Over the last few years, I've spent time each week in a local middle-school classroom. (See article here) I've also mentored high- and engineering-school kids in various ways. My experience has been that kids today don't get much exposure to computers except that involving waving a mouse. They get to be quite good at creating PowerPoint presentations, but they're clueless about how the computer gets there. <RANT>This has a lot to do with the sad state of teaching as well as the overarching goal of schools to turn out nicely conforming cattle.</RANT>

But, to your question. Perl has an easy entry curve, even though a steep back-end learning curve. As an interpreted language, it's easier to grasp than C or C++. It's also a heckofalot easier to set up Perl on a BSD/Linux machine than it is to set up Java.

I'd suggest something a bit different. Start with shell scripting! Teach kids to control their machine and their environment first, like how to insert cron jobs and .profile customizations. I'd also look into one of the little programmable microcontroller development kits. When I was a high school kid, the thing that fired my imagination was a class that used a little interpreted "assembly language" that was implemented on an IBM 360. We had to punch card decks to get at it, but the concepts of how to work the hardware directly really fired me up.

Next, load up Blender3D. Understanding graphics and the embedded Python language that drives its animation will allow the boy to get a feel for what's involved in gaming. It's the only thing I've ever used Python for, and I have to admit it's waaaay cooool.

"The right path" is to get him started. The key then is not to lead, but to get him to become self-starting. That's the critical issue in all of education, and it's the one thing schools (and television) are destroying.