Jeff Swickard, the Oregon businessman who took control of downtown Portland’s U.S. Bancorp Tower, better known as “Big Pink,” in July 2025, has quietly widened his footprint again. This time he picked up the neighboring Five Oak office building for $10.5 million, adding roughly 267,000 square feet to his portfolio at a price that is a fraction of what the property once fetched. Public and agency tenants are still in place on the block, keeping government services rooted there even as private-sector office demand continues to limp along.
Sale price, scale and how steep the decline was
According to The Oregonian/OregonLive, Swickard’s $10.5 million price tag represents roughly a two-thirds drop from the building’s 2014 sale, based on public records. Industry data puts Five Oak at about 267,000 square feet, a sizable chunk of space for an owner looking to upgrade, reconfigure or simply hold through a long recovery. The deal is one more entry in a growing list of older Portland office properties trading at sharply reduced values as the market resets.
Who’s in the building now
For now, Five Oak is still anchored by government tenants that tend to pay on time and stay put. Multnomah County lists the Department of County Human Services at the site, and the Oregon Health Authority also maintains Portland offices there. Local reporting has tied the property to the address 421 SW Oak St., and the building cycled back to its lenders during the recent wave of market turmoil before landing in Swickard’s hands. Portland Business Journal, along with county listings and state directories, all line up on those public-agency occupants.
How this fits with the Big Pink playbook
Swickard’s July 2025 purchase of U.S. Bancorp Tower, widely reported as a roughly $45 million deal, signaled early that he was willing to scoop up marquee downtown properties at heavy discounts and then spend on improvements over time rather than chase a quick flip. OPB and other outlets noted his pledge to reposition Big Pink and court new tenants. The Five Oak acquisition fits neatly into that playbook: buy locally, sit through the lean years and plan for a long holding period instead of betting on an immediate leasing boom.
Market backdrop: why prices are so low
Portland’s downtown office market has been under strain for more than a year, and it shows in the numbers. Recent reports put central business district vacancy around one-third. Colliers’ fourth-quarter 2024 research pegged CBD vacancy in the mid-30 percent range, a level that puts steady pressure on owners and lenders to either cut prices or wait out ambitious repositioning plans. Against that backdrop, it becomes easier to see how a large, government-anchored office block could change hands for a sum that would have sounded unthinkable a decade ago.
What’s next and why it matters
Swickard has told reporters he is in talks to buy other nearby properties and believes the area needs, in his words, “a little reimagination,” with an investment horizon of more than ten years, according to The Oregonian/OregonLive. Public records cited in that coverage trace prior ownership and entity transfers through institutional holders in 2025, highlighting how quickly control of downtown assets has shifted in recent quarters. For Portland’s core, this latest deal is a reminder that any comeback is likely to be uneven and driven by buyers who are prepared to wait and invest in upgrades, not by short-term trades that depend purely on a rapid rebound in office leasing.
