If not getting crushed was the goal, El Jefe should move to 50N65E, because both combatants are large. Because that was your intent, I will put El Jefe at 50N65E.
Corky turns into a statue (rolled 12 Fort save), and comes crashing down, but not as fast as you might think because the corkscrew action slows it down, but not enough to keep it from breaking into a whole lotta pieces. El Jefe can breathe again in round 443.
Round 440: Two creatures come into the arena from the Lawful side. One is an ant the size of a pony. It holds its mouthless head and thorax upright. It has humanlike arms ending in sharp claws, and its abdomen has a stinger. The other creature looks like a pony-sized spider with humanlike arms below its mandibles. The two creatures move into the arena to 60N30E and 60N35E, respectively. El Jefe feels compelled to attack any creatures that come out of the Neutral side of the arena (rolled 12 Will save).
Next in round 440 for Neutral is a gray render (Monster Manual). El Jefe is at 50N65E, the ant is at 60N30E, and the spider is at 60N35E. El Jefe has 66 HP remaining.