Arguably the greatest British hero of all time, Horatio Nelson changed the course of history not once, not twice, but on three separate occasions.
Known as “Britannia’s God of War”, Nelson lived a life characterized by duty and service to King and Country. His dominance on the seas mirrored that of Napoleon’s on land — so much so that Napoleon himself even kept a bust of Nelson on his dressing table.
On one occasion, however, Nelson flagrantly disobeyed orders, taking a major gamble in the midst of battle. For a moment, he seemed doomed for disaster.
Yet through his leadership, decision making, and jaw-dropping physical courage, Nelson led his men to an unthinkable victory — and achieved something no other British officer of the past 300 years had ever accomplished.
This is the story of the Battle of Cape St. Vincent, and how Horatio Nelson disobeyed orders to glorious results…
The Stakes
February 14, 1797. Britain’s Royal Navy faces down a massive Spanish fleet sailing near the Cape of St. Vincent, off Portugal’s southern coast. Sailing to rendezvous with the French, the Spanish fleet poses an existential threat to Britain — if the Spanish and French succeed in joining forces, they will outnumber the Royal Navy, seize control of the British channel, and launch an invasion of England.
At stake is control of the seas — and with it, Britain’s ability to defend its homeland.
Commanding the British fleet is Admiral Sir John Jervis, a seasoned leader known for his strict adherence to discipline. As the fog lifts on the day of battle, his lookouts finally spot the immensity of the Spanish fleet — no fewer than 27 ships of the line, including the 130-gun Santísima Trinidad, the largest warship in the world.
Despite having just 15 ships of the line in his own fleet, Jervis knows he has no choice but to engage the Spanish. In the admiral’s quarters of his flagship Victory, he draws up a battle plan. Intending to pursue a rigid battle formation to exploit British discipline and gunnery superiority, he sends out the order to his ships:
Form in a line of battle ahead and astern of Victory.
By maintaining a line formation, the British can split the Spanish armada, take down the main contingent first, and then tackle the remainder. But as the battle is joined and the fleets maneuver, it becomes clear that things are not going to plan.
The first half of the British line splits the Spanish fleet, but in doing so cedes the windward position to the enemy. Should the rest of the British ships hold the line of battle, the Spanish can circle around them upwind, unite their two divisions, and escape.
This is the critical moment — and it is precisely here that Horatio Nelson makes his move…
Breaking the Line
Jervis’ orders are clear: the fleet must hold formation. But Nelson, towards the end of the British line on the deck of HMS Captain, sees something others don’t.
He realizes the winds are changing — and that in the time it takes the British to turn around and tack upwind after their initial pass, the Spanish will have escaped their grasp. Defying orders, he breaks formation and heads out alone towards the Spanish fleet, seeking to cut off their retreat.
His audacity in breaking the line of battle — a decision for which he could easily be court-martialled and expelled from the Royal Navy — is matched only by his audacity in choosing which ship to attack. He heads straight for the Spanish flagship, the Santísima Trinidad.
Nelson is drastically outgunned. The HMS Captain’s 74 guns are no match for Santísima Trinidad’s 130. But that’s not the only ship Nelson takes fire from — five more Spanish ships of the line cluster in around him, battering the Captain from no fewer than six sides.
“Desperate situations require desperate measures,” Nelson later writes. But suicidal as it may seem, there’s a method to his madness. As the Captain is being torn apart by cannon fire, Admiral Jervis looks on from his flagship, and begins to recognize what Nelson is up to.
The commodore’s head-on charge into the Spanish fleet has cut off the enemy retreat and isolated a cluster of their ships. What’s more, the Spanish formation starts to break up as they converge on Captain. Jervis sees Nelson hasn’t just bought the British time — he’s bought them an opportunity.
Doing all he can to communicate through the chaos and smoke of battle, the admiral signals to a few key ships to break off and support Captain. As crazy as it is, Nelson’s gamble might be just enough to turn the tide of battle…
Two Ships, One Hero
Back on HMS Captain, Nelson collapses as a cannonball rips through wood panelling next to him, sending giant splinters flying. One of them strikes Nelson in the abdomen and punctures his stomach — leaving him with an injury that will plague him for life.
