brew install gdb

~ $ brew install gdb
Updating Homebrew...
==> Installing dependencies for gdb: openssl@1.1 and python@3.8
==> Installing gdb dependency: openssl@1.1
==> Downloading https://mirrors.cloud.tencent.com/homebrew-bottles/bottles/openssl@1.1-1.1.1g.mojave.bottle.tar.gz
######################################################################## 100.0%
==> Pouring openssl@1.1-1.1.1g.mojave.bottle.tar.gz
==> Caveats

A CA file has been bootstrapped using certificates from the system keychain. 
To add additional certificates, place .pem files in
  /usr/local/etc/openssl@1.1/certs

and run
  /usr/local/opt/openssl@1.1/bin/c_rehash

openssl@1.1 is keg-only, which means it was not symlinked into /usr/local,
because macOS provides LibreSSL.

If you need to have openssl@1.1 first in your PATH run:
  echo 'export PATH="/usr/local/opt/openssl@1.1/bin:$PATH"' >> ~/.bash_profile

For compilers to find openssl@1.1 you may need to set:
  export LDFLAGS="-L/usr/local/opt/openssl@1.1/lib"
  export CPPFLAGS="-I/usr/local/opt/openssl@1.1/include"

For pkg-config to find openssl@1.1 you may need to set:
  export PKG_CONFIG_PATH="/usr/local/opt/openssl@1.1/lib/pkgconfig"

==> Summary
🍺  /usr/local/Cellar/openssl@1.1/1.1.1g: 8,059 files, 18MB
==> Installing gdb dependency: python@3.8
==> Downloading https://mirrors.cloud.tencent.com/homebrew-bottles/bottles/python@3.8-3.8.2.mojave.bottle.tar.gz
######################################################################## 100.0%
==> Pouring python@3.8-3.8.2.mojave.bottle.tar.gz
==> /usr/local/Cellar/python@3.8/3.8.2/bin/python3 -s setup.py --no-user-cfg install --force --verbose --install-scripts=/usr/local/Cellar/python@3.8/3.8.2/bin --install-lib=/usr/local/lib/python3.8/site-pack
==> /usr/local/Cellar/python@3.8/3.8.2/bin/python3 -s setup.py --no-user-cfg install --force --verbose --install-scripts=/usr/local/Cellar/python@3.8/3.8.2/bin --install-lib=/usr/local/lib/python3.8/site-pack
==> /usr/local/Cellar/python@3.8/3.8.2/bin/python3 -s setup.py --no-user-cfg install --force --verbose --install-scripts=/usr/local/Cellar/python@3.8/3.8.2/bin --install-lib=/usr/local/lib/python3.8/site-pack
==> Caveats
Python has been installed as
  /usr/local/opt/python@3.8/bin/python3

You can install Python packages with
  /usr/local/opt/python@3.8/bin/pip3 install <package>
They will install into the site-package directory
  /usr/local/opt/python@3.8/Frameworks/Python.framework/Versions/3.8/lib/python3.8/site-packages

See: https://docs.brew.sh/Homebrew-and-Python

python@3.8 is keg-only, which means it was not symlinked into /usr/local,
because this is an alternate version of another formula.

If you need to have python@3.8 first in your PATH run:
  echo 'export PATH="/usr/local/opt/python@3.8/bin:$PATH"' >> ~/.bash_profile

For compilers to find python@3.8 you may need to set:
  export LDFLAGS="-L/usr/local/opt/python@3.8/lib"

For pkg-config to find python@3.8 you may need to set:
  export PKG_CONFIG_PATH="/usr/local/opt/python@3.8/lib/pkgconfig"

==> Summary
🍺  /usr/local/Cellar/python@3.8/3.8.2: 4,124 files, 62.7MB
==> Installing gdb
==> Downloading https://mirrors.cloud.tencent.com/homebrew-bottles/bottles/gdb-9.1_1.mojave.bottle.tar.gz
######################################################################## 100.0%
==> Pouring gdb-9.1_1.mojave.bottle.tar.gz
==> Caveats
gdb requires special privileges to access Mach ports.
You will need to codesign the binary. For instructions, see:

  https://sourceware.org/gdb/wiki/BuildingOnDarwin

On 10.12 (Sierra) or later with SIP, you need to run this:

  echo "set startup-with-shell off" >> ~/.gdbinit
==> Summary
🍺  /usr/local/Cellar/gdb/9.1_1: 55 files, 27.9MB
==> `brew cleanup` has not been run in 30 days, running now...
Removing: /usr/local/Cellar/openssl@1.1/1.1.1d... (7,983 files, 17.9MB)
Pruned 0 symbolic links and 2 directories from /usr/local
==> Caveats
==> openssl@1.1
A CA file has been bootstrapped using certificates from the system
keychain. To add additional certificates, place .pem files in
  /usr/local/etc/openssl@1.1/certs

and run
  /usr/local/opt/openssl@1.1/bin/c_rehash

openssl@1.1 is keg-only, which means it was not symlinked into /usr/local,
because macOS provides LibreSSL.

If you need to have openssl@1.1 first in your PATH run:
  echo 'export PATH="/usr/local/opt/openssl@1.1/bin:$PATH"' >> ~/.bash_profile

For compilers to find openssl@1.1 you may need to set:
  export LDFLAGS="-L/usr/local/opt/openssl@1.1/lib"
  export CPPFLAGS="-I/usr/local/opt/openssl@1.1/include"

For pkg-config to find openssl@1.1 you may need to set:
  export PKG_CONFIG_PATH="/usr/local/opt/openssl@1.1/lib/pkgconfig"

==> python@3.8
Python has been installed as
  /usr/local/opt/python@3.8/bin/python3

You can install Python packages with
  /usr/local/opt/python@3.8/bin/pip3 install <package>
They will install into the site-package directory
  /usr/local/opt/python@3.8/Frameworks/Python.framework/Versions/3.8/lib/python3.8/site-packages

See: https://docs.brew.sh/Homebrew-and-Python

python@3.8 is keg-only, which means it was not symlinked into /usr/local,
because this is an alternate version of another formula.

If you need to have python@3.8 first in your PATH run:
  echo 'export PATH="/usr/local/opt/python@3.8/bin:$PATH"' >> ~/.bash_profile

For compilers to find python@3.8 you may need to set:
  export LDFLAGS="-L/usr/local/opt/python@3.8/lib"

For pkg-config to find python@3.8 you may need to set:
  export PKG_CONFIG_PATH="/usr/local/opt/python@3.8/lib/pkgconfig"

==> gdb
gdb requires special privileges to access Mach ports.
You will need to codesign the binary. For instructions, see:

  https://sourceware.org/gdb/wiki/BuildingOnDarwin

On 10.12 (Sierra) or later with SIP, you need to run this:

  echo "set startup-with-shell off" >> ~/.gdbinit