Should New York worry about rejection?
"It takes courage to play where the lights shine the brightest," he said. "It takes leadership and character and competence to step up and say, 'I'll go first.' And it takes great skill to succeed in the No. 1 market."
Although many frustrated Knicks fans still roll their eyes whenever Dolan speaks because of what he's put the franchise through in the past decade, Dolan's words ring truer than ever now that Cliff Lee has become the second colossal free agent to spurn New York City in a matter of months.
I'm not assaulting Lee's character or other intangibles, but it's hardly a secret that being a marquee player in New York City is just as challenging as it is rewarding.
It seems as though there is no longer an ironclad rule in sports that if athletes want to prove their mettle, they go to New York.
So what happened to that New York City mystique?
"Our Plan B is patience," Yankees GM Brian Cashman told reporters during a conference call Tuesday.
The sports fan in me would have loved to see Lee take on the psychological challenge of leading the Yankees to a World Series, particularly because it would have meant battling a reloaded Red Sox team, but the realist in me understands that the psyche of today's professional athlete is centered on minimizing the possibility of failure.
Certainly no athlete of any generation liked to fail, but athletes have so much exposure now that failure comes with a harsher stigma that smart athletes want to avoid.
A star doesn't just fail a city today. He fails the world. He doesn't just fail at Yankee Stadium and in the New York tabloids. He fails on Twitter, Facebook and YouTube. Failures have become as memorable and lasting as successes.
Part of the reason LeBron James left for Miami is there was a perception he couldn't win in Cleveland, even though his push for an NBA title was just part of the process in developing into a spectacular player and winner.
Not every athlete is equipped or wants to be a savior.
Does avoiding that pressure make someone such as Lee a less dynamic player?
Kevin Garnett spent 12 seasons in Minnesota trying to build the Timberwolves into a championship team, and ultimately, he became a Celtic because he grew sick of trying to learn from losing.
Garnett, who won an NBA title with the Celtics in his first season with the team, admitted after James chose Miami that he wished he had left Minnesota sooner.
"Loyalty is something that hurts you at times, because you can't get youth back," Garnett said. "I can honestly say that if I could go back and do my situation over, knowing what I know now with this organization, I'd have done it a little sooner."
Lee is returning to Philadelphia, a city full of sports zealots who see his arrival as World Series-or-bust, and he's joining a pitching staff with Roy Oswalt, Cole Hamels and Roy Halladay. But it's not quite what the Heat have established in Miami. It's better. What Lee is required to do in Philly is magnitudes easier than what he'd have been expected to do in New York, where he and CC Sabathia would have anchored the staff and, win or lose, had every pitch scrutinized and second-guessed on TV, on radio, in print, online and at the corner bodega.
Professional athletes see safety in numbers -- as in millions of guaranteed dollars and teammates who are talented enough to pull their own weight.
Shouldering the fate and fortune of an entire franchise and city has become an overrated experience for extraordinary talents like Lee, LeBron and even Alex Rodriguez, who ironically came to New York in 2004 for the same reason Lee and LeBron avoided New York.
I don't knock either Lee or LeBron for their choices, and they certainly aren't the only star athletes to say no to New York. After the 1992 season, Greg Maddux did the same thing, choosing the Atlanta Braves over pinstripes.
But if I were a New Yorker, I'd be more concerned about what losing such heavyweights as Lee and LeBron says about the type of free agents the city can attract.
The real issue isn't who is saying no to New York but who is saying yes.
As Dolan said, it takes a special personality to lead and thrive in that town. Lately, the only athlete who has been begging to come to New York is Carmelo Anthony. And before Anthony's back-channel pleas, the biggest free agent the Knicks had landed in some time was Stoudemire.
Stoudemire and Anthony are terrific players. Stoudemire is having a marvelous season and has so far proved to be a good investment, returning the Knicks to basketball relevance. But both are also questionable leaders.
Is New York City still a desirable destination for bona fide, complete superstars such as Sabathia? Or is it now the preferred locale for wannabe, flawed or over-the-hill superstars such as Eli Manning and LaDainian Tomlinson?
Or even worse, is it for those who have no problem accepting failure?
Jemele Hill can be reached at firstname.lastname@example.org.