The City of Portland was two days away from opening up a process to replace the organization behind the troubled Portland Marathon in January when Mayor Ted Wheeler decided to delay the process for another year, emails show.

The emails, obtained from the city, show that Allison Madsen, the special events coordinator for the Portland Bureau of Transportation, was working with other city employees to draft a request for information. She was getting ready to solicit proposals for "a full-service organizer to produce a new city-owned event," when she received a call from the mayor's office, telling her the city would spend one more year working with beleaguered Portland Marathon organizers, Les Smith and Mamie Wheeler (no relation to Ted Wheeler).

"I have no words to express my disappointment," Madsen wrote in an email to colleagues after the call.

Madsen did not respond to a request for comment.

The Portland Marathon has been plagued by struggles. The Oregon Department of Justice opened an investigation in July into issues related to the group's corporate structure and possible conflicts of interest between Smith and Wheeler's nonprofit and for-profit companies they own or owned, jointly and separately.

The race itself was nearly shut down as it began in 2016 because of issues with its safety plan. The marathon was denied a permit up until several weeks before the race in 2017, something Portland Bureau of Transportation spokesperson Dylan Rivera said had never happened to another longstanding major Portland event.

And, the Portland Marathon has a history of paying fees months late and under protest, making it, Rivera wrote in an email to The Oregonian/OregonLive, "the only major event that has been far enough behind that the City warned them that they were past due, and their account could soon be sent to a collection agency."

Les Smith did not respond to multiple requests for comment. The Oregon Secretary of State's website shows he donated $500 to Friends of Ted Wheeler on March 15, 2016.

In January 2018, emails show the city was beginning the process to find a new partner.

"You are receiving this notification from the City of Portland because you have previously expressed interest in producing an athletic event in Portland," read a draft letter, dated Jan. 9, 2018, that preceded a longer packet of information requesting proposals, referred to in emails as an "RFI" or request for information.

"As you know, because of staffing shortages, no new athletic events have been permitted for the previous three years," the letter continued. "But now, a unique opportunity presents itself and you are invited to respond."

According to the letter, the event would "be a full marathon, held annually in early October."

An email references a meeting between city transportation officials and Larry Pelatt, the interim chief procurement officer who was advising officials to help outline a process for soliciting proposals, in early December. Members of the mayor's staff were made aware of the meeting and the outline that came out of the meeting.

Several drafts of the RFI passed between Pelatt and Madsen in early January. A timeline that was part of these drafts shows the letter and paperwork soliciting proposals were set to go out Jan. 12.

Even before the process began, at least three groups expressed interest in managing the event.

John Pontefract, the organizer of Portland Fit, a marathon training program, reached out to city officials in July of 2017, expressing interest in submitting "a compelling proposal" to return the event "to its proper place as one of the nation's best marathons and one of Portland's premier community events."

"I was interested in getting some more information about the process," Pontefract said Monday.

Pontefract, a runner himself, was deeply invested in the marathon. After watching the race struggle, he said, "I felt strongly that they should change ownership."

But Pontefract said that at the time it sounded like the city wasn't going to make any changes in the short term.

"I think they said we're still evaluating what we need to do," he said. He reached out again to the city after the marathon in October but never heard back.

Another group, called Capstone Events, which owns, partners with and operates marathons across the country, sent an email in August 2017, asking to meet with Mayor Wheeler to talk about "the opportunity to partner with you and the City of Portland to return the Portland Marathon to its proper place."

Capstone Events head John Kane did not respond to a request for comment.

Stephen Brown, a Portland wealth adviser, became interested in taking over the marathon last July. At that point, he created a corporation called Rose City Marathon, which is currently inactive, with two partners, Aaron Simpson and David Halliburton.

Brown said he reached out to the city about submitting a proposal to take over operations of the marathon in September 2017. He told The Oregonian/OregonLive that he spoke on the phone with both Madsen and Berk Nelson, a senior adviser to Mayor Wheeler, and met with Madsen twice in person.

He said city officials from police, transportation, the City Attorney's Office, and the mayor's office all encouraged him to keep working on his Rose City Marathon plan.

He said his group was ready to submit a proposal -- and they still are. "We have a turn-key event ready to go," Brown said. "We could still do this."

So far, he hasn't gotten a chance to submit a proposal.

On Jan. 10, Madsen got a surprising call from Nelson.

"The most recent final decision, in opposition to everything PPB and I have been told over the last several weeks, is to allow the Portland Marathon to produce the event in October this year," she wrote in an email to other city employees. "Supposedly, Les Smith will be told this is the last year and we will move forward with a competitive RFI process for 2019.

"As you can guess, I am feeling pretty deflated at the moment," she continued. "Both Police and I were told that the final decision was made last Friday, and the Mayor's PIO was working on the media release to announce the RFI process. We were on hold until Monday (1/8) for Mr. Smith to be notified in advance of the media release."

Michael Cox, spokesperson for Mayor Wheeler, said the mayor did not change his mind about opening up the process but decided to postpone it for another year.

"I know folks had what they were referring to as 'turn-key' solutions for this year," Cox wrote in an email conversation, but, he added, "the Mayor is focused on a world-class event with long-term (annual) stability, and felt the extra time is necessary."

Both Cox and Rivera emphasized that doing work in one direction and then changing or postponing plans is not unusual.

When the RFI process opens for 2019, they both said, the mayor will revisit the work done by transportation officials.

Cox also acknowledges that there is a risk in continuing to work with the Portland Marathon, risks Madsen warned about in a list she created with Portland Police Sgt. Bret Barnum, who is part of the event planning team, subject-lined "top issues with marathon."

Her list was sent to Nelson and Jennifer Arguinzoni, the mayor's director of strategic partnerships on Jan. 2, and contained six items, expressing years of frustration with the Portland Marathon organizers. It included, "Failure to communicate/coordinate effectively," "Failure to pay billings in timely manner," "DOJ investigation," and "31.8% NO SHOW rate in 2017."

"These are people who paid their registration fees ($125+ each)," wrote Madsen, "but chose not to participate in the event, or due to failures, were not confident the event would be held."

According to Rivera, "event organizers agree that a healthy event would be less than 10 percent" non-participation rate for marathons and half-marathons.

Even before the no-shows, racer numbers were already down last year. The 2017 race had 6,400 registered runners, instead of the 8,000 participants in 2016.

Cox said the mayor understood these risks.

"One side is the risk of going with the current operator in 2018," he said. "Versus the risk of trying to throw together a world-class event."

He also understands the frustration of city employees who must continue to work with an organization that has a history of failure to pay on time, a reluctance to work cooperatively, or in a timely fashion.

"It's clear that the city staff has had years of difficulties" working with the marathon, Cox said.

But ultimately, he said, for a mayor busy with more pressing "front burner" issues like housing and homelessness, "it was a judgment about risk and resources."

The question the mayor's office has to ask, said Cox, is "where are our resources best deployed for maximum effect?"

For this year, that means sticking with the status quo.

-- Lizzy Acker

503-221-8052

lacker@oregonian.com, @lizzzyacker