No. pip will not install system-level dependencies. This means pip will not install RPM(s) (Redhat based systems) or DEB(s) (Debian based systems).
To install system dependencies you will need to use one of the following methods depending on your system.
Ubuntu/Debian:
apt-get install libfreetype6-dev
To search for packages on Ubuntu/Debian based systems:
apt-cache search <string>
e.g:
apt-cache search freetype | grep dev
Redhat/CentOS/Fedora:
yum -y install freetype-devel
To search for packages on Redhat/CentOS/Fedora based systems:
yum search <string>
e.g:
yum search freetype | grep devel
Mac OS X: (via Homebrew)
brew install freetype
To search for packages on Mac OS X based systems:
brew search <string>
e.g:
brew search freetype