Why Ending Sentences with Prepositions Is Finally Okay

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For decades, a quiet but persistent anxiety has haunted many English speakers. It is the fear of the dangling preposition. We are taught from an early age that a sentence should not end with a word like “with,” “for,” or “in.” We are told to say “for whom the bell tolls” instead of “who the bell tolls for.” We are taught to say “the person with whom I spoke” rather than “the person I spoke with.”

Recently, that anxiety was shattered by an announcement from Merriam-Webster. On Instagram of all places, the dictionary announced that it is now okay to end a sentence with a preposition.

For Eli Amdur, veteran journalist and host of Vantage Point, the news was a personal earthquake. Raised by self-educated parents who wrote beautifully and schooled in the rigorous public school systems of the 1950s and 1960s, Eli had internalized the rule as law. In his fifteen years teaching graduate leadership and communication at Fairleigh Dickinson University, he admits to running out a significant amount of red ink correcting students for this very error.

But as Eli discovers in this episode, the rule was never as absolute as we were led to believe. In fact, the rejection of the rule is a testament to the unique flexibility of the English language itself.

The Churchill Anecdote

To understand why the rule is fading, Eli turns to a famous, if perhaps slightly apocryphal, story involving Winston Churchill.

According to the anecdote, Churchill was drafting a speech when his editor began returning his pages with notes asking him to move the prepositions to the beginning of the sentence. Churchill, a man who took great pride in his command of the language and his individual style, finally snapped. He wrote in the margin:

“This is the bloody sort of nonsense up with which I will not put.”

The point of the story is not just the rebellion, but the clarity. The editor’s corrections made the sentence stiff, archaic, and difficult to parse. Churchill’s version, ending in “put,” is punchy, clear, and powerful. It demonstrates that rigid adherence to grammatical formulas can sometimes sacrifice the very thing grammar is supposed to serve: effective communication.

Why English Survived

The deeper reason the preposition rule is dissolving lies in the history of the English language. Today, English is the most spoken language on earth. It is a first, second, or third language for more people than any other, the mother tongue, principal language, or official second language of no fewer than 56 countries, and spoken by an estimated three billion people.

Yet, a millennium ago, English nearly went extinct.

In the 10th century, the Norse invaded, and in 1066, the Normans arrived. Historically, when larger, stronger forces invade a region, the native language usually disappears. The dominant culture imposes its language, and the local tongue fades into obscurity. With English, the opposite happened.

How did a language limited to Northumbria, spoken by perhaps 30,000 people, come to dominate all others? Eli argues that it is because English is porous, flexible, creative, and forgiving.

Unlike languages with rigid, closed structures, English absorbs words from other languages and makes them fit. It creates more new words and idioms each year than all other languages combined. Crucially, it allows common usage to become formal rules. The acceptance of the dangling preposition is a perfect example of this organic evolution. The rule died because people stopped following it, and the language adapted to the people, not the other way around.

The Lesson from D-Day

The theme of flexibility and trust carries Eli into the “Great Minds” section of the episode, where he turns to Dwight D. Eisenhower and the D-Day invasion.

On the morning of June 6, 1944, the Allies had no business thinking they would win. The German response to the invasion had to climb the chain of command to Adolf Hitler. Hitler was a micromanager who allowed no decision without his consent. On that specific morning, he was asleep with orders not to be woken. Consequently, Field Marshal Erwin Rommel, arguably the most accomplished general alive, could not commit the German armor that was sitting just miles away from the beaches.

In contrast, the Allied commanders on the beaches had the trust of their superiors. Roosevelt, Marshall, Churchill, and King George VI trusted Eisenhower to make decisions and adapt in real-time. That day was won not just by force, but by the ability to think and act without waiting for permission from above.

Eli recalls standing on the beaches of Normandy with his family on the 50th anniversary of D-Day, reflecting on the cost remembered at the American cemetery at Colleville. The lesson for leaders today is clear: trust your team. Do not micromanage the details to the point of paralysis.

Eisenhower captured this philosophy in two enduring quotes:

“In preparing for battle I have always found that plans are useless, but planning is indispensable.”

“Pessimism never won any battle.”

Consider the alternative. What if Eisenhower had not had the trust of Roosevelt, Marshall, Churchill, and King George VI, the way Adolf Hitler would not give his trust to any of his own commanders? Think that one over.

Final Thoughts

The story of the preposition and the story of D-Day are more connected than they first appear. Both illustrate the power of adaptability and the danger of rigid control.

As Eli concludes the episode, he offers two final aphorisms to guide your thinking:

“Focus not as much on what your eye can see, but on what your mind can imagine.”

“When opportunity knocks, it doesn’t wait around very long for your answer.”

Whether you are writing a sentence or leading a team, the key is to remain flexible, trust the process, and be ready to act when the moment arrives.

Listen

If you want to hear the full discussion on language rules, the history of English, and the leadership lessons from D-Day, listen to the full episode below.

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This episode is supported by Vantage Point’s Executive Sponsor, Stephen Bozer, SVP of Human Health at Flavine Also supported by Major Sponsor Bergen Volunteers, neighbors serving neighbors across 70 towns in Bergen County since 1966 Also supported by Major Sponsor Kardam Consulting, strategic counsel for the business of making medicine

Vantage Point – the podcast for critical thinkers. We’re not political, just critical.