A lot of people wanted to know what Portland Mayor Ted Wheeler was thinking on July 22, 2020, as the country watched him choke on clouds of tear gas fired by federal officers.
It was a surreal moment – an American mayor under attack alongside thousands of his constituents after weeks of nightly racial justice protests — and covered as such by every major news outlet in the country. Footage of the mayor, wincing and teary-eyed, made the rounds on cable news. Reporters trailed him through the crowd, lobbing questions about his thoughts on the unfolding scene (“Orwellian”) and the taste of the tear gas (“nasty stuff.”)
But Michael Kessler, a computer programmer by trade and City Hall watcher by hobby, wanted a deeper look into what the mayor was thinking on one of the most chaotic nights of the city’s most tumultuous year.
Under the state’s public record law, anybody has a right to ask for any record retained by an Oregon public body related to “the public’s business.” So Kessler submitted a public records request for Wheeler’s texts.
The mayor had been busy that day.
As Wheeler prepared to make his first appearance at the protests, he texted soon-to-be Multnomah County District Attorney Mike Schmidt, inviting the prosecutor to join. Schmidt, newly elected and perhaps sensing the chaos bound to erupt when Wheeler waded into a crowd that had cursed his name nightly, declined. He had to focus on his new job, he wrote.
Others were more encouraging. E.D. Mondainé, then the president of Portland’s NAACP chapter, applauded the mayor. So did real estate developer and arts patron Brian Wannamaker, sending Wheeler a picture of the view of his Columbia Gorge vineyard, with the offer of “a place to go, that no one will ever know.” After watching a livestream of the protest, one of Wheeler’s staffers offered to deliver him food after work, which the besieged mayor praised as the “nicest thing anybody has said to me in a long time.”
The staffer would soon be one-upped by then-South Bend, Indiana, Mayor Pete Buttigieg, who had recently dropped out of the 2020 presidential race. After photos of Wheeler struggling under tear gas began circulating, Buttigieg texted his support.
“The mayor’s lot is to catch it from all sides but you are bearing it well, and it reflects well on your city,” Buttigieg, now the U.S. transportation secretary, wrote the next morning.
The two exchanged fawning texts throughout the day, commiserating on a mayor’s fate to be attacked from all angles.
“A good friend of mine told me this morning, you’re not above the fray. You are the fray,” Wheeler responded. “But nobody knows what it’s like to be under pressure like you do. I am in awe of your composure.”
That same morning, Kessler would request all of Wheeler’s messages from the night he was tear gassed through the next day. But dozens of messages – including the exchanges with Schmidt, Wannamaker and Buttigieg – were not handed over. City attorneys would later say they had no idea these texts existed.
The messages turned out to represent just a fraction of the thousands of texts sent and received by the mayor over his time in City Hall that were out of reach of the public.
During the summer of 2020, city leaders unanimously voted to name transparency one of the city’s “core values.” The word itself now appears on every job posting the city releases, at the bottom of many city employees’ email signatures, and over 400 times on the city’s website. Yet public record experts say the city has repeatedly broken the one state law aimed at promoting a transparent government: the Oregon Public Records Act.
The law, considered the bedrock of open government in the state, requires government officials to preserve their records — emails, texts, memos — and, in most cases, turn them over to the public when asked.
But an OPB investigation found the mayor and his staff sent and received thousands of text messages between 2017 and 2021 that weren’t available to people requesting city records. Thousands of messages from Portland elected officials and their staff have been erased in violation of city policy that they be kept permanently. Some experts say the city has now opened the door for every single records request for texts that came in during the mayor’s tenure to be re-examined.
It can all be traced back to a faulty system city leaders built for capturing these text messages. With a simple toggle of a button, any city employee could get around the rules.
Including the mayor.
It’s a button that should be familiar to iPhone owners.
It’s what allows the user to turn iMessage, Apple’s proprietary messaging service, on or off. Keep the toggle on, texts will be sent to other iPhone users through Wi-Fi or cellular data. Your texts, in turn, will show up inside blue bubbles. Turn iMessage off, and texts will be sent through a cell phone network and will show up inside green bubbles. If an iPhone user with iMessage on texts someone without an iPhone, texts will show up in green bubbles, regardless.
