As a player, Michael Jordan's career could be summed up in one question: How did he do that?
Unfortunately, as an exec, the question has become, "Why did he do that?"
Why did he draft that guy? Why did he sign that player? Why did he make that trade?
His inability to come anywhere near the level of success in the front office as he did on the court is probably the second-most glaring blemish on his legacy.
The worst is something he did, or rather didn't do, 20-some years ago, and it still follows him today.
Back in 1990, Harvey Gantt, a black Democrat and former mayor of Charlotte, was attempting to unseat the much despised race-baiter Sen. Jesse Helms, who opposed making Dr. Martin Luther King Jr.'s birthday a national holiday and allegedly whistled "Dixie," a song lamenting on the good old days of slavery, to purposefully antagonize a black member of Congress in the elevator with him.
In 1992 the Department of Justice said the North Carolina Republican Party and the Jesse Helms for Senate campaign sent tens of thousands of postcards to black voters, with false voter information and threats of jail during his contest with Gantt. Helms, of course, denied being involved.
Anyway, Jordan, who had played at UNC and at the time of the election was the most famous black man on the planet save for Michael Jackson, was approached by the Gantt campaign for support. Jordan declined, reportedly telling a friend later, "Republicans buy sneakers too."
Now perhaps if he hadn't been the closest thing to Muhammad Ali the black community had, or if Helms hadn't been such a blatant racist, or even if Jordan could have tweeted one of those "if I offended you" mea culpas that are popular with athletes today, Jordan might have been forgiven years ago.
But he was that close to Ali in terms of influence; Helms was that bad; and there was no Twitter.
Then there is "Republicans buy sneakers too," which started popping up on Twitter this week almost as soon as it was learned that Jordan was participating in this month's Obama Classic fundraiser and co-headlining a $20,000 a plate dinner following it.
Why did he do that -- attach his name to politics -- after so many years of being apolitical?
The black community never turned its proverbial back on No. 23 for his lack of political involvement, that's for sure. But despite all that Jordan has accomplished -- and given back -- he is still not revered quite in the same way that Jim Brown, Bill Russell and, of course, Ali are. He had his shot to be more than just a great athlete, and well he choked.
Yes, it is unfair to expect an athlete to be anything more than an athlete.
Yes, it is unfair to place the weight of an entire community on one person's shoulders.
And it is unfair to compare the civil rights struggles of the 1960s with the way society was in 1990 and how it is today.
Nonetheless, for many, "Republicans buy sneakers too" defines Jordan outside of basketball almost as much as hitting clutch shots and hoisting trophies define who he was within it.
Jordan actually donated to the Obama campaign when he ran for U.S. Senate in 2004. In fact, in an email blast that went out this week, President Obama said that when he received the check "I wasn't sure whether I should cash it or frame it."
But as black celebrities such as Oprah Winfrey and Jay-Z, as well as athletes such as LeBron James, Vince Carter, Grant Hill and others became more vocal in their support for Obama during his historic run in 2008, Jordan was predictably, painfully absent.
So why do it now?
Republicans are still buying shoes.
Did his politics change?
Forbes estimated that in 2010 Jordan made more than $60 million in endorsements, nearly 10 years after his third and final retirement. The Jordan Brand is a $1 billion industry now. Maybe he's finally in a place where he doesn't feel he needs the money of people who agreed with Helms' views.
Or maybe his friend, commissioner David Stern, who is co-hosting the dinner with him, asked him for a favor.
Or maybe he's trying to scrub off the blemishes. Winning a championship as an owner would erase what we think of his skills as an exec, but only rolling up his sleeves and and getting involved in something political can address what happened in 1990.
Black people don't have to be Democrats; I'm not.
It would be extremely shortsighted to vote for a candidate strictly for the color of his skin; I don't.
But the request from Helms' opponent wasn't about partisanship, or blindly supporting a black candidate; it was about dignity.
For decades Helms antagonized the black community for sport on the Senate floor. And in that moment when people expected Jordan, the Ali of his time, to use his considerable influence to fight, he kept quiet to sell more shoes. That's just a hard pill to swallow, even 20 years later.
Maybe that's why he decided to get more publicly involved. Perhaps after all these years, the man Jordan has become looked back on the man Jordan was back then, shook his head and wondered "why did he do that?"