Raymond's hard bargain

It took three months, $439, and a complaint to the city ombudsman, but last week Portland City Hall finally coughed up some documents that I had asked to see in a public records request. The key word being “some,” because not everything I wanted has been delivered, there are some heavy redactions in what they did send me, and the city has claimed exemptions for some material that was neither provided nor specifically identified.

Nonetheless, the files that the public records minions have released do contain some interesting tidbits about the hiring of Raymond Lee. Lee is the new city administrator who arrived in Portland after quitting or being asked to leave Greeley, Colorado, where he had been city manager for about four years. Lee and Greeley have agreed not to say anything bad about each other (although one Greeley city council member has already publicly accused him of lying), and so it’s hard to tell what happened over there. Three other Greeley bureaucrats who worked closely with Lee left city government there about the same time he did.

The newly released materials show that somebody in Portland did ask Lee, at least indirectly through the city’s headhunting consultant, why he left Greeley. Lee sent the city a copy of his severance agreement with Greeley, along with this explanation:

Clay:

As you share my separation agreement with the City of Portland, I want to provide brief context regarding my transition from the City of Greeley.

When members of my City Council became aware that I was being recruited for another City Manager opportunity in a larger city, a few expressed concern about my continued focus on Greeley while I explored external opportunities. The City has several long-term projects and initiatives underway, and the Council was seeking assurance of sustained, long-term commitment to see those efforts through.

Following that discussion, it became clear that if I intended to pursue other professional opportunities, it would be best for both the organization and me to part ways amicably.

I had already identified the City Administrator position in Portland as an opportunity I wanted to explore, and I chose to do so transparently and with integrity. The City of Greeley and I are parting on positive and professional terms with no legal or disciplinary matters involved. I have not been placed on administrative leave and remain actively working in the office as of November 21, 2025. I will take PTO during the Thanksgiving holiday week, and my final day of employment will be December 2, 2025, as outlined in the agreement.

This transition reflects a mutual and respectful decision that allows both the organization and me to move forward in alignment with our respective goals. I continue to be committed to supporting a smooth and successful transition for the City of Greeley during this period.

Please feel free to share this message directly with the City of Portland to accompany my separation agreement.

It’s interesting to compare that explanation with what Lee told the Portland media when he showed up a few weeks later to be anointed for his Portland gig. Here’s what the Oregonian reported:

Neither Greeley’s new mayor, his predecessor nor any member of its six-member council responded to questions from The Oregonian/OregonLive about Lee’s tenure and departure.

“The city of Greeley appreciates Raymond Lee’s vision and contributions to the community during his tenure as city manager,” city spokesperson Barb Hey said in an email Wednesday. “It was not unexpected that he would be moving on to serving a larger city, and we wish him well in his new position.”

Lee told The Oregonian/OregonLive on Wednesday that the decision for him and the city to part ways was mutual, providing him the chance to make his next career move while allowing Greeley leaders to make a smooth government transition.

“We agreed to manage that transition in a peaceful manner,” he said.

It’s all exceedingly vague, isn’t it? But it was good enough for Portland. The mayor, Keith Wilson, couldn’t wait to throw money at the guy.

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Which brings me to the heart of what I asked to see: documents relating to Lee’s compensation package here in the Rose City. And the documents supplied, although they don’t include the final, signed employment agreement, do show Lee being handed a sweet deal – and Lee demanding an even sweeter one, a lot of which he got.

Here was the city’s initial offer, as summarized by Ron Zito, a City Hall HR manager who was in the middle of the give-and-take:

• Annual Salary - $320k (approximately $154/hr)

o Eligible for annual Cost of Living Adjustment

o Eligible for annual Merit increase as awarded by the Mayor

• 95/5 split on Health Benefits (PPO, HMO, and HDHP options available)

• Oregon PERS retirement plan - employee and employer contributions fully paid for by the City

• Accelerated Vacation Accruals

o Top of scale - 8.31 hours per pay period or 216.06 hours per year

• 40 hours of front-loaded vacation for immediate use as needed

• 11 Paid Holidays and 3 paid personal days

• $10k relocation reimbursement agreement

• Employment Agreement – including severance offer in the case of separation without cause

o 3 year agreement - 12 months’ pay and 6 months benefit coverage if separated in first year, 6 months pay and 6 months benefits if separated in years 2 or 3

o Contingent on Council approval, would be brought as an ordinance at the time of confirmation

I love that they haven’t even hired the guy, but already they’re promising to pay him big bucks if he gets let go for being incompetent.

