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What would the Bandit King do here?

Right now, the players in my group are about 1 mile outside the hilltop fortress of a bandit king (or, a guy who fancies himself a bandit king). The game is D&D and it's 4E. The party is 6 PCs, plus one allied cleric and five allied level 7 soldiers. (The allied soldiers are currently in a different location)

The fort is pretty well defended and there are 75-80 men under the Bandit King's ("BK") command. The non-minions in the bunch are mostly either Human Outlaws or Human Dire Beast Hunters, led by several elites (an assassin/lurker, a skirmisher and a soldier). There is also a trained owlbear and two controller types, as well as several Ravenous Attack Dogs. I picked the Dire Beast Hunters, as I imagined them using the net attack to capture slaves for trading.

The players' plan was to attack supply wagons going into and out of the fort, forcing the BK to come out after them.

They managed to keep the first ambush hidden from the fort's view, but it will be more difficult going forward.

So, if you were the Bandit King and in charge of the fort, what would you do if:
(a) You saw your supply wagon being ambushed a mile outside the fort? Do you ride out with 25% of your men, 50%, all of them? (The fort also abuts a large lake, so they can get fish from the lake for food. That is currently not an issue.) My thought was 25% of their number leave the fort, and keep a few men a safe distance behind to immediately report back. 75% stay in the fort in case it's a trick.

(b) If the PCs keep the second ambush hidden, how soon do you send out men looking for what happened to the wagons? The players have already found out they sent out four wagons a week at different times and to different locations and round trip is usually 6-8 days each. If you suspect foul play, do you ride out in force?

(c) In a straight up fight, the PCs are over-matched vs all the bandits, even if you add in their allied cleric and five allied soldiers, so are looking to get them into "bite sized" groups.

(d) If the players wait too long, the BK will unite his forces with a local band of orcs, and then be able to grow their power even further.

Any other ideas, or anything I'm missing?

Thanks

Option (e) As a safety measure for the supply chain, start having some supplies brought in by boat over the lake.
 

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[MENTION=1861]Loonook[/MENTION]
Yeah but my ninja had none of your spaghetti western. Truce? ;)


Ehh, I guess :D. Honestly a caravan traveling through rough territory should have a lot of coverage if you have it available. It seems like your original BK was not ready for it. At most I'm seeing 2-3 additional minionesque soldiers on each caravan ranging near, and then just go from there with the ideas presented.

Slainte,

-Loonook.
 

Group of heavies hidden in that center cart ready to jump out and blow away any PCs who came through. Pretty common in the days of highwaymen, and could easily surprise the PCs. You have two animal/creature scouts (Druid can shapeshift right?) to run point, along with anyone who has some sort of concealment spell. Rogues also have UMD; do you have additional combat/obfuscation/travel items that these guys can handle?

After seeing Quickleaf's minute-long sniping of my post I think I need a bit more motivation to go further. What exactly is this guy's background? What skills does he have and who does he have on his side? He knows his way around or else he wouldn't survive this long... But we should know his skills.

EDIT: QUICKLEAF!!! Making me work more :).

Slainte,

-Loonook.

This is 4E D&D.

The BK is an elite skirmisher, but is pretty good at range or in melee.

His main lieutenants are two elite soldiers, an elite lurker (assassin), and two controllers.

There are a couple of human "brute" types for damage, as well as a trained owlbear.

However, most of the non-minion bandits are human outlaws (soldiers) or human archers (artillery), so they don't have a ton of "muscle" - soldiers are tough and have good defense, but don't dish out a lot of damage.

Which is why they're joining forces with the orcs.

The BK already has a bit of a small fiefdom established - several clusters of farms and families of fishermen pay tribute to him in foodstuffs and money, as well as local traders. There is not much in the way of civilization to stop him - however, the sparse population also means that money/treasure is sparse, which is why he is attempting to expand his territory. Plus, a kingdom to the north of this no man's land has fallen apart due to a civil war, so refugees are trickling south, towards the BK's domain. All the more reason for the BK to put his stamp on even more territory.

He is fairly crafty - he knows he can't squeeze the farmers & fishermen too much and he has built up a pretty good supply of foodstuffs in his fort
 

Ehh, I guess :D. Honestly a caravan traveling through rough territory should have a lot of coverage if you have it available. It seems like your original BK was not ready for it. At most I'm seeing 2-3 additional minionesque soldiers on each caravan ranging near, and then just go from there with the ideas presented.

Slainte,

-Loonook.

The turf wasn't that rough when the first supply wagon left - the BK thought he had most of the locals cowed/cowering. The PCs are new to the scene and have seemingly managed to keep the BK unaware of their presence.
 

All the more reason for his brutal reaction. In addition to skinning the mayor, he could take a few hostages (women and children) and threaten to kill them unless the culprits are turned over. Put the townspeople and players in a jam, and give them something heroic to do.
 

The turf wasn't that rough when the first supply wagon left - the BK thought he had most of the locals cowed/cowering. The PCs are new to the scene and have seemingly managed to keep the BK unaware of their presence.

Depending on if his face is readily identifiable to the PCs (and just how insidiously cunning he is) the Bandit King could infiltrate them. Set himself (or a trusted lieutenant) up as "freedom fighters" stealing from the BK, and have him meet up with the PCs ambushing one of his own wagons. Forge a bit of trust, learn how they operate and who they care about, come in with a high risk but big payoff plan which sets the PCs up to be divided and conquered OR pisses them off so much they go ahead with a direct assault.

That would take quite a bit of brass and require the Bandit King's appearance to be unknown, him to very good at disguise, or hire a mercenary to play the role.
 

Depending on if his face is readily identifiable to the PCs (and just how insidiously cunning he is) the Bandit King could infiltrate them. Set himself (or a trusted lieutenant) up as "freedom fighters" stealing from the BK, and have him meet up with the PCs ambushing one of his own wagons. Forge a bit of trust, learn how they operate and who they care about, come in with a high risk but big payoff plan which sets the PCs up to be divided and conquered OR pisses them off so much they go ahead with a direct assault.

That would take quite a bit of brass and require the Bandit King's appearance to be unknown, him to very good at disguise, or hire a mercenary to play the role.

I like the idea, but I think it may work better with the assassin I had mentioned above, as he has bluff & thievery trained.
 

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