Malta: World War II’s Most Intriguing “What If?”

The Irresistibility of World War II “What Ifs?”

History buffs love to contemplate alternative scenarios. World War II is a particularly rich trove for novices like me to indulge in such debates. Some of the more popular ‘what if?’ scenarios include assessing the war’s outcome if Hitler kept his tanks rolling to the beaches of Dunkirk in mid-1940, if the Japanese found the American aircraft carriers docked at Pearl Harbor on that infamous December 7, if Hitler focused exclusively on taking out Moscow in late summer 1941 instead of shifting forces to focus on Kiev, if the Germans reacted quicker on D-Day to crush the Allies beachhead, and if America did not have the atomic bomb and attempted an invasion of Japan. Through the years I’ve consumed countless hours reading about, mulling over, and debating with others such scenarios.

The Republic of Malta’s Embassy, captured by author during a recent trip to Washington D.C.

Yet my favorite World War II ‘what if?’ scenario is one that does not garner much interest beyond dedicated military history fans and professional historians. It revolves around the tiny Mediterranean island of Malta. The question is a simple one: what if Germany invaded Malta in the spring/summer of 1941 instead of Crete and delayed the decision on invading Russia (Germany’s Operation Barbarossa kicked off in June of that year)? I believe the answer is that World War II would’ve ended up very different, and not in a good way.

Everyone Saw the Obvious (Except for the Chief Decision Maker)

What’s scary about an Axis invasion of Malta is that many of Hitler’s best generals and his Italian ally Benito Mussolini all wanted to do just that. They named the plan Operation Hercules. And the British feared it.

In February 1941 German General Erwin Rommel arrived in Tripoli, taking command of what eventually becomes the Afrika Korps. Britain was sitting on a precarious precipice in Africa, with Sir Winston Churchill calling it, “the peg on which all else hung.” Churchill in April 1941 proclaimed losing Egypt and the Mideast “would be a disaster of the first magnitude to Great Britain, second only to successful invasion and final conquest!”

Rommel’s abilities in the field only intensified the concern of the British in Africa. The Desert Fox shared Churchill’s strategic assessment of Africa: Rommel advocated to ignore Greece, go after Malta, secure supply lines to Africa, and then take Egypt, the Suez Canal, and the Mideast oil beyond. The British Empire would be severed in two. An immediate invasion of Russia in the summer of 1941 was not necessary under this plan of attack, since once Africa and the resource-rich Mideast were secure, Germany could deal with Russia at its own choosing and across several different fronts of attack, including the Caucuses.

Rommel’s boss and rival, Field Marshal Albert Kesselring, agreed with him (the two did not care for one another; Rommel had more charisma but Kesselring was probably the better commander). So too did Grand Admiral Erich Raeder, who advised Hitler in May 1941 for a decisive Egypt-Suez offensive in autumn 1941. And Italian dictator Mussolini was fully supportive of focusing on Malta.

All understood that Malta posed a constant threat to Axis supply lines in the Mediterranean. Supply limited what Rommel could do. If the convoys had a bad week, Rommel halted; if supplies made it through, Rommel was virtually unstoppable.

In May 1941, if Germany dropped paratroopers onto Malta instead of Crete (which was strategically and tactically irrelevant) and the Italian navy kept the British Mediterranean fleet at bay for a short period of time, the exhausted and depleted island would likely fall. Malta in Axis hands would provide air superiority over the Med, which would allow Rommel better reinforcements, turning the tide of Africa to the advantage of the Axis. Egypt would fall, the Suez Canal would be seized, access to Mideast oilfields would be open, and perhaps it would’ve brought down Churchill and his government, incentivizing the British to press for peace.

Best yet for Germany under this scenario, a Malta invasion would’ve delayed or canceled the disastrous June 1941 invasion of Russia. Ironically, the reason Hitler decided to not invade Malta, so he would not need to delay Operation Barbarossa, ended up being his biggest strategic blunder of the war and led to his demise. Few decisions were as decisive as Malta in World War II: one decision has Germany likely victorious and the opposite decision leads to inevitable, crushing defeat.

What Happened Instead: Hitler’s Epic Barbarossa Blunder

Despite the chorus of voices from his leadership circle, Hitler would have none of the Malta invasion talk. Instead, in 1941 Germany went after Crete in May and invaded Russia in June with Operation Barbarossa. Hitler decided to attempt to render Malta useless by relying on constant air assaults. Once a Malta invasion was off the table, Rommel hoped he could get to Cairo without the island secured.

It’s hard to overestimate how massive of an effort Barbarossa demanded on Germany and the Axis. Over three and a half million Axis troops attacked along an 1,800-mile front. Eighty percent of the German army was assigned to the Russian front. Think about what Rommel may have accomplished if he had something even close to Barbarossa forces in Africa, and the resulting secure supply lines, that Axis control of Malta would’ve provided.

