Thursday, October 28, 2021

MadCap's Table Top Tales - Dean Winchester Build (5e)


And now, we have our final build of Horror Month 2021. Since we've spent the month dealing with monsters, I think it's only fitting that we bring in a monster hunter: namely Dean Winchester from the TV series Supernatural. Y'know, that series I've been reviewing for a while. You've probably heard of it.

Dean's a wise-cracking, ass kicking, good ol' boy in need of some major therapy. Life may get him down and even kill him on...many, many occasions, actually. . .but with Sam at his side and himself behind the wheel of his beloved '67 Impala, Dean is always ready to crank up the mullet rock and apply a boot to the ass of every demon on Earth and in Hell and more than a few other things, too.

Ready? Let's kick it in the ass!

So what do we need for Dean? Let's see.

  • Deception skills. Dean lies to the cops, to his brother, and even to himself.
  • Killing. It's Dean's business (at least when it comes to monsters) and business is good.
  • Exorcisms. Despite not particularly being inclined toward books, Dean can spin a good exorcism to send those demons back to Hell where they came from.

For Dean, we're using the standard spread from the Player's Handbook. Roll for stats if you want, as always, but keep Dexterity and Wisdom in mind for multiclassing. Picking stats for Dean was actually really hard to do, in reality, most of these should be in the upper teens, if not higher. Maybe they will be by the end of the build. We'll see.

Charisma: 15

Dean is a ladies' man and is 1/2 of the team that managed to keep Supernatural on the air for fifteen years...that is, ten years longer than it should have been...on pure estrogen. Definitely nothing to sneeze at.

Dexterity: 14

Dean is a fair shot with a pistol, rifle, and...actually, he's just a good shot in general. Just ask Yellow Eyes. Oh, right. You can't. Because he's dead. Because Dean Winchester killed him.

Wisdom: 13

No, Dean is not particularly wise, but he is observant which this reflects. He also just has a bad habit of rolling Nat 1s when it comes to Common Sense.

Strength: 12

Dean is good in a bar room brawl and his handy with melee weapons, but isn't a He-Man.

Constitution: 10

Constitution's a little low, we just need other things more.

Intelligence: 8

Dean is not much for the books, putting a lot of the research onto Bobby and Sam.

For race, Dean is a Human. Given his origins, we can call him a Variant Human. We get a +1 to two different ability scores - go for Dexterity and Wisdom. Dean also gets a skill of his choice for free, go for Religion. Just because Dean doesn't believe in God (at least in the early seasons) doesn't mean he isn't well-read up on the bastard just in case He decides to show up. Dean also gets one Feat. Go for Tough to beef him up from that bad Constitution score. Tough gives you 2 hit points for every level you have and every level you get from the time you take the feat. It's honestly just good to have regardless of how good or bad your Constitution score is.

As a Variant Human, you also get Common and one other language of your choice.

For background, we'll be dipping into Van Richten's Guide to Ravenloft for the Haunted One background - the origin story for someone who has suffered a terrible tragedy because of something supernatural, which is very appropriate for Dean. As a Haunted One, Dean can choose two languages of his choice so long as one of them is Abyssal, Celestial, Deep Speech, Draconic, Infernal, Primordial, Sylvan, or Undercommon. For flavor, I'd say pick up Abyssal and Infernal if you didn't with your one free language from being a Variant Human. If you did, then pick up Deep Speech or Primordial to reflect Dean's time in Purgatory, whichever seems more fitting. Celestial might work, though Dean couldn't understand Castiel in his true form.

For skills, you can choose two from Arcana, Investigation, Religion, or Survival. Since we got Religion from our race, let's get Arcana and Survival from our origin.

Haunted One gets the Heart of Darkness feature, which is basically the same as Rustic Hospitality from the Folk Hero origin in the Player's Handbook, just with a gothic horror twist.

For any character that you're going to multiclass, here's a free tip: if you're going to have rogue anywhere in the build, do rogue first. Therefore, Dean's first level is going to be Rogue (1). Dean gains proficiency in Dexterity and (ironically) Intelligence checks as well as four skills from the Rogue list. Go for Athletics, Deception, Investigation, and Sleight of Hand.

