After leaving Constantinople, Isaac ordered the Byzantine flag lowered and replaced with the Venetian flag of St. Mark.
Reputation meant nothing—safety came first.
Flying the Venetian flag might deter Ottoman or Mamluk naval forces from acting rashly.
In truth, Isaac's fleet wasn't weak. The St. Nicholas carried twenty naval cannons, with a large ballista mounted at both bow and stern. The crew could also engage in close-quarters boarding combat if needed.
The two merchant ships weren't lacking either—each carried ten cannons.
Out on the desolate seas, Latin merchants had always possessed a flexible moral code.
If they couldn't win: "I'm a registered merchant ship."If they could: "I'm a lawful privateer."
These were extraordinary times. Byzantine influence in the eastern Mediterranean had dwindled drastically, and its navy existed in name only.
The rising Ottomans hadn't yet had time to build a dominant fleet, relying more on overland trade routes.
That opened the door for Latin merchants and the Knights Hospitaller, who rapidly seized key trading ports and took control of the Aegean and Marmara seas.
In such an environment, pirates flourished, with participants from both the Muslim and Christian worlds, and tacit approval from both sides.
Flying the Venetian flag now could deter most pirates, including those from the Hospitallers.
They sailed by night to avoid encountering Ottoman warships.
The full moon rose, guiding the travelers at sea.
The night passed without incident, and Isaac fell into a deep sleep amid the rocking waves.
At dawn, loud voices woke him.
He flung open his door and stopped a passing sailor.
"What's going on?"
The sailor pointed out to sea.
Four Ottoman galleys, flying the crescent and star of the Ottoman navy, appeared on the horizon.
Isaac rushed to the captain's quarters, where Captain Fidel and Commander Michael were already gathered.
"Your Highness, four Ottoman galleys spotted off the port side!"
"I see them. Captain Fidel, what do you intend to do?"
"Your Highness, Venice and the Ottomans had a treaty. Normally, they don't attack each other. But Venice recently blockaded the Dardanelles, effectively breaking the pact. How they'll treat us is... uncertain."
"Their galleys are outdated. If we can strike first, and with your guards, we might be able to drive them off."
Isaac considered this and decided to observe for now.
"Your Highness, they're signaling us—they're demanding we stop for inspection!" shouted the lookout.
The four galleys spread out in a semi-circle.
Isaac examined them closely. Their design was clearly inferior—no match for the St. Nicholas.
Their sails remained up, and their oars were still.
They weren't preparing for combat. At least not yet.
Isaac made his decision.
"Have the two merchant ships prepare for battle. We'll pretend to comply to lower their guard. Tell the Venetians to wait for our signal—our cannons."
The St. Nicholas signaled back. Soon, a small boat rowed over from the Ottoman fleet.
Onboard, Captain Harsh cautiously observed the opposing fleet.
Venetian merchants rarely clashed with Ottomans—they cared more for gold than Christ's glory.
But the bastard Hospitallers sometimes flew Venetian flags to trick Muslim ships, striking once their guard was down.
The Ottoman ships stayed beyond cannon range. Harsh had been sent to inspect and collect dues.
No Christian could be trusted!
Harsh thought bitterly.
"Arslan! Why the hell are you rowing so fast?"
Harsh noticed they were nearing the big ship at alarming speed.
"Sir…" The rower's voice trembled.
"The Christian ship—it's charging at us!"
Whoosh—
A dark object flew through the air—straight at the boat.
"Abandon ship!" Harsh roared.
Boom—
The speaking sailor couldn't dodge. The cannonball took off his head.
The ball smashed through the boat.
Harsh had jumped into the sea just in time, watching his crew thrash in the water.
More cannonballs splashed nearby, sending up plumes of water.
A shockwave knocked Harsh unconscious. As he floated, his blurry vision caught sight of the St. Nicholas lowering the Venetian flag…
And raising a long-lost symbol—the purple double-headed eagle.
The St. Nicholas was at full battle readiness. Slave rowers, whipped into frenzy, strained at their oars.
"Boat destroyed! Port cannons ready! Target enemy ship right one—fire!"
The port-side cannons roared. A line of solid lead balls traced perfect arcs in the air.
Unfortunately, the Ottoman ships were just at the edge of range. The shots fell short.
"Faster! Push harder!"
Captain Fidel shouted.
All three allied ships pushed to their limits. They had to close the distance before the Ottomans reacted.
The Ottomans had taken a favorable horizontal formation.
But their ships were outdated, with too few cannons.
That gave Isaac an opening.
The St. Nicholas zigzagged across the waves, carving a giant "Z" in the sea.
Closer… closer!
The Ottomans finally responded.
Boom—
A flash of fire, a puff of smoke.
Six stone balls splashed harmlessly into the sea.
"Starboard cannons ready! Target enemy ship left one—fire!"
The St. Nicholas's starboard cannons roared. Heavy lead balls screamed toward the target.
Simultaneously, the two merchant ships opened fire.
As the smoke cleared, cheers erupted from the lookout.
"Enemy left ship hit! Mast down! Deck on fire!"
Isaac could vaguely see the broken mast and flames. The Ottoman crew cursed and fought the blaze.
With insufficient slaves to row, losing their rigging meant they were crippled.
The three remaining enemy ships fired back.
But their old-style catapults were inaccurate and weak.
The cannon duel dragged on—more a battle of incompetence than skill.
Isaac's ships focused on the Ottoman flagship, pounding it with shot after shot. It held firm but groaned under the damage.
