Senate Minority Leader Mitch McConnell (Ky.) may not be atop the GOP’s most vulnerable list this cycle, but observers say he has been recently acting like he’s got a race on his hands, and Democrats already are trying to tar McConnell with the same “obstructionist” label that Republicans used to topple then-Minority Leader Tom Daschle (D-S.D.) less than three years ago.

McConnell is one of 20 Senate GOP incumbents looking to hold onto their seats in 2008, a weighty task in a volatile political environment that proved disastrous for the GOP in November. And while McConnell has a serious advantage as a seasoned political heavyweight running for a fifth term in a conservative state, he faces difficult hurdles as a party leader trying to steer the GOP Conference through a series of controversial issues.

“I have a very high energy level and I think even my critics would agree I am pretty good at doing a lot of different things,” McConnell said Wednesday. “I am going to have no trouble at all balancing having a campaign that’s prepared, representing the people of my state and leading my party in the Senate.”

McConnell’s ability to multitask is being tested by the ongoing immigration debate in the Senate. The topic has put McConnell in a tenuous spot as he tries to balance his own misgivings about the issue and a divided Conference, while taking a leadership position that requires him to work the floor on his party’s behalf.

McConnell has appeared to be missing in action in recent days as the debate comes to a heated denouement, an absence that many Republicans view as an attempt to keep himself at arm’s length from a politically incendiary issue for fear of upsetting Kentucky voters on one side and the White House on the other.

Still, McConnell is making no apologies for his handling of the immigration bill, saying his approach fits his goal — to ensure the diverse viewpoints of his 48 fellow Senate Republicans are heard and that they have opportunities to offer amendments.

“My job as Leader is to guarantee to the maximum extent possible fair treatment for my Members,” McConnell argued. “This is an unusual issue and my Conference is [divided] right on down the middle.”

“I’m not sure that bothers his re-election as much as that bothers a split Conference,” offered Sen. Larry Craig (R-Idaho). “I think that’s maybe what he’s wrestling with more than his re-election.”

But Sen. Jeff Sessions (R-Ala.) said the issue has the potential to play a serious role in the upcoming election, warning that all Republicans — not just McConnell — should take note: “I think people make a big mistake if they take this lightly.”

Immigration aside, Senate Democrats and left-leaning organizations have wasted no time trying to exploit McConnell’s possible weaknesses this cycle and have begun putting in place a multitiered campaign to paint the Minority Leader as too closely tied to President Bush and as the architect of the Senate GOP’s “obstructionist” strategy — the same tactic used to defeat Daschle in 2004.

At the same time, the Democratic Senatorial Campaign Committee is trying to recruit a challenger who could, at the very least, force McConnell to shell out millions of dollars to defend himself and distract him from his leadership duties.

“There’s no doubt that Mitch McConnell is vulnerable and we expect to have a candidate in place who will run a strong campaign and will win,” said DSCC spokesman Matthew Miller. “This isn’t just me claiming he’s vulnerable. There’s a wealth of public polling that shows the same thing.”

But McConnell and his Republican Senate allies were quick dismiss any suggestion that Democrats could re-enact “giant-killer” Sen. John Thune’s (R-S.D.) history-making defeat of Daschle. Even with the political headwinds against the GOP, McConnell believes his record will prompt Kentucky voters to give him another term.

While he said he’s “not sailing into the wind” heading into 2008, McConnell was quick to remind that in 2002 he won re-election with 65 percent of the vote and secured 113 of Kentucky’s 120 counties.

“Clearly, that was then and this is now,” McConnell said. “But I am unaware of any political observer who has listed me in the top 10 [most vulnerable Senators]. I think you are getting a bit of spin here.”

Sen. Bob Bennett (R-Utah), McConnell’s closest Senate confidant, said the differences between Daschle and McConnell are far from insignificant: “Daschle wasn’t in tune with South Dakota; Mitch McConnell is pretty in tune with Kentucky.”

“I wouldn’t underestimate him,” Bennett said.

McConnell said he plans to raise a record $15 million for his race and already is surpassing fundraising marks in the first six months of the two-year period. As of March 31, McConnell had $4.4 million in the bank, with new fundraising numbers about to be released in the coming days.