Dean gains yet another language in Thieves' Cant, proficiency with thieves' tools, and Expertise. Expertise allows him to select two skills (or one skill and his proficiency with thieves' tools) and double his proficiency bonus for those skills. I'd personally recommend bumping up Sleight of Hand and his skill with thieves' tools - Dean did use a paperclip to break out of a pair of handcuffs in the Pilot, after all.

Dean also gains a Sneak Attack for an extra 1d6 damage against an opponent he manages to get the drop on once per turn, so long as he's using a finesse or ranged weapon.

For Dean's second level, we'll be sticking around in Rogue (2). Second level Rogues get Cunning Action, allowing them to take a bonus action to Dash, Disengage, or Hide while in combat.

For the third level, Dean will stick in and around Rogue (3) for a bit longer. At third level, Rogues pick a Roguish Archetype. Go for Thief from the Player's Handbook. No, Dean is not a thief (unless you count credit card fraud and hustling pool), but the Fast Hands ability is definitely right up Dean's alley. With it, Dean can use his bonus action from Cunning Action to make a Dexterity (Sleight of Hand) check to use his thieves' tools to open a lock or trap, or take the Use an Object action.

Also, Dean's sneak attack goes up to a 2d6! Neat!

Fourth level Dean means Rogue (4) and our first ability score improvement or feat. We're going to take the Skilled feat and pick up a few skills that we weren't able to get before, namely Insight, Perception, and Intimidation. Dean happens to be able to read people (9 times out of 10), rarely has monsters get the drop on him in combat, and can be pretty scary when the need arises.

Fifth level Dean will be leaving Rogue behind, however, to go to Fighter (1). With a Dexterity of 15, we meet one of the minimum requirements (the other being or Strength of 13+). Dean is now proficient with all armor but heavy armor, and all weapons and shields. This will reflect his combat training as a hunter.


At first level, Dean has to pick a Fighting Style. Given his proclivity for using guns, I'd recommend the Archery style. This style gives Dean a +2 to attack rolls when using ranged weapons, be they guns or something less complicated.

Dean also gets a Second Wind, allowing him to heal 1d10 + his fighter level once per short or long rest.

Fighter (2) at Dean's sixth level gets him Action Surge. On his turn, Dean can take on additional action on top of his regular action and a possible bonus action, having to finish a short or long rest before he can use this again. This ability gets another use at 17th level, though we probably aren't reaching that in this build.

Fighter (3) brings Dean to seventh level and he has to pick a Martial Archetype. We're going with Champion. Champions receive Improved Critical, meaning that a weapon attack they make can score a Critical Hit on a 19 or a 20.

While there are definitely some merits to staying in Fighter a bit longer, we're going to press on. Dean's Eighth level sees him become a Ranger (1). First level Rangers get a Favored Enemy (obviously, we're going to go with fiends to cover both demons and devils). Dean has advantage on all Survival checks to track his favored enemies as well as Intelligence checks to recall information about them. He also learns a language of his choice that is spoken by his favored enemies. So...Abyssal or Infernal? Again? Or maybe just Elvish. Who knows? He did LARP.

Dean may choose an additional enemy at 6th and 14th level of Ranger.

First level Rangers also become a Natural Explorer. Choose one type of favored terrain. If Dean makes an Intelligence or Wisdom check related to his favorite terrain, his proficiency bonus is doubled if he uses a skill that he's proficient in. It also gives the following benefits:

  • Difficult terrain in his favorite terrain will not slow his group's travel down, meaning that he and Sam can cruise through in the Impala no matter the obstacles. 
  • He and Sammy can't be lost except by magical means while traveling.
  • When Dean forages for food, he'll find twice as much as he normally would.
  • When tracking other creatures, Dean also learns their exact number, sizes, and how long ago they passed through the area.

Dean can choose an additional favored terrain type at 6th and 10th level.

