I'm going to measure this in sword units: Shiryu will go down before Mihawk, hence so will his captain.
It's interesting how Blackbeard, Shanks and Buggy are interconnected since their youth, though. Luffy is the odd one out despite knowing the three of them.
What's funny is the paths the generations took
Gen1 - Great Marines and Pirate Kings (75-80 years), romance and war
Gen2 - Admirals, Revolutionarys and Yonko (55-60 years), stale mate and weapon scrambling
Gen3 - Shichibukai, YC1, recent yonko (40-45 years old), schemers and lurkers now gunning for Pirate King
Gen4 - Supernova, RA & Yonko heirs (20-25 years), young guns going straight for the top without waiting in line
Gen1 was so strong and chaotic that they made Gen2 adopt new beliefs like RA, Absolute Justice or need of preparing 20 years for war.
Gen2 never got to claim power fully (about 5-10 years back and until now) because when they finally got power Gen3 were also ready.
Gen3 had to play the long game. They knew Gen1 would sooner or later die, they just had to be smarter than Gen2 when the time came. They have now seized power (Buggy, Mihawk, Shanks, Blackbeard) or were about to (Doflamingo, Crocodile).
Gen4 is the TikTok generation. They don't need record companies, model agencies, book publishers or whatever. No apprenticeship. They are not waiting, they will set up their own companies and try to claim the prize for themselves in their own way.