Old Tom, Red Tom, Raw and Bloody Head Tom ...

Old Tommy Rawhead
CE Advanced Redcap(10HD) Beguiler 4/Unseen Seer 10
Build
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CR Class Base Attack Bonus Fort Save Ref Save Will Save Skills Feats Class Features
2 (4HD) Redcap +2 +1 +4 +4 Hide 7, Intimidate 7, Listen 7, Move Silently 7, Search 2.5(cc), Sense Motive 3(cc), Spot 7, Survival 7 Improved Initiative, Power Attack Eldritch Stone, Powerful Build, DR 5/Cold Iron, Low-light Vision, Natural Armor +1
3 (6HD) Advanced Redcap +3 +2 +5 +5 Hide 9, Intimidate 9, Listen 9, Move Silently 9, Search 3.5(cc), Sense Motive 4(cc), Spellcraft 1(cc), Spot 9, Survival 9 Martial Study(Shadow Jaunt) +2 Str, +2 Dex, +2 Con, Natural Armor +2
4 (8HD) Advanced Redcap +4 +2 +6 +6 Hide 11, Intimidate 11, Listen 11, Move Silently 11, Profession(Sailor) 1(cc), Search 4(cc), Sense Motive 4(cc), Spellcraft 3(cc), Spot 11, Survival 10 +2 Str, +2 Dex, +2 Con, Natural Armor +3
6 (10HD) Advanced Redcap +5 +3 +7 +7 Hide 13, Intimidate 13, Listen 13, Move Silently 13, Profession(Sailor) 3(cc), Search 5(cc), Sense Motive 4(cc), Spellcraft 4(cc), Spot 13, Survival 10 Imperious Command +2 Str, +2 Dex, +2 Con, Natural Armor +4, DR 10/Cold Iron
7 (11HD) Beguiler 1 +5 +3 +7 +9 (6+Int)Hide 14, Listen 14, Move Silently 14, Profession(Sailor) 5, Search 8, Spot 14 Armored Mage, Trapfinding, Spells
8 (12HD) Beguiler 2 +6 +3 +7 +10 Hide 15, Listen 15, Move Silently 15, Profession(Sailor) 11, Spot 15 Martial Stance(Assassin's Stance) Cloaked Casting(+1 DC), Surprise Casting
9 (13HD) Unseen Seer 1 +6 +3 +7 +12 Hide 16, Listen 16, Move Silently 16, Profession(Sailor) 16, Search 9, Spot 16 Damage Bonus +1d6, +1 Level of existing arcane spellcasting class
10 (14HD) Unseen Seer 2 +7 +3 +7 +13 Hide 17, Intimidate 14.5(cc), Listen 17, Move Silently 17, Profession(Sailor) 17, Spot 17, Never Outnumbered Silent SpellB Advanced Learning (Locate Object), Silent Spell, +1 Level of existing arcane spellcasting class
11 (15HD) Unseen Seer 3 +8 +4 +8 +13 Hide 18, Intimidate 17(cc), Listen 18, Move Silently 18, Profession(Sailor) 18, Spot 18 Practiced Spellcaster Divination Spell Power +1
12 (16HD) Unseen Seer 4 +9 +4 +8 +14 Hide 19, Intimidate 17.5(cc), Knowledge(Local) 4, Listen 19, Move Silently 19, Profession(Sailor) 19, Spot 19 Damage Bonus +2d6, +1 Level of existing arcane spellcasting class
13 (17HD) Unseen Seer 5 +9 +4 +8 +14 Hide 20, Intimidate 18.5(cc), Knowledge(Local) 5, Listen 20, Move Silently 20, Profession(Sailor) 20, Spot 20, Clarity of Vision Advanced Learning (Divine Insight), Guarded Mind, +1 Level of existing arcane spellcasting class
14 (18HD) Unseen Seer 6 +10 +5 +9 +15 Hide 21, Intimidate 21(cc), Listen 21, Move Silently 21, Profession(Sailor) 21, Spot 21 Knowledge Devotion Divination Spellpower +2, +1 Level of existing arcane spellcasting class
15 (19HD) Unseen Seer 7 +11 +5 +9 +15 Hide 22, Intimidate 22(cc), Knowledge(Local) 6, Listen 22, Move Silently 22, Profession(Sailor) 22, Spot 22, Collector of Stories Damage Bonus +3d6, +1 Level of existing arcane spellcasting class
16 (20HD) Unseen Seer 8 +12 +5 +9 +16 Hide 23, Intimidate 23(cc), Knowledge(Local) 9, Listen 23, Move Silently 23, Profession(Sailor) 23, Spot 23 Advanced Learning (Commune with Nature), +1 Level of existing arcane spellcasting class
17 (21HD) Unseen Seer 9 +12 +6 +10 +16 Hide 24, Intimidate 24(cc), Knowledge(Local) 12, Listen 24, Move Silently 24, Profession(Sailor) 24, Spot 24 Trickery Devotion Divination Spellpower +3, +1 Level of existing arcane spellcasting class
18 (22HD) Unseen Seer 10 +13 +6 +10 +17 Hide 25, Intimidate 25(cc), Knowledge(Local) 15, Listen 25, Move Silently 25, Profession(Sailor) 25, Spot 25 Damage Bonus +4d6, +1 Level of existing arcane spellcasting class
19 (23HD) Beguiler 3 +13 +7 +11 +17 Hide 26, Intimidate 26(cc), Knowledge(Local) 18, Listen 26, Move Silently 26, Profession(Sailor) 26, Spot 26 Advanced Learning (Shadow Well)
20 (24HD) Beguiler 4 +14 +7 +11 +18 Hide 27, Intimidate 27(cc), Knowledge(Local) 21, Listen 27, Move Silently 27, Profession(Sailor) 27, Spot 27 Scourge of the Seas


