DnD Story: How the Phantom Thief Made Failure Look Awesome

This debonair dragonborn rogue tries to save everyone and has the absolute worst luck with attack rolls. But, man, does he always manage to fail with style!

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After being inspired by a bunch of D&D shows and podcasts, I finally decided to buy into the hype and took a friend from my office with me to a local gamestore to play D&D Adventure League.  She was a veteran player and was really excited about me getting my feet wet with the game.  I wanted to make a rogue character, but felt like doing something a little out-of-the-ordinary, so I ultimately threw together an Arcane Trickster modelled after a phantom thief.  I wanted to be an unusual race, so I went for flavor rather than optimization and chose to be a white dragonborn despite the lack of DEX and INT bonuses.  After consulting a Draconic dictionary, I decided to name him Stythr Kaldak, a play on Arsene Lupin, which means “manly wolf.”  To fit more with the clever, cat-and-mouse-game nature of a phantom thief who enjoys a battle of wits (and to make up for his terrible Wisdom rating), I also put my expertise bonuses into Perception and Insight instead of Stealth and Sleight of Hand.

Despite being really weak and being downed frequently, I had a ton of fun playing as Stythr.  I decided to roleplay him as an idealistic, morally-driven Robin Hood, so unlike the other rogue in our party, I was very open about my thieving ways, only killed NPCs to defend other people and tried to convince everyone else to resolve matters without bloodshed.  After the first encounter, we also got a box of giant toenails as a trinket drop, which, despite their usefulness as potion ingredients, nobody else wanted for some mysterious reason, so, seeing an opportunity for comedy, that quickly became one of Stythr’s quirks.  When my friend, playing a tempest cleric, had to revive me, she went through my possessions to get my healing potion, and I asked the DM if she had to roll to see if the box of toenails opened up and spilled out on her.The second time I fell, I tried to give her the box of toenails to remember me by, and when she shouted a repulsed “no,” I doubled down and said that I had already written it into my will.Naturally, everybody was cracking up by that point.  We then fought some stone giants, and I asked to add their toenails to my collection, which the DM granted, to my delight.  This isn’t the only thing I did for flavor either; despite it having no real use, I bought a Cloak of Billowing and added it to my inventory to complete my phantom thief aesthetic, since Stythr’s all about having a flair for the dramatic.  I now make use of it whenever I’m trying to look cool.  Which I guess is undermined by the toenail collection?  Anyway, I digress.

Despite his colorful antics, the thing I’ve noticed the most about Stythr is that he seems to be able to pull off the most insane stunts… but only if it doesn’t really impact combat.  The best example of this is when I went as the level 4 arcane trickster to an ongoing game of Descent into Avernis.  The particular quest I joined was extremely combat-centric, and since I was paired with a bunch of unscrupulous teammates, hilarity ensued.

We start off the quest by meeting the captain of the Flaming Fists, a group of mercenary law enforcers who keep order in Baldur’s Gate.  The man’s already embroiled in a fight against a bunch of desperate refugees, which doesn’t sit well with my character’s “help the poor and oppressed” philosophy.  Things only go from bad to worse when we find out that he had only hired us because the Flaming Fists are too busy imprisoning all the helpless refugees.  He also says we have permission to kill anyone we need to, since the Flaming Fists are above the law, which everyone but me is excited about—great, I think, I can already tell my tablemates are a bunch of loose cannons.  And to add insult to injury, he singles me out as an object of ridicule, since I’m the most unusual-looking party member.  He starts off by staring at me and saying how he “can’t believe that they’re desperate enough to hire someone of MY kind” and saying how “the stench of foul play is everywhere… although it might just be MY stink.”  Miffed, I casually ask the DM about the contents of the captain’s desk, looking for some kind of leverage to cause mayhem for this guy.  He explains that in addition to some official seals and documents, he also has an ink bottle, and I immediately think “jackpot.”  But he follows up by saying he has a collection of teeth on display, and I’m intrigued.

In a last-ditch attempt at courtesy, I tell the captain that I respect his tooth collection, since I personally have a collection of giant toenails.  At which point, the DM tells me, “You see the captain give you a judgmental look of disgust—apparently he thinks teeth are fine, but TOENAILS are too gross to collect.”And THAT’s the moment I decide to make it my mission to ruin the captain’s day.  As an arcane trickster, I get the ability Mage Hand Legerdemain, which allows me to make my Mage Hand invisible and move objects without being spotted, provided I succeed at a Sleight of Hand check.  So on the way out of the captain’s office, I tell the DM, “I use my invisible Mage Hand to tip over the bottle of ink onto his teeth collection.”  He’s completely shocked, and tells me to make a Sleight of Hand check.  I was initially appalled when I roll a 3, and am getting ready for a confrontation when suddenly the DM cracks up—the captain had rolled a natural 1 on his perception check.The ink spills onto his teeth collection, and he’s so upset that he falls backwards in his chair and lands on the floor, yelping in frustration.  Everyone cracks up, and I feel like an absolute champion despite my prank not actually helping us on our quest.