Ranger (2) sees Dean have to adopt a Fighting Style as we did in the Fighter class. While we took Archery there, we're going to take Dueling here to emphasize Dean's skill with melee weapons. Dueling grants you a +2 to damage when you're wielding a melee weapon and only a melee weapon in one hand and nothing else in the other.

Dean also gets access to Ranger Spellcasting! Sam and Dean do use magic (or powers like magic) on occasion in the show, so I'm saying that this works. No judgment. Dean knows two spells at 2nd level. Go with Hunter's Mark and Cure Wounds.

Hunter's Mark has Dean choose a creature within range and mark it as his quarry. Until the spell ends, he deals an extra 1d6 damage to it whenever he hits it with a weapon attack and he has advantage on any Perception or Survival rolls made to locate it. If the target drops to 0 hit points, he can use a bonus action to mark a different creature. This spell lasts up to an hour depending on his concentration.

When used in a spell slot of 3rd or 4th level, the concentration can be maintained for up to 8 hours. For 5th or higher, it can be maintained for up to 24.

Cure Wounds heals a creature for 1d8 + your spellcasting Ability Modifier, but has no effect on undead or constructs. You can boost this by using a slot of 2nd level or higher, adding a 1d8 for each level above 1st.

Ranger (3) must choose a Ranger Archetype. In this case, we'll be going with Horizon Walker from Xanathar's Guide to Everything. Dean is, after all, not only someone who has been to other dimensions, but does a Hell of a good job sending creatures back to them as well, pun entirely intended. 

As a third level Ranger taking the path of the Horizon Walker, Dean gains the ability to Detect Portal. As an action, Dean can detect the distance and direction of the closest planar portal within 1 mile of his current location. He regains this ability after finishing a short or long rest. Handy for finding those portals to Hell or those escape hatches from Purgatory, am I right?

Dean also gains the Planar Warrior ability. As a bonus action, choosing a target within 30 feet of him, Dean can translate all the damage he does to it on this turn to force damage and deal an extra 1d8 force damage on top of that to it. When he reaches 11th level, this increases to 2d8.

Dean also gains Primeval Awareness. For expending a spell slot, Dean can focus his awareness into the region around him. At 1 minute per level of spell slot, Dean can sense within 1 mile (or 6 if he's on his favored terrain) the following creatures: aberrations, celestials, dragons, elementals, fey, fiends, and the undead. Pretty useful for when you're trying to hunt something down.

For your spell for this level, pick up detect magic. It really would have helped Dean against that Scarecrow.

Eleventh level Dean is a Ranger (4). And Dean gets an Ability Score Improvement or a Feat. We're going to go with Sharpshooter from the Player's Handbook. Dean no longer gets disadvantage for attacking at long range, his ranged weapon attacks ignore half cover and three quarters cover, and before he makes an attack he can choose to take a -5 penalty to it in exchange for +10 to damage if he hits.


Twelfth level Dean is at Ranger (5) and he gets an Extra Attack as well as access to 2nd level Ranger spells. Pass without trace is a fun one, allowing Dean and any creature he chooses within 30 feet of him when he casts the spell to have +10 bonus to Stealth checks and being unable to be tracked except by magical means for up to 1 hour depending on his concentration. Any creature under the effects of this spell leaves no tracks or other traces of their passage, even if they want to. So now, Dean can track demons without the demons being able to track him.

Ranger (6) will see Dean get improvements to Favored Enemy and Natural Explorer. Not much else to note here.

Ranger (7) will see Dean get the Ethereal Step ability. Dean has learned how to glimpse the B-Side, now able to cast etherealness as a bonus action without expending a spell slot, but the spell ends at the end of the current turn. Once he does this, Dean can do it again after finishing a short or long rest.

Dean also gets a new spell. We'll be taking protection from evil and good from the Horizon Walker Spell List. On a touch, Dean can protect one creature from aberrations, celestials, elements, fey, fiends, and undead.

Attacks to hit that target receive disadvantage when it's committed by one of those groups. The target cannot be charmed, frightened, or possessed. The target also has advantage on any new saving throw against these effects.

Ranger (8) sees Dean rise to 15th level overall and gain another Ability Score Improvement or feat. Go ahead and beef up your Constitution and your Wisdom for more health and better spellcasting bonuses.

