The perennial gadfly has raised an impressive amount of money this year, considering he is challenging an incumbent congressman, but most of the nearly $250,000 his campaign has raised is already spent. The campaign’s overhead has been high: With more than 10 employees, payroll has been its biggest expenditure. The campaign has also spent more on printing its glossy, full-color brochures than it probably should have, considering it has not yet sent out districtwide direct mail.

Boswell used his financial advantage early, defining Fallon negatively in mailings before Fallon had a chance to define himself. Polling of the race has been sparse, but it appears that Boswell has enough of a margin for victory that even a low turnout election, in which Fallon’s enthusiastic supporters turn out in much higher numbers than Boswell’s, is not much of a threat to his claim to the Democratic nomination.

But the Des Moines Register, the largest newspaper in the district and the state, endorsed Fallon Tuesday, giving him what might be his last chance for a foothold in advance of next week’s election. Readers and contributors at the blog OpenLeft are considering a final fundraiser for Fallon, which could bring in as much as $25,000. Fallon’s offline fundraising might also be expected to pick up amid the good news.

But money is only useful to a campaign if it comes in early enough to be spent. Fallon’s attempts to earn free media attention have largely failed, because he has said little on the campaign trail that surprised anyone. His attacks on Boswell surround issues that were so thoroughly litigated by presidential candidates during the caucuses that they are hardly news anymore, and Iowa’s entire Democratic establishment has worked hard to drown out his message. To make matters worse for Fallon, Boswell has actually shifted to the left over the past year, diffusing some potential attacks.

Boswell is already on the air, and he has enough money to increase his ad buy over the next seven days. Fallon does not yet appear to have made a media buy, although his campaign did not immediately respond to a request for information about their media strategy.  A report filed with the Federal Election Commission indicates that Fallon paid about $5,000 to produce three TV ads, but with only roughly $30,000 on hand as of May 14, it is not clear that his campaign will be able to run them much.

A last-minute fundraising blitz spurred by the Register’s endorsement may be Fallon’s best shot at overcoming what appears to be an insurmountable Boswell lead. Fallon’s focus on field organizing has forced him to make a costly investment, and it will only pay dividends if his energetic staff can identify supporters to bring to the polls.

Battles aren’t just fought on the ground. A week away from election day, trailing two to one in the polls, Fallon’s ground game needs air support. His long-shot candidacy depends on how much money he raises in the next 24 to 48 hours and how much media he can buy with it.

“Even though I have a lot of respect for [Boswell] — I think he’s a man of dignity, he served well, this country and our state — we disagree on many issues,” Fallon said to a room filled to the brim by reporters, staff, and volunteers.  He cited the Iraq war, the USA PATRIOT Act, vehicle mileage standards, and bankruptcy protection issues as significant areas of disagreement.

In his announcement speech, Fallon framed his candidacy in terms of a desire among Democrats — and the electorate at large — for change.  “This fall is going to be a great year for Democrats — particularly for Democrats who represent change,” he said, emphasizing his belief that he could win in a general election.

He also noted that Boswell’s 2006 general election margin of victory was half the size of Gov. Chet Culver’s.  “That says something to me,” he said.  “It says maybe [Boswell's] style is not resonating.”But Fallon may face difficult odds in the 2008 primary.  Boswell’s most recent filing with the Federal Election Commission indicates that he has a war chest of over $600,000 ready to spend on his campaign.  The filing shows that Boswell has received donations from several members of the Democratic Congressional leadership, including Speaker Nancy Pelosi, Majority Leader Steny Hoyer, Democratic Caucus Chair (and former chair of the Democratic Congressional Campaign Committee) Rahm Emanuel, and Majority Whip James Clyburn.  Boswell has also earned the endorsement of Sen. Tom Harkin, whom Fallon had previously described as a personal hero.

“I don’t expect a lot of sitting Democratic officials to support [me],” Fallon said.  “About 73% of that money that [Boswell] raised is from political action committees.  That should be a huge red flag for everyone.”

Fallon has ambitious fundraising plans to compete with his well-funded opponent.  “I will raise money.  I will raise a lot of money,” he said.  “Our budget is $700,000, and I think we can do it.”  That goal is particularly ambitious in light of his continuing pledge not to accept money from political action committees (PACs) and lobbyists, which he called “a matter of principle.”

Citing the results of the Iowa Caucuses, in which two candidates who had similar fundraising standards placed first and second, he noted, “It’s being shown right now that you don’t have to take money from PACs to win.”

Unlike Fallon’s long-shot 2006 campaign for the Democratic nomination for Iowa governor, which was not taken very seriously by political commentators for the first several months, his 2008 congressional campaign has already earned significant attention in the media and among activists.

Prominent liberal bloggers from outside Iowa have targeted Boswell for his relatively conservative voting record.  Fallon seems happy to capitalize on their efforts.  “My campaign is one of several around the country that is going to try to change the character of the new Democratic congress,” he said.