Ability Scores
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Starting Ability Scores:

Str - 10
Dex - 12
Con - 13
Int - 15
Wis - 8
Cha - 14

Final Ability Scores after Racial modifiers, Redcap Advancement, and level bumps:

Str - 22
Dex - 20
Con - 24
Int - 18
Wis - 10
Cha - 16

Levels 4, 8, and 12 go to Int, levels 16 and 20 go to Str, level 24 goes to Con


Spells per Day/Spells Known
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Spells per Day
CR 0lvl 1st 2nd 3rd 4th 5th 6th 7th 8th 9th
7 5 3 - - - - - - - -
8 6 4 - - - - - - - -
9 6 5 - - - - - - - -
10 6 6 3 - - - - - - -
11 6 6 4 - - - - - - -
12 6 6 5 3 - - - - - -
13 6 6 6 4 - - - - - -
14 6 6 6 5 3 - - - - -
15 6 6 6 6 4 - - - - -
16 6 6 6 6 5 3 - - - -
17 6 6 6 6 6 4 - - - -
18 6 6 6 6 6 5 3 - - -
19 6 6 6 6 6 6 4 - - -
20 6 6 6 6 6 6 5 3 - -


CR 2
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Old Tom is just a Redcap. That being said, Redcaps are nasty bruisers in a fight. Their slings blow appled-sized holes in things, and any monster that wields a x4 crit weapon is just asking for a lucky crit to straight up kill a PC. At this point in his life, Old Tom has taken up residence in an abandoned lighthouse on the coast. He's a twisted and evil little fey who used to be a Klaubauterman (a beneficial ship sprite). Nowadays, he savagely defends his turf, and delights in slaughtering the survivors of any shipwrecks that occur nearby. If he can use the lighthouse to guide them to their doom, all the better.

