the Democratic nomination for United States Senate seat held by Leverett Saltonstall. Furcolo defeated O'Connor by a 3 to 1 margin at the Democratic State Convention, but O'Connor decided to remain in the race. In the primary, O'Connor upset Furcolo 48% to 39% with Edmund C. Buckley received the remaining 13%. O'Connor was able to sweep the western part of the state and top Furcolo by 10,000 in Boston. During the general election, O'Connor contrasted his youth to Saltonstall's age, calling him "yesterday's senator" and "The Late George Apley of Massachusetts politics" and attacked the senator for "fail[ing] to act for the working man". Saltonstall in turn criticized O'Connor's campaign for lacking substance. After refusing to debate O'Connor, Saltonstall stated "If my opponent would express his opinions of some of the vital national and international issues, I would then consider whether I would debate on these subjects or not". Saltonstall defeated O'Connor 1,358,556 votes to 1,050,725 to hold on to his Senate seat. Defeat for reelection A 1960 reassessment of all of real estate in the city led to a furor when 1/3 of the Springfield's homeowners saw increases over their 1959 tax. On October 11, 1960, 4,500 residents attended a meeting at Springfield Auditorium where members of the Board of Assessors attempted to explain the tax increase. Each member was booed off the stage before they could speak and O'Connor, who had no role in the property reassessment, failed to quiet the crowd and police were called in. O'Connor planned to cut 578 jobs from the 1961 budget in order to reduce the city's taxes, however he reversed this decision due to a lack of public support. In 1961, O'Connor faced eight challengers in the city's first non-partisian election. He finished first in the preliminary election with 34% of the vote. In the general election, attorney Charles V. Ryan upset O'Connor 28,999 (52%) votes to 26,271 (48%). Two weeks after O'Connor's loss, the city's percentage assessment system, which had been a major issue during the campaign, was declared unconstitutional by the Massachusetts Supreme Judicial Court. County Commissioner In 1980, O'Connor defeated incumbent Richard S. Thomas to win a seat on the Hampden County Commission. He was reelected in 1984, 1988, and 1992. Run for district attorney In 1990, Hampden County District Attorney Matthew J. Ryan, Jr. retired and O'Connor, his longtime friend, was seen as his favored successor. During