Boswell was targeted particularly because of his votes in favor of continuing to fund the Iraq war throughout 2007, but in December, he changed positions and voted against the most recent funding bill.  Asked by Iowa Independent whether Boswell’s switch would negatively impact Fallon’s ability to build a coalition of Democrats against him, Fallon indicated that he thought it might actually help his chances.  “If we’re having the effect of getting [Boswell] to do what we hoped he would do all along, that’s great,” Fallon said, touting the influence he may already have had on the direction of Congress.

“But I don’t know if it’s a very sincere conversion.  I can’t judge that.  I don’t know what’s really going through his mind,” he continued.  “But yeah, it does look interesting that [Boswell's switch] happened about the same time that the rumor was spreading about my campaign.”

Sources confirm that Boswell was aware of a possible Fallon candidacy since November, if not earlier.

According to Network Solutions’ Internet Domain Registry, on November 21, the domain names FallonForCongress.com, FallonForCongress.net, and FallonForCongress.org were registered to an organization called “Fallon for Congress.”  Although the domain names do not currently point to a campaign Web site, the physical address listed for each of them in the Internet domain registry matches Fallon’s home address in the Sherman Hill neighborhood of Des Moines.  Lynn Heuss, a former legislative aide and campaign worker for Fallon who is registered to vote at the same address, is listed as “Administrative” and “Technical” contact for the domains.  (It is possible to register domain names using fraudulent information, but given the accuracy of the contact information provided in the domain records, this scenario seems unlikely.)Fallon, who won more votes in the 3rd Congressional District than either of his opponents in the 2006 gubernatorial primary, was widely considered the most liberal candidate in that race.  He refused large contributions from all donors, and he refused any contributions from political action committees (PACs).  He was a vocal supporter of land-use policies that emphasized local control and environmental protection.  He was skeptical of the work of Iowa’s Department of Economic Development and the Iowa Values Fund, which he said served as tax giveaways for corporations with few long-term benefits to local communities, and he supported Main Street Iowa and locally-based programs as an alternative.

But Fallon received criticism from primary voters who considered him a disloyal Democrat because of his public endorsement of Green Party presidential candidate Ralph Nader in 2000.  Other critics believed — incorrectly, it turned out — that Fallon’s idealist campaign had no serious chance of winning.

After his defeat, Fallon continued to build relationships with local Democratic activists by attending fundraisers and events for local candidates and party organizations around the state.  Early on in the presidential race, he endorsed former Sen. John Edwards.

Although challenging an incumbent congressman from a candidate’s own party is uncommon and usually difficult, Fallon’s candidacy may attract support from progressives across the country.  Boswell has been designated a target by activists on several high-profile progressive blogs, including the site OpenLeft, which labeled him a “Bush Dog Democrat” in August.  The bloggers’ argument is that Boswell’s voting record — particularly his votes in favor of funding the Iraq War — make him more conservative than voters in his district.  Just as online activists helped to defeat Sen. Joe Lieberman in Connecticut’s 2006 Democratic primary, they may hope to defeat Boswell.

OpenLeft’s Chris Bowers wrote:

If [Boswell] does not correct the way he votes and continues to side with Bush over his constituents on these key matters, given Boswell’s lean Democratic district and history as a fairly weak campaigner, it is pretty easy to see him as one of the top five targets for a progressive primary challenge against a sitting Democrat in 2008. Can you imagine any lower hanging fruit? A fairly simple television ad pointing out that he voted to authorize the use of military force in Iraq in 2002, to renew the Patriot Act in 2005, to eliminate habeas corpus in 2006, to fund the war without any troop withdrawal mandate in May, and to grant the Bush administration warrant-less wiretapping powers a few weeks ago would probably cause his approval rating to crash in just a matter of weeks. Not a single one of those positions is popular in his district–especially among Democrats–and this long-term pattern paints a clear picture of Boswell as a neo-conservative. A primary challenger to Boswell would have a legitimate change of success.

Or, preferably, Boswell could just stop voting with Bush, and instead starting voting with his district. That way, no primary challenge will be necessary.

Perhaps as a reaction to the criticism he received or the threat of a primary challenge from the left, Boswell voted against the latest war funding bill in Congress on December 19.  How his latest vote will influence the online progressive community’s actions remains unknown.

Boswell, a well-entrenched incumbent, may have his own help.  The Democratic Congressional Campaign Committee may offer him money and resources out of fear that Fallon would be a weaker general election candidate.  In fact, although a primary contest between Boswell and Fallon may be close, several operatives familiar with politics in the 3rd Congressional District privately expressed reservations about Fallon’s general election chances.  In 2004, President George W. Bush narrowly won Boswell’s district.  In 2006, Boswell’s seat was targeted by the National Republican Congressional Committee and pro-GOP independent expenditure organizations as one of the Republicans’ few pickup opportunities, and the race was often mentioned as one of the most competitive in the country by national media reports.

Late Friday, neither Fallon nor Boswell could be reached for comment.