Rolly Duckfield & Lorent Caswell

There are way too many open threads and minor plotlines in ASOIAF for every single one of them to have a resolution. For instance we may never find out the fate of Weasel aka "the crying girl" and as GRRM says sometimes a "cigar is just a cigar". That said for some reason I truly do think we will get a another encounter between Rolly Duckfield & Lorent Caswell.

Background

Rolly Duckfield aka Duck is a:

exclaimed the larger of the riders, a brawny man with a shaggy beard and a shock of orange hair. -ADWD, Tyrion III

Who we first meet in ADWD as one of the travel companions of young Griff/Tyrion aboard the Shy Maid.

While formerly a member of the Golden Company (and knighted by JonCon), Rolly is a member of Young Griff's kingsguard. But formerly he grew up in Westeros.

As a child he grew up at Bitterbridge, the seat of House Caswell (and where the reader has been for Renly's great melee):

Duck had begun to regale him with his own life story. His father had been an armorer at Bitterbridge, he said, so he had been born with the sound of steel ringing in his ears and had taken to swordplay at an early age.

but after an incident with the Lord's son:

Such a large and likely lad drew the eye of old Lord Caswell, who offered him a place in his garrison, but the boy had wanted more. He watched Caswell's weakling son named a page, a squire, and finally a knight. "A weedy pinch-faced sneak, he was, but the old lord had four daughters and only the one son, so no one was allowed to say a word against him. T'other squires hardly dared to lay a finger on him in the yard."

"You were not so timid, though." Tyrion could see where this tale was going easily enough.

Rolly was forced to flee:

"My father made a longsword for me to mark my sixteenth nameday," said Duck, "but Lorent liked the look of it so much he took it for himself, and my bloody father never dared to tell him no. When I complained, Lorent told me to my face that my hand was made to hold a hammer, not a sword. So I went and got a hammer and beat him with it, till both his arms and half his ribs were broken. After that I had to leave the Reach, quick as it were. I made it across the water to the Golden Company. I did some smithing for a few years as a 'prentice, then Ser Harry Strickland took me on as squire. When Griff sent word downriver that he needed someone to help train his son to arms, Harry sent him me."

He was also knighted by Griff (with a great story for how he got his name):

"And Griff knighted you?"

"A year later."

Haldon Halfmaester smiled a thin smile. "Tell our little friend how you came by your name, why don't you?"

"A knight needs more than just the one name," the big man insisted, "and, well, we were in a field when he dubbed me, and I looked up and saw these ducks, so … don't laugh, now."

Due to Rolly's loyalty, Young Griff names him to his kingsguard:

The prince arrived to join them four days later, riding at the head of a column of a hundred horse, with three elephants lumbering in his rear. Lady Lemore was with him, garbed once more in the white robes of a septa. Before them went Ser Rolly Duckfield, a snow-white cloak streaming from his shoulders.

A solid man, and true, Connington thought as he watched Duck dismount, but not worthy of the Kingsguard. He had tried his best to dissuade the prince from giving Duckfield that cloak, pointing out that the honor might best be held in reserve for warriors of greater renown whose fealty would add luster to their cause, and the younger sons of great lords whose support they would need in the coming struggle, but the boy would not be moved. "Duck will die for me if need be," he had said, "and that's all I require in my Kingsguard. The Kingslayer was a warrior of great renown, and the son of a great lord as well."-ADWD, The Griffin Reborn

Current Status of Lorent Caswell

Since Rolly fled Lorent has become Lord of Bitterbridge and we see him support Renly early on:

Renly grinned. "Go softly, Lord Randyll, I fear you're overmatched." He summoned a steward in the livery of Storm's End. "Find a place for the lady's companions, and see that they have every comfort. Lady Catelyn shall have my own pavilion. Since Lord Caswell has been so kind as to give me use of his castle, I have no need of it. My lady, when you are rested, I would be honored if you would share our meat and mead at the feast Lord Caswell is giving us tonight. A farewell feast. I fear his lordship is eager to see the heels of my hungry horde."

"Not true, Your Grace," protested a wispy young man who must have been Caswell. "What is mine is yours." -ACOK, Catelyn II

but after Renly's death, wispy Lorent proves even more coward:

Lord Tarly has seized Renly's stores and put a great many to the sword; Florents, chiefly. Lord Caswell has shut himself up in his castle." -ACOK, Tyrion X

Brienne does see centaurs (sigil of House Caswell) in Tarly's host in AFFC, so it does seem he has at least sworn for Joffrey/Tommen. That is the last we hear of Lorent.

Encounter between them?

Now this is where we get speculative. Young Griff and the Golden Company are invading Westeros via the Stormlands And have likely taken Storm's End (through "Guile"). And there is currently an army marching down on them:

There is an army descending on Storm’s End from King’s Landing. You will want to be safe inside the walls before the battle.” -TWOW, Arianne II

Its possible that when this battle occurs we could get an encounter between the two, especially if we look at how the upcoming battle could potentially go. u/BryndenBFish did a much better job than I ever could pointing out how the upcoming battle could mirror the Battle of Agincourt due to:

• the utilization of mixed units
• the terrain (muddy/rainy in the Stormlands currently)
• Mace Tyrell's overconfidence
• JonCon's change in nature

The theory is amazing (one of my favorites) and at the end in order to make sure of the loyalty of the Reach, JonCon resorts to savagery (he is willing to be the butcher now):

"There is where you're wrong," Myles Toyne had replied. "Lord Tywin would not have bothered with a search. He would have burned that town and every living creature in it. Men and boys, babes at the breast, noble knights and holy septons, pigs and whores, rats and rebels, he would have burned them all. When the fires guttered out and only ash and cinders remained, he would have sent his men in to find the bones of Robert Baratheon. Later, when Stark and Tully turned up with their host, he would have offered pardons to the both of them, and they would have accepted and turned for home with their tails between their legs."

He was not wrong, Jon Connington reflected, leaning on the battlements of his forebears. I wanted the glory of slaying Robert in single combat, and I did not want the name of butcher. So Robert escaped me and cut down Rhaegar on the Trident. "I failed the father," he said, "but I will not fail the son." -ADWD, The Griffin Reborn

so like at Agincourt, numerous lords could be butchered after surrendering in order to maintain control, etc. It is quite possible that one of those lords could be... Lorent Caswell.

Other

In the Mystery Knight there is another "sideplot" at Bitterbridge where Kyle the Cat claimed to have made Lord Caswell (another wispy man) his first sword:

Joffrey Caswell will be at this wedding, the Lord of Bitterbridge. When he was three, I made him his first sword. I carved it out of pine, to fit his hand. In my greener days my sword was sworn to his father."

and then Kyle the Cat "throws" his joust against the drunk Lord Caswell:

"I know that feeling well." Ser Kyle sighed. "Lord Caswell did not know me. When I told him how I carved his first sword, he stared at me as if I'd lost my wits. He said there was no place at Bitterbridge for knights as feeble as I had shown myself to be." -The Mystery Knight

Probably nothing, I just thought it was interesting there was a somewhat similar plotline about a sword being made involving a young Lord Caswell in history.

Again I just want to point out that I don't think every loose end is going to tie up. While I have made numerous similar posts about Jon/Ser Alliser Thorne, Gregor/Loras, even SwannBowl, I don't expect all of them to happen, but just pointing out possibilities.

TLDR: Ser Rolly Duckfield aka Duck is going to meet his nemesis from is childhood, Lord Lorent Caswell and could potentially execute him.