WASHINGTON -- Imagine that your boss is disliked by about half the people who know him, doesn't get along particularly well with the business community, is viewed unenthusiastically by some of his own supporters, and has still tasked you with raising as much as $1 billion in a year and a half.
Meet Rufus Gifford, fundraiser in chief and informal LGBT ambassador for President Barack Obama's reelection campaign.
As finance director for Obama for America, Gifford is playing a crucial, behind-the-scenes role in securing the president a second term. The task is a daunting one: run the most expensive campaign in history at a time when the economy is bearing down on people's wallets and when public support for the president -- while higher than other elected officials in Washington -- is still in the troubling range.
And if that weren't enough, the expectations couldn't be higher. Gifford, just 37, is doing his job against the backdrop of Obama's 2008 run for office -- which featured a revolutionary fundraising approach that brought in roughly $750 million, shattering all previous records.
The Massachusetts native certainly has the capacity for the challenge. He has a knack for raising money. And a lot of it.
In 2004, he helped to raise $30 million for Sen. John Kerry (D-Mass.) in his failed bid for the presidency. Gifford was Kerry's deputy finance director for the western region at the time and ultimately became one of Kerry's most successful fundraisers. In 2007, he helped to lead Obama's southern California fundraising operation, which brought in $80 million -- among the largest amounts from any state for Obama.
"He'll be a warrior for this president," Kerry said of Gifford's fundraising prowess.
"The outcome in 2004 was a kick in the gut for Rufus but he didn't cry in his teacup, he moved on to the next battle and that was getting Barack Obama elected, and now he's still at it," the senator said. "This guy is just passion personified and that's infectious."
Kerry has an unusual perspective on the matter: His daughter Alexandra was classmates with Gifford at Brown University. After college, Gifford went to Hollywood and found work as a creative executive affiliated with 20th Century Fox, where he served as a liaison between the studio and the writers, director and actors. He worked on a number of commercially successful films, but none that foreshadowed a future in election politics. "Dr. Dolittle 2" with Eddie Murphy, "First Daughter" with Katie Holmes and "Life or Something Like It" with Angelina Jolie are among his credits. He also played a dog owner in "Garfield," the 2004 movie starring Jennifer Love Hewitt and a computer-generated, lasagna-loving cat named Garfield, based on the comic strip with the same name.
But after several years in Hollywood, Gifford became disillusioned with the movie industry and wanted to try something different. When Kerry won the Democratic nomination in 2004, Gifford decided his frustration with the Bush administration was enough to reassociate with his college classmate and head to the Kerry campaign.
"He cared about films but he cared a lot more about the direction of his country so he dropped it all, quit, and moved to my campaign with little more than a wish and a hope and he became an instant legend among the fundraisers," Kerry said. "He was a pied piper on our campaign."
Gifford cemented his status as a big-time fundraiser a few years later when he began raising money for Obama. Gifford, who is openly gay, teamed up with his then-partner Jeremy Bernard to raise tens of millions of dollars for Obama through their consulting firm, B&G Associates. Their combined fundraising success has been written about in several publications, most notably in a 2008 piece in L.A. Weekly titled, "Obama's Gay Gold Mine." Bernard has since gone on to become the first openly gay White House social secretary.
The Obama campaign declined a request to interview Gifford. But former colleagues offered testimonials on his behalf. Bill Burton, who was Obama's campaign spokesman in 2008, got to know Gifford at fundraisers during the first campaign and described him as "one of the most diligent, hardworking and, most of all, conscientious people I've ever worked with."
At the Democratic National Committee, which works with Obama's reelection campaign to raise money, some officials were eager to praise Gifford even at the expense of his predecessors. Gifford was the DNC finance director from January 2009 to April 2011.
"Make no mistake. Compared to past finance directors, Rufus is such a breath of fresh air," said one top DNC fundraiser who spoke on the condition of anonymity.
