Jennie's appearance was unexpected. Caleb didn't think he could meet again with someone he used to work with.
Caleb and Jennie had met once, it happened when Caleb's alliance successfully advanced to the next round.
Not only them, but other alliance members also gathered to discuss other strategies outside of their discussions in the game. During that time, Caleb met Jennie a few times.
Unfortunately, when the tournament started, Jennie was forced to die as her kingdom was invaded by tens of thousands of troops, just as Caleb's alliance troops were attacking the enemy alliance center.
At that time, Caleb realized Jennie would not win against the invasion. Yet, Caleb did not expect that Jennie could withstand the enemy invasion for several hours, disrupting the enemy's plans.