The Venetian Harrier was hit a few times but remained afloat.
Realizing their disadvantage, the Ottomans tried to close the distance and engage with crossbows.
Captain Fidel wouldn't allow it. He ordered the fleet to hold formation, presenting broadsides for maximum firepower.
The battle shifted instantly.
Midway through, one Ottoman galley took a direct hit to its powder store. It listed and sank.
Now the Ottoman flagship charged forward through smoke and fire.
Crossbowmen on deck braced for battle, eyes blazing.
Then they saw something terrifying.
On the St. Nicholas's deck, rested and ready, Isaac's royal guards drew their longbows.
The outcome was no longer in doubt.
After a volley exchange, the Ottoman flagship raised a white flag.
Their remaining crew—dead or wounded. Isaac had lost two men, with over a dozen injured.
Isaac then forced another Ottoman ship to surrender, approached the crippled galley, and—after failed negotiations—ordered a full assault. Archers first, then boarding parties. No survivors, except slave rowers.
"Your Highness! In this skirmish, under your wise command, we sank one enemy ship, captured two by surrender, and seized one more. We captured 104 sailors and 138 slaves. What are your orders?" shouted Captain Fidel.
Isaac looked at him deeply.
He had only issued basic commands—tactical decisions had been Fidel's. Yet the captain claimed no credit.
This kid had potential.
Sharp tactics, solid discipline, and smooth people skills?
How many drinks had he poured for his previous superiors?
Isaac patted Fidel's broad shoulder, stepped onto the platform, and shouted:
"Soldiers of Rome! Today, we defeated the Turks and brought glory to the Empire!"
The royal guards cheered wildly. The sailors less so.
"But a victory deserves a reward! Fidel, Michael—three hundred ducats for you. Treat the men well once we're ashore!"
He tossed his last money pouch onto the deck. Gold ducats scattered everywhere.
"Long live the Prince!"
Everyone cheered.
The fleet pressed on. The St. Nicholas towed the disabled enemy ship. The merchant ships flanked it, with the two captured vessels in the center.
Their weapons removed, their oars manned by a third of their slaves, and closely watched by Isaac's guards.
On the third day at noon, the fleet arrived at Negroponte—a Venetian colony on the Greek peninsula.
There, news arrived of the Varna Crusade's defeat, casting a shadow over their naval victory.
Still, the soldiers and sailors were delighted to disembark, ready to spend Isaac's 300 ducats.
Isaac seized the moment to meet the Ottoman flagship's captain—the fleet's commander.
To his surprise, the man, Captain Kerman, was Greek—and Orthodox.
After some conversation, Isaac learned Kerman's backstory.
Once part of the Byzantine fleet stationed in Thessalonica, Kerman had even studied astronomy at the University of Constantinople.
When the Empire abandoned Thessalonica, its remaining ships were absorbed by Venice and the Ottomans.
A local Bey took a liking to Kerman, making him commander of a private fleet.
Kerman's job was to pose as an Ottoman official, stop merchant ships in the northern Aegean, and collect tolls.
Most merchants didn't resist—at worst, they grumbled.
Until Isaac showed up and broke the rules.
"You're Orthodox. The Ottomans didn't discriminate?"
"No," Kerman bowed his head.
"They suggested I convert to Islam, but didn't pressure me. There are still many Orthodox in Thessalonica. Though… many have converted."
Isaac was silent.
It was true—the Ottomans were relatively tolerant. Many Orthodox and Catholic Europeans served the Sultan or his Beys. Converted Greeks often gained high status. Sultan Mehmed II's favorite advisor, Zaganos Pasha, had once been Christian.
The Ottoman claim to be "Sultan of the Romans" wasn't baseless. Their rule resembled a dynastic succession more than a foreign conquest. Many Byzantine policies lived on under Ottoman rule. Their religious tolerance drew talent from all over the world.
Isaac's enemy was a thriving, rapidly rising empire.
He made his decision.
"Kerman, I am Isaac Palaiologos, a prince of the Empire. I now appoint you captain once again. Keep your trusted men—recruit more if needed. Do you accept?"
"I do, Your Highness," Kerman stood tall, hand to chest.
He had no other choice. Refusal meant slavery.
Escape was impossible—Ottomans tolerated infidels, but they despised traitors.
This was his last chance.
"Your Highness, the other captain is Bulgarian and also Orthodox. I can persuade him to join us."
Isaac nodded with satisfaction. Smart move!
That evening, Isaac dined with Michael, Fidel, Kerman, and the Bulgarian captain, Novich.
He unveiled his plans.
Of the three captured warships, the disabled galley would be sold. The other two would be upgraded and added to Isaac's private fleet.
Captured sailors who were Greek or Bulgarian Orthodox would be retained. Ottomans would become slaves.
Isaac's guard would expand to 140 men. New recruits would come from Negroponte—and must be Orthodox.
Fidel became fleet commander and captain of the flagship St. Nicholas.Kerman took command of the Northumbria, a captured galley.Novich took the Manuel, another captured galley.
Junior officers on the new ships would rotate in from the St. Nicholas crew.
Looted goods and surplus slaves would be sold to fund new cannons for the fleet.
The dinner ended on a high note.
As Isaac looked at the docked ships, his chest swelled with pride.
In just two weeks, he had become master of three warships.
Mehmed? I'll twist your skull off and drink soup from it!
My name is Isaac. Let the Ottomans beware!