Sure to his word, Hitler had the Luftwaffe and Italian air forces pound Malta relentlessly in 1941 and early 1942 (by December 1941 the island sustained over 1,000 bombing raids). The first half of 1942 saw German and Italian air raids ruin Malta’s capacity to function, and Rommel received 90% of his reinforcements during this time. But in late April 1942, Kesselring lost many of his squadrons in the Med to reassignment on the Russian front.

Churchill saw his opening and did not hesitate to act decisively to supply Malta. The Allies put together a massive convoy destined for Malta and named the effort Operation Pedestal. Statistically, the Axis won the battle of Pedestal, and the convoy took a brutal beating in the summer of 1942. But enough of the Pedestal supply made it to the island to buy her valuable time until the late 1942 Allied victories of the invasion of North Africa (Operation Torch) and Field Marshal Bernard Law Montgomery at El Alamein. Churchill knew what Pedestal meant when he said, “when this war is a misty memory in the minds of old men, they will still talk of the convoy for Malta which entered the Mediterranean in August 1942.”

Four Lessons the Malta Decision Teaches Us

The events surrounding Malta in World War II inform us of four vital lessons that are applicable today.

Lesson #1: Know Thy Opposition

First, although Hitler made strategic blunders (perhaps the biggest being Malta/Barbarossa), often refused to listen to his generals, and was a monster, there was one arena where he was unrivaled in his ability: reading and understanding the politics of his allies, rivals, and enemies.

Hitler understood the Allies’ weakness wasn’t in technology, industry, weaponry, or strategic positioning. Instead, he knew the weakness lay in the democracies’ longing for peace, leaders who were idealists, and populations desiring to be left alone. Hitler saw this and used those traits against his rivals and ultimate enemies to grow his power to the point where it altered the course of history and ruined millions of lives.

This first lesson has parallels today. A new axis aligned against the western democracies is taking shape with China, Russia, and Iran. Instead of Chamberlain willing to appease Germany to secure “peace in our time” to save Europe, we have Climate Czar Kerry willing to appease China to secure nonbinding carbon reduction pledges to save the planet. If leaders like Xi are paying attention and can read rivals, I fear the outcome today might be similar to that in the 1930s.

Lesson #2: Allies Matter

Second, allies can look good on paper or on a map, but they can make situations complicated and end up being a net detriment. Such was the case with Italy and Germany in World War II. These two nations had a complex relationship.

Approaches to Mediterranean sea power differed greatly. Germany was constantly frustrated with Italy’s unwillingness to commit its capital ships in battle. The Italian navy was formidable, but constantly torn between viewing taking on the British navy as a historic opportunity or a mortal threat. The British suffered no such hesitation, and saw the purpose of capital ships to engage in battle.

Mussolini regretted by spring 1942 the alliance with Germany (prior to throwing his full support behind Hitler, Mussolini attempted to forestall the outbreak of war and considered allying Italy with Britain and France) and the empty promises that came with it. Conversely, Hitler viewed Italy as a burden, not an ally, and ultimately preferred Italy had remained neutral. Amazingly, the alliance placed both nations in a worse off position during the war and helped lead to their demise.

The lessons here are to choose allies carefully, think through what you expect to gain from them, and preserve your reputation of living up to your promises once in the alliance. The Italian-German pairing in World War II shares traits with the current debacle in Afghanistan, with the now exposed/fallen Afghan government in exile and the lost credibility of the U.S. through the Biden administration’s broken promises. Like Italy and Germany in World War II, we somehow managed to make each other worse off.

Lesson #3: Don’t Let Ideology Trump the Rational

Third, Hitler should’ve known history better back in 1941. Instead, he played right into Britain’s hands. By invading Russia, and not sticking it out in the Med, Hitler obliged Britain’s historic strategy of how to deal with powerful adversaries on continental Europe: ally yourself with a land locked nation with a large army to open a multi-front war against your enemy. Germany enabled that British strategy into action with Barbarossa.

Germany did so because Hitler allowed ideology to trump practicality in his decision making. He saw Russia and communism as the great evils to vanquish. The sooner he went on the attack against the Soviets the better – the consequences be damned. That cost Germany everything in the end, not just Malta and the Med.

Hitler’s placing ideology over rational decision making when it came to Barbarossa brings to mind the recent U.S. failed experiments in nation building and our current leaders’ obsession with placing climate change objectives over national strategic interests. A democratically elected president in a modern, free society can make as big of a blundering mess as a madman heading a fascist regime in the 1940s when ideology reigns over reality in strategic decision making.

