Even Democrats acknowledge that flipping retiring Rep. Kenny Hulshof’s (R-Mo.) seat is a long shot. But after achieving the once-unthinkable last month in ex-Speaker Dennis Hastert’s (R-Ill.) district, Democrats boast that these are no ordinary political times.

“It’s been a long time since a focused Democrat has gone in with a focused message and tried to win this district,” a Missouri Democratic operative said. “It’s like the old Missouri Lottery slogan: ‘You Can’t Win if You Don’t Play.’ Well, we’re going to be playing.”

After Show Me State Gov. Matt Blunt (R) unexpectedly called it quits early this year, Hulshof, long-rumored to have grown tired of Congress, announced his run for governor, creating an open-seat opportunity in his district for the first time in more than a generation — and perhaps pushing the bounds for what’s politically possible for Democrats this cycle.

Held by Democrats for 30-plus years until Hulshof knocked off conservative Rep. Harold Volkmer (D) in 1996, the district has been politically dormant for the past decade. The intrigue typically tapers off by the filing deadline when no primary candidates step forward and the popular Hulshof could be rest assured of another two-year term.

Hulshof defeated Volkmer 49 percent to 47 percent in 1996. Since then, only once has he received less than 60 percent of the general election vote — in 2000, when he won with 59 percent. Democrats know that the calculus for victory is complicated, but in such a favorable political climate — and with what they claim is an unexpectedly weak collection of GOP candidates — interest by the party and outside activists like EMILY’s List is growing.

“There are parts of this district that during middle-class turmoil and an economic squeeze, there’s a way to piece this together,” a Missouri Democratic operative said. “It’s not a model district for a Democrat to win, but there is a way to weave your way through.”

The Democratic Congressional Campaign Committee echoed that prediction, suggesting that potential frontrunner Jason Van Eaton’s (R) decision not to run hints that some Republicans are uncertain of their chances this cycle. Van Eaton, a former top aide to Sen. Kit Bond (R-Mo.), likely would have walked away with the nomination, but let the filing deadline lapse last month after telling local media in February that he wasn’t interested.

Still, five Republicans and four Democrats did make the March 25 filing deadline. And party officials and operatives agree that there are two standouts on either side: State Rep. Judy Baker and former state Speaker Steve Gaw for the Democrats, and state Rep. Bob Onder and former state tourism director Blaine Luetkemeyer for the Republicans. Missouri’s primary is Aug. 5.

Baker, who is expected to report within days that she’s raised $200,000 this year, is under consideration for an endorsement by Democratic fundraising powerhouse EMILY’s List, the group confirmed Monday. But with few metrics available for the once-out-of-reach district, which takes up most of northeastern Missouri, the group is holding off on an endorsement for now.

“We think she’s a really good candidate. We haven’t endorsed yet because we’re trying to get a handle on what this primary looks like and what the general election looks like,” said Jonathan Parker, political director for EMILY’s List. “This is a potentially winnable seat, we’re just still analyzing it.”

Democratic operatives in the state say Baker’s early fundraising advantage, coupled with her support in the Democratic-heavy Columbia area, give her the early edge. But her ability to make sizable gains in those areas, Democrats claim, largely hinges on how former state Sen. Ken Jacob (D) matures as a candidate. If Jacob’s campaign flops, a Democratic insider said, Baker could walk away with the primary with 30 percent to 40 percent of the vote.

“The wildcard for her is what Ken does,” a Democratic operative said. “Ken has limitations [as a candidate], but he could seriously dilute what could be an advantage for Judy in Boone County.”

Despite Baker’s potential fundraising appeal, some Democrats argue that Gaw’s perceived support in rural northeastern portions of the district suggest that “he has the strongest profile to win in the general election,” one operative said.

“It’s going to take a special kind of Democrat [to win],” the consultant said. “He is best positioned to do that.”

Democrats point to Sen. Claire McCaskill’s (D-Mo.) performance in the district last cycle to illustrate the significant obstacles they would need to overcome in November. Despite campaigning heavily in rural areas, McCaskill lost the 9th district by more than 5 percent of the vote in 2006.

By contrast, in Rep. Sam Graves’ (R-Mo.) neighboring district, McCaskill marginally defeated then-Sen. Jim Talent (R-Mo.) in a heavily suburban district with sizable numbers of swing voters.

“There is no place to run up the score,” a Democratic operative in the state said. “The improvement that a Democrat has to make in [Hulshof’s district] is spread across a larger piece of geography than [in Graves’ district].”

Marion County Commissioner Lyndon Bode (D) also filed for the primary, but he is not expected to alter the race.

Republicans are counting on Hulshof’s popularity, and his likely appearance on the November ballot as the GOP nominee for governor, to perhaps offset any recruiting disappointments.

“The district is a GOP stronghold, and with Kenny Hulshof as the potential nominee in the governor’s race, the winner of the Republican primary could be very well situated for the fall,” National Republican Congressional Committee spokesman Ken Spain said.

Onder and Luetkemeyer are both expected to give their campaigns at least $250,000 apiece before the primary — for a GOP contest with an expected $750,000 per candidate price tag, a Republican operative in the state said.

The operative said that intrigue could build in the Republican contest if former professional football player Brock Olivo (R) decides to self-finance his campaign. Olivo stumbled badly after announcing his candidacy a month ago — garnering Keith Olbermann’s “Worst Person in the World” notoriety — and offended some Republicans by suggesting that he was only a Republican “for now.”

Still, Olivo has the highest name recognition of the bunch, the operative said, particularly in the Republican stronghold of Franklin County, where neither Onder nor Luetkemeyer have particularly strong support. Franklin County is home to the regional metropolis of Washington, where Olivo’s alma mater, St. Francis Borgia High School, is — and where he is still a household name.

“That’s why early on he’s a factor,” the operative said.

State Rep. Danie Moore (R) and former state Rep. Dan Bishir (R), who both filed for the primary, are not expected to garner significant support.