Unfortunately ruby-install won’t let you install Ruby version 1.8.7 any more. Here’s how to install it using ruby-build so that it could still be used by chruby:
brew install ruby-build
brew install openssl libyaml libffi
brew install apple-gcc42
brew install openssl098
# dependencies
mkdir -p ~/.rubies
# if doesn't exist
brew link openssl098 --force
# 1.8.7 requires OpenSSL 0.9.8 (or lower)
ruby-build 1.8.7-p375 ~/.rubies/ruby-1.8.7
# compile 1.8.7-head (p375 is the same as HEAD)
brew unlink openssl098
# revert symlinking
chruby 1.8.7
# switch to 1.8.7