Nevertheless, Nelson is back on his feet in no time. Seeing his ship falling apart around him, he knows he can’t hold out much longer. So he orders his captain to take what’s left of the wheel and ram their vessel into the nearest Spanish ship of the line.
Within striking distance is the San Nicolás, and soon HMS Captain’s bow smashes into the rear end of her starboard side. Having armed his men with everything from cutlasses to kitchen knives, Nelson and his men swarm the ship:
The first man who jumped into the enemy's mizen chains was Commander Berry, late my First Lieutenant; he was supported from our spritsail yard, which hooked in the mizen rigging. A soldier of the 69th Regiment having broken the upper quarter-gallery window, I jumped in myself, and was followed by others as fast as possible. I found the cabin doors fastened, and some Spanish officers fired their pistols: but having broke open the doors the soldiers fired, and the Spanish Brigadier fell, as retreating to the quarter-deck. I pushed immediately onwards for the quarter-deck, where I found Commander Berry in possession of the poop, and the Spanish ensign hauling down. I passed with my people, and Lieutenant Pearson, on the larboard gangway, to the forecastle, where I met two or three Spanish officers, prisoners to my seamen: they delivered me their swords.
-Horatio Nelson, recounting the boarding of the San Nicolás.
For the first time in 300 years, a British officer has taken an enemy ship by boarding. This alone merits being welcomed home a national hero — but it’s a feat that’s about to be topped.
As Nelson receives the swords of the surrendered Spanish officers, musket fire suddenly rains down from above. Another Spanish ship, the even larger San Josef, has become entangled with the San Nicolás in the confusion of battle.
San Josef’s deck is raised a level above that of the San Nicolás, making it impregnable to assault — or so it seems. In a scene even Hollywood would hesitate to film for fear of seeming unbelievable, Nelson leads his men on another charge — this time jumping from the deck of San Nicolás onto the hull of San Josef, using the external chains and rigging to pull themselves onto the deck.

The feat is so remarkable that the Spaniards are too stunned to react, and they surrender the moment Nelson steps on deck. Just like that, Nelson has taken not one but two Spanish ships of the line by boarding.
As he celebrates what is arguably the most remarkable feat of daring in Royal Navy history, Nelson looks around him. As far as he can see, his gamble has paid off — two other Spanish ships of the line and over 3,000 troops have surrendered, and English losses are minimal.
Nelson breathes out a sigh of relief. The battle has gone decisively to the British. For now, England is secure.
Takeaways
1) See the Bigger Picture
Nelson's position towards the rear of the British line allowed him to see how the battle was developing. He only broke orders because he understood the stakes better than anyone else at that moment. Only disobey an order if you’re fully confident your reading of the situation is the right one.
2) Act on Experience
Nelson’s decision to break from the line of battle wasn’t as reckless as it seemed. His confidence came from years of experience and a deep understanding of naval warfare. If you’re going to disobey, make sure you know why you’re doing so — bold actions succeed when they are rooted in expertise, not arrogance.
3) Lead the Boarding Party
Nelson’s courage on deck inspired his men to follow him into what seemed like an impossible situation. His physical courage during battle — whether in pushing through his stomach injury or jumping onto enemy ships — gave his men the fire they needed to do the same. True leadership isn’t about issuing commands from safety, it’s about standing shoulder to shoulder with your men when they need you most.
Want to dive deeper?
I hope you enjoyed this email — it took me much longer to write than usual, thanks to the time I spent researching the ins and outs of naval combat in order to better share this story with you.
Tomorrow, James and I go live on X at 9am ET to dive into the life of Horatio Nelson, and the 3 moments in which he turned the tide of history (this battle being the first!)
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Tomorrow, paid subscribers will receive a deep dive analysis of Nelson’s life — and why his heroic deeds still resonate with us so powerfully today…
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Hope to catch you on the stream tomorrow!
Ad finem fidelis,
-Evan