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NEW YORK -- After Andy Roddick announced his retirement, the analysis of his career began. He was asked what he will miss the most, what he is most proud of -- and then came the wild-card question.

Roddick was asked about his favorite news conference.

Having covered a number of retirement pressers (Kim Clijsters, Andre Agassi and Pete Sampras), I know you could almost take bets on how long it would be before a player makes a reference to how annoying dealing with the media has been. Sometimes, a player like Roddick will good-naturedly throw the writers a bone about respecting the job the media does, but it's clear that news conferences rank somewhere near being on hold with tech support in terms of fun.

So Roddick's favorite news conference? A reporter prompted Roddick by saying he had one in mind. It was late last Friday night, after a second-round win at the Open, that Roddick stopped playing the game.

[+] EnlargeCameron Spencer/Getty ImagesAndy Roddick bid a fond farewell to the New York crowd after losing in the fourth round of the Open to end his career.

"What do you want me to say to make you look better in your story?" Roddick asked. "You tell me. You're searching for something. Maybe we can just cut the s--- and you can tell me what you're looking for."

Roddick, who was not angry so much as direct, had a point. He can be funny, smart, irascible or engaging, depending on the moment, but he isn't always cooperative, nor should he be. I can't count the number of times I've heard -- or said -- "The story is written, now all I need is the quote."

And then a news conference consists of trying to get an athlete to fill in that blank. A question might begin, "Don't you think ... " Or a short preamble from a reporter tries to lead a player to a conclusion already made on deadline.

Tracy Austin, a former tennis great who transitioned into television after her career, said she has experienced that as an athlete, and from the other side. She heard another player say something similar this week.

"You're just asking the same question but you're asking it differently," Austin heard. "Are you looking for a certain answer?"

Sometimes Roddick -- or Serena Williams, or Maria Sharapova, or any number of other savvy, intelligent athletes -- doesn't want to be led.

Are those athletes difficult, or are reporters just playing with them, as though they are fictional characters in a written narrative? There are times when Roddick is right that a reporter isn't listening to his answers as much as looking for confirmation of an opinion already held. Roddick joked with the reporter Friday night that he was finally cool with that now that he's retiring.

"But make up whatever and I'm good with whatever," Roddick said. "No problem. I have no consequences now."

Roddick has been reflective and engaging since announcing his retirement. It's freed him to open up a bit more. His announcement started a bit of a lovefest among Roddick and his fans, the tennis community, and even the media, in its own way.

"Andy is one of the most quotable guys in the history of tennis," Austin said.

Roddick was rarely so easy midcareer, particularly after a loss. After a win, he was revealing and charming, and often extremely funny, with a sardonic wit. But after a defeat, he could be cutting and short, unnecessarily so.

Former player Lindsay Davenport said news conferences aren't easy for every player.

"You know going in there, win or lose, what the tone is going to be," Davenport said. "It's really hard to want to deal with it. Some people let it wear them down, and other people don't. You can see Roger [Federer], even when he wasn't winning every Slam and getting to No. 1, he was still handling it with grace. He's very understanding that everyone has their role to fill and job to do, and he didn't take it personally."

The postmatch news conference may not be the best way to get to know a player, anyway.

Imagine your worst day at the office. Now imagine being asked to stand in front of a group of people who are not your friends, and dissect every mistake. They may ask for reflection, accountability and regret in a three-minute interrogation.

Said Austin, "[Athletes might wonder], is this an attacking question? 'Should you have won more? Could you improve more? Are you retiring?' That's kind of what the job is as of the press. At the same time, you're asking -- we, I guess I'm part of the press -- are asking those questions to someone who has just come off a loss or is dealing with all these things."

Davenport said stepping away from the game gives players more perspective when it comes to the back-and-forth.

"I never felt like I had a strained relationship with the media and I never felt like I had a chip on my shoulder about it," Davenport said. "Other people do, and that's the interesting transition. But I think any player, once they step away from the game, and whether it's one year, three years, four years, you start to see it in a different light, and see there's more that goes into it than just two people playing tennis."

Or, more likely, Roddick might start to look at the media now more as an opportunity than a foe. He already has a sports radio show. Tennis is a sport where the transition from player to commentator is well paved, from personalities as prickly as John McEnroe to Austin and Davenport, who works for the Tennis Channel.

"If he wants that, that world is definitely open for him," Austin said. "It'd be an easy transition."