Some in the past have been "unbelievably bad" and even "textbook-case depressive," the official added. Gifford, on the other hand, is "enthusiastic" and "unflappable," qualities the official said are "exactly what you need for this job."
Whether Gifford can translate that personal enthusiasm to Obama's donors is the prevailing and critical question.
A look at Obama's fundraising numbers since April, when he officially launched his reelection bid, shows him well on his way to surpassing his 2008 campaign earnings, despite the tough economic and political conditions working against his reelection.
The campaign pulled in $42 million in the third fundraising quarter of the year, which runs from July through the end of September, according to campaign records. That total is more than twice the amount ($17.2 million) raised by Rick Perry, Obama's highest fundraising GOP challenger, during that period and is just shy of the combined total raised by all Republican presidential candidates in that same period.
That doesn't count the money raised by the DNC during those months. All combined, the two groups brought in more than $70 million, which put them well over their $55 million target.
"We had a record-setting quarter," said a campaign official who spoke on the condition of anonymity. "The narrative out there is that the base is disenchanted, but actually we don't see that in our fundraising."
The day before the third-quarter fundraising deadline, Gifford appealed directly to supporters to give even $3.
"The staff and I are working around the clock, powered by too much coffee," Gifford wrote in a Sept. 29 campaign email to supporters. "No one's complaining; that's what we signed up for. And we're not doing this just because it's our job to make sure the campaign has the resources it needs. We're doing this because it's part of what defines this movement."
The campaign is also forging new ground with donors. More than 606,000 people gave between July and September -- a number that tops what was a record-breaking 552,000 donors in the second fundraising quarter and reflects more than 257,000 first-time donors, according to campaign records. In another milestone, in mid-October, Obama hit 1 million donors.
But not all news on this front has been positive. Obama isn't bringing in the same millions of dollars from former donors in Democratic strongholds and in districts that he won narrowly four years ago, according to an Associated Press analysis of the most recent campaign finance data.
Tens of thousands of supporters who gave him hundreds of dollars or more in the early stages of the 2008 campaign haven't offered him similar amounts of cash so far in this campaign, the AP analysis found. And in some cases, former Obama donors are now giving to Republican candidates like former Massachusetts Gov. Mitt Romney.
For now, though, Gifford is driving the most powerful fundraising operation in the country. Obama campaign officials say they don't have a set goal of raising $1 billion, or any fixed amount for that matter, despite that figure circulating in the press. But the trajectory of fundraising levels for past presidents suggests that's where the campaign may be headed.
"We're doing pretty well," the campaign official said.
FOCUSING ON THE BIG PICTURE
Early gains on the fundraising front don't necessarily portend overall success, however. And like Obama, one of the things Gifford must contend with is a party and country that just aren't excited about the direction of the administration.
The president's approval rating is hovering at 43 percent, in part because of a growing dissatisfaction among his left flank. A July CNN/ORC poll found that roughly one in four Americans who disapprove of Obama say it's because he hasn't been liberal enough. The poll also put his approval rating among liberals at 71 percent, the lowest point in his presidency.
With that audience in mind, the campaign has chosen to deliver a simple pitch: focus on the big picture.
A Republican in the White House would mean progress on some of Obama's key initiatives -- health care reform, gay rights, Wall Street reform -- would be halted, if not reversed, said the DNC fundraiser. It would also mean more conservative Supreme Court appointments.
"That's one-third of the government for the rest of our lives," the fundraiser said. "For many people, it's just showing them money is needed, especially early money, and getting them to see the big picture."
And that's the message that will be driving a whirlwind of fundraising activity over the next year, all orchestrated by Gifford. Overseeing a staff of dozens, Gifford divides his time between working the phones at campaign headquarters in Chicago and being on the ground at the fundraisers he organizes -- shaking hands, overseeing the event's minute-to-minute operations. He has one deputy in the Chicago office, at least half a dozen regional finance directors and a smattering of others who report to him at various levels of operations.
