Note first that Portland does NOT HAVE A SHERIFF. So the fact check is false — this guy is not the sheriff of the city of portland, so he cannot “refute” an endorsement that doesn’t mention him.
Second, Trump clearly meant the Westmoreland Sheriff, not the Portland Sheriff. There IS a Westmoreland Sheriff, he was a democrat, and he just endorsed Trump and became a republican.
So the CORRECT fact check would be “Trump confuses Portland and Westmoreland when touting a Sheriff endorsement.”
Portland doesn’t have a sheriff. Sheriff is a county position, not city. Mike Reese is sheriff of Multnomah County, Portland is in Multnomah.