Regardless of sizing issues, there is one way to protect yourself from most pickpockets- roll initiative! Sleight of Hand can't be used in combat if the target is aware of your presence. If you want to steal something in combat from someone who is aware of your presence, you need to use the steal maneuver. If you have a free hand, succeed on a check and the object isn't heavily secured, you jack their item.
On the subject of stealing, here's an interesting feat: Agile Tongue. It's a racial feat designed for the Grippli, a race of little frog dudes.
Adorable little frog dudes
Agile Tongue does what it says, giving your frog-man a 10 foot long tongue with enough agility to pick up items weighing five pounds or less, make Sleight of Hand checks, steal from or disarm opponents and make melee touch attacks. Due to the wording of the feat, while it may be designed for moving five pound or lighter objects normally, there are no restrictions on Sleight of Hand, disarm or steal other than what the abilities normally have, allowing you to grab whatever the hell your opponent is carrying, even if it's a titan with a hammer bigger than you are (assuming you succeed on the check, of course). The Sleight of Hand function brings up the mental image of just how a frog manages to stealthily stand 10 feet away from you, stick out its tongue, reach around in your pockets and then steal your keys without you noticing, but that is only the beginning.
do dodo do do dooo do dodooo
Since you can use your tongues to deliver touch attacks, you can also use them to deliver spells that require your touch. A grippli cleric gains a distinct tactical advantage by standing in the back row and licking allies to deliver healing abilities and buff spells such as bull's strength or shield of faith. A grippli can even go full on BattleToads and use its tongue to deliver touch attack spells like shocking grasp or frigid touch. Then there are the times when you have to deliver a touch attack spell to a zombie or gelatinous cube .
But maybe your DM is a dick and won't you play a two foot tall little frog dude. Don't worry, we have a solution- be a human and take the Racial Heritage feat, which allows you to pick a humanoid race as one of your ancestors and count as both races for the purpose of game mechanics, including what feats you're eligible for. Then go hang out with the rest of your mutant brotherhood.
As you may have noticed, Racial Heritage has some weird effects based on the fact that it lets you take any racial feat that does not have a specific racial trait requirement. Among the things you can pick up:
-The ability to flip the fuck out at Levar Burton or bite everyone like an infant throwing a tantrum
-Fully functioning wings
-An undead animal companion that recovers swiftly from any injury, and the ability to drink blood or befriend the shit out of people
-A tail that can hit people and even carry weapons, or other functioning wings
-Spell Resistance or increased durability
-The ability to planeshift
-The ability to turn into a fox or waste a gigantic number of feats on spell-like abilities and growing fluffy tails
-The ability to spit poison
-The ability to swim through dirt and even lava
-The ability to live without breathing
-A prehensile tail
-The ability to breathe water
Also worth mentioning is that Pathfinder condensed the creature types, making elementals a subset of outsiders, and giants a subset of humanoids. Thus with Racial Heritage, you can pick up tremorsense through your stone giant ancestry.
Let's make a grippli rogue and have our frog be an excellent thief with an amazing tongue! So, how does our frog mutant go about stealing things?
Steal works like most Combat Maneuvers, in this case the would-be thief makes a Combat Maneuver check using the thief's Combat Maneuver Bonus (CMB) against the target's Combat Maneuver Defense (CMD). If the would-be thief has an empty and and the check is successful, the thief swipes the item.
This may seem simple, as Pathfinder's Combat Maneuver system was an attempt to simplify streamline the wonky 3e system before it, but unfortunately it went horribly wrong.
The basic Combat Maneuver Check is 1d20 + your CMB bonus = 1d20 + Base Attack Bonus + Strength modifier + special size bonus + miscellaneous bonuses
The basic Combat Maneuver Defense is equal to 10 + your Base Attack Bonus + Strength modifier + Dexterity Modifier + special size bonus + miscellaneous bonuses
The size bonus is based on the character's size, with Medium creatures like humans having a +0 modifier, and it scaling with size from +1, +2, +4, to +8 at Colossal, and down with size from -1, -2, -4, to -8 at Fine.
