But DuPree, the first black gubernatorial nominee from a major party in the state's history, remains optimistic. And he is not your typical underdog, refusing to go negative against his opponents, regardless of their party or platform. During the Democratic primary, DuPree refrained from criticizing his rivals, even when he was matched up in a runoff against a much better financed opponent, businessman Bill Luckett.
DuPree plans to continue this strategy in the general election, despite Bryant's major advantage in both money and name recognition. DuPree doesn't even have a negative word for the man he is seeking to replace, Gov. Haley Barbour. Lobbing criticism at Barbour could allow DuPree to indirectly go after Bryant, but that just isn't in the Hattiesburg mayor's make-up.
"I think that people have enough of that kind of campaigning in other places in America," DuPree said. "I don't do that, never have done that. I'm not going to start now."
DuPree also differs from most candidates in his top campaign issue. While most focus squarely on the economy in these down times, Dupree tells voters that his top priority is fixing Mississippi's education system, particularly in terms of early-age development. He said a strong education program will lay the foundation for the state to improve across the board.
That's not to say he doesn't have an economic platform. DuPree also emphasizes job creation, citing his positive record on jobs in Hattiesburg in the wake of Hurricane Katrina. He said he wants to create a more hospitable environment for small businesses.
When it comes to experience, Dupree is happy to contrast himself with Bryant. Before being elected mayor in 2001, Dupree served stints on the Forest County Board of Supervisors and the Hattiesburg School Board. Bryant, on the other hand, has spent the majority of his career serving in state government -- as a member of the state House, state auditor and lieutenant governor.
"My experience dwarfs his experience, DuPree said. "We deal with things in real time and reality. He sets policy, legislation, and then they go home. And then we deal with what they do. And it's not a vote and then it's over."
Realistic about the very tough road ahead, DuPree is now concentrating on raising enough money to compete with the deep-pocketed Bryant. He won the Democratic nomination despite being outspent in that race.
DuPree's advisers have told him he needs to raise about $2 million for the general election. The mayor said the Democratic Governors Association, with whom he met in Washington this week, pledged to spend about $90,000 on the race.
The goal is to amass enough cash to go up on the air with statewide television ads to raise his name identification. Before the primary, the DuPree campaign could only afford to run TV ads during the week before the election -- and with very limited circulation. This time, DuPree said he wants to have his spots running at a much higher frequency at least three weeks before Election Day.
To pull off what would be a major election night upset, DuPree will need to depend on strong turnout among blacks, who make up 37 percent of the state's population and tend to vote Democratic. DuPree also is focused on increasing his visibility in the rural areas in the Northeast and Northwest parts of the state.
Despite a national political climate consumed by partisan rancor, DuPree has confidence that voters in Mississippi will have open minds and vote for the candidate who best understands and seeks to address the state's problems. He said that while many local voters might be disillusioned with the national parties, they have more riding on the outcome of the gubernatorial race.
"Washington is some far away land," DuPree said. "Jackson is not. It's right there."
Despite the long odds, DuPree remains hopeful and confident. The product of a single family home, he regularly references his mother who raised him. He credits her with instilling in him the resiliency that he hopes will carry him into the governor's mansion
"My momma taught us how to do more with less," DuPree said.