About 4 years ago, I started playing D&D with a new group.

It really got me back into the game and we’ve been playing weekly ever since.

At the time, there were three DMs in the group. Each DM had their own campaign in the rotation and worked to tie in some common threads between all three stories. Effectively, each story took place in the same world but at different locations.

The DMs would rotate when the group expressed interest in a different story or if the DM just really wanted to play again.

When I first started playing with this group, I rolled up a character – a timid young wizard. Three weeks later, the DMs were rotating which meant I got to make another new character for this campaign.

Where the first character was a timid academic, this next character was anything but!

Having gotten used to playing with this group, I decided to play a character that’s a little more my style when it comes to roleplaying.

I presented them with my new character: the rascally thief with a heart of gold, “Prince” Jiffy Halfstep.

To this day, I don’t think I’ve ever had a character quite as polarizing for the table as this guy.

“Prince” Jiffy Halfstep

The Halfling thief known as “Prince Jiffy Halfstep” was no royalty. Still, he came to be viewed with princely respect and admiration by many of the downtrodden people in the slums of Waterdeep’s Field Ward.

In time, the title stuck.

Jiffy was a “Robin Hood” type character. At a young age, he grew tired of the rules in the orphanage that he was raised in. He escaped and chose to make his own way on the streets. Finding new friends and family, it took no time at all for Jiffy to learn how to survive.

His small size and quick-thinking made him exceptionally good at getting into places unnoticed. As he got older, he began to view cat-burglary and pickpocketing as a type of art form.

Still, these talents were exclusively used at the expense of those who “could stand to make a donation” to the city’s poor.

These activities gave Jiffy a rush that he could never get enough of. It was hard to tell if it was the smiles on peoples’ faces when he would return with his latest score that he found so addicting or if it was the ever-increasing reward for his capture.

The jobs would continue to get harder and Jiffy would get bolder with each heist. He developed a flair for theatrics, taunting the guards who consistently failed to capture him before he escaped to one of his many safehouses in the Waterdeep slums.

Unfortunately, however, it was only a matter of time before Jiffy’s overconfidence got the better of him and his luck ran out.

Falling for a “honeypot” set by the city guard, Jiffy was arrested and imprisoned.

But perhaps his luck hadn’t run out just yet after all…

The Party Gains a Rogue

While “Prince” Jiffy had been a constant source of headaches for the Court, it was hard to deny his skill.

Though his crimes were numerous, a case was made on Jiffy’s behalf. Rather than facing punishment of life in prison or execution, a group that was being assembled to handle an important mission could benefit from Jiffy’s skill.

If he were to survive this dangerous mission, Jiffy would get a clean slate for his service to Waterdeep. While he wouldn’t receive any of the praise and reward that the others have been promised, he would be free to start a new life elsewhere without pursuit.

If he didn’t survive this mission, it’s the same result (though less humane) as him facing justice for his crimes.

The Court agreed and Jiffy was handed over to the party to join them on their quest. If Jiffy were to try and escape, the party was instructed to execute him on the spot.

Ever the dashing rogue, Jiffy insisted that he didn’t plan to make a run for it. The party cautiously trusted him…

The Mission

The party was tasked with acquiring a powerful item, a tome that contained the Word of Making. This tome would enable anyone who could harness the Word of Making’s power to channel the magic of the gods.

Think of it as the Wish spell but with even less restrictions.

Each of the group’s 3 DMs were using these Words of Making as the MacGuffins in their stories. Honestly, I thought it was pretty cool and it led to a type of “All-Star” campaign once the three storylines converged.

A rift had opened to some other dark plane. Somewhere within the massive, dark tower that stood amongst the barren wastelands of this plane was the tome.

The mission was seemingly simple enough: find and acquire the tome then bring it back to Waterdeep.

Other groups had been sent through the rift, but none had yet to return. All things considered, our group wasn’t particularly expected to return either.

Heading into the rift towards unknown danger and almost-certain peril, the party set out on their mission.

The Party Braves the Tower of Death

Jiffy made good on his word to the party.

Not only did he not try to escape, he gleefully threw himself at certain danger to help his allies. He couldn’t help but show off, but the party came to admire his flamboyant swagger and general panache.

