It's not so much that it's 'Hilarious', but the line 'I've covered wars you know?' has just become the catch-all argument for anything regarding the character. Like "How the hell does a normal guy with a baseball bat stand up against someone like Gold Lightan?", "Well, he's covered wars you know..."
And also, those characters all look alike, but they have pretty different personalities and traits. Someone like Nico Bellic I can't stand, and I thought Chris from RE5 was pretty dull too. I don't even know who half those other guys are, so... no comment I guess. I did think it was strange they used the scrapped design for Sam Fisher in Conviction though, considering that look never came to light.
Anyway, this is getting kinda off-topic, but at the same time I can't really think of any first party developed Sega characters apart from Kazuma I particualrly liked in recent years.