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How Trump's 'anaconda' tactics put the squeeze on Iran an...
Glenn H. Rey · 2026-05-12 · via New York Post
President Donald Trump speaking at a podium with coach Curt Cignetti standing beside him, welcoming the Indiana University football team to the White House.
President Donald Trump's strategy mirrors Gen. Winfield Scott, America's preeminent military mind, and his Civil War "Anaconda Plan". AP

President Donald Trump has been compared to many historical figures, by opponents (who claim he’s another Adolf Hitler) and by boosters (who cite Andrew Jackson or Teddy Roosevelt). 

With his blockade of Iran, though, maybe we should start comparing him to Gen. Winfield Scott. 

In the mid-19th century, Scott was America’s preeminent military mind, the architect of victory in the Mexican War and the “Grand Old Man of the Army.” 

As the Civil War loomed, he developed a plan to defeat the Confederacy with the smallest number of casualties possible. 

He called it the Anaconda Plan — and like its namesake it was about applying a squeeze, and squeezing hard, until its object was squeezed to death.

Rather than winning a single decisive battle or a series of major confrontations, Scott wanted to cut the Confederacy in two by seizing control of the Mississippi River, while choking off the South’s foreign trade — upon which it was enormously dependent for both money and materiel — with a naval blockade of its Atlantic and Gulf ports. 

Scott’s plan had few takers at the beginning, when enthusiasts on both sides thought the war would be finished in months, with daring cavalry charges and the like. 

But when that didn’t happen, the plan became the basis for the Union war strategy — and it worked. 

The South was beaten on the battlefield, but its loss came in no small part because it was being economically squeezed on all sides.

Today, Trump is following a similar strategy both at home and abroad.

With Iran, he’s choking off the regime’s oil money — and secondarily, he’s restricting China’s oil supply.

The US blockade of the Strait of Hormuz means Iran’s oil exports are stuck and piling up, with little room to store the accumulating product; shutting down the wells could do permanent damage. 

Iran’s alternative trade routes — with Russia via the Caspian Sea, and with China via road and rail — are meager in comparison.

The regime cares little for its suffering people, but the blockade means money isn’t coming in, the Revolutionary Guards aren’t being paid and foreign militias are getting restive.

By keeping Iranian oil from reaching its destination, chiefly China, Iran’s former customers now must pay market price — in dollars — for the oil they need.

Meanwhile, Trump has also cut deals giving the United States control of vital maritime chokeholds in the Indian Ocean, the Pacific and the Caribbean, all of them essential for going anaconda on China, should that become necessary. 

China has put a lot of effort into getting ready to invade Taiwan; Trump has been putting effort into gaining the ability to strangle China if it does. 

And here at home, Trump is pursuing a similar strangulation strategy against his opponents. 

Even after his Department of Government Efficiency was disbanded, he has been cutting off the shady transfer of billions of taxpayer dollars to programs and organizations that enriched Democratic Party cronies while seeding political warfare against Republicans.

Through redistricting in states like Texas, Florida and Tennessee, Trump is squeezing the Democrats’ built-in margin of safe seats, making Democratic control of the House more difficult. 

Colleges and universities, which have long served as money laundries and sources of activists and sinecures for the left, are now facing audits and federal lawsuits over censorship and race discrimination.

And of course Trump’s media opponents are choking, too, though that part’s mostly self-inflicted. 

Obviously fake stories and exaggeration have trust in major media plummeting — but they can’t seem to help themselves.

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They, along with many of their readers and viewers, have become hooked on the thrill of fake news, regardless of the dangers — a sort of auto-erotic self-strangulation, I suppose. 

Like the people who wanted a single decisive battle to settle the Civil War, many of Trump’s supporters, and even some of his opponents, are mystified at why he’s pursued such an indirect series of strategies. 

But Trump is a businessman, and he sees matters of policy from a business perspective. 

It’s no surprise that his attacks on his enemies, and America’s, operate along economic lines.

“No bucks, no Buck Rogers,” as a character in Tom Wolfe’s “The Right Stuff” famously put it in a passage about NASA’s gigantic moon-shot budget. 

Trump understands that thoroughly. Others will do so in time.

Glenn Harlan Reynolds is a professor of law at the University of Tennessee and founder of the InstaPundit.com blog.