As the Trial of the Purse concluded, neither the party nor Isabellas’s team had little time to breathe as the next trial was already upon them.
Trial 2: Trial of the Tongue
Pitting Orlando against the smooth talking Elven Pirate: Vaelis Thanrodil in a contest to convince Jarek Mill, a captured city clerk, to give up the target location of the Daisyguard’s next raid.

Orlando start of by assessing the situation, whilest Vaelis went full “bad cop” on Jarek.

Unfortunately, Jarek was used to threats so the attempt failed, but Vaelis skillfully changed threats into flattery leaving him smiling as he left the table. DM Note, Valelis scored the first of 3 successes needed.
Orlando realised Jarek was no fool and used to people trying to pry information out of him and decided to appeal to the professionalism of the city clerk instead.
It worked and Jarek concluded that Orlando ofcourse was smart enough to realise the raid would not be a tavern again like last raid, but something more commercial, maybe storage.

Vaelis had a mix of fails and successes while Orlando learned that Jarek was just stamping the order, but had seen the harbour stamp on the order as well.
Vaelis in a desperate attempt tried to undermine Orlando by claiming Orlando to be a plant, but it backfired and Orlando learned that the target location was Warehouse 7 by the northern docks.
Alfein’s outfit scored another “Favour of the Hand” making it 2-0 against Isabella’s pirate crew.
Trial 3: Trial of the Lock
Next up was Fenrir against the Goblin Pirate Grip Grimtooth.
The two contestants face an iron safe with no less than 4 doors, one on each side.

Fenrir, while not particularly skilled at lock picking, had seen enough locks being picked and successfully opened the first door.. only to find it was fake leading directly to a sturdy iron wall.
Grib, was having no luck and the foul swearing from the increasingly nervous goblin was enough to make the criminal audience watching blush.
As Fenrir moved on to the second door and successfully started to pick it, Grib decided to rush over and push the Aasimar druid away to capitalise on the progress Fenrir had made.
This made Fenrir turn into a Werewolf and ripped the door off its hinges… only to find it was another fake.

Grib, scare of the lycanthrope, rushed back to his original door and through a compination of terror of what Isabella would do to him if he failed, and luck, he managed to open the door.
With a short triumphant shout, the door opened into the safe. But Grim’s shouts turned quickly to surprised screams of shock as the safe contained a multi-legged Mimic!

Both Fenrir and Grim was chasing the fast Mimic and eventually Grim got hold of the speedy creature, but continuing his streak of bad luck, he got himself entangled in his lasso and knocked himself out.
Fenrir grabbed the unconscious Goblin and used him as bait for the Mimic and was able to grab the key winning this trial.
As the Mimic was led out with Grib’s leg in its jaw, the Goblin Pirate shouted curses and threats of revenge at Fenrir.
Trial 3 also went to Alfein and her outfit making the score 3-0
Trial 4: Trial of the Breech
Trial 4 faced off our Cleric, Amelia against Torren “Stonebelly” Underbough a very sturdy and muscular Halfling.

The two contestants stood back to back and each had a door in front of them to knock down with brute force. However, they were tied together with a 20ft robe.
Torren was bracing himself for the first attempt at his door, when Amelia instantly rushed to her door dragging the unfortunate Halfling with her.
With a massive crash her door started giving away.
Recovering, Torren yanked the rope back in an effort to knock the Cleric over, but while she was dragged along, she stayed on her feet.

The muscular Halfling reached his door with a mighty crash. It was already starting to give up.
With a few more slams at their doors, Torren slipped leaving Amelia in the lead and ready for the last blow to her door.
As she pulled the prone Halfing with her as extra weight behind her final attempt, Torren launched a small fireworks that called a favour in from one of his Hafling mates.
Suddenly a fat, naked Halfling jumped into the arena only wearing boots and a ninja hood. The Halfling streaker ran up and down shouting insults at the audience.
The spectacle almost made Amelia stop her momentum, but in the end she resolutly continued and smashed down her door winning another “Favour of the Hand”.

The score stood at 4-0 to Alfein and her outfit before the final trial.
Trial 5: Trial of the Eye
The fifth and final trial pitted Alfein against The Pirate Queen Isabella, the Blood Rose of the Seven Seas, herself.

The contestants started side by side and had to run to an ancient stone statue at the other end of the arena, climb it and take the Ruby Eye in its left eye socket and return it to the start point.

Alfein got the jump on Isabella and legged it half way to the statue.
Isabella instead tried to rile the audience but to her surprise it backfired and she was left rattled by the fact that not all were on her side. Preposterous!
Alfein used Isabella’s distraction to throw a line of ball bearings across the arena floor.
As Isabella caught up with Alfein, she skid on the ball bearings but kept her posture.
Alfein reached the statue, climbed it and pried out the Ruby Eye with her knife.
Isabella reaching the statue saw this with anger in her eyes, but only for a brief moment as the huge statue woke up as a fully animated Golem trying to take back the Ruby Eye.

Isabella jumped to grab Alfein’s leg. While she failed, Alfein used the opportunity to let herself fall down on Isabella kneeing her in her ribs in the fall.
Alfein was running back with the Ruby, but Isabella and the Golem caught up. Outnumbered, Alfein lost the Ruby to the Golem, that started walking back.
Isabella jumped on the Golem to take the Ruby, but in all the kerfuffle, the Ruby was dropped on the floor for the taking.
And Alfein didn’t miss the beat. She skillfully kicked the Ruby with her feet into her hand and ran to the finishing line.
It was over!
Alfein had won not only Orlando’s thievery gang back, but also acquired Isabella’s Pirate fleet in the progress.

Epilogue
Isabella’s crew quickly turned their back on her as she humiliated disappeared quietly into the crowd.
Alfein turned to Orlando and told him that he could have his gang and The Golden Carnation back.
Orlando, taken back by the display of charity, fell on his knees and proposed to Alfein, who said “yes”.

DM notes: 100+ games and this is the first time we will have a wedding.
DM notes: Final thoughts
So far our campaign has been a tough and serious one with big stakes and not a lot of clear paths forward to make the players think.
However, The Five Trials of Thievery gave me an opportunity to create something a bit more lighthearted and something where each player would have to stand on their own.
I really enjoyed running these two sessions and here are my DM notes of how I planned them out.
