Jeff Swickard keeps buying buildings in downtown Portland.
The Portland Trail Blazers keep telling city officials how difficult it's become to do business there.
So it was worth noticing who Tom Dundon met with when he returned to Portland this week.
Swickard was among several business and political figures who met with the Blazers owner, as KGW reported.
Dundon also met with Mayor Keith Wilson on Sunday before watching Monday's preseason game against the London Lions from courtside. It marked his first public appearance in the city since June.
Swickard, meanwhile, has been on quite the shopping spree.
The car dealership magnate purchased Portland's iconic Big Pink office tower for $45 million in 2025. He also acquired the Five Oak Building for $10.5 million, partnered on a $70 million purchase of another downtown property and bought a majority stake in Park Avenue West.
Willamette Week reported that Swickard now controls approximately 2.4 million square feet of downtown real estate through transactions worth a combined $250 million.
That's a lot of property in a city whose economic problems have become part of the Blazers' argument for a better arena deal.
During a July City Council hearing, team president Dewayne Hankins criticized Portland's taxes, business climate and political environment, arguing those conditions made it difficult to attract corporate partners and recruit players.
Swickard isn't exactly disputing those concerns.
He's acknowledged the city's struggling office market, shortage of tenants and disappearing middle-class jobs. Much of his real estate portfolio was purchased through transactions involving lenders looking to unload distressed properties.
He's just buying the buildings anyway.
But his thoughts on Dundon might be even more interesting than his property portfolio.
In an October 7 interview with Willamette Week, Swickard offered a pretty enthusiastic endorsement of the Blazers' new owner.
"I love Tom Dundon," he said.
Swickard described Dundon as a reasonable businessman and expressed confidence that negotiations would eventually produce an agreement keeping the franchise in Portland.
"I think the Blazers stay," he said.
Those comments came before the two met this week.
There's no public account of their conversation or indication that Swickard has any formal involvement in the proposed $600 million Moda Center renovation. The arena negotiations still face a December deadline.
And buying discounted office towers is a different business from running an NBA franchise. Swickard's investments don't make the Blazers' concerns disappear.
But after months of hearing why Portland has become such a difficult place to do business, Dundon has now met someone spending millions on the belief that its future is worth investing in.
Swickard has about 2.4 million square feet riding on that belief.
He might be worth listening to.