Navigating the massive Tower of Death, Jiffy was able to expertly disarm every trap and poke his nose into every locked room. Like an over-caffeinated ferret, he was able to quickly sniff out every piece of treasure within the tower and store it for later in the party’s Bag of Holding.

In combat, he was able to weave in and out to deliver decisive Sneak Attacks on enemies. Calling out quick one-liners isn’t necessarily a must-have mechanic for Rogues, but the theatric Jiffy liked that it kept attention on him.

That would change slightly in the next area of the Tower, however.

The Tower of Death. The symbols in the circular rooms will make sense in a bit…

The party came to a large circular room with a massive pillar in the middle of it. The room was intersected by four hallways and had four sets of double doors.

The air seemed to pulse with energy and everyone’s hairs began to stand on end.

Coming down the hallways, the party was attacked by a large group of undead soldiers and their Death Knight commander.

“This is bad. This is very bad.” one of the players said. “Should we run?”

But initiatives were already being rolled and we were very nearly surrounded.

With a smirk, Jiffy began getting creative.

“Nah” he chuckled, “we can take ‘em!”

The Quick-Thinking Thief

If you asked Jiffy, he always had a plan for everything that could possibly happen.

In truth, he hated planning and preferred more spur-of-the-moment actions. His gut feelings and quick reflexes had never steered him wrong!

Well… except for when they got him arrested and sent on this mission, but who’s keeping score?

The first couple rounds of combat, Jiffy helped take out a couple of the undead soldiers while making his way to the Northeast side of the room. The party’s Paladin was squaring up with the Death Knight while the others were focusing down the minions.

They were holding on, but everyone at the table knew that this was a virtually impossible fight. (We were like level 10 or so. The Death Knight alone is a CR 17 and he had over a dozen minions helping him.)

But Jiffy had that gut feeling pulling him towards that set of double doors on the Northeast side of the room.

Because the Thief subclass allowed Jiffy to pick the lock on the doors as a bonus action, he was able to get them open pretty quickly.

“What are you doing?!” the party’s Ranger says.

As the doors fling open, a rush of intense heat bursts forth.

In a loud booming yell, a deep voice calls out:

“Who are you?!”

Jiffy and the Genies

Opening the door, Prince Jiffy found himself face-to-face with an Efreet. These are powerful and cruel genies from the Elemental Plane of Fire.

“What are you doing?!?!” the Ranger says louder this time.

The Efreet was magically restrained and chained to some kind of device. Needless to say, even by Efreeti standards, this genie was in a very bad mood.

Thinking quickly, Jiffy immediately dropped to his knees and bowed.

“My lord! I’m here to save you!” he calls out with all of the conviction he could muster.

Half of the table (including the DM) burst into laughter. The other half are staring at me with a unique mixture of confusion and anger.

Jiffy makes a Deception check and aces it.

“Then set me free, Halfling! I shall bring my vengeance upon those who have captured me!”

Undoing the restraints, Jiffy releases the Efreet into the combat.

“You just killed us. We’re screwed!” the Paladin says.

Combat continues until it comes back to Jiffy’s turn. I couldn’t help but grin from ear to ear as the DM asks me, laughing, “Jiffy, what are you going to do?”

The table was silent as I chuckled, “I’m going to the next room!”

Just like his interaction with the Efreet, Jiffy found a Marid in a similar restraint. (These are genies from the Elemental Plane of Water. They typically have a better disposition than Efreet.)

Once again rolling high on his Deception check, the Halfling Rogue swore himself to the Marid. Freeing his second new lord from its shackles, he released the Marid into the fight.

The rest of the table were positive that this would bite them, but the genie were at least helping.

“We’re so screwed” the Paladin kept saying under his breath.

A Prince He Shall Be!

By the time Jiffy released the third genie, a Dao from the Elemental Plane of Earth, the combat was coming to an end. As before, Jiffy successfully convinced the genie that he and his allies had come to free her.

Not one to leave a locked door unopened, Jiffy freed the fourth and final genie, a Djinn from the Elemental Plane of Air.

As the other three genies began carving their way through the Tower of Death, the Djinn took a moment to thank Jiffy. It explained that they had been captured by the BBEG of the adventure. Their power was being siphoned to power… something bad…

Jiffy was invited to join the Djinn back to the Elemental Plane of Air.

I looked away from the DM to everyone else at the table. Their eyes were wide with anticipation. The Paladin kept shaking his head and mouthing “please don’t” towards me.