Those of you capable of doing basic pattern recognition might have already noticed one discrepancy- the Combat Maneuver Bonus check uses one score for calculations (Strength) while the Combat Maneuver Defense check uses two (Strength, Dexterity) with an "and" rather than an "or". Conceptually, few creatures with high Strength have high Dexterity and vice versa, but there are always exceptions. High-end outsiders in general tend to have all around high ability scores- a balor has good Strength and Dexterity, with an end result that its Combat Maneuver Bonus is +33 while its Combat Maneuver Defense is 54, meaning that if two balors fought, neither could do anything to the other since both require a roll of 21 on a 20 sided die to succeed. The Balor Abyss-Wide Wrestling Federation is doomed before it even starts.
Breaking it down further, your base attack bonus is a function of your hit dice or level- a Good bonus scales at a rate equal to your hit dice/levels, while an Average attack bonus scales at a rate of three points every four dice/levels, and a Poor attack bonus scales at a rate equal to one point every two dice/levels. Our rogue has an Average bonus, while late-game enemies like Outsiders and Dragons not only have a Good bonus, but also tend to have more hit dice than a character has levels- all things equal, our grippli rogue would be behind 5 points just based on BAB differences (20 levels of average is +15, while 20 levels of good is +20), and things are nowhere near equal at higher levels.
Making matters worse, your combat maneuver bonus is normally Strength-based, and grippli have a Strength penalty because they're skinny frogs. You can spend a feat on Agile Maneuvers to make your CMB Dex-based and use the grippli's Dexterity bonus, but that means you're down a feat. Even then, grippli are Small, and thus take a -1 penalty to Combat Maneuver Bonus checks and their Combat Maneuver Defense. Large and larger creatures get a bonus to those same checks, and at high levels almost every enemy that isn't a humanoid with class levels is larger than a humanoid. Dragons, outsiders, magical beasts even undead can have Colossal representatives with a +8 bonus. They also tend to have larger Strength scores than you have Strength or Dexterity, and sometimes both are higher than anything you can cook up under normal conditions. It's an uphill battle.
The other big thing with Combat Maneuvers is that despite being designed as a system that anyone can use, it's really a bad idea for anyone to use them. By default, making a Combat Maneuver provokes an Attack of Opportunity, meaning your enemy gets a free chance to hit you in the face for daring to interfere with them. You can prevent this by investing in the "Improved [MANEUVER NAME]" feats, which prevent you from provoking AoOs and also grant you a +2 bonus on your CMB when performing that particular maneuver. Unfortunately for the Talented Mr. Grippli, Improved Steal has a prerequisite- Combat Expertise, a feat that lets you sacrifice your attack bonus (and subsequently your CMB) for defensive bonuses (which also boosts your CMD). Unfortunately in 3e/PF, defense does not end fights- it merely prolongs them, and in most situations it's better to hit people more accurately so you can end the fight sooner. So not only is this a feat that the grippli rogue won't use, it also requires an Intelligence score of 13 or more.
So we're three feats down and now we can make an attempt to steal without getting punched in the face, and our chances of success have moved from "miserable" to "mediocre". Problem is that even if we successfully steal something from our enemy with our free hand, we didn't do it stealthily, and we didn't do anything else this turn. The solution to that is... more feats. Greater Steal means that the target won't know what happened until the end of the fight or until the target attempts to use the item, while Quick Steal lets you steal something and fight on the same turn. So that's five feats down (out of ten) and while Quick Steal may let you steal and fight in the same turn, it does not let you steal and fight well on the same turn, since you spent your best attack to make a steal attempt and must use your considerably less-good attacks to hurt your foes, made even more less-good because you're a rogue, not a fighter (and since you needed a free hand to steal, you probably aren't wielding two weapons to double your damage each round barring you having more than two arms).