If his team's fundamental task is re-patching the framework of donors that helped propel Obama to office initially -- whether by direct outreach or warning of a Republican takeover -- Gifford offers the reelection team a unique vehicle for doing so. While unintentional, his hiring as campaign finance director has proven to be a helpful entree into one of the party's most politically generous constituencies.
"It certainly doesn't hurt that Rufus is from the [gay] community," the DNC fundraiser said. "It is absolutely a plus."
Under Gifford, the campaign's Lesbian, Gay, Bisexual and Transgender Council -- a high-powered panel of about 20 fundraisers with strong ties to the gay community -- has strengthened its role since it was formed during the 2008 campaign. The council holds conference calls with the campaign every other week, sometimes with Gifford on the line and sometimes not, and it requires one thing from each member: raise at least $350,000 from the gay community.
Barry Karas, a co-chair of the council, said he was somewhat active in Obama's 2008 campaign but decided to step up his involvement this time after talking to Gifford, his personal friend. A Human Rights Campaign board member for 20 years until stepping down this year, he has already raised more than $500,000 on the council.
"When it came to 2012, I felt that it was very crucial to step in," Karas said. "I feel that we have a very strong ally, a stronger ally than we've ever had in the White House, and I want to keep that forward energy going."
The council has pulled off several fundraisers around the country, but its biggest success was a sold-out LGBT dinner in New York City in June. The event was specifically organized for the gay community and brought in roughly 600 donors at $1,250 a head -- a huge number of attendees for an event organized around a specific community of people versus a region. Highlights of the night included an address by Obama and introductory remarks by openly gay actor Neal Patrick Harris. Total money brought in: $750,000.
Karas said the format of the event was such a hit that the campaign is looking at putting together a similar fundraiser next spring in Los Angeles.
"I think it's easier in the LGBT community to have events specifically geared to the LGBT community for the feeling of being engaged by the administration and by the campaign," he said. "That's why that one was so very successful."
But when it comes to raising money from the gay community, Democratic officials say what has contributed more than Gifford's personal story is all that Obama has done in the past three years. Among the victories he has delivered: the "don't ask, don't tell" repeal, hate crimes legislation, new hospital visitation rights for gay couples, a lifted immigration ban against people with HIV, and the decision to no longer defend the Defense of Marriage Act, which defines marriage as a legal union between a man and a woman.
"These are the main reasons why the LGBT community should be more generous than usual and more generous than others," the DNC fundraiser said. "The gay community falls somewhere between grudgingly enthusiastic and wildly enthusiastic. That translates into dollars."
The campaign has also found other ways to play up its successes in ways that subtly tug at LGBT donors' hearts and wallets.
On the day "don't ask, don't tell" was repealed, the campaign released a moving video profiling gay veterans who suffered under the policy. One woman who nearly died in the Sept. 11 attack on the Pentagon describes how her lesbian partner "would have been quite literally the last to know" because she couldn't put her name in her emergency contact information. Another fast-rising naval officer says he was discharged for telling his commanding officer he was gay.
After clips of the president denouncing the policy and signing the repeal into law are shown, with an upbeat rock music soundtrack in the background, the Obama campaign logo appears on the screen under the message, "You should be with us in 2012," and features a link to the campaign website.
The campaign also created an "Obama Pride" page on Facebook. The page, which has more than 64,000 "likes," highlights activities the president is doing for the gay community. They include initiatives to combat bullying and to honor the loss of a gay rights pioneer, as well as news of the second openly gay judge getting confirmed under Obama.
Other outreach to the gay community has included maintaining "a large presence" at gay pride parades, said the campaign official, and addressing the annual Human Rights Campaign dinner in October, where Obama was wildly cheered for repealing "don't ask, don't tell."
It is for all these reasons, Karas said, that his job is pretty simple: just get people into the room with Obama. Gifford's job is more complex, daunting and, potentially, historic.
"He never does talk about the task," Karas said. "He's so positive, he keeps very upbeat. And he's got a great smile."