Isaac's fleet stayed at Negroponte for three days.
During that time, forty new guards were recruited from nearby villages, and the disabled galley was successfully sold to a Venetian private owner for 2,000 ducats.
With minor repairs, he could easily resell it for 3,000 ducats.
The Ottoman sailors who had been reduced to slaves were sold to local nobles, destined to labor in the fields until death—or be sold off elsewhere.
There were no naval cannons available locally, so the plan to purchase additional artillery was postponed.
Recruiting new crew members, repairing damage, and replenishing supplies for the three ships cost Isaac another 500 ducats.
Now, Isaac had just over 2,000 ducats remaining.
Three days later, at dawn, the fleet set sail.
Negroponte was quite close to Athens, and by noon, the Acropolis was already visible on the horizon.
Flying the Byzantine flag, the fleet soon received a small boat sent to welcome them.
Isaac stepped onto the deck as the harbor drew nearer.
The crowd onshore cheered—they had clearly been informed of the incoming supplies.
At the front of the group stood a man in a purple cloak, sword at his waist, with a commanding gaze and heroic stature.
Constantine Palaiologos, future Basileus of the Empire, and the last emperor of Rome.
The ship docked.
Isaac was the first to leap ashore, striding toward the father he had not seen for some time.
"Salute to you, noble Lord of Mystras and Despot of the Morea,""By order of His Majesty, I have escorted provisions and military supplies to reinforce your campaign. En route, we encountered an Ottoman squadron—one ship sunk, two captured. Here is their military banner!"
Isaac took the Ottoman flag from a squire and threw it to the ground.
Cheers erupted from the crowd, and a rare smile lit up Constantine's stern face.
"Behold the Prince of Palaiologos! Behold the fleet of the Roman Empire!"
The five warships lined up, their dark gunports facing the shore.
The people roared even louder, some instinctively ducking their heads.
"All who have distinguished themselves shall be rewarded! Tonight, we feast!"
Constantine declared.
At the banquet, Isaac soon excused himself and headed to Constantine's command tent.
His father had been waiting.
Only now did Isaac have a chance to properly study this legendary final emperor.
Constantine resembled his brother Ioannes but appeared more lively and energetic.
Handsome, resolute, with piercing black eyes and a jaw covered in stubble. His healthy bronze complexion stood in stark contrast to the usual pallor of other Palaiologoi.
At this moment, Constantine was riding high.
After years of effort in the Morea and Corinth, he had assembled a force of 5,000 and, in coordination with the northern Crusaders, conquered Lepanto and Athens. The ruling Medici family had submitted, and his forces now threatened Thebes.
This was the largest military operation of Byzantium's twilight, meant to open a corridor from the Peloponnese to Constantinople and relieve the capital from isolation.
The campaign had gone well, even reaching Thessaloniki.
Had the Crusade at Varna succeeded—or even stalemated—Constantine might have succeeded.
But history had no "if." News of the Crusaders' annihilation had already reached his camp.
Local nobles who had only recently submitted were now growing restless, paying lip service while secretly defiant.
Isaac's timely arrival, along with the military success, had shocked the fence-sitters.
Some previously reluctant landlords now "generously" provided supplies.
Constantine looked upon his twelve-year-old son with satisfaction.
Voluntarily leaving the capital, selling off his inheritance, and joining the military campaign.
His eyes now sharp, his bearing calm, and his every movement brimming with confidence.
Was this really the same timid, bookish child?
Perhaps the Empire's worsening condition had awakened something within him.
So thought Constantine.
"The war is progressing smoothly. Your uncle Thomas is overseeing the siege. Thebes should fall soon."
Constantine traced the military map with his finger, stopping at Thessaloniki.
Once a major city of the Empire, Thessaloniki had briefly been reclaimed during the Ottoman interregnum.
But the emperor couldn't muster enough troops to resist the growing Ottoman threat and sold the city to the Venetians.
It didn't help. The Venetians couldn't hold it either, and in 1430, the Ottomans took full control.
Recapturing this commercial and strategic hub would improve Byzantium's dire position and fortify the new territories.
"What do you think, Isaac?"
"Father, we must not attack Thessaloniki."
Isaac answered without hesitation.
"Oh? Why not? Many officers are advising we strike while the Ottomans are still regrouping."
Constantine was composed.
Isaac cleared his throat.
"Thessaloniki has strong fortifications and is garrisoned by Ottoman regulars. Even if we take it, the losses will be severe. When the main Ottoman force returns, how will we defend it?"
"The region has a large Orthodox population. We could raise new militias—"
"Please abandon that thought, Father."
Isaac bluntly cut him off.
"The people may reminisce about the old Empire, but to expect them to rise against the Ottomans? Unlikely."
"From what I've learned, the Ottomans treat Orthodox Christians relatively well. There's no major oppression—people have little reason to resist."
Isaac paused and added,
"In fact, they might be living better than before."
Constantine's face turned red, then pale.
There was no shame in it.
In the final days of the Empire, war, internal conflict, and crushing taxation had devastated the people.
The Ottomans' enlightened policies helped them consolidate new territories quickly.
They were, in some ways, more Roman than the Romans.
"What do you propose, then?"
At last, the question Isaac had hoped for.
He'd been preparing an answer all the way here, fearing Constantine might be too stubborn to listen.
"Father, I have four major proposals."
Isaac stood up.
"First, after Uncle Thomas takes Thebes, halt the advance and pacify the people."
