“He’s running out of time, but I think he can win one more.”

There are three athletes who come to mind when I think about that quote, which is uttered almost hourly on every sports talk radio and television talking head show in America. For me, the three athletes who define that quote are Roger Federer, Tom Brady, and Phil Mickelson.

Each guy is in the news. Federer had a disappointing run at the French Open and now prepares for Wimbledon, just a month after his wife gave birth to their second set of twins. Brady has been dissected in light of a well-conceived, poorly-executed column by a rabble rousing troll who admittedly is all about numbers and completely ignores wins. And Mickelson tries yet again for his first US Open championship starting tomorrow at Pinehurst. Oh, Mickelson’s also under investigation by the FBI and SEC for his alleged role in an insider trading scheme. Let’s just say he’s stressed.

Federer, Brady, and Mickelson all have one primary rival with whom they’ve co-defined their sports over the past 15 years. For various reasons, each rival has a better shot at reaching the mountain top again before these three.

The questions are clear. Will Federer win another Grand Slam event? Will Brady capture another Super Bowl? Will Mickelson win another Major, but much more importantly, will he ever win the US Open?

The levels of wondering and hoping have reached nearly mythical heights. Let’s take a closer look at each member of the triumvirate:


He’s the one closest to a lock for “Greatest of All Time” status. Another Grand Slam win would help, as would a better head to head record with his younger rivals, but Rafael Nadal backers rely too heavily on Nadal’s French Open success. In a couple years, maybe Nadal surpasses Federer, but not yet.

Even though Federer could retire tomorrow as the greatest, he presses on. Thousands of columns have been written on the odd experience of watching Federer remain an elite, top-5 player, yet one who can’t beat the top two guys. And it is an odd experience. It’s strange watching Federer not reach Grand Slam finals anymore, but at the same time, why should a top-5 player retire? Federer shouldn’t be punished for his past greatness. Instead, fans and media should do a better job of adjusting the current reality that Federer is merely a very good player who still has a puncher’s chance to win.

For Federer to win, a lot of things have to go right. He needs a forgiving draw, one pitting Novak Djokovic against Nadal in the semifinals so Federer won’t have to face both. He’s got to beat other guys he’s struggled against, like Juan Martin del Potro and Tomas Berdych. He’s got to be well rested yet in top form. He needs to play short matches. And of course, he needs some luck.

Thankfully for the Swiss Maestro, he gets four chances a year to win another. A relatively healthy 32 (soon to be 33), he should have at least 10 more cracks at it before he declines even further, at which point he could still make a Jimmy Connors-like run in his late 30s.


The only one of these three guys who plays a team sport, Brady’s case is a bit different. Yes, he’s still an elite, top-5 quarterback capable of taking crappy teams to the conference championship. Working most strongly against Brady is simply his age, as he’ll be 37 this season. He’s famous for insisting on playing into his 40s, and maybe he will. Should he follow up on that promise, he’ll not only need to delay his decline, he’ll actually need to improve in some areas, like throwing the deep ball and reacting under pressure. Tall tasks, but Brady isn’t one to be doubted.

Brady does, however, have a couple items working in his favor. He plays in a weak division and what has been a weak conference for three years now. The Patriots may not have been one of the four best teams in the NFC, but they were, by far, the second best team in the AFC. If it weren’t for the Broncos, the Patriots would be the heavy favorite to reach the Super Bowl this year. Speaking of the Broncos, both they and the Patriots have “loaded up” this season, which helps Brady. His receiving corp still leaves much to be desired, but the commitment to improving the defense should increase New England’s chances. This year should prove Brady’s best chance at winning it all since 2011, with the enhanced defense playing a big role, and the AFC playing a major role. He’d run into an NFC buzz saw in the big game should he get there, but as most Patriots fans know, this year has got to be the year.

Phil Mickelson


Phil is the most complicated of the bunch. He’s the oldest, yet his career will last longer than the other two. He was the last to get over the hump, in 2004, and he’s also the most recent, winning the 2013 British Open, the Major his game is least suited to, with a scorching Sunday that came out of nowhere. Assuming he stays out of prison for this Wall Street snafu, Phil inspires the most confidence that he’ll win another big event.

Instead of looking at his, say, 30 or so upcoming chances to win one of the four Majors, let’s instead look at his US Open chances. Given the disparities in their sports, and the effect age has on each, Federer has about the same chances left to win any of the Grand Slams as Mickelson does to win one US Open. It’s tougher to extrapolate Brady’s chances, given he plays a team sport with only one chance per year. However, Brady should have two or three legitimate chances to win, and that’s about what the other guys have left, too. Phil has finished 2nd a whopping six times at America’s championship, and may only finish in the top two a few more times, much in the same way Federer may only reach a few more Grand Slam finals.

Despite not winning it yet, Phil Mickelson is the US Open. He has been since 1999 at Pinehurst, where he collapsed on the final few holes and lost to the late Payne Stewart. That US Open, like all others since, ended on Father’s Day. That particular Father’s Day saw Mickelson becoming a father for the first time, and left many with the memory of Stewart simultaneously consoling Mickelson on a golf level and congratulating him on a personal level.

On those Sundays when he’s coming in second, the cameras fixate on his wife and kids, and we all think back to that first US Open letdown, fatherhood, and wonder if this is the year Phil comes full circle. If the nostalgia of Father’s Day isn’t enough, Mickelson’s birthday is June 16 and usually falls during the tournament. Phil finished second in both 2002 and 2013, when the competition’s final day fell on June 16, meaning it was US Open Sunday, Father’s Day, and his birthday. If you think about what must go on in his head during those days, it’s pretty hard to blame the guy for a bogey here or there.

Is this the year? Hell, I hope so. I’m a Phil fan, and it makes for a great story. Does he have a better shot of winning a US Open than Federer and Brady do of winning a title? It’s damn close, but with the aura of Pinehurst looming large, how can you not go with Phil?