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In paragraph 2, what does the phrase “summered him and wintered him” mean?

Squire Lee is hopeful that Bobby will succeed.
Squire Lee is hopeful that Bobby will succeed.

Squire Lee has lent Bobby money many times.
Squire Lee has lent Bobby money many times.

Squire Lee and Bobby have been friends for many years.
Squire Lee and Bobby have been friends for many years.

Squire Lee has invested time and energy in Bobby.
Squire Lee has invested time and energy in Bobby.