These bubbles have earned an outsized role in the zeitgeist – with green bubbles seen, particularly among certain young people, as a touch lamer than their blue counterparts. This January, the Wall Street Journal profiled iPhone-addicted teens who “dread the ostracism that comes with a green text.” Tech columnists have urged iPhone owners to please remember “that a green bubble is a person.” Superstar rapper Jack Harlow has been featured on a track titled “Green Bubble,” detailing the trials and tribulations of dating a girl with, you guessed it, green bubbles.
In Portland City Hall, that divide between green and blue was more than a niche aesthetic preference. Since 2017, green bubbles have been stored in the city’s archiving system, the texts readily available to anyone who asked. Blue bubbles were not.
Most governmental bodies in Oregon — including the city — consider text messages a public record. Under the city’s policy, all bureau directors, elected officials and their staff must retain their texts and emails related to city business permanently. (There are exceptions for “transitory texts,” ephemeral messages such as “running late” or “be right back.”)
Oregon’s law is notably weak when it comes to enforcement. While some state public record laws threaten agencies with thousands of dollars of fines or even misdemeanor criminal charges for egregious violations, in Oregon, there’s no real punishment for a difficult agency. If a public body ignores a record request or drags their feet too long, a district attorney can fine them $200 — a drop in the bucket for most places.
In 2016, when city leaders began thinking about purchasing a text archiving system, the inability to capture texts sent via iMessage was not viewed as a problem. The alternative was already a mess. Whenever a request rolled in for an official’s texts, city attorneys would have to track down that official and either make them screenshot their texts or pry away their phone to pull the messages manually. Worried the city was “risking non-compliance” with public record laws, then-city attorney Tracy Reeve recommended an archiving contract with a company called Smarsh, a darling of Portland’s small tech scene.
Headquartered just a few blocks from City Hall, Smarsh specializes in storing electronic communications for thousands of companies and government agencies; its clients range from the U.S. Department of Commerce to the Florida Department of Citrus. In December 2016, the city of Portland joined the list, inking a $95,000-a-year contract for software that would capture employee texts directly from cell carriers, such as Verizon, AT&T or T-Mobile. Once an employee enrolled in the program on their city phone, every text they sent or received would upload to an online archive, at the fingertip of the city’s lawyers and IT staff. Mayor Wheeler would later call the software “a game changer in terms of text messages.”
“It saves everything,” Wheeler raved to his colleagues at a February 2020 council meeting when the topic of public records requests arose. “It’s easy: Push the button, out you go.”
Almost everything. The software can pull nearly any electronic message into the portal — emails, WhatsApps, texts, Slack messages, Microsoft Teams chat. But it can’t touch iMessages. Encrypted by Apple, those blue bubbles have always remained out of reach of the software.
This created an obvious problem: Any employee who wanted their texts off the radar could simply turn iMessage on. For that reason, Smarsh recommends their public sector clients go elsewhere for a separate program that blocks iMessage. OPB reached out to several city governments that use Smarsh — Orlando, Jacksonville, Spokane. All say they pair it with a program that either restricts the use of iMessage or prevents public employees from blocking text archiving.
In 2016, the city had bought a program that could block iMessage for the Portland Police Bureau. Senior Deputy City Attorney Jenifer Johnston, the city’s point person for public records, said the city had to buy the technology for the police to comply with federal law, which tightly regulates how criminal justice information can be handled. But she said city officials didn’t think it would be the “best use of the funding” to purchase the iMessage-blocking technology for everyone else. The program currently costs the police bureau roughly $37,000 per year.
For the other thousands of employees with city-provided iPhones, Portland leaders would choose a different tact: Trust them to keep iMessage turned off.
It’s a strategy that, while beneficial to the city’s bottom line, some inside City Hall now recognize as overly naive. One longtime staffer would later compare it to building a barn with no walls.
The mayor + iMessage
On his third day in office, the mayor signed a form acknowledging the city’s policy to stay away from the messaging service. The document informed him, in bold lettering, that city officials may “not use iMessage on your City devices because these messages cannot be captured and archived by Smarsh.” On the back were instructions on how to toggle off iMessage with picture aids: green-bubbled texts about crowdsourcing a proposal (good!) and blue-bubbled texts about picking up a pad thai order (bad!).
