How can a pugilist deal with flying enemies?

Question

I started playing D&D a couple of months ago and I'm getting used to my pugilist character in my GM's homebrew campaign.

But I always have a problem when we face flying opponents, and I know for a fact (based on my characters past), that there might be a moment when I need to face a flying opponent (a warlock) alone.

But I can't see a way to even begin battling such a foe.
I have Ironbelly Brawler , Belligerent Bruiser, Openfist Disciple and Salty Shipwrecker as fight clubs, and at this moment do not have a side arm and I don't see my character getting one anytime soon.

Answer 1

Adding on to what has been said already:

• You might be able to simply jump up, using a box, table, or cart like a ramp, grabbing your opponent's feet and initiating a grapple maneuver of some kind.

• It's possible (depending on GM ruling and the Warlock's behavior) that they will have to stand on the floor or get near you for an attack. This could also open them up for a grapple action or sword strike.

• While you said you didn't see your character getting a sidearm anytime soon, if you get a chance to prepare for the fight it's not unreasonable to get one anyway, as your character seems to be aware of the Warlock's ability to fly. (I read your question this way, I hope my assumption is correct)

• If nothing else works you can try to throw things at them, be it your sword, a chair, a spear used as wall decoration, or whatever else is near you. If you hit them there's a chance of their concentration being broken and they might fall to the ground.

  The following factors can break concentration:

  • Casting another spell that requires concentration. [...]
  • Taking damage. Whenever you take damage while you are concentrating on a spell, you must make a Constitution saving throw to maintain your concentration. [...]
  • Being incapacitated or killed. [...]

  Source: DnD 5e basic rules page 79/80: http://dnd.wizards.com/articles/features/basicrules

Ultimately you can (hopefully) trust your GM to not throw you into unresolvable situations as long as you don't do anything silly. If you can't run away or defeat your enemy, then there's the possibility of a plot line where you get defeated - but not killed - and saved, so next time you will be prepared for this strong opponent, either in the form of a crossbow or something else.

Answer 2

Control the battlefield

If you have no way to reach a flying opponent, which is quite feasible, then you need to make sure to fight them in a location where flight is not an advantage.

This includes indoors or outdoors while there are high winds / lightning storms to make his flight difficult.

Fly yourself

Not sure what level you are but you could get a flying mount, jumping from the back of your Pegasus to grapple the warlock to the ground would be epic.

Don't go alone

If you know something is coming you do not need to wait for it to happen. Force the issue and have the fight before the warlock is ready, ideally while you have some companions with you who can assist.

Run away

Nothing says you have to stand and fight an opponent you cannot reach, just run and hide. If you mix this with controlling the battlefield the warlock might have to land to search for you.

Answer 3

Hand Crossbow

The Pugilist already has an option built-in for ranged attacks: Proficiency in Hand Crossbows.

You did say you had no intention of going with a sidearm and have heavily invested in melee. That's a perfectly acceptable build decision - but it does have it's drawbacks (no ranged option) that you will need to compensate for in other ways.

You're not always going to be in the spotlight

It's also important to remember that you have a character that excels in martial melee combat. Encountering a flying creature absolutely puts you at a disadvantage - but maybe it's where other party members excel. If you always expect to be able to fight at and with your optimum level, you may get frustrated when things don't go your way. But that's okay, those are opportunities where other party members can step up.

I've played a Great Weapon Fighting Paladin with no ranged options and in those fights against flyers, I sat there throwing spears. It was sub-optimal, but that was because I didn't make a build that was good at ranged.

In those cases, I also found other things to do (helping allies, healing, etc.) that actually helped me realize more about my character and his capabilities.