“Mitch McConnell will do everything that’s necessary to win re-election,” said National Republican Senatorial Committee Chairman John Ensign (Nev.). “He’s done a great job representing Kentucky. Obviously we’ll be there if we’re needed, but at this point, we don’t plan on him needing us.”

For its part, the DSCC won’t provide details about how much it plans to spend, nor has it yet recruited a top-tier candidate to take on McConnell. But two Democrats have been mentioned as possible contenders — Charlie Owen, a wealthy businessman, and Attorney General Greg Stumbo.

Whomever they recruit, the DSCC insists it can give the GOP leader a legitimate race by portraying him as a barrier to a series of politically popular initiatives, from an end to the Iraq War to lobbying and ethics reform. What’s more, the committee believes any Democrat who jumps in the contest will have no trouble harnessing millions of dollars as the candidate seeking to topple a leading face of the Republican Party.

Kentucky has not been easy pickings for Republicans in recent years. Sen. Jim Bunning (R) was re-elected with just 51 percent in 2004, in a more favorable environment than the current one for the national GOP, and embattled Gov. Ernie Fletcher (R) is fighting an uphill battle for re-election this year.

A recent Democratically commissioned poll in Kentucky signaled that McConnell may not be invincible, showing only 47 percent would vote to re-elect him while 44 percent would prefer someone else. Other polling has fueled left-leaning groups to go after him, including Americans United for Change, a liberal anti-war group that already has spent close to $200,000 in paid advertising to criticize him over his support of Iraq conflict. The group is planning another ad campaign in the coming weeks to highlight McConnell’s “obstructing” popular priorities from national security to ethics to the economy.

“The situation with Daschle is certainly not a parallel in any respect, but there are similarities,” said Americans United President Brad Woodhouse, who added that despite the differences between the two Senate leaders, “It doesn’t mean that the obstructionist label won’t have some resonance.”

But Senate Minority Whip Trent Lott (R-Miss.) said Democrats won’t be able to make the “obstructionist” label stick, “unless they do a lot better job than they’ve been doing, because the American people broadly support the fact that we’ve been stopping this Democrat agenda.”

Still, Senate Republicans said Wednesday that regardless of whether McConnell proves vulnerable, all GOP incumbents are watching their backs heading into 2008.

“I think [McConnell] would be foolish, as we all would, if we weren’t worried about our re-elections, because as we saw from the last year, even potential presidential candidates can lose their Senate seat if they don’t pay attention to business,” said Sen. John Cornyn (R-Texas).

“Every person should run scared,” agreed Ensign. “We shouldn’t take anything for granted. Mitch McConnell is not. He’s doing what’s necessary to win.”

And McConnell himself doesn’t appear to be assuming electoral safety, telling Kentucky supporters in a recent fundraising letter that he is “facing the most difficult re-election campaign of my career.”

“At a time when our nation needs solid conservative leadership, the national Democrat Party and their liberal allies are going out of their way to make me a ‘Republican Tom Daschle’ — a Senate leader defeated in a long, difficult and expensive campaign,” McConnell wrote.

Daschle spent $19 million in the 2004 campaign to try to fend off Thune, but lost nonetheless by a narrow 51 percent to 49 percent.

Thune said Wednesday that he doesn’t believe the political dynamics will square up in 2008 as they did when he ousted Daschle from office. “We were successful in pointing out that Daschle’s leadership positions were at odds with where South Dakotans were,” he said. “I don’t think that works with McConnell. His positions are our party’s positions.”

Still, the climate is changing, and even Republican Senators acknowledge that shock waves are still being felt from the 2006 election, when they lost a surprising six seats.

“The last election was not good for the Republican Party, and the next election looks like it’s going to be a challenge,” acknowledged Sen. Judd Gregg (R-N.H.).

Republicans said McConnell faces a tall order as he balances leading the party and looking out for his own political survival.

“I think it’s always more complicated for the leader because he’s got to be … cognizant of the desires and needs of a Conference, and on something, for example, as divisive and contentious as immigration, it’s really hard,” Cornyn said.

Ensign expressed confidence that McConnell “can handle his position here just as well has his re-election. He’s a very capable leader.”