I think the hat thing was clearly meant to be a joke...that was just being funny, and not an undermining attempt.
However, the other things mentioned in the article have some validity. I realize that the DailyWire certainly has a political leaning (that they've been pretty open about, Ben Shapiro has never really pretended to be a "moderate")
These stand out as potentially valid critiques...not sure if they were "intentional undermining", but at the very least, they're mixed messaging and potentially politically damaging.
Harris slammed Florida Governor Ron DeSantis for not taking her phone calls about the impending storm, calling him “utterly irresponsible” and “selfish” and accusing him of playing political games.
Then a few days later...
Biden posted a photo of himself next to a phone and said he had spoken to both DeSantis and the Tampa mayor about recovery from Hurricane Helene and preparations for Hurricane Milton.
Biden then went on to say:
saying DeSantis had been “cooperative” and was “doing a great job.”
Biden saying "DeSantis is doing a great job" (after Harris just called him irresponsible and selfish) isn't a great look. One could even say that Biden complimenting DeSantis at all (a figure who many on the left hate) isn't a great look in the eyes of Democrats either.
Biden's declaration that he wouldn't step in and intervene in the port strike (after having intervened not long ago when the rail workers did it), knowing the economic implications of a major disruption this close to election time and holiday shopping season could've spelled disaster.
That risk was exacerbated when the ILA president was saying things like this on his social (referring to how his meeting with Trump went):
"
We had a wonderful, productive 90-minute meeting where I expressed to President Trump the threat of automation to American workers," Daggett said. "President Trump promised to support the ILA in its opposition to automated terminals in the U.S. Mr. Trump also listened to my concerns about Federal 'Right To Work' laws which undermines unions and their ability to represent and fight for its membership."
(and then posted a picture of himself with Trump on his ILA social media account from when he flew down to Mar A Lago to meet with him)
A union threatening to upend an economy right before election time, and then their leader posting pictures of himself palling around with Trump and saying flattering things about him... and Biden does nothing. Had that labor dispute not resolved on its own, an extended port strike could've seriously damaged the Harris campaign.
Perhaps their fear was that Harris was already walking the tightrope with regards to unions after the blow that was dealt by the Teamsters declined to endorse her, and any further actions perceived as "anti-labor" (like a forced strike stoppage) could've hurt that even further. But either way, it wasn't a great look and the risks of non-action could've come with serious liabilities.
