Consider that by the time the US Open gets underway just over two weeks from now, tennis’ Big Three of Novak Djokovic, Rafael Nadal and Roger Federer will likely only have collectively played two matches on North American hardcourts prior to arrival in New York – two for Nadal, zero for Djokovic and Federer. Surely, this creates significant opportunity for a prime contender like Daniil Medvedev.

Tonight, at the National Bank Open in Toronto, an event where Medvedev is the top seed, the 25-year-old Russian had little difficulty versus qualifier James Duckworth, a scrappy, net-rushing Australian ranked no. 85 in the world. It took 68 minutes for Medvedev to earn the win, 6-2, 6-4, and advance to the quarterfinals. Medvedev’s only hiccup came when he was broken when serving at 5-2 in the second set. But the final game went swiftly, Medvedev closing it out at 30 with a sharp wide ace.

Much of Medvedev’s eclectic arsenal was on display in this match. His backhand is impregnable. Be it driven hard and flat, whipped with a hint of topspin, on the run or from a comfortable position, Medvedev rarely misses on that side. The forehand, a shot subject to breakdown versus high topspin – especially on clay – was well-behaved and also forceful. But Duckworth lacks enough power or spin to trouble Medvedev, especially on a hard court. Perhaps Duckworth was also worn out from having made his way through the qualifying and then earned impressive wins over Taylor Fritz and Jannik Sinner.

As often happens, Medvedev also bedeviled his opponent with a few custom specialties, these being shots where Medvedev’s technique appears straight out of your local park. Serving at 5-4, 30-15, Medvedev came to net and hit a backhand volley with excessive sidespin. He is among those rare stylists who can make something apparently ugly turn out beautiful.

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Medvedev is among those rare stylists who can make something apparently ugly turn out beautiful.

Medvedev is among those rare stylists who can make something apparently ugly turn out beautiful.

What needs to happen for Medvedev win a major? To date, he’s been in two finals. Back in 2019, off the heels of a terrific summer that included runner-up showings in Washington and Montreal, followed by a title run in Cincinnati, Medvedev reached the finals of the US Open. Down two sets to love versus Nadal, he levelled the match and only ended up losing, 6-4 in the fifth. This February, Medvedev was beaten 7-5, 6-2, 6-2, in the finals of the Australian Open by Djokovic.

The defeat to Nadal ranks among the great efforts of recent tennis history, spiced up by Medvedev completely winning over the New York crowd just over a week after he’d earned its ire. The loss to Djokovic was a bit more disturbing. Having beaten Djokovic three of the previous four times they’d played, it seemed logical to expect Medvedev to offer a tougher test. Then again, the Australian Open’s Rod Laver Arena is to Djokovic what Roland Garros’ Court Philippe Chatrier is to Nadal: home, sweet home.

Comparing those two finals just after losing to Djokovic, Medvedev’s sharp analytical skills revealed much. As he said in Melbourne, “was two different matches, for sure. Just they play differently. One is a lefty, the other is a right-handed, straightaway. And Rafa gives you more time to think on the court. But then, you know, he's amazing in defense. He's amazing with his forehand. You feel like you won the point, he makes some crazy shots. But you have time to think and you have time to adapt to things. Today with Novak, I felt like I wanted to mix up things, I wanted to try to do something different, but I felt like he took all the time from me, he took all the advantage in his side straightaway.”

Medvedev erased a two set deficit in the 2019 US Open final only to end up losing, 6-4 in the fifth

Medvedev erased a two set deficit in the 2019 US Open final only to end up losing, 6-4 in the fifth

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But the bigger mental challenge for Medvedev is on the emotional front. Two days ago in Toronto, Medvedev admitted after his opening match – a three-set struggle versus another keen disrupter, Alexander Bublik -- conceded he is a work-in-progress. “Very far from perfect in my mental strengths,” he said following the Bublik match, “but I think I am also 50 times ahead of what I have been even few years ago. So that's the main goal: to improve, improve, and improve.”

More than a great many players, Medvedev pays attention to his opponents and finds way to dissect and dissemble. That interactive quality is part of what makes him so compelling to watch, Medvedev operating like a safecracker as he turns and twists the dial to find the combination that will pry open the vault. As Medvedev said this evening, “If it's an opponent you don't like to play and you know about it, you're not going to say it here to you, but you're gonna feel a bit tougher, because you're gonna be, like, Well, I don't like to play this guy, what can I do better?”

With little troubling him this evening, Medvedev faced zero demons. But come the US Open, over the course of longer matches and the added pressure of increased expectation and opponents looking to earn a big win over him, it will be fascinating to see what happens to Medvedev round by round as he attempts to navigate the tricky transition between contender and champion.