Things take a turn for the worse, however, as soon as we go to a local bar to get some info out of an informant, a violent female Halfling rogue.  My other office friend, a gnome wizard, joins me in playing games at the bar while everyone else gets drunk and causes trouble.  Once the other players endear themselves with the woman by suggesting that she takes the man she catches cheating in her dice game as a slave, then subsequently encouraging her to cut off his finger, I hear the scream of agony and run up to try to diffuse the situation.  Suddenly, the pirate captain who’s out for revenge against this woman storms into the bar with his crew, and an encounter begins when he spots her with us in the balcony.

The fight starts when a white dragonborn, a Lv. 1 fighter, decides to breath-weapon a whole bunch of the pirate’s goons without provocation, completely freeze-drying two of them.The rest of the party springs into action, instantaneously murdering two more.  When I get my turn, I shout “Why do I always have to work with a bunch of murder hobos!?” and start knocking people out with the flat of my rapier.To try to end the fight quickly, I decide to do a crazy jump off of the upper floor balcony to sneak attack the leader nonlethally before the rest of my group brutally murders him.  I roll a NAT 20 acrobatics and land a hit while sailing through the air like a magnificent eagle. I roll d8 + 2d6 for sneak attack.  The dice land… THREE ONES.  I try to escape by jumping over the table, and roll… ANOTHER NAT 20 ACROBATICS.  So basically, I’m leaping around like Legolas in an antigravity chamber, but my rapier’s hitting him like a wet noodle.The pirate is so confused that he asks me what I’m doing, so I shout “Trust me, I’m trying to save your life! Everyone else is gonna murder you!”  I attack him again for d8… ANOTHER ONE.  At this point, I can’t even believe it.  The DM announces that he’s at 1 HP now; if i had literally rolled 1 better at ANY TIME, I would have successfully knocked him out.

Meanwhile, one of my comrades, a barbarian, gets his turn, and decides to do something REALLY helpful… slam his axe into the neck of the goon I had nonlethally felled in my first turn.  He actually MISSES the first time despite having advantage, which is crazy, but the second time he lands.  The DM describes how blood starts gushing down the stairs.  Meanwhile, our warlock looks at the captain I wanted to spare and decides to Eldritch Blast him in the face for 8 damage.  As his headless body hits the floor, I shout “You should have let me knock you out!” followed by, “Well, at least I managed to save that one guy!”  Cue me spotting the blood on the stairs.  I run up to see the barbarian covered in blood and grinning like a madman, and I just facepalm.

This trend continued for the rest of the quest, including a bathhouse, where the same barbarian buried his axe into the shoulder of a seemingly defenseless woman clad in nothing but a bathrobe, while the dragonborn fighter physically assaulted another one and wrestled her to the ground.  To be fair, they were actually assassins, but nobody else in the bathhouse, including my character, knew anything besides the fact that our group had stormed into a bathhouse with weapons and started randomly attacking a group of vulnerable women.  Then, later, when we encounter two cult members torturing a prisoner, our party members decide we need to do a rapid surprise attack… on the person being tortured.  To “put him out of his misery quicker.”  Yeah, this is literally their plan.  Then, once we do manage to non-lethally capture one of the cult members and restrain her in the former prisoner’s shackles, our party members ruthlessly kill her as soon as she tells us what’s up ahead in the dungeon.  Meanwhile, I’m helpless to stop any of this because I can’t use my normal methods like rapier sneak attacks or the Sleep spell in these confined quarters with nowhere to hide.

But the kicker comes when we get to the final battle against one of the cult leaders being blessed by a triad of evil altars, where my attack rolls all whiff horribly.  I get fed up with being terrible, remembering how I made two nat 20 acrobatics checks earlier, so I decided, for flavor, to gratuitously backflip over one of the altars to land in front of the cult leader.The DM makes me roll for acrobatics…it’s a NAT 20. AGAIN.  Nobody can believe it; I’ve literally natted every single acrobatics check I made that day.I go to make my attack, inspired by new confidence… And MISS AGAIN.  I groan, pan around and do a hide check behind one of the altars… A NAT 20.  The table erupts in a roar of disbelief.  Once again, I’m Solid Snaking this guy with insane jumping and stealth moves, but can’t do anything TO him.

When I finally land a sneak attack hit as I jump out of my hiding place and dealt decent damage, it feels great.  I have my character triumphantly shout “Look, I can do things!!!”… and then I’m promptly engulfed in an explosion of darkness along with the rest of the party as the cultist’s bare skull self-destructs from being killed, blasting everyone in a 30-foot radius.  And from there, having blown up everyone because I finally landed a good hit on an NPC for once, our adventure came to a cliffhanger ending… or at least until next week, when we’ll hopefully finish the dungeon.

So basically, Stythr’s a debonair dragonborn in a cape who’s extremely bad at combat and whose efforts to resolve things nonlethally are constantly thwarted by his bloodthirsty party members.  But I guess he looked incredible and suave while failing miserably in battle, which I guess is how a phantom thief is supposed to act, so… yay?


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