Jake Paul and team are picking and choosing the fighters where they think is their best choice to win and make millions per fight and till now they are successful in finding opponents and promoting the fight and make millions per fight
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I wouldn't be critical of this too much, this happens in boxing frequently even with bigger names. Anthony Joshua, Fury all had to go through journeymen before getting to where they are, and they likely cherry picked names along the way, in fact I'd say it was in the boxing promoters interest to keep the hype train of Anthony Joshua going as long as possible, since there was clearly holes in his boxing, but wasn't exploited until recently.
The day Joshua lost the fight against Ruiz, and seemly lost his confidence is the day boxing took a big hit to their wallets. Yeah, he's still a big name, but he definitely isn't bringing in the same type of money he once was.
Jake can't be expected to come into a new sport, and take on the hardest opponents that he can. Yeah, that would make a statement, but I think beating Woodley is a statement enough. He has at least beat a professional fighter who had won a few accolades along the way. Though, it makes sense to progress from close to amateur level fighters, to a fighter who isn't trained specifically in boxing, but has some reputation attached to his name.