Thousands of text messages sent by Portland mayor’s government phone went missing

Thousands of text messages from Portland Mayor Ted Wheeler’s city-issued iPhone and the phones of other top officials went missing for years from the public record, including texts he sent after former President Donald Trump directed federal agents to the city to quell nightly racial justice protests.

Oregon Public Broadcasting reports the city uses specialized software to capture text messaging on city-issued phones so they can be retained for public record requests, but the software can’t capture encrypted messages sent using Apple’s iMessage service.

OPB’s investigation found the mayor and his staff sent and received thousands of iMessage texts between 2017 and 2021 and those messages were not captured — and therefore not included — in key public records requests about the protests, policing and other issues.

Users can turn iMessage off and instead send texts outside Apple’s proprietary system by toggling a button in the iPhone’s settings. Wheeler and other city officials signed a document saying they understood they must toggle iMessage to the off position and Wheeler was repeatedly reminded of that, OPB reported.

Ten months after Wheeler signed the form, iMessage was turned on on the mayor’s iPhone, the outlet reported. The mayor then received over 6,400 iMessages between January 2019 and September 2021, according to a spreadsheet of all Wheeler’s texts from that period requested by OPB.

Wheeler declined to comment to OPB. His spokesman, Cody Bowman, said in an email to The Associated Press on Tuesday that the mayor ‘never manually turned on iMessage’ and was fully compliant with the archiving system.

‘Mayor Wheeler made his phone available to ensure that texts were manually captured,’ Bowman said.

OPB obtained the spreadsheet of the missing texts after it discovered city attorneys, concerned about his non-compliance, used special software in late 2021 to export all the content on the mayor’s phone — but iMessages sent on Wheeler’s previous city-issued phones are lost forever.

Senior Deputy City Attorney Jenifer Johnston told OPB that ‘all messages on (his) iPhone are essentially iMessage.’

The lost messages include from several former city commissioners and Wheeler’s former police advisor Robert King. They all used iMessage and left before Portland realized the problem and extracted iMessages from current phones.

King advised the mayor on the racial justice protests, two fatal police shootings and clashes between far-right and far-left groups during the time in question. The city received a dozen fruitless public records requests seeking King’s texts.

From 2018 to 2021, the mayor’s office alone received over 130 requests for text messages from both press and constituents. For example, the city omitted 1,300 relevant texts spanning nearly every pivotal protest moment after a public records request by a local activist group because they had been sent in iMessage, OPB reported.

‘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.’

By 2021, staff with the city’s technology bureau, were sending increasingly frantic emails about the mayor’s conduct. They wrote that he was ‘re-enabling iMessage every time’ even though he had been told repeatedly that doing so made the automatic text archiving impossible.

Bowman, Wheeler’s spokesman, said Tuesday that while city staff initially thought Wheeler disabled iMessage himself, they now know that’s not the case.

iMessage could have been turned on on the mayor’s phone without his knowledge when he got a new phone; when he changed his SIM card; when he synced his work phone with iTunes; or when he sent a message to a non-city employee who did use iMessage, Bowman said.

‘What the City did not realize until very recently was all the ways that iMessage could unintentionally and inadvertently be turned on when using the Apple device,’ he said in an email to the AP.

Johnston, Portland’s senior deputy city attorney, said she is confident the city operated in good faith.

‘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.’

By December 2021, all elected officials had iMessage irreversibly blocked.