Despite losing her first two elections, Healey became popular among Republicans and was elected to the post of chairwoman of the Massachusetts Republican State Committee in 2001; this made Healey only the second woman to head the Massachusetts GOP. Soon after beginning her term as Chairwoman, the Massachusetts GOP began courting Mitt Romney – then the President and CEO of the 2002 Winter Olympics – to take over acting-Governor Jane Swift's position as the Republican candidate in the upcoming gubernatorial election. Healey discreetly flew to Salt Lake to meet with Romney and, soon after the Olympics, Romney expressed his intention to challenge Swift in a Republican primary.