Possible Encounter:
The Lighthouse Keeper (EL 2) - The party is hired by the local lord to clear out and secure an old abandoned lighthouse on the edge of his domain. If the peasantry is to be believed, the vengeful spirit of a long dead sailor pining for his lost love haunts the lighthouse, and none who have ventured there ever return. Unfortunately for the party, it's no spirit, but Old Tom that has taken up residence. He uses hit and run tactics to soften the party up with Eldritch Stones before moving in to finish off the last one or two in melee with his scythe. GM's are encouraged to make the lighthouse dangerous in and of itself. Crumbling stairs, bits of falling masonry, close quarters, and terrible lighting conditions help set the atmosphere. Bonus points if there's a storm that drives the party to seek shelter in the lighthouse.


CR 6
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By this point, not only has Old Tom secured himself a homebase in a (now fortified) lighthouse on the coast, he's also managed to salvage a pinnace that crashed up on the shore, and secured himself a small crew of redcaps. He uses intimidation and the promise of murder, mayhem, and treasure to keep them in line. When they aren't out pillaging small vessels sailing along the coast, they are counting their ill-gotten goods or torturing some prisoners back at the lighthouse. Old Tom is no pushover either. For a small old man, he's got tremendous strength, DR that is hard to punch through, and (with Imperious Command), the ability to terrify everyone on deck of whatever ship he boards.

Possible Encounter:
The Crew of the Callous Shrew (EL 8) - This encounter can happen any time the party is travelling by sea along the coast. Seeing a ship ripe for the plucking, Old Tommy Rawhead and his crew (2 or 4 young redcaps) come upon the PC's vessel at dusk. They board the vessel quickly and stealthily, doing their best to kill the crew quietly. Unfortunately, the young redcaps much prefer murder to looting, and so will attempt to kill everyone aboard before they even think to steal any treasure. If the fight goes badly, Old Tom will roar curses and threats to keep the young redcaps fighting for longer than they'd like before they break and run. If his crew starts running, Old Tom wisely retreats as well.


CR 16
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Old Tommy Rawhead quite the captain now. He's a stealthy killer, and delights in leaving only a single survivor of his attacks tied to the main mast and clad in the freshly skinned flesh of his fellow crewmates. Old Tom's spells aid in establishing a larger crew, subduing victims for later torture, and finding targets on the high seas. Advanced Learning from Unseen Seer gives him access to divination spells from any class list. While you could probably cheese this out by picking from some of the more tasty prestige class spell lists, I've gone for a slightly more tame approach, and the two spells of note are Divine Insight (which makes Old Tom really good at a few skill checks per day), and Commune With Nature (which lets him know what people, sea life, and ships are beyond the horizon so he can plan his attack, or make his escape).

Possible Encounter:
Rawhead and Bloody Bones - The Callous Shrew has become a problem. As trade has increased between neighboring nations, more and more vessels have fallen victim to Old Tom and his crew, which in turn has made the fey captain far more bold. Recently, a ship that was secretly carrying the King's daughter and a sizeable dowry to a neighboring kingdom in order to cement a peace treaty was lost. The PC's are hired to track down the princess, the gold, and the ne'er-do-wells that are responsible for the attack and make them pay. Old Tom has had decades to train his crew, outfit his ship, and secure his hideout. Old Tom will not only have a sizeable crew of redcaps (young and advanced) in his employ, but he'll also have a number of other dangerous creatures he's enchanted to ensure his safety. The PCs will need to track Old Tom down before he kills the princess, otherwise it could mean war between the two neighboring nations.


References
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Monster Manual III - Redcap
Player's Handbook II - Beguiler
Stormwrack - Scourge of the Seas
Spell Compendium - Divine Insight, Shadow Well
Tome of Battle - Martial Study, Martial Stance, Assassin's Stance, Shadow Jaunt
Complete Champion - Knowledge Devotion, Water Devotion
Complete Scoundrel - Skill Tricks (Never Outnumbered, Clarity of Vision, Collector of Stories)
Complete Mage - Unseen Seer
Complete Arcane - Practiced Spellcaster
Drow of the Underdark - Imperious Command