Anyway, that package is mighty juicy. Five weeks and two days’ vacation, plus three personal days, comes to six weeks off. Then they throw in an additional week, available immediately, for a total of seven weeks paid not to show up through the first week of 2027. Plus a salary that tops that of the outgoing city manager, a highly experienced, long-time Portland bureaucrat. Not bad for a guy you just met a few weeks ago.

But Lee, a bold self-promoter with a 10-page résumé and letters after his name like “LSSGB,” countered for more money. A lot more money.

With the responsibilities and expectations of this role in mind, I would like to propose several adjustments that align the package with comparable executive positions.

I currently serve as the City Manager for the City of Greeley, Colorado, a full-service municipality of approximately 116,000 residents. My annual base salary is $318,474.69, supplemented by a 12 percent retirement contribution (approximately $38,216.96 annually), a $7,200 vehicle allowance, and approximately $68,000 in City-paid benefits, for a total annual compensation of roughly $424,000.

While I have not yet received Portland’s complete benefits breakdown, it is evident that the total compensation offered is below my current compensation in a much smaller and less complex city.

Given Portland’s significantly larger scale, higher cost of living, broader service footprint, and the substantial responsibility of implementing a new form of government, the offer should reflect the expectations and scope of the role.

Compensation in comparable large-metro jurisdictions demonstrates the appropriate market level for this role.

He then lists what he says are the salaries and benefits of the comparable city officials in Sacramento, Oakland, San Francisco, Vancouver (Washington), Fort Worth, Tacoma, Charlotte (North Carolina), El Paso, and Oklahoma City, summing them up as follows:

Across these jurisdictions, base salaries generally range from the low $300,000s to the high $400,000s, and total compensation frequently reaches $450,000 to $500,000 or more. Portland’s size, complexity, cost of living, and governance transition place this role within the upper tier of this market.

Then comes the pitch. Lee is asking for a starting salary of between $370,000 and $390,000, depending on the benefits attached. And for benefits, he comes up with some proposals that even for Portland City Hall would be crazy, like a deferred compensation plan and a 401(k) account. Importantly, he’s extremely keen on getting paid on his way out the door from Portland:

To support stability and continuity of leadership, the agreement should include a renewal decision point 18 months before the expiration of the contract term. At that point, the contract would automatically extend for an additional year unless the City provides notice of non-renewal. If the City elects not to renew at that time, the remaining term of the contract would be paid out. This structure provides predictability for both the City and the City Administrator and ensures steady leadership during Portland’s transition.

Wilson passed on the crazier stuff, but he did give Lee the $370,000 salary he wanted, along with an explanation of how valuable the city’s pension plan would be for him. As told by Zito:

[H]ere are the updated elements the Mayor was willing to modify under the City’s offer…

• Increased base salary of $370k

• Mayor’s interested in supporting Raymond’s ongoing professional development

o E.g. covering Black Belt certification

• Open to supporting Raymond on 2 house hunting trips, we would book for him and would need to put a cap on total costs.

• We would likely look to use the December 10th confirmation hearing as one of those trips.

Just to reiterate the value of our offer in the total comp terms Raymond uses below…

• $370k base salary

• Benefits (Health and Dental) valued at $31,500 per year investment by the City

• PERS contribution roll-ups (38.67%) made by the City is valued at $143k

• So total compensation on just these three inputs is over $540k in salary and benefits.

For ease of reference, I am including the additional benefits I shared earlier, that continue to be a part of this offer…

• Eligible for annual Cost of Living Adjustment

• Eligible for annual Merit increase as awarded by the Mayor

• 95/5 split on Health Benefits (PPO, HMO, and HDHP options available)

• Oregon PERS retirement plan - employee and employer contributions fully paid for by the City

• Accelerated Vacation Accruals

• Top of scale - 8.31 hours per pay period or 216.06 hours per year

• 40 hours of front-loaded vacation for immediate use as needed

• 11 Paid Holidays and 3 paid personal days

• $10k relocation reimbursement agreement

• Employment Agreement – including severance offer in the case of separation without cause

o Contingent on Council approval, would be brought as an ordinance at the time of confirmation

As for the PERS benefit, check it out, city taxpayers. On top of his salary, the city pays another 38.67 percent into the pension maw, or another $143,000, for Lee. Throw in health insurance coverage at, say, $1,300 a month for a family (although Zito’s figure is more than twice that, at $2,625), and my friends, old Raymond’s picking up a cool $528,600 a year in cash and prizes to go with six weeks off the first year. (The documents on the City Council agenda when he was confirmed valued the package at $535,700.)

The bit about the “Black Belt” certification in Zito’s message is a little alarming. This is not a martial arts thing, but instead part of some kind of management training run by an outfit called Lean Six Sigma. They give out two certifications, Green Belt and Black Belt. Lee, who is a relentless collector of training certificates, currently has the Green.

