Definitely in.

Initiative Roll: 13

Zashier enters the pit still in weathered clothing, but looking positively chipper. "One more aughta do it. Then... then we get to that." He half-mutters to himself as he takes that final step inside.

Initiative: 20.

(@JMBeckwith: Ooooo~ Ominious!)

Gilrosh is in. 

Initiative: 15

Thargan will join
Initiative: 11

Iarus's burden never ends.

Initiative: 4

Boozy Jon is in 

Initiative: 4

Barrington Bigsby is here!

Initiative: 17

You all stand inside the dark room behind the gate waiting for your moment to move, the arena is silent as you wait and the gates are pushed open and you see before you an Ogre! It stands tall and walks around looking unsure of its self, it has 2 heads though one being much smaller then the other, they bicker between each other until they meet your eyes.

The Pit is a thick layer of sand and a scattering of large rocks, nothing else.

=    1      2       3      4       5      6       7      8      9     10     11    12    13    14    15

A  .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . 

B  .     . .      . .     . .      . .     . .      . .     . .      . .     . .      .+   . .      . .     . .      . .     . 

C  .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . 

D  .     . .      . .   +. .      . .     . .      . .     . .+    . .     . .      . .     . .      . .     . .      . .     . 

E  .     . .      . .     . .      . .     . .      . .     . .      . .     . .   !. .     . .      . .  !   . .      . .     . 

F  .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .     . .     . .      . .     . 

G  .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .     . .     . .      . .     . 

H  .     . .      . . +  . .      . .     . .      . .     . .  O. .O   . .    ! . .     . .      . . !   . .      . .     . 

I  .     . .      . .     . .      . .     . .      . .     . .    O. .O   . .    B. .     . .      . .     . .      . .     . 

J  .     . .      . .     . .      . .     . .      . .     . .   Z . .  E . .    I . .       . .      . .     . .      . .   Te. 

K  .     . .      . .     . .      . .     . .      . .     . .      . .     . .  Th . .      . .      . . + . .      . .     . 

L  .     . .      . .     . .      . .      . .   + . .     . .      . .      . .      . .      . .    G. .     . .      . .     . 

M  .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . 

N  .     . .      . .+ J. .      . .     . .      . .     . .      . .     . .      . .     . .      . .   +. .  . .     . 

O  .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . .      . .     . 

----------------------------------[                                                    ]--------------------------------------

Boulder +(Half cover)

For Initiative I have split you into 2 groups.

Group 1: Boozy Jon, Tenacity, Barrington Bigsby, Gilrosh.

Group 2: Elwin, Zashier, Thargan, Iarus.

The Ogre will go after you all.

1st group take your turns!

Boozy Jon will move to L6, focus all his senses on the Ogre, notch an arrow, and hide behind the boulder. stealth 22

(Just for clarity, maybe change Thargan from yellow as it is hard to read. I almost thought I was missed off until I highlighted it)

Tenacity will move to N13 for the cover of the boulder and pull out her shortbow to take a shot at the Ogre. 

To hit: 5 Damage: 4

Gilrosh moves to N13
"A big guy eh? Let's slow this down a bit, and make these rocks a little more colorful"

Casts Entangle centered on the Ogre.

As a bonus action he grabs a handful of pebbles from the ground and casts Magic Stone on them

Barrington Bigsby moves up to J10, casts Shield of Faith on himself and readies an attack with his Longsword if the Ogre moves within melee

"Come on, then! Hit me, right here!"

Group 2 your turn! 

Iarus will move up next to Barrington (J11) and fire off a ray of frost at the ogre.

Attack: 17 Damage: 2

"Our bodies shall be the shields for the fragile."

"Hooo--that's a big one." Zashier shakes himself slaps his cheeks, then runs off to 8J and whips one of his smaller throwing darts at the Ogre."Take that!" 

Attack: 20 Damage: 7.

It was time.

Elwin ran out, quickly glancing around at his comrades. After noting the position of those taking cover, he moved into the front line, nodding at the one's admonition--Iarus, if he remembered correctly.

His hand was already closed around his crystal again, and as he moved his fist and whispered, once again a thin layer of frost spread from his hand to cover his body. Pocketing the crystal, he gripped his spear firmly, then gazed at the filthy ogre that was quickly being surrounded by entangling foliage. One more quick utterance under his breath--a curse, this time--and he again felt his patron's power flow through him. He stood alert, ready to strike should the creature free itself.

Elwin will move up to J9, then use his action to cast Armor of Agathys at level 1. His bonus action will be spent activating his Hexblade's Curse, targeting the ogre. He'll use his reaction to activate his Polearm Master feat and make an opportunity attack should the ogre get within 5 feet.

Reaction Attack: 15, Damage: 11

((Stupid question: considering Ogres are large, should he take up 4 squares instead of one? If so, it might make a slight difference when it comes to range.))

Thargan will cast Hunters Mark and run to K10 with both shortswords drawn and will dodge 

When the large gates open a cheer is heard from the crowd as everyone begins to run in and take position!

Strength save: 23

 The vines begin to wrap around the ogres legs but it is to strong and 4 begins to charge at Zashier.

 It uses its club to slam down on Zashier

Attack: 21 Damage: 14

 Boozy Jon you get advantage from stealth, not even a Nat20 would let the ogre see you.

 Group 1 your turn is up!

Tenacity will move to J15 to get a better line of sight with her shortbow and she'll take another shot.

As a bonus action, she will cast Bardic Inspiration on Iarus

To hit: 5 Damage: 3