Eighth-level Rangers get Land's Stride. Nonmagical difficult terrain costs no extra movement, passing through nonmagical plants no longer slows you down or causes hazard damage and you have advantage on saving throws against plants that are magically created or manipulated to impede movement such as entangle.

Ranger (9) gets no benefits beyond a new spell and unlocking the 3rd level of Ranger Spells. Haste is a fun one that we get from Horizon Walker, so let's do that. By concentration for up to 1 minute, Dean can double a target's speed, grant them +2 to their AC, give them advantage on Dexterity saving throws, and give them an additional action each round. That action can only be used to Attack (one weapon), Dash, Disengage, Hide, or Use an Object. When the spell ends, the target can't move or take actions until the next turn as they're essentially "slowing down" from being at a faster speed.

Ranger (10) sees Dean at 17th level overall and get another Natural Explorer improvement as well as the ability to Hide in Plain Sight. Dean spends one minute covering himself in camouflage, granting him +10 to Stealth so long as he does nothing.

Ranger (11) will bring Dean the power of a Distant Strike. When Dean takes the Attack action, he can teleport up to 10 feet before each attack to an unoccupied space that he can see. If he attacks two different creatures with the action, he can make one additional attack with it against a third creature. So, under the right conditions, three attacks in one go. Not bad!

Ranger (12) brings Dean his final Ability Score Improvement or Feat. Crossbow Expert is probably something that should have been gained at a lower level, but here we are. As a Crossbow Expert, Dean can ignore the reloading property of crossbows that he's proficient in, being within 5 feet of a creature does not impose disadvantage on a ranged attack, and when he uses the Attack action and attacks with a one handed weapon, he can use a bonus action to attack with a hand crossbow that he is holding.

Otherwise, pump up the Constitution and the Wisdom for reasons already discussed.

Our capstone is going to be Ranger (13), bringing Dean to 20th level and granting him a new spell slot as well as access to 4th level spells. Banishment from the Horizon Walker spell list is our goal and we have achieved it. 

Dean can attempt to send one creature within range to another plane of existence, able to do so if they fail their Charisma saving throw. If the target is native to the plane they're already on, they hover around in a harmless demiplane until the spell ends.

If the target is not native to the current plane and fails its save, it's sent back to its own native plane and remains there unless Concentration is broken. If it is broken before 1 minute is up, then they return and will probably be very pissed about it. Make sure you learn your Latin, Dean!


Now that we're at level 20, let's see how good this build is.

Pros:

  • You have some good choice of combat skills. Dean is comfortable enough with a blade or a gun, though obviously favors the gun. Between Favored Enemy, Hunter's Mark, Planar Warrior, and some others, you have the potential to be utterly terrifying in a fight. And that's just from one attack, you have two (technically three with Distant Strike)! And that's not even getting into your Action Surge!
  • You're a skill and language monkey. You have a bunch of skills and can speak at least half the languages in the game by the time you finish this build. Not bad!
  • You have a high Wisdom, which is one of the most called for saving throws in the game. Even without proficiency, that's nothing but a good thing.

Cons:

  • You have a lot of spells that require Concentration and your Constitution...really sucks. This is really a build where I'd suggest rolling for your stats and using the above spread as a guide for where to put your scores. You also can do banishment...but you've only got the one spell slot for it, meaning if somebody resists, you're all out of luck.
  • Speaking of your Constitution, your health is going to be averaging 119, meaning that a really vengeful demon or witch might be able to wear you down and get a power word kill on you. Tough helps with this, putting you at around 159 instead, but Dean deals with a lot of heavy hitters and those hit points could dry up real fast.
  • You unfortunately also have a limit to your damage options. Planar Warrior helps with the Force damage, but you have basically no magical backup if things get really hairy.

But you're Dean Winchester. Knock back a couple of brews, get your guns ready, pick up Sammy and Cas in the Impala, and go kick it in the ass! Just be careful if you cross the guy who's been writing your story. You may end up all out of Chuck and no amount of Jack will help you.

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