Nelson wakes up, from a nap after instructing Lolita of what he would do given the circumstance...
He compared it to, a David vs Goliath situation. He knew Lolita in the long run could not win, but could win in other ways.
To his surprise, Lolita did not follow suit. He found out his original plan had succeeded but after that - Lolita developed Scurvy or something...
She did not follow his advice through and as such, took losses herself. Losses of which, she could not take if she wanted to win in 'other ways'.
There still be hope; as Meliva pointed out Lolita being a tad bit crafty.