Roskelly Winterleaf

Summary

Roskelly Winterleaf is a Halfling lieutenant and toll collector operating under Phlebotomas Plumthorn in the pyramid approaches. He manages checkpoints, demands an “Adventuring License” fee and a tithe from delvers, and keeps Phlebotomas Plumthorn’s interest protected with a mix of charm and muscle.

Appears In

• Session 2 - Halfling Rent-Seekers
• Session 3 - Dragons and Baboons and Beastmen, Oh My!
• Session 4 - Cheese and Crackers and Thoth and Demons
• Session 6 - Good Ghost, Bad Ghost
• Session 8a - Never Trust a Scorpion
• Session 8a - Never Trust a Scorpion
• Session 24b - The Set Cult Strikes Back, Larel’s Stuff, and the Hall of Shrines
• Session 26 - The Scouring of the Shire

Roles & Influence

• Lieutenant for Phlebotomas Plumthorn; oversees halfling toll operations near the pyramid landings.
• Local fixer for small deals and access arrangements; responsive to gifts/favors.

Relationships

• Phlebotomas Plumthorn: boss and protector; Roskelly enforces his turf.
• PCs (various): pragmatic rapport built through repeated toll negotiations and information exchange.

History

• Session 2 - Halfling Rent-Seekers — # DFRPG Arden Vul Session 2: Halfling Rent-Seekers Date: Demmasday, 21st of Toternios, 2993 AEP Weather: Cool, cloudy Player Characters: Ioannes Grammatikos Byzantios, Archontean cleric of Demma (Demented Avenger) Vaelethron ‘Vael’ Sunshadow, Half-El…
  • Session 2 - Halfling Rent-Seekers — The lead halfling was named Roskelly, and he informed the party that this area under the pyramid was the turf of his boss, Phlebotomas Phlebotomas Plumthorn, and that Mr.
• Session 3 - Dragons and Baboons and Beastmen, Oh My! — Date: Demmasday, 28th of Toternios, 2993 AEP Weather: Cool, overcast, light rain Player Characters: Ioannes Grammatikos Byzantios, Archontean cleric of Demma (Demented Avenger) Michael J Dundee, Thorcin barbarian (Adam) Vaelethron ‘Vael’ Sunshadow, H…
  • Session 3 - Dragons and Baboons and Beastmen, Oh My! — Vallium produced the sweetroll he had purchased early that morning in Gosterwick and gave it to Roskelly, the halfling lieutenant, as a gift.
• Session 4 - Cheese and Crackers and Thoth and Demons — # DFRPG Arden Vul Session 4: Cheese and Crackers and Thoth and Demons Date: Demmasday, 5th of Lucrios, 2993 AEP Weather: Cool, overcast, rainy Player Characters: Ioannes Grammatikos Byzantios, Archontean cleric of Demma (Demented Avenger…
• Session 5 - Parleys and The Great Cavern — # DFRPG Arden Vul Session 5: Parleys and The Great Cavern Date: Demmasday, 11th of Lucrios, 2993 AEP Weather: Cool, overcast, rainy Player Char…
  • Session 5 - Parleys and The Great Cavern — On the large landing room halfway down the steps inside the pyramid, they encountered Roskelly and a couple of his halfling toll collectors.
• Session 6 - Good Ghost, Bad Ghost — # DFRPG Arden Vul Session 6: Good Ghost, Bad Ghost Date: Demmasday, 18th of Lucrios, 2993 AEP Weather: Warm, sunny Player Characters: Ioannes Grammatikos Byzantios, Archontean cleric of Demma (Demented Avenger) Vallium Halcyon, Archontea…
  • Session 6 - Good Ghost, Bad Ghost — (Roskelly generously allowed the goats and swarms to adventure for free.) Since Ashe Maykum had Water Vision, the group headed south through the gray-green mist to the smelly murky pool, hoping the spell would reveal some treasure.
• Session 8a - Never Trust a Scorpion — Dundee, Thorcin barbarian (Adam) Vaelethron ‘Vael’ Sunshadow, Half-Elven mage (Kyle) Significant NPCs: Lyssandra and Pelteon, wizards of the Arcane Practitioners’ Club Lady Alexia Basileon Basileon, ruler of Gosterwick Freydis the Stern, steward to Lady Alexia Basileon [[factio…
  • Session 8a - Never Trust a Scorpion — Meanwhile, the Wizard Eye emerged into the Glory of Thoth, where Roskelly and five other halflings were standing guard in the shadows near the central statue, watching the various entrances to the room mor…
• Session 8b and 9 - Muirasso’s Tomb and the Broken Head — Dundee, Thorcin barbarian (Adam) Vaelethron ‘Vael’ Sunshadow, Half-Elven mage (Kyle) Uvash Edzuson, Dwarven cleric of Zodarrim (Based Cosmo) Merenuithiel “Merenuithiel Lacrymosa Merenuithiel Lacrymosa Armaris” Merenuithiel Lacrymosa Armaris, Elven mercenary archer (Archon Shiva) Significant NPCs: Muirasso, wight, fo…
• Session 24b - The Set Cult Strikes Back, Larel’s Stuff, and the Shrines.md|Hall of Shrines]] — Dundee, Thorcin barbarian (Adam) Uvash Edzuson, Dwarven cleric of Zodarrim (Cosmo) Significant NPCs: Many Set guards Several Set acolytes Several Set sergeants Some Set Guild of Service fighters
  • Session 24b - The Set Cult Strikes Back, Larel’s Stuff, and the Shrines.md|Hall of Shrines]] — Unfortunately, right as the lead PCs came out the secret door, Roskelly and several of his halfling toll collector thugs were standing right in that area, looking at the statue.
• Session 26 - The Scouring of the Shire — Dundee, Thorcin barbarian (Adam) Merenuithiel Lacrymosa Merenuithiel Lacrymosa Armaris, Elf Grudge Brigade mercenary archer (Archon Shiva) Significant NPCs: Craastonistorex, green dragon Briar, Wyvern Giant Tick Phlebotomas Phlebotomas Plumthorn, Halfling mob bo…
  • Session 26 - The Scouring of the Shire — Roskelly led his followers from the Glory of Thoth through the portcullis.

Notes

Death

• Session 26 — The Scouring of the Shire: During the confrontation near the Glory of Thoth, Roskelly attempted to flee as Phlebotomas Plumthorn negotiated surrender. Lacrymosa shot him repeatedly with arrows, killing him.

Discord Insights

• GM was told the name Roskelly Winterleaf, implying it is an entity recognized in the game. (Discord Summary 2025-W12)