The Columbia River Crossing—the proposed $3.5 billion project to replace the Interstate 5 connection between Portland and Vancouver—died many deaths. It was finally laid to rest in 2014, after Washington officials pulled out and Oregon officials realized they couldn't make it pencil on their own.

Now its ghost is haunting the Portland mayor's race.

The two candidates for mayor with the most experience and money—Oregon Treasurer Ted Wheeler and Multnomah County Commissioner Jules Bailey—have many similarities.

Both graduated from Lincoln High School, then collected graduate degrees from Ivy League universities. Both have worked at the county and the state (Wheeler was Multnomah County chairman, and Bailey was a state legislator). As mayor, both want to house the homeless, build denser neighborhoods and raise the minimum wage.

And on the Columbia River Crossing, both managed to avoid taking strong positions that would create permanent enemies among CRC factions, including the construction unions that supported the massive infrastructure project and the environmentalists who railed against widening the highway.

"You can't paint one as a wide-eyed supporter and the other as a staunch opponent," says Joe Cortright, a Portland economist who was among the biggest critics of the CRC. "They both hewed the middle road."

Here's a look at what they did—and why it matters now:

Ted Wheeler

What he did: As Oregon treasurer, Wheeler had responsibility for making sure Oregon could sell bonds to finance the CRC. In July 2011, two consultants Wheeler hired to examine the project's funding dropped a firebomb on the project.

Oregon would have to rely on tolls to repay debt on the bonds. But the consultants found that project backers were relying on toll revenue projections that were so overly optimistic they'd leave the project hundreds of millions of dollars short.

Then Washington pulled out of the bi-state partnership.

Then-Gov. John Kitzhaber reworked the project, making it an Oregon-only one, and tried to fast-track it in 2013, hoping to secure federal funds. In a three-page letter issued four days before Kitzhaber's Sept. 30 deadline, Wheeler said it couldn't be done. "It is premature to conclude the project can work," he wrote.

Why it mattered then: Wheeler's announcement that he still had questions that couldn't be answered in time to meet the governor's deadline meant he effectively killed the project without actually having to declare that he opposed it. "He played it very coy," says former state Rep. Katie Eyre (R-Hillsboro), who opposed the project. "He challenged the debt, but he certainly avoided coming out either for or against it."

What he told the Northwest Oregon Labor Council on Jan. 25: "I testified with the governor of the state of Oregon in support of the Oregon-Washington Columbia River Crossing project, and I even laid out the plan to get it done, but I opposed the Oregon-only solution because the financial plan that the Legislature…tasked me with evaluating didn't add up," he said. "I support the Columbia River Crossing, and as mayor of Portland I will advocate for it, but it will be a joint Oregon-Washington proposal if it passes."

Why it matters now: Wheeler doesn't want trade unions who supported the CRC to back his primary opponent, Bailey. Early endorsements suggest he shouldn't worry. The International Brotherhood of Electrical Workers Local 48 and Columbia Pacific Building Trades Council, two private-sector unions that strongly supported the CRC, endorsed Wheeler months before Bailey got into the race.

Jules Bailey

What he did: Bailey won election to the Oregon House in 2008. A year later, the freshman lawmaker from Southeast Portland penned an op-ed with state Reps. Brian Clem and Cliff Bentz questioning the CRC. "We have yet to hear why adding more traffic lanes will not make a bad situation worse," the legislators wrote in The Oregonian on Sept. 8, 2009. "We have not heard why this expenditure should be made now, in the midst of a recession, when the money could be spent in a more effective job-generating way. And most importantly, we have not heard how the commissions and the governors plan to bring the people of this state to the table to weigh in on a project that will affect every Oregonian."

In 2011, lawmakers who supported the CRC put forward a feel-good measure, House Joint Memorial 22, urging the federal government to help fund the project. Katie Eyre, who as a Republican representative from Hillsboro was among the CRC's staunchest opponents, says Bailey bucked Democratic leadership to help scuttle the joint memorial. "Jules Bailey was an instigator," she says. "I believe he acted very courageously."

But then Bailey reversed his position.

In 2013, Bailey supported House Bill 2800, which pushed the project forward but included some safeguards to protect Oregon taxpayers. "With these changes to the project, I believe this bridge can be part of that 21st-century transportation system, and it is time to move forward," Bailey told supporters.

Why it mattered then: Bailey's conversion to CRC supporter angered some environmentalists. When he later attended a forum sponsored by the Oregon League of Conservation Voters, activists crashed the event to present Bailey with a mock award—a Cars Rejuvenating Carbon award for "courageously increasing the carbon and car capacity" of the region, The Portland Mercury reported March 1, 2013.

What he told the Northwest Oregon Labor Council on Jan. 25: "My opponent…has attacked me for supporting the Columbia River Crossing and the jobs and transportation it would create, while on the other hand stating that he supported it. I'm not sure which is actually true."

Why it matters now: Bailey is walking a razor's edge. He has limited his campaign contributions to $250 per person or organization. In order to offset Wheeler's enormous fundraising advantage, he'll need independent expenditures from environmental groups such as the Oregon League of Conservation Voters, which opposed the CRC, as well as union groups that were friendly to the project. That may mean having to describe his position on the CRC in creative, ambiguous ways.