I'd bet on Jake just because he's the one who initiated this fight and for his previous bouts against MMA legends, he won those with questionable performances from his enemies. Might be the same outcome in here if Silva is motivated only by money, which somewhat shows on some interviews that were done to him. +100 isn't also a bad odd to bet on considering that Jake Paul is also a capable boxer in his own regard. If skills and grit I'd say Silva, but again this is a Paul initiated fight and that should suggest you something.
I would bet otherwise- even if Anderson Silva is at least 45 years old, experience will take you further compared to someone who is relatively new to this sport.
Anderson Silva is known by many as a legend in UFC. He is a former middleweight champion and his techniques are surprisingly deadly. Though he is against a 25+ year old with more stamina, he can outsmart Jake Paul with his experience and training from all the fights that he'd experience on the field. Not to mention, just one grapple and the fight could be over in an instant.
Of course, this is all situational but if I were to bet my money, I would most likely go all in for Anderson Silva.