Shanks and Mihawk – The Failed Generation
There’s an interesting parallel between the Luffy/Zoro relationship and the Shanks/Mihawk one. Both Shanks and Luffy set out looking for a crew at 17 (Shanks was 15 at Roger’s execution and according to chapter 0 he recruited Yasopp 2 years later).
Mihawk started making a name for himself before the death of Roger and traveled around seeking out stronger and stronger opponents. Before he met Luffy, Zoro had already made a name for himself in the East Blue while traveling around seeking out stronger and stronger opponents.
‘So where does the failure lie?’ you may ask, and rightly so because both Shanks and Mihawk seem pretty successful at what they do. Luffy tried to recruit the future World’s Strongest Swordsman, why wouldn’t Shanks? In chapter 0 it’s clear that Shanks sought out Yasopp based on reputation and we’ve already established that Mihawk had a reputation of his own at this point. But where Luffy gained a crewmate Shanks got a rival.
Now to Mihawk’s failure. At age 19 Zoro met and dueled his greatest opponent Dracule Mihawk. At age 19 Mihawk witnessed the execution of Gol D. Roger.
From what we’ve seen in the story Roger was obviously a swordsman, meaning he could potentially have been the previous World’s Strongest Swordsman (if it wasn’t Roger then there existed an even stronger swordsman at the time which is hard to believe). I believe that’s part of the reason why Mihawk seems so bored and unfulfilled (beyond the whole suffering from success thing), I also think that’s why he became a rival of Shanks rather than a crewmate (sure he’s also a loner, but so was Zoro and he still joined a crew), he saw someone strong enough to truly test his strength and without Roger around to defeat he needed, more than ever, to prove himself against other swordsmen.