But hey, rogues have rogue talents, gained at each even level, some of which can be spent to subsidize your feat requirements. Combat Swipe lets you get Improved Steal, and Combat Trick can be used to pick up one of the other combat feats. And what's this? Weapon Snatcher lets you use your skill with Sleight of Hand in place of your Combat Maneuver Bonus on disarm maneuvers.
Thus instead of making a 1d20 + Strength (or Dex) + BAB + size modifier + miscellaneous bonuses check for CMB, you can make a Sleight of Hand check of 1d20 + level + 3 + Dex + miscellaneous bonuses, dropping your size penalty and increasing the chances of you coming up with bonus like a +5 Sleight of Hand bonus from gloves of larceny. Something of a move in your favor then... except for the fact that it uses your skill at stealing things to disarm weapons, not steal items, so that's five different feats you have to pick up if you want disarm and fight in the same round without getting punched in the face (well, three, since you already have Combat Expertise and don't need Agile Maneuvers).
But whatever, we're committed to this, the Talented Mr. Grippli is going to steal the shit out of things.
We're a level 20 grippli rogue. We've spent the following feats:
-Weapon Finesse
-Agile Maneuvers
-Agile Tongue
-Combat Expertise
-Improved Steal
-Greater Steal
-Quick Steal
-Improved Disarm
-Greater Disarm
-Quick Disarm
That's 10 out of 10, but we can also spend rogue talents on Weapon Finesse, a Combat Trick, Improved Steal and maybe some other feats via our advanced Rogue Talents. We're probably going to want Skill Focus (Sleight of Hand) in there as well.
We've got 15 BAB from our 20 levels, and let's say we've got 28 Dexterity (16 base + 2 race + 4 level bonuses + 6 item) for a +9 bonus.
That makes our Steal CMB= 15 BAB + 9 Dex + 4 feats -1 size = +27, and our Disarm Sleight of Hand bonus= 20 ranks + 3 class skill + 9 Dex + 5 item + 6 feat = +43. Now let's go find some level-appropriate foes.
Let's see... Red Dragon Great Wyrm, winged world-ending spawn of destruction, tor linnorm... ah, Thanatotic Titan. We can make a disarm attempt using our tongue at a +43 bonus against a CMD of 60, which means 20% of the time we can successfully use our little tongue to grab a 100 pound battle axe that's larger than we are. The other 80% of the time, we do jack shit and remain within 10 feet of a army-killing monster with a 30 foot reach using a 100 pound battle axe that's larger than we are.
Now if we wanted to increase our odds we could pick up miscellaneous bonuses to skills and attack rolls such as luck bonuses, insight bonuses and morale bonuses from spells and magic items. If we wanted to increase our odds of successfully stealing things even further, we'd have to completely overhaul our character concept.
First, replace our average BAB with good BAB by rolling something like a barbarian or fighter, and pounding our Strength up with levels, race (we can still have our Agile Tongue as a human with Racial Heritage), items, and maybe even stuff like sorcerer bloodlines. We pay our damn feat taxes (the fighter hurts less when doing this) and pick up our respective tricks- fighters have weapon training and weapon focus to up attack bonuses while a barbarian can just flat-out add your class level to one maneuver check per rage. We use enlarge person and the like to bulk up and increase our CMB and CMD. We can pump our CMB into the 50s or 60s, proving that if you want to steal something in the heat of battle and not get spotted, the best way to do so isn't to be a light and lithe little rogue, but a berserk twenty foot tall mountain of muscle screaming in fury. They'll never see you coming.
Of course, even after we've devoted a pile of feats and character resources into being able to swipe shit with our tongues, we run into one tiny little problem... there's nothing worth taking.
The titan had a weapon, but nothing that you could affect with the Steal maneuver- and the titan was something of a rarity at higher levels. Dragons and other monstrous land-shaking beasts are not only huge and possess ridiculous CMDs, but also generally don't fight with manufactured weapons and don't carry much in the way of personal belongings that could swing the fight if stolen away- you can't use disarm on a creature with fangs and claws. And even if you could disarm or steal something, while you're doing that you're not dealing HP damage and ending the fight, while also remaining well within the reach of the creature's own weaponry, leaving it free to chew on you instead (not only are you giving less than you're receiving, you probably don't have as much HP either). Thus if you want to take something from opponents in a high level game, about the most efficient way is just to beat them into the ground and loot their bodies.
