Got any hard evidence to back that up? Anyone can take a guess, but it means nothing unless you can prove it. Anecdotal evidence isn't proof. While I agree that many people do pirate apps I don't throw around bogus stats and opinions like they are facts.
The jailbreakers I know personally do not pirate apps. There are some very compelling - and obvious - reasons for uncrippling iOS devices that do not involve "getting free stuff". Do you really think Jay Freeman (Saurik) and the other JB pioneers decided to free their Apple crippled products with the motive of installing a few cracked $0.99 apps?
FWIW, one thing I have noticed is that the pirating demographic tends to skew toward high school age/early 20s males, while people in their mid-20s and older tend to jailbreak for other reasons. Anecdotal so YMMV of course.
Take your own advice. Just because the jailbreakers you know personally don't doesn't mean that jailbreakers as a whole group don't. Again, anecdotal evidence.
Btw, Saurik isn't a jailbreak pioneer. He runs Cydia, which amongst other things is primarily an app store for jailbroken devices. That is very different from being a hacker who finds exploits and writes programs to actually jailbreak devices. People like musclenerd, ipod4g and geohot are jailbreak pioneers.
Calling my "anecdotal" evidence worthless is the same as calling your entire post worthless. Your demographic is actually incorrect and if you ask politely, I will share with you some legitimate sources.
Another thing, it's much easier to hack into a jailbroken device than one in "Apple's jail", even if you have changed the root password and other security measures people sometimes take after jailbreaking. That jail is protecting you from the malware and other malicious stuff that plagues Android. Speaking as someone who knows a great deal about computer security. So while you get the ability to tweak your device, install apps both pirated and not, install themes and other customizations, you give up security. Some find it worth it, some (like myself) don't.