As alert readers of this blog know, Lee is addicted to executive coaching, bringing in one guru after another to teach him and his underlings how to manage. In four years in Greeley, the city paid for at least five of these consultants, and sometimes Lee’s continuing education took place far from his City Hall desk. 

Wilson is not just tolerating a continuation of those practices here in Portland, but affirmatively encouraging it. In an email message to Zito around the time the offer was made to Lee, Wilson said, “I would love for Raymond to consider moving from a Green Belt to a Black Belt. The city will cover the expense. It is a nominal cost with large upside system improvement benefits.” We’ll see about the nominal costs and upside benefits in due course, I suppose.

Between getting his “Black Belt,” attending conferences of bureaucrats, and hosting periodic off-site retreats for bureaucrats and elected politicians, it’s reasonable to expect Lee to be out of the office, and probably out of town, at least three “business” days a month, for a total of about seven weeks a year. Coupled with the vacation and personal time he’s got coming to him, that’s at least 13 weeks, or a quarter of the year, when he won’t be taking your call. But he’s going to manage the city bureaus, all of them, in three-quarter time. Not to worry.

Anyway, to return to the salary negotiations, it was Thanksgiving Week, and the back-and-forth moved quickly. Lee signed the city’s revised offer sheet that Wednesday. He was confirmed by the City Council a couple of weeks later.

* * * * * * * * * *

As I say, I don’t have his final employment contract. The public records clerks at City Hall, having taken three months to fulfill my request, didn’t look for documents dated after my request. And so the latest I have is from December 18. I guess I’ll have to put in another demand to get what’s been generated since then. And who knows? Maybe they’ll take another three months to get the records to me. Fortunately, my transparency war chest still has funds available. (Thank you, readers.)

What they did send me has some pretty big redactions. Two incidents apparently triggered document blackouts. One involved some sort of medical episode Lee had in mid-December which made him postpone a meeting with Zito to go over the draft employment agreement:

There was another, much bigger redaction, apparently relating to Lee’s travel arrangements. That one’s harder to figure out:

The city claimed exemptions from disclosure on several grounds. They cite state statutes, and you have to look them up. Such sweethearts, these folks are. The claimed exemptions were: 

ORS 192.355(9)(a) incorporating ORS 40.225 (OEC 503(2)) - Attorney-client privilege.

ORS 192.398(1) - Medical records.

ORS 192.345(22) - Information that, if disclosed, would allow a person to gain unauthorized access to property; identify areas of structural or operational vulnerability that would permit disruption to, or interference with, services; or disrupt, interfere with or gain unauthorized access to public funds or to information processing, communication or telecommunication systems.

ORS 192.345(23) - Security-sensitive information.

I'm not sure what travel documents could contain that would fit within any of those exemptions.

* * * * * * * * * *

Anyway, if you want to see what we’re paying $535,000 a year for, there’s a mildly entertaining clip posted on YouTube from a KGW talk show from earlier this month. Lee goes one-on-one with a reporter for about 12 minutes. It's here.

It’s clear that Lee is a politician. He can recite the talking points at high speed. Portland’s in a “renaissance.” Downtown is the “heartbeat.” And people are going to want to “live, work, and raise a family” downtown.

All flaws of city government are the fault of the “old charter.” We have a “new form of government” now, and that will solve our problems. Fifteen months old is still “new,” apparently.

But there’s a weak note in Lee’s flowery speeches. In his zeal to sound more managerial, he constantly refers to city government as “our organization.” Our organization this, our organization that. In the first 10 minutes of that clip, he says “organization” 15 times. I counted. It got so bad that the interviewer caught the bug and called his own employer an “organization,” too. 

If someone tries to get you into a drinking game where you down a shot every time Lee says “organization,” don’t dare do it. You will wind up in rehab.

When I get some time, I’ll take you through some of his expense account reports from Greeley. They may provide more chuckles to go with those from his early files here in Portlandia. And of course, if anything else turns up on his Portland deal, I’ll report it as well. But don’t hold your breath waiting for that one. They're slow-walking me.

* * * * * * * * * *

Meanwhile, the “Clay” headhunter guy who brought Lee to Portland and vice versa is an interesting dude. His name is Clay Pearson. Like Lee, he has a master’s in public administration from the University of Kansas. Fascinating! And just this month his firm, Strategic Government Resources, happened to be hired by the city to run, you guessed it, an all-day Saturday retreat for the City Council members on March 7. It’s touted on SGR’s website, here. A “Council Strategic Priority Setting Session,” it was reportedly held at a nondescript location downtown. Lord knows how much Clay’s crew were paid to “facilitate.” The Lee Era has clearly begun.