This is an issue we are carrying since 0.13 (or maybe earlier, that was the first time I have seen it) - I just checked on the current codebase and discovered it is still there, so finally time to report.
On OSX the make deploy is working properly only the first time it is executed on a "virgin" system. All subsequent deployments are missing the libboost_system-mt.dylib which is definitely needed to run without dev environment. Obviously it thinks that the file is already in place:
libboost_system-mt.dylib already deployed, skipping.