How can a halfling wrestle the tarrasque?

Question

Against a typical foe that's two or more size categories bigger than the attacker's own, a typical attacker's attempt to grapple stops at Step 3: Hold because the attacker "automatically lose[s] an attempt to hold if the target is two or more size categories larger than" the attacker (Player's Handbook 156). The typical attacker's bonus on grapple checks can be literally infinite, yet even infinity is insufficient to allow the attacker to take hold of a foe two or more size categories bigger than it. The best halfling grappler that ever existed can't suplex the tarrasque—or even a lowly ogre—without your help.

So, without changing the attacker's or the defender's size category or form—and without Pun-pun style shenanigans—, is there a way for an attacker to hold a foe two or more size categories bigger than the attacker?

Allow me clarify that I'm not looking for that one race that can grapple too-big creatures but for generally applicable options available to any creature after it enters play as not that race. Workarounds are unacceptable—for example, no committing suicide on a boon trap of last breath until the DM rewrites the reincarnate chart to include goliath then gaining XP sufficient to advance a level then taking the goliath barbarian 1 substitution level.

The spirit of the question would have answers locate in a text a feat, spell, magic item, or similar material that doesn't change the creature's size or form yet allows the creature to get a hold on too-big foes. A class that permits this is a last resort and shouldn't have a race as a requirement for entry.

(Be nice to answers posted prior to 5 Sept. 2017 at 1 PM PST—those answers were posted prior to the previous two paragraphs.)

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Note: The Races of Faerûn feat Jotunbrud (166) is no help here: it only increases the modifiers due to size and doesn't change the creature's size category. Similarly, the Dragon #303 martial arts style Stonegrind Wrestling (57–8) says that the creature is only "one size category larger for the purposes of grapple checks," rather than grappling generally. Further, the Dragon #300 prestige class flesheater (68–9) at level 2 gains the special ability flesh rip that makes it so the creature only no longer suffers size penalties on grapple checks. Even the game's finest mundane rasslin' class, the Champions of Ruin prestige class Black Blood cultist (44–8), doesn't normally overcome this size category limit. The fan-made grappling handbook "Hulkmania Is Runnin' Wild" focuses (albeit rightly) much of its attention on becoming bigger, bypassing—not altering—this limitation it. The closest I've found is the Dragon #342 halfling barbarian 1 substitution level special ability halfling rage that lets a halfling (only) while raging (only) count as Medium (only) "whenever doing so would be beneficial, such as while in a grapple" (90–1), which is pretty darn restrictive… and, given the wording, the DM may or may not allow the special ability to work for this purpose.

It was the special ability of the prestige class flesheater that reminded me once more of this limitation: it's a halfling-only prestige class that's good at grappling… yet that doesn't really seem to take into account that some of its best abilities are unusable on creatures with a size category bigger than Medium—like bigger creatures don't have flesh to eat or something. Does anything actually change—or even eliminate—this limitation on grappling for a halfling hungry for some tasty, tasty tarrasque?

Answer 1

So, I don't read the rules the same way you are. It seems to me that establishing a hold is a grapple check, just a certain specific kind of grapple check, and so these abilities that make you larger for grapple checks make you larger for that purpose as well. In any case, I think it's clear that the authors thought it did so: that there is no benefit anywhere listed that explicitly increases one's size for the purpose of establishing a hold is telling.

Powerful Build (and the similarly-worded "Larger than Small" class feature) are clearly meant to make you count as larger for basically everything combat-maneuver-y (combat maneuvers aren't a defined thing in 3.5 but "subject to a size modifier or special size modifier for an opposed check (such as during grapple checks, bull rush attempts, and trip attempts)" is pretty clearly trying to evoke that sort of stuff, as opposed to stuff like Intimidate checks or whatever that might also work out as side benefits), and grappling is so exemplarily combat maneuver-y that it's even called out specifically in the parenthetical in most of these upgrades.

Basically, there's nothing other than straight up size-alteration that will let you do this, but I think that's because the designers thought they already had that covered (and I would argue they do already have it covered), rather than because they actually wanted small creatures to really never-ever-ever be able to initiate grapples with bigger opponents.

That said, even with this restrictive interpretation of the text, we can still grapple enormous opponents quite handily, if we can provoke them:

The step required to establish a hold only applies when one is seeking to initiate a grapple. That means the size restriction can be ignored in the prominent case of an opponent having already initiated the grapple.

The Tarrasque is built to grapple its opponents: it possesses Improved Grab, Swallow Whole, and a +81 grapple modifier. It shouldn't be terribly difficult to get it to initiate a grapple with your halfling without any effort on your part, but suggestion et. al would certainly be effective should the Tarrasque prove hesitant to bite.

