Its financial troubles run so deep, 80 police officers were laid off earlier this year and 120 more could lose their jobs in a matter of months.
In spite of, or perhaps because of, Oakland's long list of problems the race to run the city is a crowded one this election year. Ten people want to be mayor.
Four have emerged as the clear front runners, leading the pack in fundraising, endorsements and support in the polls.
"This is not an easy job, but it is a doable job," Rebecca Kaplan said.
Kaplan is the City Council's most junior member. She believes Oakland's potential can be seen in the revitalization of the Uptown neighborhood, now home to thriving restaurants and a theater. She says that could happen all over the city and create jobs if business permits were easier and faster to come by.
Kaplan also wants to sell off city-owned properties that are not being used and she is leading the charge to expand the medical marijuana industry as a way to bring Oakland out of the red and into the green.
As for one of the most controversial topics in Oakland this year -- laying off cops -- she voted against it.
"I voted no on the layoffs and they absolutely could have been avoided," she said. "We should have instead pushed for a deal where the police would have contributed 9 percent toward their pension in exchange for agreeing to no layoffs."
Councilmember Jean Quan voted for the police layoffs. She says the only way the layoffs could have been avoided was if the police union agreed to a pension deal. And despite city negotiators repeated attempts, no deal was reached.
"I'd actually like to have more officers, but until you get the cost of officers down that's not going to happen," Quan said.
After serving two terms on the City Council and before that a school board member, Quan says City Hall has too many administrators. If she is elected mayor, she promises fewer bureaucrat jobs, either through retirements, or if necessary, forced layoffs.
The one thing Quan is not willing to cut are neighborhood programs for young people. Even if saving them comes at the expense of laying off more police.
"One cop is a quarter million dollars. One after school program could be a quarter million dollars," she said. "And if you pit them against each other and have no after school programs and nothing for kids to do, crime will only go up."
In addition to battling Oakland's crime problem, the next mayor of Oakland will take charge of a city facing a $45 million deficit
"Oakland City Hall doesn't work, this city does not work, money is paid and it goes into a black hole," former state Sen. Don Perata said.
After four years with a mayor widely accused of being absent on the job, Perata says he has the leadership skills Oakland needs.
His plan to save money and bring back laid off officers involves cutting what he calls "redundancies" in City Hall. That means immediately freezing dozens of city boards and commissions, including the ethics commission, responsible for investigating campaign and ethics law violations.
With a new Kaiser hospital under construction, Perata says Oakland's economic future lies in health care. He also wants local government to be more business friendly.
But he says residents need to do their part too. If he becomes mayor, he plans to ask voters to approve a one-half cent sales tax.
"We're going to have to go back to the voters, I think within half a year, and say, 'OK, this is what we've done, this is what we need just to stay even,'" Perata said.
Joe Tuman is considered the race's dark horse thanks to ranked choice voting this year. It is a label the college professor and TV political analyst welcomes.
"If we don't fix the pension problem all other bets are off," Tuman said. "This is the ticking time bomb; the crime problem we have will pale by comparison because city government won't be able to provide any of its core functions."
The fact that Oakland needs a fix and soon may be the one thing all the candidates agree on.