Ten months after Wheeler signed the form, iMessage would be turned on on the mayor’s iPhone, according to an automated email he received from Apple on Oct. 2, 2017.
When OPB began reporting this story, Johnston said she believed Wheeler had iMessage turned on – and so his messages were not pulled into the city’s text archive – for roughly two weeks during a brief period in 2021 when he switched phones. After requesting and reviewing hundreds of pages of emails, cellphone records, and phone data exports, OPB determined that the mayor’s iMessage had, in reality, been on for much of the period between October 2017 and December 2021. During that time, the mayor sent and received a steady stream of text messages that were never searched.
The mayor declined repeated requests to be interviewed for this story. OPB was able to pinpoint some of the period in which the mayor was using iMessage on his iPhone through a series of public records requests: OPB learned that city attorneys used special software in late 2021 to export all the content on the mayor’s phone, including iMessages that Smarsh could not capture. The software exports text messages in a format that makes it easy to distinguish iMessages on the phone from traditional text messages. OPB requested the date and sender of every iMessage on the download.
The spreadsheet OPB received back shows the mayor sent and received over 6,400 iMessages between January 2019 and the date of the download, September 2021. Johnston, the senior deputy city attorney, would later write in an email that “all messages on [his] iPhone are essentially iMessage.”
OPB then requested a selection of the mayor’s messages. The collection underscores why reporters and curious constituents seek out text messages: the city’s leaders and their staffers say a lot privately that you would never hear from them publicly.
For example, you probably would not have gotten the mayor’s staff to entertain a conversation about the political merits of speaking out about a police officer’s friendly texts with a Patriot Prayer leader — as his communication director did on Feb. 16, 2019.
At the time, much of Portland was seething over recently-surfaced text messages between Lt. Jeff Niiya, an officer assigned to manage protests, and Joey Gibson, leader of Vancouver-based far-right group Patriot Prayer. Leftist activists, civil rights groups, and two council members had called for an independent investigation over messages they perceived as overly sympathetic. Wheeler joined the chorus in a public statement on Feb. 14, calling the texts “disturbing” and saying they “appear to cross several boundaries.”
Two days later, his then-communications director Eileen Park reminded Wheeler about the political strategy behind the statement in a text: “We joined in the outrage, which was necessary. Then when the dust settles and the investigation yields results and new information - we move with the flow - not against it.”
During the racial justice protests of 2020, Wheeler declined to speak to reporters after Commissioner Jo Ann Hardesty called on him to give her control of the police bureau. While his office dodged press inquiries on her accusations that he had lost control of the force and put “our community in danger,” Wheeler followed up privately with her within 30 minutes:
“I feel deeply betrayed by you,” he texted. “I’m not going to respond right now.”
Wheeler was similarly quiet about what could have caused the abrupt resignation of Brian Hunzeker, the president of the Portland Police Association – or PPA – in March 2021. Hunzeker left the post due to what he called a “serious, isolated mistake” related to a police investigation of an alleged hit and run involving Hardesty. Two weeks earlier, the Oregonian had published an article incorrectly linking her to the incident through an unnamed source. Rumors immediately swirled that Hunzeker was that source.
Wheeler did not speculate publicly. But he did text Hardesty immediately after news of the resignation broke: “It’s a shitshow at PPA.”
“Doesn’t take a genius to read between the lines on this one,” he wrote.
None of these messages would turn up in records requests.
The mayor’s persistent iMessage use on his publicly provided phone came in spite of repeated warnings from city attorneys and technology staff that these texts could not be archived.
In addition to making every iPhone user sign a form acknowledging the city’s no iMessage policy, Johnston says an attorney or phone coordinator would also check with the employee when they got a new iPhone to make sure iMessage was actually off. Employees were handed an FAQ dedicated to iMessage explaining the difference between blue and green bubbles, and technology staff would send out periodic reminders to council offices and bureaus to confirm the messaging service was still disabled.
