HCL, Sr. was friendly with TR, but he was still a stalwart Conservative, regardless (although more of the Paleo variety by today’s standards). Junior marked the change from Conservative Republicanism to liberalism that would ultimately lead to the death of the MA GOP. Even if Brown is elected, that won’t resurrect the party. His is a victory for an anti-Democrat establishment Oppositionist coalition, but not the state party.
Massachusetts does seem to like divided government. Patrick’s poor performance in office ought to be a caution that might persuade the Independents to give Brown a chance.