Can Rosie O’Donnell Destroy The Presidency? Well…

This past week Donald Trump launched another fusillade…not toward Iran, but Ireland.

Photo: commons.wikimedia.org by David Shankbone, https://creativecommons.org/licenses/by-sa/3.0/

Rosie O'Donnell by David Shankbone

For reasons basically inexplicable, the President took aim at FORMER personality Rosie O'Donnell.

To the extent anyone is unaware, Donnie and Rosie had a feud of sorts many years ago when she appeared on a daily talk show titled "The View”.

Now, to be crystal, during that era O'Donnell was — for most people — somewhat radical. At the same time, it was the premise of the program; to have a group of chatty women represent various "types” voicing opinions, of which O'Donnell was the "extreme Liberal”.

It was, and remains (now with Whoopie Goldberg playing the part), a schtick that succeeds — folks both Liberal and Conservative get all "worked up” over some trifling nonsense said by someone with minor power while advertisers major bank.

No harm there, not really.

Rosie Is Retired — Not Cancelled

The issue here is that O'Donnell departed "The View” from her first stint as a Host in 2007 and last participated as Host for a single season in 2014 and then…not much.

She did a couple films in 2015 and 2016 which were essentially cameos. A searing episode of the 2022 remake of "A League of their Own” a few years back. Some other marginal programs, etc.

Her most recent denouncement of Trump of any consequence was in 2018 when she made a speech against him outside the White House.

In 2025 she moved from the U. S. to Ireland, pursuing Citizenship, with intent to begin a new life with her family.

Most would say, "Fare Thee Well, Old Adversary!”

Trump Grasping at Former Vainglory

During the last Presidential Cycle at one debate Trump made reference to O'Donnell and everyone — myself included — laughed in a "Greatest Hits” sort of way because…well, it's always fun to reminisce.

Except, for some reason, Trump seemingly could not let it go.

When the Irish Prime Minister visited in March 2025, our President took the opportunity to gratuitously make a "dig” at O'Donnell. The Prime Minister was mystified by the exchange.

Then last week — COINCIDENTALLY — while trying to distract from The Great Epstein File F*ck Up, our President took time out of his busy day to AGAIN randomly berate O'Donnell by implying he would revoke her Citizenship. (Offensive on MANY levels, even if you absolutely LOATHE the woman.)

Importantly, while there may be a few random internet posts or social media comments made by O'Donnell (of which, this author is not deeply aware, because as most, I don't pay much attention to her) the image of a sitting President arbitrarily tossing insults is unseemly.

Only, it gets worse…

Rosie May Be A Riveter

First, it is not my place to defend Rosie O'Donnell. Basically we would agree on EXTREMELY little.

That may be important to establish given the polarized nature of American politics. Except, I can look at a person minding their own business — in ANOTHER COUNTRY — and find it distasteful she be attacked.

Two, evidently Rosie O'Donnell had a pretty rough life.

I have encountered several individuals in this world but never even met O'Donnell. So I do not know her other than what has appeared in the Press, but that is enough to see there have been "issues”.

No insults are intended, but this woman has either dealt with or is dealing with some psychological matters of pretty heavy consequence. So, as totally an observer, it seems cruel to make fun of her.

Okay, maybe she put out insulting Tweets…but that's not enough to attempt to destroy someone.

Three, unjustified attacks on Rosie O'Donnell are beginning to rankle The Base.

I know the apparently unwarranted insults are not offensive to myself alone. Many are feeling comfortable with the situation.

Picking up a dispute from 15 years ago by picking on a woman with mental health concerns mostly trying to raise her family is not Right. It just isn't. Any normal person is going to agree, or at least inquire, "Okay, what did she do to you?”

If the answer is, "She made me angry almost twenty years ago!” that is…embarrassing for you.

Trump Is Building A Bombshell

Anyway, let's say someone despises O'Donnell. I do not, but let's say that is the extremist position.

Until the past week Rosie was largely silent. She was going about her own concerns. Mainly not involved in politics aside from the proverbial "angry Tweet” that many casual voters post.

But there is this — Rosie O'Donnell, no matter what MAGA thinks of her, is popular in Hollywood.

She is reputationally (there, at least) considered a kind person who is basically decent.

Knowing that, by repeatedly antagonizing Rosie he makes her a Figurehead in any opposition.

Despite appearances, many in Entertainment are reluctant to get into the whole Culture War scenario. Many just want to work. To make money. Be famous. Whatever. NOT to fight all the time.

So a lot of Entertainers aware of some things have not mentioned any of them for that reason.

BUT…if Trump makes O'Donnell (not top personality, but prominent) a Figurehead of resistance?

Maybe some, or in worst case many, of those Hollywood people who know some things will begin funneling anecdotes to Rosie to distribute on their behalf.

One woman is one thing. One woman being a conduit for half of Entertainment is something else.

Hollywood Is Not As Eager To Rumble As You Believe…Until Now

Trump is rousing O'Donnell into a very public fight — and into becoming a walking Blind Item.

For those uninitiated, a Blind Item is an "unsourced rumor” without attribution, that is often true.

Someone knows something they want to get out, but can not have their identity attached to it.

Remember, Trump spent decades in Entertainment and at least eight years on his own show — that's a lot of Crew, Staff and Talent who had interactions with them. Do they all have "secrets”? No. But if even some of them have tidbits, all those could be directed to a singular individual to publicly air.

And who to do that? A well-regarded former colleague in another country being unfairly hounded.

Trump — Always The Wrong Battle

To a certain extent Trump already woke the wildebeest.

The other day O'Donnell finally responded — after YEARS of ridicule — with some pretty inflammatory insults and imagery.

Again, I don't agree with much of it and I do not agree with much of her philosophy.

Our purpose today is to ask — What possible intent, Trump?

How are you served by this nonsense? Rosie was quiet. No one else remembered her last week.

Today you've got a motivated enemy with potential support of those who know lots of things.

Distracting from the Epstein dumpster fire by creating another fire is no distraction at all — it's merely two fires.

So will Rosie end the Presidency of Trump? Likely not.

Yet these are exactly the sort of stupid errors often the Beginning of the End for any Administration.

Guy Somerset writes from somewhere in America