The lawyers responsible for steering city leaders away from behavior that could invite a lawsuit took extra steps with the mayor. At least twice, Johnston told OPB, the city attorney’s office manually turned iMessage off on the mayor’s phone, though she said others may have done it as well. Each time, she said, the mayor indicated “his understanding that iMessage had to be turned off.”
It never stayed off for long.
Wheeler received a Black iPhone 7 from the city when he entered office and switched out his phone twice over his first term — each time for a gray iPhone 8 Plus. On these two iPhone 8s, records show iMessage was on within a few months of Wheeler getting the phone. iMessage was also turned on once on his Apple Watch.
By 2021, staff with the city’s technology bureau, well-aware of the public records implications of having iMessage on, were sending increasingly frantic emails about the mayor’s conduct. They wrote that he was “re-enabling iMessage every time.”
“The mayor…. keeps enabling iMessage, despite instructions, which puts him in non-compliance with records retention laws,” the city’s cellular services supervisor wrote in an email to technology bureau higher-ups on Oct. 20, 2021.
“One of the issues with Mayor Wheeler has been that he doesn’t want to use the approved/standard apps,” the staffer wrote again in a Dec. 6, 2021, email. “For example, he kept turning on iMessage as his preference, even though both Jenifer [Johnston] and I made sure he and his staff knew that it wasn’t allowed because it broke text message archiving.”
The emails raise questions as to whether the mayor, reportedly warned multiple times that turning on iMessage would mean his texts wouldn’t be available for public records requests, was intentionally trying to skirt scrutiny by keeping iMessage turned on. The mayor’s office referred OPB to the city attorney for questions regarding the mayor’s text messages.
Staff who worked under Wheeler scoff at the idea that he was purposely trying to circumvent public records rules. They say the mayor has always appeared at ease with the fact that his texts could make headlines at any point — some say unnervingly so.
“A few times, I would caution him about the contents of a text because it was a public record, and he would say, ‘I know that’s why I sent it,’” said Jim Middaugh, the mayor’s former communications director, who left in the spring of 2021.
Former mayoral staffers also say using iMessage to keep texts private would have required a level of technological finesse the mayor simply did not possess. Middaugh said Wheeler was not particularly tech-savvy and never appeared invested in the technology undergirding City Hall.
“He did not seem to be the kind of 60-year-old man who embodied a young person’s knowledge and awareness of technological trends or tools — similar to myself,” he said.
The conclusion among people who’ve worked under Wheeler: He must have just liked iMessage.
After all, there are reasons Apple’s messaging service is so popular. Users can seamlessly form group chats and see when their texts are delivered or someone else is typing. They can easily text from their Mac computer or iPad. Perhaps the lure of these features, former staff reasoned, outweighed city lawyers’ warnings.
Emails show the city’s technology staff landed on a similar explanation.
“Mayor Wheeler doesn’t want to give up iMessage and he doesn’t trust BTS [the Bureau of Technology Services],” the person who oversees city government’s cellular services wrote colleagues on Nov. 18, 2021. “City Attorney’s have even helped with messaging as part of the SMARSH compliance issue. The Mayor likes and wants to keep iMessage.”
Like other city staff, Johnston acknowledged in a September 2021 email that the mayor was “turning on and off iMessage.” But, months later, in an interview with OPB, she offered a different explanation. She said, while she’d initially been confused by the mayor’s iMessage use, she’d come to realize later it wasn’t the mayor’s fault — it was Apple’s.
Each time Apple updated its software, she said, iMessage would get turned on.
“At first I thought he was toggling it on and off, because we would find it on when I had met with him, and I know he had turned it off,” she said. “This is how I discovered that it got turned on with updates. … That’s when I realized it was not a deliberate thing.”
“Even though the mayor was taking every step we asked to comply, Apple was turning it on,” she continued.
According to an Apple spokesperson, that’s not the way iPhones work. OPB asked Apple if software updates could have reset the iMessage function on an iPhone between 2017 and 2021. A company spokesperson said that in the event iMessage is turned off, the setting would be preserved after updates.
