
Gnomezrule |

Just a word of warning. If you have monk fight Owlbear he will own the poor guy. I suggest whoever fights Owlbear you let the PC roll the perception to notice hes blind in one eye. If he takes the cue and tries to position himself to stay on the blind side you roll the skill check. That way you can keep the fight exciting by letting Owlbear be more exciting.
At the very least raise yhe DC on the skill checks.

deathbydice |
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Owlbear will easily be beaten by most main-line warrior oriented opponents, due to his miserable AC. Our dwarfish Barbarian beat him within an inch of his life on round 3 grabbing a windlass spar and battering him with that two handed weapon (and power attack).
The point to me was : he should be beaten, but spared. teaching them that some mercy will get them allies.

Uri Meca |

Ditto, our monk PC schooled Owlbear mercifully. (Though I fully expect it would have been an easy fight regardless of who took him on.) It was such a one-sided fight I didn't even bother with the skill check to notice the partial blindness. He simultaneously made an ally out of Conchobar by winning him enough gold off the side bet to buy Rosie's violin back from Grok.
The monk then skipped Plugg in the chain of command and asked Harrigan, directly, using *words* for a thumbs up/thumbs down regarding whether or not Owlbear should be left conscious. (I had Harrigan come out to see the sport.) Harrigan promptly ignored the monk, turned to Plugg and asked him why some scum was talking to him in spite of the Day 1 directive to never talk to him.
Plugg blanched in (sense motive 10) fear at the threat-laden rebuke. Plugg had the monk immediately sentenced to the sweat box. He paid up his gold, spitefully ramming the bag of coins in the sweat box, cramming the lid shut with the gold pressing against the monk's head. (The monk nearly died over the next day and easily could have were it not for Sandara surreptitiously channeling in his vicinity.)
Plugg then finished beating the living tar out of Owlbear. He and his cronies had taken to cruelly calling him Chickenbear over the next few days, tarring and feathering him all over again. Owlbear made it all the more pathetic trying to gain favour by clowning around as a chicken in a blatant need for approval. One of the PCs made him friendly, another made him helpful. The monk has begun training Owlbear. We'll see how that turns out.
Good times.

Shaun |

In my game, Owlbear actually won against a fighter (unarmed archetype). I played it cautiously and had Owlbear attack defensively most of the time, like actual boxing. No one bothered to size him up for his blindspot. When he got tossed the club, he KO'd the fighter with it. A different PC made friends with him later with promises of crab. He's now a gunner's mate and an idiot savant at taking apart and assembling ballistae in record time.

Gnomezrule |

A pair of solid punches or one club could take down a first level PC. The blind in one eye mechanic was put in so that the PC had to hit multiple times but Owlbear hit only once or twice.
Now maybe its the mechanic that makes it too easy. If I were to run it over I would run without it or up tge dc and hide the process behind the DM screen.

Lamontius |

Completely disagree with the OP.
I have had plenty of nail-biting moments occur in my campaign so far, but the monk in my game won the fight handily, showed mercy and built a strong ally for the party.
In the process of winning so handily, the party monk garnered a great deal of hate from Plugg and Scourge, singling himself out to be the target of much more scary situations later on, such as the:
Since that initial fight with him, every person in the party has grown to love Owlbear, who:

Story Archer |
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Just a word of warning. If you have monk fight Owlbear he will own the poor guy. I suggest whoever fights Owlbear you let the PC roll the perception to notice hes blind in one eye. If he takes the cue and tries to position himself to stay on the blind side you roll the skill check. That way you can keep the fight exciting by letting Owlbear be more exciting.
At the very least raise yhe DC on the skill checks.
.
I have to tell you, our Owlbear fight was absolutely epic. We have a big Barbarian whom Plugg attempted to goad into fighting Owlbear; even that early on Plugg was viewing him as a potential rival since he had excelled at the tasks put before him and earned praise from other officers. The truth is that the Barb would have plastered Owlbear (the group started out at 2nd level and he was an Invulnerable Rager, so he would have had DR 2/- against non-lethal damage, a decided advantage). Instead, the party Rogue, a lithsome and petite female with incredibly high Dexterity forstalled him, telling him that's exactly what they wanted him to do and that they needed to do something to put Plugg's 'faction' off-balance... so she stepped forward to fight him instead while the Wormwood's crew jeered and placed their bets.She had good Perception and had already noted Owlbear's bad eye and had a high enough Acrobatics skill that he would only hit her if she rolled a 1, so she used Bluff to set up sneak attacks (which I allowed her to use unarmed to deal non-lethal damage) in the form of hitting vital areas like the knee, groin or eyes. The fight lasted a good long while with her getting the better of him across the board - until Owlbear was tossed the club and he hit her hard enough to almost kill her with a single blow. She got up off the ground and promptly crit'ed him, roleplayed as a kick to the knee and then a knee to the jaw when it buckled... she jumped on him to claw his good eye out but the Barbarian pulled her off. A staredown between he and Plugg commenced while the crew murmurred about what a wildcat she was and Sandara led her off to heal her broken ribs. The party Bard (a Sea Singer who would later become our captain) later visited Owlbear in secret to soothe over any hurt feelings and laid the groundwork for Owlbear's switch in loyalty in the fight against Plugg.
It was one of the highlights of the WWM for us and really gave a PC the chance to effectively use skills in combat. It started a trend too, of the rogue becoming known as the most deadly member of the crew because of her unpredictability and her willingness to do anything it took. Another scene much later featured a one-on-one battle between the Barbarian and Avinarr Sorenesh (sp?) where the werewolf was defeated in solo combat before the assembled pirate council members to the surprise of most in attendance... one of the other pirate crew members pointed out the rogue and murmurred 'And I hear she's the dangerous one...'

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We restarted Skull & Shackles and I am now a player.
A halfling gunslinger (buccaneer). Plugg goaded me into the arena, but it was obvious that Owlbear had taken some serious brain damage. So rather than attack him, I started talking to him like he was a big labrador.
"Who's a good boy? Stay! Staaaay!"
Refused to throw a single punch, when Plugg got frustrated and threw the club in I grabbed it and tossed it across the deck saying: "Fetch!"
When Owlbear returned the club I scratched him behind the ear and he fell over as I rubbed his belly. "Who's a good boy then?"
Owlbear likes me a lot more than Plugg now, but Plugg refused to pay up. Which is fine, I'll get my payment yet.

Martial, Martial, Martial! |

We restarted Skull & Shackles and I am now a player.
A halfling gunslinger (buccaneer). Plugg goaded me into the arena, but it was obvious that Owlbear had taken some serious brain damage. So rather than attack him, I started talking to him like he was a big labrador.
"Who's a good boy? Stay! Staaaay!"
Refused to throw a single punch, when Plugg got frustrated and threw the club in I grabbed it and tossed it across the deck saying: "Fetch!"
When Owlbear returned the club I scratched him behind the ear and he fell over as I rubbed his belly. "Who's a good boy then?"
Owlbear likes me a lot more than Plugg now, but Plugg refused to pay up. Which is fine, I'll get my payment yet.
Just like a pirate of legend!
:-P

Nidra |

In my campaign, I have Owlbear throw a barrel nearby at PC in an attempt to show how powerful owlbear is. It turns to critical which cause my PC barbarian to knock prone and near death before he could manage to do anything.
It's funny that my PCs attitude toward Owlbear improve greatly after Owlbear defeat them. He has gained some respect from PCs which I think this is really good :)

Obbu |

Yep, Our raging barbarian annihilated Owlbear.
with an AC that low, you can only really expect him to threaten non-fighter types.
I would suggest, for drama, if he is getting defeated fast enough that his HP is dropping past more than one of the thresholds per turn, that you give him at least a few extra health to regulate the pace of the fight. i.e. if he goes from 15+ to below 10 in one attack, for example.
If you want to make him more of a challenge, you'd need to raise his AC, or his health: but be careful with that if you're going to use him later on, as he will suddenly be much less powerful.

