In the days that followed, Isaac continued his routine—training with his guards every morning, sharing meals with them at noon, and leaving his afternoons free.
The Venetian magistrate Miloto did not make things difficult. On the third morning, the large galley St. Nicholas arrived at the harbor of Constantinople.
"Captain Fidel of the St. Nicholas sends his regards, Your Highness."
Led by Captain Fidel, the entire crew presented themselves to their new employer.
Miloto had prepaid six months' wages and included two months' worth of provisions.The galley was almost fully manned with well-trained slaves.The ship's overall condition was excellent.
Such was the Venetian way—greedy but efficient.If it had been their Genoese rivals, they would have sailed their fleet up to your face, aimed cannons at your nose, and asked if you wanted to buy one of their scrap ships.
Isaac gave a customary speech to encourage the sailors, handed over five ducats for them to drink to the emperor's health, and allocated another hundred ducats to the captain to recruit more sailors and slaves, and buy additional supplies.
There was still ample space on the ship—it could hold at least a hundred slaves.
In times of war, galley slaves were strategic resources. The more you had, the less you had to worry about their lives, and the faster your ship could go.
A hundred ducats was more than enough for this, and whatever remained served as Isaac's welcome gift to the captain and his lieutenants.
You couldn't afford to be stingy with unruly sailors—one had to constantly ensure they wouldn't sell you out to the Ottomans for a bag of gold.
If someone offered a price for my head, remember—I'll pay double.
That's how Isaac would stay alive—and how the dream of reviving Rome could continue.
However, at this point, Isaac was left with only a few hundred ducats.
Looking at his rapidly shrinking fortune, he felt like crying.
That evening, Isaac again visited his uncle, Emperor John VIII. The emperor was still immersed in joy, and the dinner was pleasant and cheerful.
Taking the opportunity, Isaac requested to expand his personal guard to a hundred men—keeping the original twenty cavalry and adding eighty infantry and archers.
He had a solid reason: he would be joining the campaign in Corinth in the south.
By this time, the Byzantine Empire had completely lost its pool of quality soldiers. Both the themata and tagmata systems had collapsed. Constantinople's defense relied on fewer than 3,000 men, with some walls guarded by local militias and church wardens.
A hundred men wasn't much—but it wasn't small either.
The emperor hesitated, but eventually agreed. However, he only promised to help recruit the soldiers—the costs would fall to Isaac.
Isaac gritted his teeth and handed over 300 ducats.
"Please, Your Majesty, find me some strong lads. We're going to war at sea—malnourished peasants and untrained citizens won't help us."
"I'll see to it," John VIII promised.
Over the next few days, recruits arrived steadily. Isaac's personal guard was relieved of patrol and sentry duties.
To be fair, John gave Isaac face. Of the 60 new infantry, many were of lower noble birth. They came equipped with chainmail, helmets, spears, round shields, and swords—and were all sturdy, devout Orthodox Greeks loyal to the empire.
The 20 archers were descendants of Serbians from the mountains who had long served the empire as mercenaries. They were armed with powerful bows, leather armor, and curved swords.
John even selected horses from the royal stables for the cavalry to rotate.
Uncle still doted on Isaac—just the cost of these soldiers' equipment far exceeded 300 ducats.
Once the troops were assembled, Isaac rushed them out to sea for drills, hoping to help them adapt to the motion of the waves as soon as possible.
Isaac trained alongside them.
The Aegean and Marmara Seas lacked violent waves—the whole Mediterranean was known for its calm waters and high salinity. Most of the time, it looked like a sparkling pond.
Still, the ordeal was enough to make any land-bound man seasick. Isaac was no exception.
After vomiting up both breakfast and lunch, Isaac deeply regretted everything.
On deck, seasoned sailors pointed and laughed uproariously.
The soldiers weren't pleased, but seeing their twelve-year-old prince hurling beside them silenced any curses they might have had.
Back on solid ground, everyone's souls seemed to sing.
"My brave soldiers—tonight's drinks are on me. May His Majesty live forever!"
Isaac pulled out five shiny ducats and asked Captain Michael to arrange a banquet.
The troops had heard about the sailors enjoying the prince's wine—no doubt they were expecting the same.
Fairness was essential—there could be no favoritism.
Watching the cheering soldiers, Isaac wiped the sweat from his brow.
Everything was ready—now they just had to wait for the supply ships.
Two days later, on November 11th, 1444, Emperor John VIII reached an agreement with the Latin merchants: Venice would lease two merchant ships to transport supplies and equipment.
Thus, Isaac's core force—including his 100-man guard led by Michael, his retinue led by Andre, and the galley St. Nicholas captained by Fidel (with 53 sailors and 56 slaves)—was fully assembled and ready to escort the convoy.
By dusk, sailors were loading crates of food, barrels of fresh water, arrows, and gunpowder onto the deck. Soldiers boarded the ship, waving goodbye to the crowd ashore.
Slaves, under harsh supervisors, checked cannon magazines and maintained sails and rigging.
The two merchant ships—Independence from Pisa and Harrier from Venice—were also prepared. Captains and officers conducted their final inspections.
Isaac was the last to board St. Nicholas, gazing at the city.
The port was Prosphorion on the Golden Horn. To the north lay the Genoese colony of Galata; to the east, the ancient acropolis was just visible.
A crowd of citizens had gathered to send the fleet off, cheering "Long live the Emperor!" and praying for victory.
"Your Highness, all is ready," Captain Fidel whispered.
Isaac took one long look at Constantinople, now fading into twilight, then turned.
"Set sail!"
At the emperor's request, the fleet first circled the city, so more citizens could see the imperial purple double-headed eagle on the prow, stirring national pride.
The ships glided past the acropolis, Hagia Sophia, and the Grand Palace. The church bells rang to send them off.
Rounding the peninsula, the convoy entered the Sea of Marmara. More crowds had gathered at the southern ports to bid farewell.
The people had been oppressed for too long. The Byzantine Empire had not known military victory in ages. Raised on tales of Constantinople's past glory, they now lived under the looming shadow of Ottoman cannon fire.
The recent victory by Isaac's father in Corinth and the northern crusader campaign had stirred national hope.
"Let's go!" Isaac commanded.
The fleet, bearing the hopes of the people, raised its sails and headed south.
Shortly after Isaac's departure, citizens slowly dispersed, still buzzing with excitement.
On the northern road, a courier lashed his horse with desperate urgency, his face twisted in terror.
At the city gate, a guard blocked his path.
"No entry after dark!"
The courier collapsed, gasping for breath.
"Varna... defeated... the Polish king... dead... the army... all gone..."
The guard stood stunned, mind blank.
More people gathered. Cries and prayers began to spread.
At that moment, the last rays of sunlight swept reluctantly over Hagia Sophia's dome.
Darkness engulfed the city.