Lesson #4: Energy Security is Vital

Fourth, so much of World War II (and, for that matter, all major global conflicts) was about logistics, supply lines, and energy security. Japan invaded southeast Asia to get oil. The U.S. imposed an oil embargo on Japan to check the Rising Sun’s march. Japan attacked Pearl Harbor in response.

The same held for the European and Mediterranean theatres. Germany had to deliver oil to Rommel from Romania, which was a long and exposed supply chain. The Achilles’ heel of the Italian navy in the Med was lack of reliable oil supply from Germany via Romania, thus the Italian fleet was never able to assume full operational range.

Yes, Barbarossa held the promise of oil in the Caucuses, but also presented existential risk to the invader. But sticking to the Med and not invading Russia would have secured oil in the Mideast and split the British supply lines in two. All of it undertaken with the same risk Germany and Italy already had signed on for.

Today, energy security drives geopolitics more than ever. Russia uses energy, particularly fossil fuels, as a tactical lever and strategic fulcrum. China fully embraces the carbon atom to grow its manufacturing prowess. Meanwhile, both nations laugh as the United States and western Europe erode their strategic positioning and stretch their energy supply lines by pursuing obtuse climate change goals into the distant future, and do so by mandating energy derived from materials, components, and equipment that can only be found and made in places like Russia and China.


In early 1941, Hitler had four ways to break Germany out and win the war; two might’ve succeeded, one likely would’ve succeeded, and one would’ve certainly destroyed Germany (and indeed, did). Fortunately, Hitler chose the last.

His first option was to invade Britain. It was risky, but if successful would win the war lock, stock, and barrel. His second option was to strangle Britain by doubling down on waging submarine warfare on shipping. That was already working and, with singular focus, could’ve brought Britain to its knees.

His third option was the best for Germany: win the Mediterranean to get into the Mideast and Asia. That would cut the British in two, link up with Japan, and secure valuable resources. Taking Malta would’ve made the pivotal difference.

His last option was invading Russia and pouring his armies east. A two-front war, with one front against a legendary foe. History showed that decision to be disastrous for prior invaders, and Hitler made sure history repeated itself.

The crucial turning point of World War II? Not the miracle at Dunkirk in summer 1940. Not summer 1942 when Rommel was stopped at El Alamein and the battle of Stalingrad commenced. Not even Japan’s attack on Pearl Harbor in December 1941.

Instead, the crucial turning point was the summer of 1941 when Hitler turned his attention away from the Med, declined to seize a little island named Malta, and instead launched Operation Barbarossa. In that light, Douglas Porch put it best with, “The Med was not the decisive theatre of the war, [but] it was the pivotal theatre, a requirement for allied success.”

For two great reads on the topics of Malta and the Mediterranean theatre in World War II, check out:

Operation Pedestal: The Fleet That Battled to Malta, 1942 by Max Hastings and The Italian Campaign by John Strawson.

Who’s Big Tech’s Daddy? Vanderbilt, Rockefeller, and Carnegie

Over the past 150 years, starting with post-Civil War Reconstruction, America has delivered to the world the largest improvement in quality of life in history. Capitalism, free enterprise, and individual rights were the ideological columns that allowed the edifice of the human condition to rise.

As you sit in your climate controlled home, streaming movies, using Door Dash for dinner, and waiting for your vaccine of choice, you might ascribe all this technological innovation and progress to the behemoths of big tech: Apple, Google, Amazon, and so on. Certainly, these modern-day FAANG titans sit at the fore of the idea economy.

Yet our modern economy of services and ideas consists of tiered levels, with the prior tier serving as a necessary and supporting base to the next tier. No internet, no digital streaming. No electricity, no internet. No carbon, no electricity. And so on, back to the most fundamental building blocks of an economy.

Americans have lost sight of this fundamental economic truth, blinded by the mesmerizing clicks and taps of apps. Add to the mix fabricated mistruths about the demise of the “old economy” spewed by the elite and the Left in academia, government, and monied foundations, and many of us today are transitioned from uninformed to misinformed when it comes to drivers of the economy and our lives.

A historical refresher is in order.

Our modern economy is built upon five successive pillars, each one rests atop predecessor pillars and supports subsequent pillars. Lose one pillar and you lose the pillars above it. Let’s meet the new bosses, same as the old bosses.

Pillar #1: Don’t Call Them Robber Barons

Everything we enjoy in our modern life traces its roots back to, and continues to depend on, the founding fathers of our economy. Most of them rose to prominence in the period of American history after the Civil War and before World War I; a time where industry rebuilt and then drove America to global prominence.

The three faces that sit on this pillar’s Mount Rushmore are Cornelius Vanderbilt, John Rockefeller, and Andrew Carnegie. Vanderbilt built, integrated, and consolidated the transportation network, specifically rail, that allowed a nation to grow and its industry to thrive. Rockefeller took the fragmented and disorganized industries of oil and refineries and brought order that spurred the innovation of new products, including gasoline. Carnegie was the visionary who saw the need for a new product to build our cities and structures: steel.

