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Obama and Clinton (Getty Images)

(The Root) -- The same week that a controversial new article landed former President Clinton in the headlines for allegedly making a remark that could be interpreted as racially insensitive about President Barack Obama, the man once described as "the first black president" grabbed the front pages again, for possibly saving the Obama presidency. This week of Clinton extremes sum up President Clinton's relationship with black Americans. You could say that like a lot of relationships, it's complicated.

Should President Barack Obama be re-elected to a second term, his Democratic predecessor -- particularly his convention speech -- will receive some of the credit. In Clinton's convention speech -- which will likely end up winning the award for the longest of the week -- the former commander-in-chief, nicknamed "Bubba" for his down-home, Southern persona, sought to help President Obama with the demographic with which he needs the most help: white men.

Recent polls have President Obama trailing Gov. Mitt Romney among white men with college degrees by 13 points and by white men without college degrees by nearly 30. In other words, President Obama has a serious Bubba gap.

Former President Clinton was speaking directly to his fellow "Bubbas" and making a pitch for the real first black president when he said, "More than 500,000 manufacturing jobs have been created under President Obama -- the first time manufacturing jobs have increased since the 1990s. The auto industry restructuring worked. It saved more than a million jobs, not just at GM, Chrysler and their dealerships, but in auto parts manufacturing all over the country ... Now there are 250,000 more people working in the auto industry than the day the companies were restructured. Gov. Romney opposed the plan to save GM and Chrysler. So here's another jobs score: Obama, 250,000; Romney, zero."

It remains to be seen if his speech will be enough to bridge the Bubba gap, but few white politicians have spent more of their public life trying to bridge the gap between black Americans and white Americans in politics than Clinton has, though his track record shows he has had nearly as many stumbles as successes along the way in his efforts to do so.

Below, a look back at some of Bill Clinton's greatest hits and misses in black history:

Sept. 5, 2012: Former President Clinton delivers a rousing keynote speech formally nominating President Barack Obama as the 2012 Democratic presidential candidate.

September 2012: On the eve of his address before the Democratic National Convention, the New Yorker publishes a report in which President Clinton is quoted as telling the late Sen. Ted Kennedy, "A few years ago, this guy would have been carrying our bags" during the heated Hillary Clinton versus Barack Obama primary battle. The comment is decried as racially insensitive.

Jan. 26, 2008: Following his wife's presidential primary loss to then-Sen. Barack Obama, former President Clinton draws the ire of some black Americans by appearing to dismiss the significance of Obama's win by comparing Obama's campaign to Jesse Jackson's: "Jesse Jackson won South Carolina in '84 and '88. Jackson ran a good campaign. And Obama ran a good campaign here."

June 24, 2004: The day of the release of his highly anticipated memoir, My Life, President Clinton signs copies at Hue-Man Bookstore, a Harlem-based bookstore specializing in serving African-American audiences.

July 30, 2001: The former president opens his post-presidency offices, housing the Clinton Foundation, in America's most famous predominantly black neighborhood: Harlem.

Oct. 5, 1998: Celebrated author Toni Morrison dubs him "the first black president" in an essay for the New Yorker. The moniker would stick for years until his wife's campaign against the man running to become the first real black president tarnished Bill Clinton's reputation in the eyes of some black Americans.

April 1993: President Clinton nominates African-American Harvard law professor Lani Guinier for assistant attorney general for civil rights. After a backlash sparked by conservative critics who labeled Guinier one of "Clinton's Quota Queens" for her writing on affirmative action, the president withdrew her nomination, drawing criticism from some in the African-American and civil rights community.

1993: In his first year in office, President Clinton appoints five black Americans to Cabinet posts, the most of any president up until that time. They were Mike Espy (secretary of Agriculture), Ron Brown (Secretary of Commerce), Hazel O'Leary (Secretary of Energy), Jesse Brown (Secretary of Veteran Affairs) and Lee Brown, who served as drug czar, which today is no longer a Cabinet position.

1992-1993: His longtime friend, African-American civil rights activist and businessman Vernon Jordan, leads newly elected President Clinton's White House transition team and plays a key role as adviser throughout his presidency.

June 1992: During his campaign for the presidency, then-Arkansas Gov. Bill Clinton blasts hip-hop artist Sister Souljah for her comments about the Los Angeles riots. Clinton's comments were seen as an attempt to distance himself from Rev. Jesse Jackson in a subtle way that would resonate with white voters, since Jackson had invited Souljah and Clinton to a Rainbow Coalition event. The moment coined a still-used political phrase, "Sister Souljah moment," to describe a politician pulling a stunt to distance himself from a person or entity that has become a political liability.

1940s-1950s: Clinton lives with his grandparents, who are among the only Southern storeowners who cater to an integrated clientele. The former president would recall to O Magazine that growing up around black Americans would shape his interactions with them for a lifetime. He said: "My grandfather had a store in the predominantly black area of town. I'd play with the kids and just listen and look. My grandfather didn't have a racist bone in his body, which was highly unusual for a lower-middle-class white man. He and my grandmother were strongly for integrating Little Rock Central High School in the '50s. My grandfather taught me to look up to people others look down on. We're not so different after all.

"Once, a conservative Republican -- a congressman I had a good relationship with -- genuinely asked me, 'Why do black people like you so much?' I said, 'We like people who like us. They like me 'cause I like them and they know it.' "

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