When Senator Robert Byrd endorsed then candidate and Senate colleague Barack Obama for president, the historical significance was lost on no one. A former Ku Klux Klan (KKK) member, who was elected to the highest level of his local chapter of the KKK, Byrd was endorsing the man who could become the first African-American President of the United States.

On May 19, 2008 Byrd endorsed Obama calling him “a shining young statesman” in a paper statement and cited then Senator Obama’s opposition to the war in Iraq as a deciding factor in his endorsement. And while Byrd had long ago repudiated his KKK membership, the unlikely alignment of the two men still made for an interesting political match.

On Monday, shortly after the death of Byrd, President Obama released a paper statement never mentioning Byrd’s KKK past, but noting his evolved views over the years. “He had the courage to stand firm in his principles, but also the courage to change over time,” the statement read in part.

Pundits say the friendship between the two men demonstrates that politics does make strange bedfellows, but that while some saw black and white, Obama saw more.

“Obama was obviously the youngest member of the Senate and Byrd the oldest. What was intriguing about the relationship from the beginning is that Obama had tremendous respect for Byrd’s knowledge of Senate rules and thought, with no inkling of a presidential future, thought one way he could maximize his power of a junior member of the Senate was to align himself with Byrd and the rules so he could manipulate the Senate to his advantage,” says Juan Williams, News Analyst for National Public Radio and a Fox News contributor. “It was an intriguing relationship.”

And the relationship clearly meant a lot to the president. In the Monday statement, Obama mentioned his appreciation for Byrd reaching out to new senators, “He held the deepest respect of members of both parties, and he was generous with his time and advice, something I appreciated greatly as a young senator.”

It is well documented that Byrd was an active and high-level KKK member, and there are plenty of examples of Byrd’s early statements about African-American population. In a 1944 letter to then-Mississippi Senator Theodore Bilbo, Byrd wrote “I shall never fight in the armed forces with a Negro by my side... Rather I should die a thousand times, and see Old Glory trampled in the dirt never to rise again, than to see this beloved land of ours become degraded by race mongrels, a throwback to the blackest specimen from the wilds.” Byrd spent the latter part of his life talking about the “mistake” he made by participating in the KKK. In his book “Robert C. Byrd: Child of the Appalachian Coalfields” Byrd wrote "It has emerged throughout my life to haunt and embarrass me and has taught me in a very graphic way what one major mistake can do to one's life, career, and reputation.”

But some critics are not as forgiving of the “mistake” of Senator Byrd and say democrats, including President Obama use the past to their advantage.

“For decades now, Democrats have pretended that Robert Byrd’s community organizing for the KKK wasn’t relevant, even as they insist routinely that conservatives are crypto-racists. The only time the Democrats and their media friends really remembered Byrd’s Klan days was when it could be exploited: like when Byrd endorsed Obama for president. Then it was super-momentous,” said Tim Graham, Director of Media Analysis of the Media Research Center, a group that says it brings balance to the news media.

In 2006, the high level of regard Obama had for Byrd was evident when the junior senator went to West Virginia and campaigned for Byrd. “Senator Byrd has been a dear friend ever since I arrived,” Obama said referring to his arrival on Capitol Hill.

In October 2008, just weeks before Obama was elected president, Fox News Senior House producer Chad Pergram saw the two man in the hallways of Congress. Pergram reported that Obama, on the Hill for a vote during the campaign, specifically stopped to address the wheelchair bound Byrd. “Hey, how are you?” exclaimed Obama, as he took a chair next to Byrd, grabbing his hand and clasping it for almost 45 seconds,” Pergram recounted to his Fox News colleagues. Obama then signed a copy of Senator Byrd’s latest book “A Letter to the President” before heading off the Hill and back to the campaign.

However, once Obama was elected to the presidency, the two men found little to agree on politically. Byrd opposed the line item veto, the repeal of “Don’t Ask, Don’t Tell”, the appointment of “czars” to White House positions and the nomination of Treasury Secretary Tim Geithner (Byrd voted against Geithner) but the history of their friendship remained.

Williams says in the case of Obama and Byrd, the history of the KKK had no relevance, despite what others on the Hill thought.

“The black caucus viewed it [the relationship] through a racial lens, “ Williams says. “But it [history] had no relevance. It was just history given that Obama was interested in learning the rules of the game from the master of the game.”

For more on Senator Byrd, click over to "The Speakers Lobby"  and read some stories by our colleagues.