Wonder how he learned how toke on Cuban stogies -- from his Tio Tico, perhaps?

The trip took place in December 2012, so Jessie was still a minor. Cuba does not have a legal drinking or smoking age, and the age of sexual consent is 16 (though prostitution and pimping are officially illegal). It all comes down to whether it was a properly-financed official "class trip" or not -- but if Jesse hadn't graduated at that time, he, Andersen, and Jon still had a student-teacher-parent relationship. And just as the school's 25-year-old sex abuse scandal was becoming a memory...not that the high school Jon went to did any better. I guess scholastic sex scandals run in Jon's family along with fragile legs!