Innovating from their home bases of New York, Cleveland, and Pittsburgh, these three men along with others fused a backbone of the American economy that we depend upon to this day. They were far from perfect, as incidents like the Homestead Strike painfully illustrated. But they were great, and we owe them a debt of gratitude.

Most importantly, they set the stage for Pillar #2 of our modern economy.

Pillar #2: Finance Powers Innovation

As railroads, steel mills, and refineries grew into industrial titans, finance evolved into a powerful catalyst to accelerate progress and spur more innovation.

J.P. Morgan revolutionized finance as an instrument to optimize commerce, and he was not afraid to get in between Rockefeller and Carnegie where he saw opportunity to create value (for example, Morgan bought out Carnegie and created U.S. Steel). Morgan showed how the purse could be a force to be reckoned with, even for the world’s most powerful industrialists.

J.P. Morgan also funded new innovators and innovations, playing Thomas Edison and George Westinghouse against each other as they demonstrated and commercialized electricity generation. Edison brought us light, he and his competitor Westinghouse established electricity generation at scale, and Morgan provided the capital to enable all of it (Morgan eventually took control of Edison’s company and recast it as General Electric).

But if no rail, oil, or steel, then no modern finance and electricity. Once these two pillars were in place, it set the stage for the next pillar that would fundamentally reshape the world.

Pillar #3: The Societal Impact of the Modern Assembly Line

Thankfully, at about the time politicians and bureaucrats were working to take down the Standard Oils of the world, a new breed of creators appeared on the scene to keep progress moving. Henry Ford took the recipe ingredients of steel, gasoline, finance, and electricity to revolutionize manufacturing with the modern assembly line.

Ford’s assembly line made automobiles affordable. His manufacturing innovations also established an eight-hour workday and a living wage for workers, who would then have both the time and money to purchase and enjoy cars. That drove up the demand for cars, making Ford more profitable. Policy makers have been trying to replicate this virtuous circle ever since.

Others took note of what Ford was doing in autos and looked to copy it for other products. Hershey figured it out for candy while others applied it across a spectrum of industries. The worker and consumer both benefitted, with increasingly worker and consumer being one in the same. In many ways, the American middle class was the most impactful innovation of this pillar.

All of Ford’s necessary ingredients came from predecessor pillars. Without them, there would be no assembly line, all the consumer benefits that derived from it, or a middle class. Nor would there be the benefits of the next pillar that Ford and his peers made possible.

Pillar #4: Rise of the Service Economy

The prior three pillars of the economy provided the feedstocks to efficiently manufacture consumer goods. Workers increasingly were able to enjoy and afford these products, driving up demand. And technology expanded the gameboard of what and when things could be enjoyed.

All of this birthed what we know today as the service sector of the economy. Mechanics were in demand to repair cars. Beauticians were wanted to assist with application of makeup and hair care products. Entertainment became a massive industry as movie theaters and television became ubiquitous.

Before you knew it, the service economy was as big, or perhaps bigger than, the manufacturing sector of the economy. But without a strong manufacturing base, there would be no service economy. If you don’t build it, you won’t service it. If you lose the large number of high paying jobs in manufacturing, people won’t be able to afford services. Obvious to most, but frustratingly foreign to many politicians and policy makers today.

Everything was now in place for the fifth and final pillar.

Pillar #5: The Idea Economy

The prior four pillars set the stage for increased specialization, innovation, and widespread technology diffusion. Suddenly everyone had computers, cell phones, and internet access. Entrepreneurship blossomed and the largest corporations in history were created by thinkers tinkering in garages.

Big tech and the idea economy are awesome innovators and innovations. Yes, at times their power needs to be checked when impeding individual rights such as free speech. And these entities must be constantly reminded that their initial and ongoing success hinge on the underlying pillars they rest upon. But like Rockefeller and Carnegie before them, we are much better off with today’s tech titans than without them.

What’s Next?

Donald Rumsfeld famously referenced “known knowns” (things we know that we know) and “known unknowns” (we know there are some things we do not know). Our 150-year American economic journey of prosperity has definitively proven Rumsfeld’s two axioms true.

Our “known knowns” are that if you sabotage any of the underlying economic pillars, you will unleash the widespread collateral damage of ruining the subsequent pillars. That’s true even when the aspiring destroyers are trumpeting the need to do so under the banner of the public good or saving the planet.

The “known unknowns” are the future pillars to be created and brought to society. We don’t know what they are or when they will appear. But we do know the frequency and timeliness of them will hinge on our ability to protect the current pillars and nurture the ideological columns that made them possible: capitalism, free enterprise, and individual rights.

Post that in your app and stream it.