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To give the short version about Sears and Kariotis... Sears was probably the last prominent Boston Republican. He was a descendant of the early MA Governor John Winthrop (for whom he was named). When the Boston Mayorship came open in 1967, he placed a respectable 3rd for the top two slots (a swing of only 3,000 votes would’ve had him reach the runoff, and Kevin White would’ve been the loser — it was the infamous Louise Day Hicks who placed 1st and who lost to White in the runoff, so had Sears faced Hicks, he might’ve prevailed, and likely would’ve been the last GOP Mayor of Boston — rather than Malcolm Nichols, who left office in 1930).

Gov. Volpe appointed Sears as Sheriff of Suffolk County in 1968, but he lost the general election for it later. He then was elected to the Boston Common Council where he was the sole Republican (and was the first and only one since the 1940s, I believe) and was a thorn in the butt of Kevin White. He was part of the liberal ticket of 1978 (which featured Frank Hatch for Governor and William Weld for Atty General) where he was the Sec of State nominee. He was entirely centered on challenging King for Governor in 1982, but when Dukakis beat King, 53-47% in the Dem primary, he lost focus and bombed out (Barone didn’t even mention him in the description of the race), and Dukakis stomped him by a 59-37% margin.

As for George Kariotis, he was the default nominee after umpteen candidates took a pass (including Ed King, who after switching to the GOP chose not to run. Ed Shamie passed on it, too). Kariotis wasn’t even on the primary ballot in 1986. The race was between Greg Hyatt and Royall Switzer, both of whom were, shall we say, horrible. Hyatt forged names on his nomination papers and solicited money from a mob boss (and a bizarre charge that he was naked at his place of work). Switzler lied about his military record, claiming to be a decorated officer in Vietnam. He was, in fact, only a Sargeant (and served in Korea, not ‘Nam), and had only visited ‘Nam while on leave for a couple weeks. Hyatt and Switzler effectively ceased campaigning as the GOP leadership made it plain that Kariotis, an untainted businessman, would be the party’s preferred choice, but he’d have to run as a write-in. Hyatt won the primary in a VERY low turnout with 48% to Switzler’s 32%. Kariotis got 18% as a write-in. Hyatt immediately withdrew as the nominee and Kariotis substituted, but the damage was done, and Kariotis was regarded as desultory opposition to Dukakis, and lost the general, 69-31%.