Bill O'Reilly
May 22, 2026
Our Optimist-in-Chief
Our Optimist-in-Chief

The Afternoon Dispatch is written by BillOReilly.com staff.

‘The glass is always half-full’ … ‘a silver lining in every cloud.’  Pick any cliché you like about unbridled optimism, and it applies to President Donald Trump.  When it comes to looking at the bright side, he ranks up there with Dale Carnegie and Forrest Gump.  But while confidence in the future is a worthy trait, it can also backfire and give ammunition to one’s critics.

One case in point, while not especially significant, is the White House Correspondents’ Dinner that was abruptly canceled when the armed madman stormed the event.  Trump’s immediate instinct was to vow that the dinner would be rescheduled and take place within 30 days.  Even though a president has no real control over the event, he assured everyone that the second edition would be bigger, safer, and better.  That 30-day deadline is here, and it seems increasingly doubtful that there will even be a dinner, let alone one that is bigger and better.  To most Americans, that is no great loss, and this unfulfilled pledge is trivial.

Far more consequential are Trump’s always-confident predictions about the war in Iran and the U.S. economy.  The war’s end is always a few days or a week off, he assures us, after which there will be a golden age of peace, prosperity, cheap gas, and a boom unlike any in American history.  Every patriotic American hopes the president is correct – just imagine a world in which Iran’s terror threats are finally neutered, and Israel can live in relative peace (‘relative’ because the world is filled with too many Jew-haters for Israel to exist unthreatened).

That tendency to look at the world through rose-colored glasses differs by political party.  With America nearing its 250th birthday, Pew Research conducted a poll about Americans and the future.  Most adults in this country feel the country’s best years are behind us, but there is a sharp divergence on different sides of the political divide.  2 in 3 Democrats believe the country has seen its best days, and the most pessimistic Americans of all are self-described liberal Democrats.  Their gloom is no doubt affected by hatred for the guy in the White House, but even before Trump, Democrats warned of impending doom from ‘climate change,’ AIDS, acid rain, overpopulation, pestilence, nuclear annihilation, starvation, and a host of other perils.  There seems to be something in the progressive DNA that worries and warns, warns and worries.  Today’s most prominent progressives, whether Kamala Harris or Gavin Newsom or Alexandria Ocasio-Cortez, always remind us that the very survival of our democracy, even our planet, is teetering on the edge.

President Trump might be well-advised to tone it down a bit, but that’s extremely unlikely.  Optimism has worked for him in business and in life for more than half a century, and he’s not going to suddenly morph into a modern-day Cassandra, the doomsayer of Greek mythology.   Donald Trump seems to follow the thinking of Albert Einstein:  ‘I’d rather be an optimist and a fool than a pessimist and right.’  Of course, the most desirable outcome is to be both optimistic and correct. 

Naturally, Donald Trump’s legion of enemies accuse him of blatantly lying when he makes grandiose predictions, but they might remember the wise words of that famed philosopher George Costanza, son of Frank and Estelle of Queens, New York.  ‘Jerry, just remember,’ George told his best friend, ‘it’s not a lie … if you believe it!’

The views expressed in the Afternoon Dispatch are those of BillOReilly.com staff.
Posted by BillOReilly.com Staff