LeesusFreak |

I rebuilt him as a Brawler, kept his HP the same. The increased damage from his UAS and the fact that he is now proficient in them made him more than a threat to the PC that was elected for the fight (it wasn't a hard decision for the party, between the Rum Rations (even nerfed to 1d4-1) and the Filth Fever from the dire rats that 5 of the 6 PCs contracted, it went to the Kasatha gunslinger). It was a decent fight, for sure (had to fudge the end and stall Owlbear for a round, but otherwise it went pretty well).

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In my campaign, the scarred rager barbarian stepped up, won initiative, raged, and immediately critted. Owlbear didn't last long after that. The raging barbarian kept hitting him past unconscious, and the rest of the PC's had to pull him off. Owlbear became the party's enemy due to the barbarian's lack of mercy. Which caused party tension since one of the PC's had already tried to befriend Owlbear in the hold previously.
I leveled him up and used him in the final battle for the Man's Promise. He fared poorly there as well. A sad tale.

Game Master |

I didn't tweak him, since I was rushed for time. The party was terrified of him, and basically assumed, for some reason, that he was at least a ninth-level barbarian and would slaughter them all. Our strangler grapple-focused brawler stepped up, grabbed his throat, and only a lucky 20 on Owlbear's part let him stagger out of the grapple at 1 hit point. When it became clear that Owlbear didn't want to fight anymore (being prodded and shouted back into the ring by the pirates), the grappler just walked off. Owlbear became their friend because he didn't quite understand that the grappler's disgust wasn't mercy.

GM Xan Nes |

Personally, I have altered Owlbear to be far more cunning and Insideous because the players found him to easy to beat and while they like him, there characters aren't the most respectful of characters, and most of the time treat him with just a bit more respect than Plugg ever did, ie no more tarring and feathering. They did make him helpful after the fight, but after how they treated him Owlbear will get his revenge....

Jondera |

When I ran it, the party rogue had gotten in trouble earlier in the day, so I used that as an excuse to force him into the fight instead of letting the party pick. I also tweaked the blind in one eye mechanic where instead of just being a DC 15 acrobatics to not be hittable, I made his acrobatics roll his AC for the round (since it was nominally an improvement over his regular AC).
It took him long enough to get Owlbear down that it was a pretty tense fight, but as a rogue he never had much trouble keeping ahead of the guy.

Kileanna |

We had a different take on this fight.
Our bard was forced to fight him, as some kind of punishment for having a big mouth. She had already been making some friends among the crew and inciting them against Plugg and Scourge. So Plugg wanted to maje Owlbear humble her.
She refused to fight. At all. She kept avoiding all attacks while calling Plugg a coward and accusing him of hiding behind a poor simpleton. She also started talking to Owlbear telling him things like «if Plugg forces you to do things then he is not your friend».
At first the crew was mad because they weren't getting the fight they wanted to see. But a few ronds and diplomacy rolls later, Owlbear was confused and starting to believe the bard, and many people among the crew changed their mind and started to feel hatred for Plugg and pity for Owlbear.
So Plugg realized that if he allowed the show to continue the bard could turn the crew against him. He stopped the fight and said aloud that the bard had ruined the game before leaving with Owlbear.
Half the crew was pissed at her for not having a good fight, the other half was pissed at Plugg, so the basics of the mutiny were probably set at that time. Plugg hated the bard since then and decided to take his revenge on her when she wasn't among her friends. Owlbear was loyal to her since then, and when the mutiny took place he helped the PCs to fight Plugg.

Cevah |

It has been too long for me to recall the fight. I don't think it was a big deal either way. Owlbear was still Plugg's after that.
It all changed when the party mutinied. The party was sent to Bonewrack Island. We snuck back in the middle of the night. When the limited officers realized what was happening, they came out and fought. Owlbear arrived at the doorway just after an officer was killed there from above. He then heard my voice, from above: If you want to live, go back to sleep. He didn't think twice. He turned around and went back to bed. Ever since, he has been my friend, and my first 2nd level follower [leadership]. I upgraded his armor and arms, and he is much better at fighting. He's liked me ever since.
/cevah