I have little experience with melee classes. What would a "best" grappler look like?
I am aiming for an NPC of 10th level or less. 20 point buy for ability scores. Normal wealth per character level.
But I admit that I do not even know how to start defining a "best grappler", other than a warrior who uses grapple effectively in the widest range of situations. This gladiator will have earned his fame fighting both solo warriors and groups of monsters.
What weapon and armor does he use? Why does he grapple all the time? What strategies does he employ besides "grab and start smacking"?
What would you do and why?
(a) Six levels of Brutal Pugilist Barbarian
That provides Savage Grapple (Ex), Pit Fighter (Ex) with both grappling CMB and CMD improved, and Improved Savage Grapple (Ex), as well as 3 rage powers.
(b) The Improved Grapple and Greater Grapple feats
They require a mediocre INT but provide a lot for grappling.
(c) Perhaps a single Weapon Adept Monk level to be able to full attack while grappling and use Perfect Strike?
Eh, wrote a long post that got eaten.
Short version:
My suggestion would be Monk (Empty Hand, Sacred Mountain, Hungry Ghost) 2/Barbarian (Pugilist) 5/Rogue (Rake) 3. Important feats: Improved initiative, improved/greater grapple, preferably improved dirty trick
Use improved initiative to get a sneak attack in (with a thrown object if needed - empty hand is useful), used for demoralizing opponent (rake). Then grapple, bite, beat and kick his heart out. You can wear light or medium armor without losing much except for evasion (and barbarian speed), so going up against a wizard you might skip the armor but in a fight against a monster or warrior you want the heaviest thing you can wear.
Vary in style with what maneuvers you use, and don't be afraid to dirty trick to blind him, allowing more sneak attacks/demoralizations. Don't forget to Punishing Kick him around (or down) a bit, you have it 4/day and even though chance of success will be pretty low there's no penalty to use it and it can be used in armor. Then pin him down and SA his heart out with a spoon (counts as a light hammer!)
EDIT: And you'll have good saves too - F8/R7/W5 base.
note that you will have trouble being a monk and a barbarian due to alignment issues, lawful barbarians can't rage and chaotic monks lose all their class features.
also, "This gladiator will have earned his fame fighting both solo warriors and groups of monsters" is counter-intuitive as once you grapple something you're going to get shredded by a gang of monsters as you lose some dex and the ability to defend yourself properly. As a straight grappler I'm fond of monks with greater grapple and vital strike. If you're going to do something more all around you'll have to explore a lot more options.
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I will be sure to guide my grappling, Dwarven ally to this discussion. I can still tell you what I have pieced together from merely watching him grapple things as difficult as an Antlion.
*Brutal Pugalist all the way, and he could have had Imp Grapple if he was Human. Also, the only thing he "loses" for being in a grapple is AoOs. He doesn't lose dex or anything else.
*He has some Ion Stone that adds to his grappling.
*Armour Spikes can be used to make a "Light" attack while grappling or uses the grapple attempt as it's "to-hit."
Keeping both hands open for pinning makes the spikes useful later in the grapple.
*"Strength Surge" is awesomesauce. "Does a 38 get out of your grapple?"
"Not this round! Thanks, Strength Surge!" Sad DM was sad.
note that you will have trouble being a monk and a barbarian due to alignment issues, lawful barbarians can't rage and chaotic monks lose all their class features.
Unless some errata I didn't see changed that, Monks do NOT lose class abilities due to becoming non-lawful. They just can't progress as monks anymore.
Brutal Pugilist Barbarian / Bear Shaman Druid