pull off a spectacular run somewhere, and if Nadal attains no more than one major somewhere along the line, Djokovic would almost inevitably secure one more major in 2021, and possibly two. 

He will not turn 34 until that spring. By every barometer, he is a young man physically for his age. He has taken exceedingly good care of his body. 

And now he is driven more than ever before to go after the majors zealously, to win one after another with an eye towards the ultimate prize of standing alone at the top of the list.

I will give him five more majors out of the next seven. If that is the case, he will make an immense push in 2021 to win at least one more. If he does not get there, he would go full tilt after the 21st in 2022 as he approaches and then turns 35. 

He can realize that feat. I believe one way or another, he will make it to 21 and perhaps 22.

It is not difficult to envision Djokovic amassing a cluster of additional majors, as long as he remains healthy and avoids serious injuries like the elbow ailment that harmed him substantially over the second half of 2016 and all the way into the early stages of 2018. 

Barring any long absences from the sport, knowing how fully committed he is to hitting such an important milestone, carefully assessing it all, Novak Djokovic in my view is going to break Roger Federer’s record.