The next bounty increase we see for Luffy comes after Punk Hazard and Dressrosa. Much like the previous bounty increase, we only see Luffy’s bounty jump 100M(now totaling 500M) for the capture of Caesar Clown (300M bounty) and the defeat of Doflamingo (who’s bounty was locked at the astonishingly low value of 340M once he became a Warlord). While Luffy’s bounty at the end of Dressrosa was still 166% of Caesar’s and just under 150% of Doffy’s, Dressrosa acts as another intensely narrative driven bounty increase.
As a stand alone arc, we could argue that Luffy’s bounty increase for Dressrosa ought to be significantly higher given the threat Doflamingo posed to the Straw Hat crew but there are two narrative elements that are essential to put this bounty increase in context. First, Punk Hazard and Dressrosa are simply small stepping stones on the plan to take down Kaido – again it is important to rehash that while Doffy does pose a major threat, the “Big Bad” of the Post TS OP is not the Warlords any longer but the Yonko. Defeating yet another Warlord after already taking down 1. Crocodile and 2. Moria facing off against 3. Kuma becoming allies with 4. Jinbe, 5. Mihawk, 6. Boa, 7. Buggy (?), and 8. Law, the weight that was once placed behind the title of Shichibukai is now dwarfed by the danger and power of the Yonko.
Recognizing this, it wouldn’t make a ton of sense for Luffy’s bounty to double or triple here because while the stakes are high, this is not the culmination of the New World and the build up that Oda has been planning. Additionally the second narrative element to note is that in an SBS Oda states that bounties have little to do with actual correlative strength as opposed to the threat that one poses to the World Government from their perspective. Oda also noted that captains of the crew get larger increases than the rest of the crew or allies. In this vein, we see an application of this principle in Dressrosa, where Luffy clearly has the aid of the Grand Fleet and the former Warlord Trafalgar Law in his victory over Doflamingo. Each of the members of the Grand Fleet see their bounties increase by 50M. Luffy’s bounty however increases twice that, jumping 100M. This narratively sets Luffy apart from the rest of the crew, the Grand Fleet, and his allies but also foundationally answers criticisms about Luffy “needing help” to take down the big bad. Law’s bounty before being a warlord was 440M (40M higher than Luffy’s at the time we are reintroduced to him in Punk Hazard) but after Dressrosa they both ended with a 500M berry bounty. This means not only did Luffy’s bounty jump more than Law’s even though Law aided Luffy in defeating Doffy, it once again narratively sets Luffy above the rest – the Grand Fleet gets 50M increase, Law a former Warlord and ally gets a 60M increase while Luffy’s jumps an entire 100M – even though their ending value is the same this sets Luffy apart from Law in terms of bounty progression.
The final bounty jump we have to analyze takes place after Whole Cake Island were Luffy makes an incredible leap in terms of bounty value. Luffy increases his bounty by 300%, from 500M before the arc to a crazy 1.5B after escaping Big Mom’s territory. This jump represents the largest numerical leap in Luffy’s bounties (1B) and ties his 2nd greatest increase in percentages with Enies Lobby (Fitting since in one we get Nico Robin back and the other we get Sanji back).
While in Whole Cake Island, Luffy defeats two of Big Mom’s Sweet Commanders Cracker (860M Bounty) with the help of Nami and Katakuri (the man with the bounty of 1B). Again we see that not once has Luffy defeated an opponent and recieved a bounty lower than his adversary’s. While it is important to understand that Luffy did not receive the bounty within the context of OP lore because he defeated Katakuri, it very much feels that way narratively. This is Luffy’s biggest challenge yet facing someone who was superior in all categories except sheer grit shown by refusing to stay down. A few important things to note about the narrative of Whole Cake Island revolves around the idea that Luffy has now outright challenged and clashed with a Yonko for the first time. While Luffy does not defeat a Yonko, only besting a first Commander, we still see that after that arc Luffy’s bounty is 150% that of Katakuri’s.
Also Luffy again drastically outpaces his allies in terms of how much their bounties climb. Gang Bege started the Whole Cake Island arc in Zou where it was established he had a bounty of 300M and after the arcs conclusion he has a bounty of 350M. This 50M jump again is intentional to set Luffy apart as the ring leader, the man with the plan, the influential young upstart who encourages others to challenge the Yonko along side him. This narrative is important to keep in mind when looking at Wano and now that we have established Luffy’s progression with bounties we can try and make an estimated guess as to what Luffy’s bounty will be after Wano.