Retiring Sen. Jim Webb, D-Va., said Monday charged that President Obama's handling of the sweeping healthcare overhaul unnecessarily caused a great deal of fear in the country.

The Virginia Democrat, in a wide-ranging interview on MSNBC's "Daily Rundown," told host Chuck Todd that it was his "great regret" that the Obama administration scared Americans with a large bill that lacked direction.

"My great regret on that is I believe the whole healthcare issue could have been handled differently by the administration and over here [in the Senate]," said Webb, who is retiring after just one term. "I think the way that the process was put forward without a clear set of principles from the administration caused a lot of fear in the country. We had five different committees boiling down 7,000 pages of contradictory information at a time when the country was in a recession and people were talking about this other stuff."

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"So you regret voting for it?" Todd asked.

"No. In the end, I voted with Republicans 18 times, but in the end I voted for it. But we do need to move forward. We need to find different ways to work with these issues. We could have had a smaller, more focused package and the country would have been a lot more comfortable with the process."

Webb, who has stumped for Obama in the critical swing state of Virginia, said he recently talked with the president about the direction of the Democratic Party and why it's failing to capture middle-class voters.

"I said that directly to the president about two weeks ago: How in the name of the Lord can the Democratic Party, the party of Andrew Jackson, only be getting 28 percent of the white male working class vote?" Webb said. "From my perspective, it's because of interest-group politics of the Democratic Party, that particular culture doesn't think Democrats like them."

Webb's decision to retire after six years has sparked a hotly contested battle between Democrat Tim Kaine and Republican George Allen, two former governors, to replace him. Webb, a Marine who served in Vietnam and an Emmy award winning journalist who served in President Ronald Reagan's administration, defeated then-Sen. Allen in 2006.