There were two things that Jiffy held as being supremely important: his word and a bit of showmanship. With a wink and grin, he turned back to the genie.

“I would like to join you, dear Djinn, but I’m afraid my place is here. I am Prince Jiffy Halfstep of Waterdeep’s Field Ward and I have given these, my subjects, my word that I would assist them on their quest.”

The noble Djinn nodded his head.

“Perhaps some other time then?” the Djinn said in a booming and noble voice. “No other guest to my home has received the welcoming that awaits Prince Jiffy Halfstep of Waterdeep!”

With that, the Djinn made his escape from the tower.

The rest of the table (including the DM) were staring in disbelief.

“Let’s go! Time’s a-wasting and those other genies cleared the way for us!” Jiffy said as he began cheerfully walking towards the next set of stairs and whistling a little tune.

Unfinished Business

The party was still not quite calm about what had just happened. To ease the tension, Jiffy explained himself.

He figured that the genies wouldn’t have any reason to attack the party. After all, who are they going to be angry at: the ones who captured them or the ones who freed them?

The Cleric chimed in that the dear Prince had just pledged himself to three different powerful beings.

“Nah. My fingers were crossed when I said all that!”

Sure enough, when approached by the genies (thankfully at different times), Jiffy talked his way out of more possible trouble. For each one, he said that he was wrapping up some business and could get his way back “home.”

I’m so thankful that my charisma rolls were on fire this session. This could have backfired so spectacularly at so many points…

The rest of the Tower of Death was a breeze. There were a few enemies that hadn’t been annihilated by the now-free genies, but we dealt with them quickly.

Sure enough, we ended up recovering the tome that possessed the Word of Making. It was right next to what we assumed was the BBEG of this adventure.

Gathering the tome and with a heavy sigh of relief from everyone at the table, the DM rotation passed to the next person.

“I love you, but that could have gone so wrong!” the Paladin said to me.

What Became of Prince Jiffy Halfstep?

Several months later after the third Dungeon Master’s campaign and “all-star game” that came from all three campaign parties acquiring their Words of Making, we were having a “cool down session” as I call it.

With the huge story being finished, we got to talking about each of our characters. What became of them now that the story was over?

My first character with this group, the wizard, went back to pursuing a quiet life of academia. The character that I played for the third DM’s game, honestly deserves his own write up similar to this one. (So I’ll save what happened to him for that story!)

But Jiffy had the most shocking epilogue of all.

None of the genies ever came to collect on his claims of servitude. Presumably, none of them knew that they would only have a couple years to do it.

With a clean slate, Jiffy returned to Waterdeep. He shared his stories and newfound wealth (from selling the treasures he acquired in the Tower of Death) with the others in the Field Ward. With some assistance from many of the city’s merchants, he even set up a charity organization that existed to offer help to the city’s poor.

But old habits die hard…

Constantly looking to prove himself as the greatest thief who ever lived, Jiffy sought to pull off something truly legendary: he would steal the masks of the Masked Lords of Waterdeep.

Unfortunately, this didn’t go as well as his legendary overconfidence led him to believe.

Having blown his second chance, Jiffy was executed.

However, his actions have inspired very popular legends of both song and the written word. In the slums of the Field Ward, a statue of the dashing and daring “Prince of the Paupers” was erected in Jiffy’s honor.

Want More?

I hope you enjoyed this little storytime!

The memories and antics are one of my personal favorite things about playing D&D. They’re those kinds of moments in a campaign that you know you and your group will always be able to look back on.

Writing this out brought me back to that moment at the table. Yeah, it was definitely a reckless way to play, but I’m personally the kind of player who likes to poke at the world and see what happens.

It resulted in a legendary moment with my group that we still joke about 4 years later!

It also taught me an important unspoken rule about DM-ing: “Use Genies with Care.”

This article came about because I’ve been getting a ton of traffic on my tale of another character I played, the gnome artificer who basically built a Death Star. If you liked this article, go check that one out!

If Jiffy sounds like the kind of Rogue that you would like to play, check out my guide to the Thief Rogue subclass!

You might also want to check out my Complete Guide to the Rogue Class in D&D 5e!

But that’s all for now!

Let me know if these stories are something you’d like to see more of. I’ve got tons from both side of the DM screen that I can’t wait to share!

Until next time!