In paragraph 2, the phrase “summered him and wintered him” means that: Squire Lee has invested time and energy in Bobby.
<h3>Meaning of the Phrase</h3>
The passage says that Squire Lee was very efficient at studying people. It also mentioned that he had summered and wintered Boby and was satisfied with him.
This means that he had spent time and energy studying Bobby and was satisfied with his personality.