What phone is better for a 14 year old boy who know how 2 mess with phones?sidekick 2008 or blackberry pearl?

Neither. They are expensive delicate phones which tend to break very easily. For someone your age, I would recommend a much sturdier phone.

neither......a 14yr old does not need anything like that....a razr would work just fine

sidekick.

both are too much phone for a kid your age i wouldnt get my son either of those phones at 14 just because he likes to mess with them but if your into texting then any phone with a unlimited texting plan from verizon would do just fine