Cody Bowman, a mayoral spokesperson, later followed up with other potential ways iMessage could have been turned on on the mayor’s phone without his involvement or knowledge including: the mayor getting a new phone, the mayor changing his SIM card, the mayor syncing his phone with iTunes, and the mayor sending a message “to a non-city employee who had iMessage turned on.” He emphasized that Wheeler “never manually turned on iMessage” and was “not familiar with these settings.” City Chief Technology Officer Jeff Baer also emailed OPB to say that though his staff initially thought the mayor was turning on iMessage on city phones, the “assumption is invalid.”
Regardless of how iMessage was turned on, there should have been a bright blue visual cue for Wheeler that iMessage was on anytime he went to read or send texts. The meaning of green vs. blue bubbles is highlighted in the training material given to city employees and on the form he signed when he entered office.
Johnston said she wasn’t aware of the significance of the colors until recently. She said she had other things to focus on. Similarly, she said, the mayor and his colleagues had loftier matters requiring their attention.
“I think it’s an unreasonable expectation to quiz commissioners and them to know the colors of iMessages,” she said. “I am hoping that they are focusing on other more important issues for the city of Portland than the colors of their text messages.”
It wasn’t just the mayor.
Three of his senior policy advisors, his police advisor, his deputy chief of staff, his director of strategic initiatives, and his business operations manager all had iMessage on for at least a year. Wheeler’s chief of staff, Bobby Lee, and mayoral aide Sam Adams, himself a former mayor, also used the messaging service between February 2021, the month they both entered City Hall, and August 2021, the month city attorneys told them to turn it off.
According to emails, Wheeler’s office had been warned to stop before.
“Several of the people in the Mayor’s ofﬁce use iMessage, but shouldn’t,” a technology bureau employee wrote in an email to department head Jeff Baer on Sept. 10, 2021. “They know they are supposed to have it disabled but we are told by the City Attorney’s ofﬁce that they toggle it off and on because they like it better. The problem with this is that Smarsh can’t see the messages in iMessage.”
Staff within the mayor’s office, the employee continued, were “0% ﬂexible.”
“Elected[s] are very demanding and difﬁcult to work with,” they noted.
The problem extended beyond Wheeler’s office. Former Commissioner Chloe Eudaly signed the same form as the mayor vowing not to use iMessage within her first few days in office. She would later say she “vaguely” remembered being told not to use it.
iMessage was turned on on Eudaly’s phone in March 2018, according to an automated email from Apple. She kept using it until her last week in office at the end of December 2020. Much of her staff did as well, at her encouragement.
“Good morning!” the commissioner texted her staff on March 16, 2020. “Please make sure iMessage is enabled on your work phones so that I can text you from my iPad.”
Like every other elected official, Hardesty was asked by city attorneys to sign a form pledging to not use iMessage when she entered office. It’s not clear that she ever did. Neither her office nor city attorneys could find the form when OPB asked, though Hardesty said she signed every form the city requested. Directions on iMessage, she said, had been “confusing and often buried amongst the hundreds of emails” that flood her inbox each week.
By the start of the racial justice protests in June 2020, Hardesty too had reverted to blue bubbles. She kept using the encrypted service until late 2021.
iMessages obtained from the mayor’s phone show Hardesty also occasionally used her personal phone to backchannel with the mayor. On Feb 3, 2021, for example, she prodded Wheeler to confront Commissioner Mingus Mapps after what she perceived as a possible attempt to “undermine my leadership and yours.” (Wheeler and her agreed to talk one-on-one: “Just want to make sure there [is] no coup. ; )” he responded.) On Dec. 13, 2020 she asked the mayor to please stop using the expression “by any means necessary” — a phrase popularized by Malcolm X — in his police-related press releases.
City of Portland employees are not allowed to use personal phones for city business. Private cellphones are rarely examined for public record requests.
Hardesty said one possible explanation for sending work texts on her private phone was that she occasionally lost her city-provided cell. She also said city commissioners have “more leeway to discuss the politics of issues compared to other City employees.”
“It was never my intention to discuss city business on my personal phone,” she said.
OPB was able to obtain these iMessages because the city’s lawyers took steps to download them after realizing in late 2021 just how many blue bubbles were on the mayor’s phone. They took the same step around that time with many elected officials and top bureaucrats who also had been using iMessage.
