In a spectacular flameout after he retired from tennis, Roscoe Tanner deceived his friends and family and ended up penniless and in jail.

ROCK BOTTOM? That’s tough to pinpoint, he says, sighing. So many lows to choose from. Rock bottom might have come when he walked into that Stygian cell in a German prison and realized that for the length of his stay he would be defecating in front of his cellmate. “Man,” he says, “that was humiliating.” The time he was arrested in front of all those fans at a senior tennis event, that was pretty embarrassing, too. And when his father, once his most ardent supporter, turned uncommunicative, that one really stung. No, wait, I’ve got it, he says. Here’s the lowest moment of his odyssey: Immediately after he finished serving four months in a maximum security county jail in Florida on a grand theft charge, he was transferred to a New Jersey jail where he would serve five months for willfully withholding child support. For two weeks he sat on a TransCor bus–think Con Air on the interstate–that zigzagged along the Eastern Seaboard picking up other criminals who were being reassigned from one jail to another. The bus, with no air conditioning, was hotter than hell. At night the convicts either slept in their seats or, if they were lucky, bunked down at a county jail en route. They were allotted three meals a day, but there was a catch: Their hands never came out of restraints. Ever try eating McDonald’s with your wrists locked at your waist? he asks. It’s not real pleasant.

The history of grunting during matches, and an interview with the woman who pioneered it:

I tracked down the 66-year-old Victoria Palmer Heinicke in Colorado Springs, Col., where she’s a retired tech support consultant. (Though the papers referred to her as Vicki, Heinicke says she’s always preferred Victoria.) Heinicke says she can’t recall anybody ever interviewing her about how she changed the sound of tennis. “The top players grunted occasionally, but I was the only one who did it consistently,” she says.

The wayward phenom is dazzling crowds at Flushing Meadows. But have we already heaped too much on Donald Young?

There are more than 160 different types of tennis surfaces. An investigation into how they impact play on the court.

A profile of 19-year-old Ryan Harrison, the latest hope for the future of American men’s tennis, who lost yesterday in straight sets.

What happens when all of a man’s intelligence and athleticism is focused on placing a fuzzy yellow ball where his opponent is not? An obsessive inquiry (with footnotes), into the physics and metaphysics of tennis.

This is the first installment of Five on One, a new weekly feature on SportsFeat collecting the best writing on the biggest story of the weekend.

“Nothing changes faster than share prices in the tennis stock market, and now everything looks different again after Djokovic held up the Challenge Cup,” writes Mark Hodgkinson in The Daily Telegraph.

Novak Djokovic would have been No. 1 in the world regardless of his performance Sunday. That’s because he’s had the best year of any tennis player in the world, a season so remarkable that, even had Rafael Nadal held three Grand Slam titles at once, Djokovic still would have ranked ahead.

With that in mind, here are five highly intelligent and measured writings on Wimbledon’s final weekend. None is particularly long, but all offer considerate points from premier tennis writers.

It should be noted that this list was more difficult to compile than it would have been five years ago—the American media is finding a difficult time getting people across the pond for Wimbledon. But that doesn’t mean quality tennis writing is dead.

On the end of the Federer Era at Wimbledon.

A profile of the transgender tennis player and surgeon, and a look into the complicated politics of gender and sports.

“I was a quiet person. I mean, I’m not a shrinking violet, but I was a very private person. I was very well-liked, and I was very well-respected. And a lot of that was thrown away because I became a caricature, a public notorious figure. I was undressed in front of the world.”

An excerpt from Tignor’s High Strung: Bjorn Borg, John McEnroe, and the Untold Story of Tennis’s Fiercest Rivalry.

On Roger Federer’s long autumn:

Roger Federer has spent longer as a "still" athlete than any great player I can remember. You could even argue that it’s one of the signs of his greatness. Other top players hit the "still" moment, hang around for a little longer, and then whoosh, they’re gone, broken up into memorial clips and Hall of Fame inductions, classic rock bands who’ve sold their copyrights. Federer, after three straight years of diminished results — 11 to 12 singles titles a year from 2004 to 2006, then eight in 2007, and four to five every year since — is … well, still really amazing. He’s still near his best, which means he’s still playing some of the best tennis the world has ever seen. If anything, he’s improved his serve to compensate for what’s maybe been a slight decline in his movement and shot-making — although, as McEnroe pointed out during the French Open, his movement is "still great." Heading into Wimbledon, historically his best tournament, he warmed up at the French by sensationally ending Djokovic’s 41-match winning streak and playing as well as Paris has ever seen him play against Nadal.

The definitive profile of Jimmy Connors, written two months after he won just seven games against Borg in the 1978 Wimbledon final.

A selection from our Wimbledon roundup for Deadspin.