This is the fundamental problem with Combat Maneuvers in Pathfinder. If you want to do them well, you have to sink a huge chunk of resources into doing them, and doing them leaves you exposed in the process for a negligible benefit, assuming it works at all- each maneuver has one or more ways to completely no-sell it through some form of defense or trait. If you can't use them, you've wasted a bunch of character resources on an attempt at making combat more interesting and memorable when you should have focused on hitting things for more damage for maximum efficiency. And if you've spent all those resources, you're probably going to want to use that maneuver as often as possible to get your money's worth, and risk turning your character into a one button gimmick. Pity about all the things that can stop you:
-Bull Rush doesn't work on anything much bigger than you are, and it's just going to move dudes around if you don't have an interesting hazard to stuff them into (and when fighting a monster on its home turf, the environment is probably more dangerous to you than the monster)
-Dirty Trick requires that you tailor your trick to the environment and the monster, and while it isn't as easy to no-sell as the rest of the powers, it can still be a hassle if your DM doesn't want to play ball.
-Disarm doesn't work on anything not carrying a weapon, and even if you do disarm them, they can still pick up their weapons if you don't do something about that (good luck catching swords larger than you are).
-Drag moves dudes around, can't be used on really big foes, and can't be used to drag foes through dangerous terrain
-Grapple is completely negated by freedom of movement and similar abilities and can't be used on much bigger foes. It's also the most complicated maneuver in the game, best demonstrated by the two pages of flow charts.
-Overrun can't be used against much bigger foes and requires room to charge and maneuver, which can be pretty dangerous
-Reposition is like Drag and has similar restrictions on size and hazardous terrain
-Steal requires that the target have gear other than weapons and that the gear be worth stealing, as we have demonstrated
-Sunder requires that the target have weapons or gear valuable enough to make a difference, but smashing such gear means you have to repair it after battle if you want to sell it as loot
-Trip can't be used on much bigger foes, or foes without legs or flying enemies
The last one in particular is interesting because of a long bit of Murphy's Rules-esque kerfuffling. See, D&D 4th Edition uses an abstract power system for delivering its various status effects and conditions, so a cleric and a fighter might both make attack rolls, and on a hit they do damage and knock the target prone, but a fighter might do it with a melee weapon that hits the target's AC while a cleric compels the target's will and do mental damage. This system annoyed a bunch of people, because not only did they feel as though it made all the classes the same, but that it smashed verisimilitude- how the hell could you knock an ooze or snake prone? This ignores that 3e allowed the same things to happen by virtue of not explicitly disallowing the use of trip mechanics on oozes and snakes and whatnot, and that there could be different interpretations based on the situation that use different specifics to create the same general situation of "creature can't move until it takes an action and regains its bearings."
Paizo decided they'd learn from that and create the most verisimilitudinous edition, so oozes and snakes and other creatures without legs or creatures that are currently flying are immune to being tripped. And the day was saved forever. Except... well, they're specifically immune to being tripped, not to being knocked prone. Thus, you can freely do things such as... say... turn on speak with animals (which any class can get by being a gnome) then walk up to a snake and yell "ON THE GROUND, MOTHERFUCKER!" and that snake will go prone. It'll take a penalty to its melee attacks, won't be able to use ranged attacks, have a penalty to AC against melee but a bonus to AC against ranged, and won't be able to move normally without standing up, an action that will allow its nearby enemies to get a free shot at it, reaching the same end state as if it were tripped. Even if it's an ooze that's immune to mental effects as well as trip attacks, you can hit it with rocks, or knock it over with grease or any one of a half dozen other abilities. It's not even a complete ban on physical attacks, you can still punt the thing or just run the fucker over. Or you can shapeshift into a critter immune to being tripped and lie prone of your own volition.
You just can't trip it.
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