"Second, forcibly relocate the population, grain, and wealth from Athens and Thebes to Corinth and the Morea. Use captured spoils to fund the resettlement. Demand contributions from merchants."
"Third, mobilize laborers to quarry stone and rebuild the six-mile wall at the Isthmus of Corinth. Enhance it with artillery."
"Fourth, contact the Venetians and Genoese to see if they'd be interested in buying access to the newly captured ports."
It was a clear plan to abandon the new conquests and consolidate defensively.
But giving up months of hard-won gains would require immense resolve—and face strong opposition.
Constantine remained silent.
"Tomorrow, you'll accompany me north. I'll see to your fleet's artillery. Bring your guards as well."
He waved his hand.
Sigh. He still can't make up his mind.
Isaac had no choice but to comply and leave the tent.
It was to be expected.
Historians later described Constantine XI as a noble knight, a steadfast commander, a competent statesman—and a poor diplomat.
His grasp of the broader world was shallow; he often made assumptions—a flaw of idealists.
Historically, Constantine's rule in Athens and Thebes remained shaky. He failed to utilize local resources.
When the Ottomans recovered and launched a counteroffensive, Constantine was forced to abandon both cities and retreat behind the Isthmus Wall.
Local forces in Athens and Thebes promptly defected to the Sultan, becoming his vanguard in the attack.
Isaac couldn't allow history to repeat itself.
He summoned Andre, his steward, and headed for Athens' slave market by carriage.
Christianity's stance on slavery was murky at best. The Church opposed enslaving fellow Christians but turned a blind eye toward non-believers.
The market was filled with Muslim slaves—men, women, and children. Many were Ottoman civilians, others captured soldiers.
Isaac was looking for both.
It was easy to distinguish between them.
The soldiers bore scornful expressions, mocking their Christian captors, convinced the Sultan would rescue them soon.
The civilians clung to their families, eyes hollow and filled with fear.
Slaves were valuable labor, and rarely killed. But they feared being separated from loved ones.
Young men were in high demand. Beautiful women even more so.
The elderly and children were discarded.
Those taken often begged buyers to purchase their family too—usually in vain.
Isaac walked the rows, occasionally stopping to inspect a promising candidate—checking their teeth, muscles, and signs of illness.
None satisfied him.
Then, a commotion broke out.
A father, refusing to be separated from his wife and daughter, broke his shackles and attacked a slaver.
"Scum!" the slaver yelled, clutching his bleeding eye. Guards quickly surrounded the man.
"Kill him!" the slaver roared in Latin.
The daughter buried her face in fear.
Isaac stepped forward.
He stood between the guards and the man.
The guards recognized the crest on Isaac's robes and saluted.
"Salutations, young prince. Third Squad Leader Leo of the Athens Security Battalion, at your command!"
The slaver also recognized him and ran forward to plead.
"Your Highness, this man must be a spy. He should be executed!"
"I'll take the entire family."
The slaver pretended to hesitate.
"I'm afraid that's not possible, Your Highness. The two women are quite valuable..."
Isaac turned his head.
The man clutched the broken shackle, shielding his wife and daughter with a fierce glare.
The women were indeed striking. The slaver likely intended them as gifts for nobles.
"How much are they?"
The slaver grinned, his beady eyes squinting with joy. His wounded eye seemed miraculously healed.
"If Your Highness desires them, I would gift them to you—however..."
"How much?"
"Not much, not much... The two women together—100 ducats. The man, I'll throw in for free..."
Isaac tossed him a pouch.
The gesture was dashing, though his heart bled.
As the crowd dispersed, Isaac brought the family back to his residence, providing them with food, new clothes, and baths.
Once they were cleaned up, Isaac summoned them.
The man remained wary, shielding his family.
Seeing him, Isaac was immediately annoyed.
"Hello, 100 ducats."
Isaac said in broken Turkish.
The man blinked, confused.
"Infidel, what do you want?"
"If you use that insult again, I'll sell your wife to a brothel."
The man fell silent.
"You were once a soldier, weren't you?"
Isaac sipped wine and stated calmly.
"My lord, I'm a deserter."
As expected, he had military training. His stance with the shackle had been textbook Ottoman.
"Why did you run?"
"The Bey ordered a retreat—but wouldn't let us take our families."
Clearly, his family was his weakness.
Isaac made a decision.
"I'm setting you free."
He clapped, and a squire unlocked his shackles.
"What do you want me to do?" the man asked, stunned.
"I'll give you 1,500 ducats. Recruit deserters and brigands. Fly the Ottoman banner. Raid Christian villages and caravans. Drive the people southward."
The man froze, then shifted his gaze.
"Your wife and daughter stay with me. They will convert to Orthodoxy. Your daughter will attend school here in Athens."
"How do I know you're telling the truth?"
"You can refuse. I'll keep you, and your family will be sold to noblemen's beds."
His eyes burned with rage. Isaac met his glare coolly.
"Papa…" the daughter whispered.
His fury turned to sorrow.
"How do you know I won't run off with the money?"
"You already fled once. The Ottomans won't take you back."
"I can't raise an army on my own."
"I'll arrange it."
At that moment, Andre returned with fifty newly bought slaves—runaways, fugitives, and men with similar pasts.
They would become bandits in disguise, driving civilians southward, preserving Byzantine strength.
"What's your name?"
"Ibrahim, Your Highness," the man said, kneeling. His wife and daughter followed suit.
"Very well, Ibrahim. I wish you success."
Isaac raised his glass. The wine shimmered like blood.