Once the grapple is initiated, your halfling can pin the Tarraque, move it about, damage it, prevent it from leaving the grapple, and all that good stuff without having to worry about size limitations. The size limitations are only a problem against opponents the halfling can't taunt into initiating a grapple.

Answer 2

At the outset, I want to argue that options which increase your effective size while attempting a grapple check, or for the purposes of grapple checks, or similar, actually do help with avoiding the “automatically lose” clause of step 3. This comes down to two points:

• “Automatically lose” is not the same thing as “does not happen at all.” You still are actually attempting a grapple check; it’s just that you lose no matter how the rolls turn out.

• Whether or not you “automatically lose” a check falls under “for the purposes of that check.”

Given these points, effective size increases for the purposes of a grapple check, or during a grapple attempt, or when subject to opposed size modifiers, or what have you can be used to overcome the size limitation on grappling. However, improvements to size modifiers, removal of size penalties, and the like, do not help since those only touch the numbers: we have to really count as larger in order to bypass the limit, not merely get the numbers of someone who is larger. Thus flesheater and Jotunbrud do not help, as noted in the question. On the other hand, these things do:

• Halfling barbarian 1st substitution level, Dragon vol. 342 pg. 90. The halfling rage ability states that “Whenever a halfling barbarian rages, treat him as a Medium creature whenever doing so would be beneficial, such as while in a grapple.”

• Stonegrind Wrestling martial arts style, Dragon vol. 303 pg 57. You are making a grapple check, and so you are considered larger for the purposes of that check.

• Battle Jump feat, Unapproachable East pg. 42. Provides a number of benefits if you attack a target if you drop from at least 5 feet above them first. One of these is that if you attempt to start a grapple after such a drop, “you are treated as one size category larger than normal for the first grapple check following the battle jump.” Note that Battle Jump is a regional feat, specifically with respect to Taer.

• Wary swordknight halfling paladin 3rd substitution level, Champions of Valor pg. 51. The tougher than small feature offers, among other things, “When a wary swordknight is subject to a size modifier or special size modifier for an opposed check (such as during grapple checks, bull rush attempts, and trip attempts), she is treated as one size larger if doing so is advantageous to her.” Replaces aura of courage. Requires worshiping Avoreen.

• Stonebone acquired template (LA +2), Dragon vol. 350 pg. 36. Grants the powerful build feature, to count “in many ways” as a size category larger. In particular, “Whenever a stonebone creature is subject to a size modifier for an opposed check (such as during grapple checks [...]), the stonebone creature is considered to be one size larger if doing so is advantageous to it.” This wording is identical to the wording used by the wary swordknight’s tougher than small, but since the two abilities have different names, it does not seem to me that they would run afoul of any same-source limitations. Stonebone is acquired due to corruption caused by magical pollution, but the precise circumstances of acquiring it are left to the DM. It also changes the creature’s bones, making them, well, stone, and also results in some bony outgrowths protruding from the creature’s skin, but it doesn’t change the creature’s size or shape and only has minor affects on its appearance overall.

I was not able to find any spells or magic items that assisted in this matter.

However, these five actually allow a halfling (Small) to count as Colossal for grappling. Halfling rage allows us to start our count from Medium, and each of the subsequent options allows us to count as one size larger. Since creatures can grapple things a size category larger than themselves, we can actually get away with skipping one of these.

Note that even if enforcing alignment restrictions, you could be a wary swordknight sentinel, rather than paladin: sentinel is a Neutral Good variant paladin from Dragon vol. 310 pg. 50. Since Avoreen is LG, you can be NG and still worship her, and sentinel is otherwise compatible with wary swordknight. That allows you to combine tougher than small with halfling rage.

However, in an alignment-enforcing game, I have not found enough options to allow a halfling to grapple the Tarrasque while completing both black blood cultist and flesh eater. Since flesh eater requires Chaotic Evil, the sentinel approach is completely out and worshiping Avoreen is impossible under the rules of the Forgotten Realms. If we replace wary swordknight with stonebone, the LA of stonebone prevents us from getting the 8 ranks needed for either class on time. Rank-pumping shenanigans are possible, I suppose, but at that point you might as well just manipulate form yourself into the character you want.

For this reason and others, when ignoring alignment requirements, or when not interested in options that are incompatible with Neutral Good alignment, stonebone is almost-certainly the aspect to ditch: while it burns two levels instead of wary swordknight’s three, wary swordknight gives decent benefits on the first two levels (if nothing else, HD and full BAB), while LA is pure waste. Plus how one actually becomes stonebone is left entirely up to the DM beyond the association with magical pollution.

So if we ignore alignment requirements, a halfling barbarian/wary swordknight/black blood cultist/flesh eater can grapple the Tarrasque while completing both prestige classes, and actually even has a level to spare to dip something else if desired.