03/02/2009 05:12 am ET | Updated May 25, 2011

What If: Would Obama be Living in the White House Today if . . .

When someone reaches the pinnacle of power or fame, it's always interesting to consider the "what-ifs"--the smallish--relative to later events, at least--circumstances that might have derailed that person's track to the top.

Having just finished a profile of Michelle Obama (the cover story in February's Chicago magazine), I interviewed and researched in depth the Obamas' life before the 2008 campaign, and particularly Michelle's skepticism about, and disdain for, her husband's choice to remain in the Illinois State Senate, to which he was elected in 1996.

"Barack, this business is not noble," she once told him. Although she believed in community service and had disliked the private practice of law when she did it at Chicago's Sidley & Austin, she was still irritated that her husband, who had been president of the Harvard Law Review, had stuck his family with a $60,000 salary-- and forced her to remain in the workforce after her second daughter was born--when he could have been making $800,000 or more as a partner in a law firm.

Here are some "what ifs" that could have had us waking today to a President John McCain or, more likely, a President Hillary Clinton and a First Gentleman Bill Clinton.

Mid-1980s: What if Harvard Law School had rejected him?

It was his earliest election victory--becoming the first African American President (i.e. editor-in-chief) of the Harvard Law Review-- that brought Barack Obama brief national fame and a contract to write his memoir; that memoir, Dreams from My Father, sold poorly when it was first published but later became a blockbuster best seller, making the Obamas rich and Michelle a willing participant in her husband's quest for the presidency.

The background: Then a Chicago community organizer, in his mid-20s with a college degree from Columbia, by way of Occidental College, Barack decided that law school was his route to elective office. Jody Kretzmann, an old friend and colleague of Michelle's and Co-Director of a research project at Northwestern University's Institute for Policy Research, told me that his colleague, Northwestern professor John McKnight, wrote Barack a letter of recommendation to Harvard. "At that point he was feeling sort of frustrated with organizing," said Kretzmann. "[He] wasn't making change on a big enough scale." According to Kretzmann, Obama told McKnight that Harvard was the only law school to which he was applying. "It's either Harvard or nothing."

2000: What if Obama had won his race against Bobby Rush for a seat in the U.S. House of Representatives?

What if Obama won when he decided to trade up from the Illinois Senate to the U.S. Congress? He might not be "the one" today, but one of 435. Rush had been weakened by an inept attempt to replace Richard M. Daley as mayor. (We last saw Congressman Rush as the man who called resistance to the appointment of Roland Burris to the U.S. Senate a "lynching.") Obama was obviously the better candidate, should have won that race against the former Black Panther, but hey, this is politics--may the worst man win!

2001: What if Barack Obama had taken the job running the Joyce Foundation?

A former aide who worked closely with Obama back then, told me that Obama was "kind of morose" after the loss to Bobby Rush in 2000. "I don't really know...[politics is] what I want to do and it's not going well," Obama confided to this man. Still in the State Senate--Obama had not given up his seat to challenge Rush--Obama interviewed for the job heading the liberal Chicago think tank, which describes its goals as "to reduce poverty and violence in the region, and to ensure its residents good schools, decent jobs, a strong democracy, and a diverse and thriving culture."

"He basically had the Joyce job," this aide told me. The two men started to chart out "a plan. If he took the Joyce thing ... he would do Joyce, make your contacts, get yourself financially secure. Five years, you go back in and then try to run for something. `It's very doable, Barack. ... It's a good move ... build these national contacts, all fund raising.'"

After the interview was over, Barack called the aide. "You know what? I went into the interview and I was shaking with fear that I would actually get the job." Barack told the aide that he feared that if he had taken that job "he might have been out of the game." He remained in the State Senate, continued teaching at the University of Chicago but turned down a chance to become a full-time, tenured professor there.

2004: What if Obama's opponent in the Democratic primary for the U.S. Senate and his opponent in the general election had not imploded in divorce and sex scandals?

Barack did not look like a winner in that 2004 primary until an opponent's divorce records were opened. During the general election, Obama's attractive opponent was hobbled by ugly allegations involving his former wife and sex clubs and public sex. He was forced to drop out. He might have given Obama a real contest. Instead Obama won the primary and was a general election shoo-in against the right-wing extremist and talk show regular, Alan Keyes. (Mike Ditka, whom the Republicans asked to run--he flirted with the idea but ultimately turned it down-- might have given Obama cause to at least to break a light sweat.)

2004: What if John Kerry, the Democratic nominee for president, had not asked Barack Obama--by then obviously on his way to the U.S. Senate from Illinois--to give the keynote speech at the Democratic National Convention?

The speech was such a hit. It turned Barack Obama into a celebrity and his book into a bestseller. He was mobbed at every book signing and he was by then not the only one who saw himself as a serious candidate for the presidency.

There are others: what if Bill Clinton had not made so many bloopers in campaigning for his wife in the primaries and caucuses; for example managing, with insensitive comments, to turn majority support among African Americans for Hillary to 90 percent support for Obama?

Or, what if Hillary strategists had recognized the importance of the caucuses?

Or, what if the economic meltdown had waited until mid-November instead of mid-September to hit? And what if that September day as the markets plunged Sen. John McCain had thrown away his prepared text and not declared that the fundamentals of the American economy strong?