The site claims its legal. A statement on JailbaitGallery (now on its new domain, TeenGallery.com) reads:
This site combines archiving abilities of sites such as tinypic.com and imageshack.com as well as the rate functions of sites such as ratemybody.com and facethejury.com. Most of the pictures found on TeenGallery.com can also be found on all of the sites listed above, as well as other sites of the same type, therefore the terms and conditions of all of those sites, and other sites of this nature, apply to TeenGallery.com. An approval process is in place to ensure that all content available is legal. Definitions of US Laws can be found here. Please send notification of any pictures you feel violates these laws here and said pictures will be reviewed and removed immediately.
But a 2009 Forbes article calls it a "nasty stuff" and a "dodgy" site.
According to the report, JailbaitGallery frequently scrapes the Web for its content–in other words, pulling pictures from sites where people might have posted provocative or alluring pictures of themselves or their friends.
JailbaitGallery’s main stock in trade: It aggregates picture of semi-nude and scantily clad girls and encourages users to vote on how young they think the subjects are. The pictures that wound up as part of the Facebook ad campaign were voted by the JailbaitGallery crowd to be around 16 years old.
It’s likely, however, that the affiliate that illegally ran the photo made money from the abuse and, unless the girls in the photo saw the ad and filed a formal complaint, no one could have done much about it.
Tip: You can filter explicit search results on Google, like pornography, using the SafeSearch setting. Find out how you can do it here.