A kettle of fish
Are private, corporations allowed to send out campaign endorsements that encourage their members to vote for a slate of candidates? At the very least, it seems like the candidates would have to claim the mailings as an in-kind contribution, unless their campaigns paid for the endorsements, but that's another kettle of fish.
The Lake Oswego Corporation represents every business and homeowner whose lot touches the main Lake, Lakewood Bay, West Bay, Blue Heron Bay, and the main canal to the Tualatin River. They also represent the jointly-owned easements that dot the rim of the Lake, Sundeleaf Park and Millennium Park Plaza. There are lots in a large portion of the city that have deeded rights to one or more of the established easements but don't use them.
All together, the aforementioned households number around 5,000. Lake Oswego has about 16,000 households, which makes those with some connection (though tenuous) to the Lake just under 1/3 (31%) of the households in the city. How much does a mailing like that cost?
According to long-time Lake Corp members, this is the first time they can remember in over 40 years that the Lake Corp has endorsed candidates. In a mass mailing to 5,000 households, almost 1/3 of the households in the city, the Lake Oswego Corporation endorsed 4 candidates. Why did they make this unprecedented move?
I can't read minds, and I wasn't a fly on the wall
Kent Studebaker and Skip O'Neill have lakefront properties and are part of the Lake Corp. The majority of Studebaker's campaign contributions are from Lake Corporation members. They all have overlapping interests, so their endorsements were in the bag.
Why do endorsements at all? If I had to guess, it would be because the Lake Corp is frightened that in a three-way race, Dave Berg would take votes from Kent, and Jon Gustafson would win. The Studebaker campaign has been taking shots at and insulting Berg for months, aiming not at their true opponent, Jon Gustafson, but at a strong competitor with a compelling message.
If Studebaker had been using nis energy (and money) to fight the "Progressive Majority," the city would be much better off and the worst outcome would have been avoided. Perhaps there are too many influential names in Gustafson's camp to go at him directly. Or his fear of Berg was just too strong. Thank goodness Berg is for the citizens and is independent of these political machinations!
Correction: In my mailbox today I received a mailer from the Studebaker campaign comparing Kent to Jon. OK effort but too little too late?