Four years ago, Roger Federer was asked to assess the new generation of players who were moving—tentatively—up the rankings ladder behind him. Federer wasted no time in singling out a then-22-year-old Milos Raonic.

What did he think set the 6'5" Canadian apart? His missile serve? His unflappable demeanor? His flawless coif?

No, Federer sounded more impressed with what Raonic was doing off the court than anything he was doing on it.

“What I like about Milos,” Federer said, “he seems very committed and he seems like he has his team set up...you feel like he’s focused on the matches and the practice. The rest is sort of taken care of.”

Those words must have been music to Raonic’s ears.

Since the age of 8, when he began rising at 5:00 A.M. to go toe-to-toe with a ball machine, Raonic has prided himself on his willingness to “leave no stone unturned” and “give every ounce of energy” to his career. As Raonic puts it, he was out there “Every. Single. Day.” Some players make it in the pros because of their precocious talent; Raonic seems to have made it because of his precocious ambition. When he reached the fourth round at a Grand Slam tournament for the first time, at the 2011 Australian Open, a 20-year-old Raonic said, “I’m not really shocked I am here.”

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Milos Raonic needs a little madness to push him over the edge

Milos Raonic needs a little madness to push him over the edge

In the years since, Raonic’s ambition has only grown, and so have the lengths he goes to satisfy it. He has worked with nine coaches, hired a trainer and a physio, gone gluten-free and back again, and has tried meditating, journal writing and art-appreciation to relax. He has studied Steve Jobs’ philosophies on global success. He’s worn a mouth guard to keep his spine aligned and an arm-length sleeve to, among other things, bring him good luck.

Despite suffering a string of injuries, Raonic makes it seem as if everything is going to plan. Since 2012, he has steadily risen in the rankings—peaking at No. 3—and last year he reached his first major final, at Wimbledon. After losing it handily to Andy Murray, he said: “I’m going to try to get fitter, stronger. I’m going to try to improve my return game, improve my serve, improve my efficiency coming forward. There’s not one thing I’m not going to try to improve.”

Raonic, again, was as good as his word. He came within a point of beating Murray at the ATP World Tour Finals, and he started the 2017 season by beating Rafael Nadal in Brisbane. Yet as he heads back to Wimbledon, last year’s runner-up is something of an afterthought. Raonic, at 26, is squeezed between the legendary Big Four and the swaggering Next Gen.

Now he confronts the possibility that his window of Grand Slam title-winning opportunity has shrunk.

“Suddenly,” Raonic wrote in ‘Letter to My Future Self’ for The Players’ Tribune, “the road from No. 4 to No. 1 feels longer than any road you’ve ever taken.”

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Raonic has learned to volley and improved his return. He has made his forehand a weapon and become a better defender. But is there still something missing from this carefully-constructed tennis-playing machine?

“Growing up, Milos always seemed to be on the verge of breaking through,” Mia Gordon, a friend of Raonic’s from juniors, told TSN. “He would have close three-set matches with the top players in Canada, but as a junior he just wasn’t able to get that big win under his belt.”

The upside to Raonic’s frustration was that it made him get to the courts earlier and practice later, and he has long since left his old Canadian rivals in the dust. But he has struggled again at the pro level to deliver a big win at a big event. He's currently 8–33 against Federer, Nadal, Novak Djokovic and Murray.

Injuries have slowed Raonic’s progress. In the last year alone, he has been hobbled by problems with his right adductor, left wrist, left hip, right ankle, right quad and right hamstring. By now Raonic is cautious in practice; he tends to hurt himself during matches, when he can’t hold back. There’s some concern that Raonic’s recent injuries all involve his right leg, the same side where he had hip surgery in 2011.

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Milos Raonic needs a little madness to push him over the edge

Milos Raonic needs a little madness to push him over the edge

Last year at Wimbledon, Raonic was fully healthy. A few weeks earlier, he had hired John McEnroe to mentor him during the grass-court swing.  Raonic, McEnroe believed, had ignored the emotional side of tennis for too long.

“He’s tried to make sure I show my presence,” Raonic said of McEnroe.

A vocal Raonic did that in coming back to stun Federer in the semifinals—his first win over a member of the Big Four at a major. But rather than ride that wave of emotion into the final, Raonic went back to even-keel.

“I tried to treat the Wimbledon final like any other match,” Raonic wrote in The Players’ Tribune. “I could see a big difference in my on-court intensity between the final and the semifinal.”

As Federer said, Raonic’s strength is how methodical he is. But to reach his goal of being No. 1, and to take the last step at Wimbledon, he may have to add a little madness to his method.

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Milos Raonic needs a little madness to push him over the edge

Milos Raonic needs a little madness to push him over the edge

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