Mayor Wheeler’s use of encrypted iMessages costs city $166K

John Ross Ferrara
·3 min read
3

PORTLAND, Ore. (KOIN) — Mayor Ted Wheeler’s continued use of the iMessage feature on his city-issued iPhone between 2017 and 2021 cost the City of Portland $166,893 Wednesday, when the city council unanimously agreed to settle a lawsuit filed over the city’s inability to fulfill a public records request for Wheeler’s text messages.

The suit, filed by attorney Michael Kessler, a resident of North Vancouver, British Columbia, Canada, states that Kessler submitted a records request in July 2020 for all texts sent to and from Wheeler’s iPhone between July 21 and July 23 — the period after former President Donald Trump ordered federal agents to suppress nightly racial justice protests in Portland.

“On Nov. 14, 2022, Oregon Public Broadcasting reported that the city’s text message archiving system Smarsh did not capture messages sent over the Apple’s text-messaging protocol, iMessage,” the lawsuit reads. “This was problematic, because text messages are subject to the Public Records Law as well as the City of Portland’s retention policies and must be preserved.”

15-year-old boy accused of assaulting Gresham man with skateboard turns himself in

While the city purchased additional software in 2016 to block the iMessage feature on Portland Police Bureau equipment, it did not implement this protocol for other city bureaus. After taking office in 2017, Wheeler signed a form agreeing not to use iMessage because the archiving system was unable to record them, OPB reported. However, iMessage was turned on on the mayor’s iPhone 10 months later, causing Wheeler to receive more than 6,400 iMessages between January 2019 and September 2021.

By 2021, staff with the city’s technology bureau were reportedly becoming increasingly frantic about the mayor’s use of iMessage. According to emails sent by the technology bureau staff, Wheeler was “re-enabling iMessage every time,” even though he was repeatedly told that doing so evaded the city’s archiving system.

The city informed elected officials that they could manually turn off the iMessaging feature using their iPhone settings, which would be apparent by the text bubbles changing from blue to green. However, nearly all of the text messages sent by Wheeler between January 2019 and September 2021 were iMessages, Senior Deputy City Attorney Jenifer Johnston told OPB.

In December 2021, the City of Portland addressed the issue by irreversibly blocking the iMessage feature on phones used by elected officials. The mayor’s spokesperson Cody Bowman told reporters in 2022 that Wheeler “never manually turned on iMessage,” and that he was fully compliant with the archiving system.

In response to the lawsuit filed in response to the records issue, the City Attorney’s Office recommended that the city council approve the agreed-upon settlement of $166,893 “as a compromise from the full demand to resolve the matter without further legal proceedings.”
By approving the settlement, the city has agreed to pay $1,893 for Kessler’s cost of filing the lawsuit against the city, plus an additional sum of $5,000, and $160,000 to cover his attorney’s fees. The checks are to be made out to Kessler’s brother Alan Kessler, who served as Michael Kessler’s attorney in the settlement. The settlement will be paid using the city’s Legal Priorities Reserve Fund.

For the latest news, weather, sports, and streaming video, head to KOIN.com.