With money tight, Djokovic’s parents made the painful choice to put their limited resources behind Novak, while brothers Marko and Djordje saw their own tennis ambitions pushed aside. His rise came with a cost the entire family had to carry. Now 39, Djokovic has admitted he was too young to fully grasp what that decision meant at the time. Behind the trophies and records is a much harsher reality. Novak’s dream was given the best chance to survive, while his brothers were forced to sacrifice parts of their own.

“I’m trying to balance the roles of a professional tennis player and a father and a husband and son, and brother,” he said during a press conference. “I’m trying to be the best I can be in all these different roles. And it takes time and energy, so it’s a work in progress. I’ve kind of underestimated of how big of a support and sacrifice was from all the family members around me. In order for them to allow me to create space for 20+ years to do my thing.”

Though the Tour once consumed Djokovic’s life and left his family fighting for scraps of his time, that excuse no longer holds. The Serb has already stepped away from competition multiple times this season, even escaping to Montenegro with his family before beginning his hard-court campaign. Djokovic admits his world can no longer revolve around his career alone. These days, the trophies can wait. Making up for lost family time cannot.

“It does depend on family, the tempo of life, and things that might surface and need addressing, requiring my time and attention. So, I’ve done quite a bit of traveling within Europe to be with family members and do some of the things my family did for me all these years. It’s not really as straightforward as it was for most of my career and most of my life, when everything revolved around me. It’s not really like that anymore, and I like that because I need to get out of that kind of role as well,” he added.

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Djokovic picked up tennis at 11, but this was never just a childhood dream. He knew his brothers were watching their own tennis ambitions fade while the family poured its limited resources into his future. That reality gave Djokovic something far more powerful than motivation: pressure. He wanted to win, make money, and repay a family that had gambled heavily on him.

Even in the documentary Wolf in Winter, that edge comes through loud and clear. Directed by The Last Dance filmmaker Jason Hehir, the documentary digs into Djokovic’s harsh upbringing in Serbia, the sacrifices his family made, and his rise during the Federer-Nadal era. It also explores the emotional intensity that has shaped how fans view him, with Jelena describing a man who can be gentle at home but fiercely driven on court.

Away from the court, Djokovic’s family has been the one constant that tennis could not replace. He has known Jelena since their school days in Serbia, and they married in 2014 before welcoming Stefan that year and Tara in 2017. Jelena has stood beside him through the relentless travel, pressure, and scrutiny that came with becoming one of the sport’s biggest stars. Their children now shape a different side of his life.

Stefan has shown an interest in tennis, while Tara has largely stayed away from it. Djokovic has made one thing clear. He will not push either of them toward the sport that consumed so much of his own childhood.

Djokovic’s story may be his own, but the path behind it was built on family sacrifice, and he is hardly the only champion who came up that way. Venus and Serena Williams trained in Compton under Richard Williams and Oracene Price before the family moved to Florida to take their development further. Venus helped open doors for Serena, and together they changed women’s tennis. Maria Sharapova’s rise came with a similar family gamble.

In 1994, the seven-year-old moved to Florida with her father, Yuri, who reportedly arrived with only $700 in borrowed money. Neither spoke English, but the family believed access to elite training could turn her talent into something bigger.

Today, the Serb has 24 Grand Slams, the most for any male player, and has won countless other honors. While the 2026 season certainly hasn’t gone his way, he doesn’t have anything left to prove to anyone. But despite struggling with his form and fitness, Djokovic has still managed to rack up strong results at times this season.

This includes an appearance in the Australian Open final and a semifinal run at Wimbledon. Djokovic is currently ranked No. 5 with 3,760 points. Despite easily being the oldest player in the top 10, he can still provide a great challenge to any player in the world. His impressive performance at SW19 pretty much proved that.

Now, as he enters the hard-court season, Djokovic will begin his Cincinnati Masters campaign against Thiago Agustin Tirante in the second round, but his opponents in the next rounds can prove to be very challenging.

Novak Djokovic handed a tough draw at the Cincinnati Masters

Playing at the event after three years, Djokovic can face trouble from the third round. He can be up against either Jack Draper or Matteo Arnaldi. Notably, Draper had defeated Djokovic earlier this season at the Indian Wells Masters and can prove to be a challenge despite his injury concerns.

Things would not get any easier for Djokovic in the Round of 16, where he could potentially face either Jakub Mensik or Luciano Darderi. Both have enough firepower to push the Serb and are capable of turning that matchup into a real upset threat.

If Djokovic gets through, Alex de Minaur is his projected quarterfinal opponent. Djokovic owns a 3-1 head-to-head advantage, but de Minaur’s speed, consistency and comfort on hard courts could make that a difficult matchup for the veteran.

A win there could set up a semifinal clash with Alexander Zverev, which would be their first meeting of the year. Djokovic leads their head-to-head 9-5 and has generally had the better of the matchup, but Zverev’s recent form could make this one far less comfortable. The World No. 5 could also run into Rafael Jódar, one of the hottest players on Tour after his semifinal run at the National Bank Open.

If Djokovic reaches the final, Taylor Fritz or Ben Shelton could be waiting. Both Americans would have the home crowd firmly behind them, adding another challenge for Djokovic. Shelton, in particular, would arrive with plenty of confidence after his title-winning run in Montreal.

Djokovic may not have received the easiest draw, but the tournament still presents a major opportunity to claim his first title of the season. With Jannik Sinner and Carlos Alcaraz both absent because of fitness concerns, the path to the Masters crown is far more open than usual.