Some of those contributions were made by other people. The Edward Lampert from Greenwich gave to Republicans much more than to Democrats (if he gave anything to Democrats).
Of course, if you gave to Bush, Romney, and Forbes, people today will see you as a RINO, almost a Democrat, but it certainly wasn't like that at the time.
Looks like the Sears thing was just too far outside of his level of expertise... in short he bit off more than he could chew.
See the "How Sears Was Gutted by Its Own CEO" thread today.
He wasn't incompetent. It was intentional.
I guess he probably stayed on the right side of the law, but the shady characters aren't all on one side in politics.
I believe he gave Romney $2,000 - which is like most of us tossing someone a nickle... The link I provided has all his political donations.