The Gator definitely fits inside the CPA as long as it isn't bulging too much. I got my CPA because I needed something smaller than my Air Boss, but I still need to carry a bunch of stuff. The CPA became my go to carry on for week long trips that didn't require a suit or an extra pair of shoes. The chief advantage of the CPA for me is the fact that it is sized as a briefcase and has semi-rigid sides which allows me to carry folders, papers, manuals effectively without having them crushed or twisted. Each of the inside walls has a mesh section to keep your papers and/or laptop upright and secure so nothing gets damaged.