But for any official who used iMessage and left the city before the crackdown, their texts have likely disappeared. City phones were often wiped and either reused or donated when their owners left City Hall.
City archivist Diana Banning, who is in charge of preserving the records of elected officials and their staff once they leave office, said she’d only been told there was a “little hiccup” with iMessages, but did not know the extent. After an OPB inquiry, she confirmed there were no iMessages in the city’s archives from Eudaly, who used the messaging platform throughout her term in office.
Nor were there any from the phone of former Commissioner Amanda Fritz, who had iMessage on for a year between spring of 2019 and 2020. Texts Wheeler sent using iMessage on his first and second phone in office have disappeared, too. That period stretched from October 2017 to January 2019, long before the city’s lawyers realized they had a problem.
iMessages sent by Wheeler’s police advisor Robert King, who left the city in the summer of 2021, are similarly lost. Because King had iMessage for much of his time in office, no one-on-one conversation between him and the mayor sent between April 2020 and May 2021 was ever turned over. In that period — in which King advised the mayor on the monthslong racial justice protests, two fatal police shootings, and multiple violent clashes between rival far-right and left groups — the city received a dozen public record requests seeking King’s texts.
The mayor’s office was typically flooded with these requests. From 2018 to 2021, the mayor’s office received over 130 requests for text messages from both press and constituents. For nearly all requests, city attorneys only provided what was in Smarsh. That means many people seeking public records got some texts, but nowhere near all.
For example, when a local activist group requested all of Wheeler’s texts during the 2020 racial justice protests, the city omitted over 1,300 relevant texts spanning nearly every pivotal protest moment (”My favorite sign so far is the big one that says ‘Ted Wheeler is a pig fucker’,” Wheeler texted the night of June 17, 2020 after a hundred protesters set up an “autonomous zone” outside his Pearl District apartment. “My neighbors will kill me if the demonstrators don’t.” )
When OPB requested all texts between Adams and Wheeler from June 2021, the city only turned over messages from group chats. Both men had been using iMessage and so OPB did not get any texts sent directly between the two men.
“I don’t see that there’s any way that this isn’t a violation of law,” said Ginger McCall, Oregon’s first-ever Public Records Advocate who now works at a progressive advocacy group in Washington D.C. “... They clearly didn’t fulfill their legal obligation. That’s a nice way of putting it.”
Johnston, Portland’s senior deputy city attorney, said she is confident the city operated in good faith and had done “everything reasonable” to retain the hundreds of text messages sent by City Hall staffers each day. She said there had been no violation of public records law, because city lawyers and public records staff didn’t know the iMessages existed.
“What I understand the law requires is that we perform a reasonable search,” she said. “And our search was reasonable based on what we knew at the time.”
As things stand
In late 2021, after four years of Smarsh and countless blue bubbles, alarm bells began to blare within City Hall.
Tech bureau staff had been working on a project, known as “Enterprise Mobility Management” or EMM, that would make it much easier to oversee the city’s thousands of iPhones. By enrolling all city phones onto a platform called Workspace ONE, technology staff could control the settings of every employee phone from afar, for example, downloading or blocking certain apps.
Some technology bureau staff said they’d long suspected iMessages were widely used across city government. The new software project, which brought them up close and personal with the phones, confirmed that there were blue bubbles everywhere.
Workspace ONE quickly took on a new significance. With the software, the city could now block iMessage.
Originally, elected officials were scheduled to be some of the last city employees to receive the new software. But, technology staff moved them to the top of the list due “their non-compliance with text archiving,” per emails. Staff would note the “surprising number” of “elected and VIP” officials whose texts had not been properly saved.
By December 2021, the mayor — along with every other elected official — had iMessage irreversibly blocked. Where the iMessages toggle used to be, there is now just a blank space.
The remaining city employees have slowly followed suit. When OPB began reporting on the topic earlier this year, about 150 of the city’s roughly 3,300 employees with iPhones still had iMessage on, including the fire chief, the chief deputy city attorney and the directors of the housing and water bureau. OPB determined that number by using an iPhone to draft text messages to each city employee.
That same week, staff from the city attorney’s office told OPB that “all City phones have iMessage disabled.”