Gandalf had been watching Frodo closely.
From the moment Bilbo handed over the mithril shirt and the pouch filled with a mountain of gold, Gandalf had scrutinized Frodo's expression.
Not once did Frodo show greed, only worry for Bilbo.
A quiet admiration flickered in Gandalf's eyes… and alongside it, the spark of a plan.
Sylas noticed it as well. He didn't comment, but he understood.
Then Gandalf's voice brushed against Sylas' mind, clear as a whisper:
"Sylas, what do you think of Frodo as the Ring-bearer?"
Sylas turned, surprised, meeting Gandalf's steady gaze. The wizard was speaking through telepathy.
"Explain."
"I feel the wheels of fate turning again," Gandalf replied silently. "A war far worse than the last is coming. Sauron's power… it's no longer dormant. It feels heightened, perhaps stronger than in his former prime."
Sylas narrowed his eyes as Gandalf continued:
"And the One Ring is stirring as well. Its link to Sauron is deepening. Even Tom Bombadil can't suppress it anymore."
The idea made Sylas uneasy. Bombadil was practically untouchable, if even he was struggling, then the Ring's corruption had reached a frightening level.
Gandalf's mental voice softened.
"Tom does not belong to our conflicts, we can't drag him and Goldberry into this. We need to remove the Ring from the Old Forest and finally destroy it."
Sylas asked aloud, "And how exactly do you intend to do that?"
Gandalf glanced toward Frodo, who was helping Bilbo fold one of the old cloaks.
"We assemble another Fellowship," he said quietly. "We escort the Ring back to Mount Doom. That is where it was forged, only the fires of Orodruin can unmake it."
Sylas frowned.
"You're talking about the very heart of Mordor. Sauron's domain. He's stronger now, he'll feel the Ring the moment it approaches."
In the original timeline, Frodo's journey succeeded only because Sauron lacked a physical body, and his connection to the Ring was faint.
Now, that connection had clearly returned, perhaps even strengthened.
Delivering the Ring secretly… may no longer be possible.
Gandalf nodded grimly.
"Which is why we must pull Sauron out of Mordor."
Sylas blinked, surprised by the boldness of the idea.
Gandalf leaned closer, speaking in a low voice:
"Galadriel, Elrond, Círdan, you, myself… the entire White Council. We'll confront Sauron directly, far from Mordor. If we force him to focus on us, he won't sense the Ring being carried into his land."
He paused, eyes gleaming with that familiar cunning.
"We'll spread a rumor: that the One Ring is to be sent west across the sea to the Blessed Realm, to be purified by the Valar."
Sylas let out a sharp breath.
"Clever."
"Sauron will panic," Gandalf said, smiling slyly. "He will never allow the Ring to reach the West. He will chase it himself."
"Leaving Mordor wide open," Sylas finished.
Both men understood the implications.
It was possible.
A Fellowship could sneak into Mordor while Sauron himself was drawn away, enraged, distracted, desperate.
Sylas looked again at Frodo, kind, steady, gentle, untempted even when handed more wealth than the Shire had ever seen.
"So you mean to choose Frodo as the Ring-bearer," Sylas murmured.
"To carry the Ring all the way to Mount Doom."
Gandalf nodded slowly, glancing at Bilbo and Frodo. A quiet sigh escaped him.
"To be honest, I would still choose Bilbo if I could. He has experience, he has will, and he resisted the Ring. He was the ideal Ring-bearer."
Then his expression softened with regret.
"But though his body remains youthful, his spirit has grown weary. He no longer has the strength for such a burden."
He looked toward Frodo.
"Frodo is much like Bilbo once was. Their mothers both come from adventurous bloodlines, their fathers from the steady Baggins line. They share the same birthday, the same temperament, the same quiet courage. Sometimes I feel it was meant to be, that Bilbo adopted Frodo because this day was always destined to arrive."
Sylas thought privately:
'He isn't wrong. These two really are the protagonists across decades, and Middle-earth bends around them.'
Aloud, Sylas asked, "But how do you intend to persuade Frodo?"His tone was serious.
"Taking the Ring to Mount Doom is not simply difficult, it's fatal. One mistake and he dies. And the closer he gets to Mordor, the stronger the Ring's corruption will become. That's agony even the strongest minds fail to endure. Why would he agree?"
In the original timeline, Frodo was forced into the journey, hunted by Ringwraiths, driven from his home, and desperate to protect the Shire.
But now, Frodo wasn't under threat.
And with the treasure Bilbo had handed him, he could live a peaceful, ridiculously wealthy life.
Why risk everything for a burden that offered no reward?
Gandalf let out another long breath.
"I don't want him to carry this burden, Sylas."
"But there is no one else who can resist the Ring. Not truly."
Hobbits were gentle, content, and unambitious, which also made them uniquely resistant to the Ring.
But it also meant they hated leaving home.
"Only Bilbo and Frodo," Gandalf continued, "have that balance, hobbit resilience mixed with an adventurer's courage. They are the only ones who can carry the Ring without falling immediately to its temptation."
Sylas remained silent. He knew Gandalf was right.
And he also knew Gandalf had already made his decision.
Sylas didn't interfere with the choosing of the Ring-bearer.
He didn't help persuade Frodo. He left that entirely to Gandalf.
When Bilbo finally finished packing and said his emotional goodbye to Frodo, Sylas placed a gentle hand on Bilbo's shoulder. With Elseth and Elroth beside him, he stepped into the green Floo flames and vanished toward Hogwarts.
Gandalf, meanwhile, stayed behind in Bag End, preparing for the hardest conversation of Frodo's life.