@Huon:
To stick to the dumb predictions thing: Jewelry Bonney is actually much older and when she was young she was a member of the Rumbar pirates. Later she found her devil fruit, which she uses to look young again (who wouldn't?). At some point in the future she will meet Laboon and it will be a very emotional moment.
To build on this- When Bonney sees Humming Brook's new bounty poster, one that reveals he's now a member of the SHS, she will go find them and join. Reason?
Simple just like several characters were influenced by the real life Edward Teach aka Blackbeard (Edward Newgate & Marshall D Teach) there are 2 characters based on Calico Jack.
We know about Calico Yorki, but Brook was also based on Calico Jack. You see, just as Calico Jack and Anne Bonney were on the same crew and were lovers, so are Brook and Jewelry Bonney.
Aslo Jack & Anne eventually married, therefore so will Brook and Bonney one day marry
–- Update From New Post Merge ---
On a different note... I just found an article by Forbes from 2008 on "top-earning Pirates" link Using this as an inspiration =
Reason why Doffy has kept Bellamy around so much is that Bellamy is one of the richest pirates there is. That golden pillar he brought from Skypeia was really solid gold and he already had 120 million berri before that.