A piece of political history:
In 1996, then Governor William F. Weld (R) gave incumbent Senator John Kerry (D) a pretty good fight but it wasn’t enough. The problem for Weld was that Senate Majority Leader Robert Dole (R) was at the top of the ticket and William J. Clinton (D) prevailed for a second term. Ross Perot (Ref) was also on the ballot that year and the economy was in good shape.
Although Weld did well in Worcester County, he could not decisively build a demanding lead in the traditionally Republican-leaning county of Essex.
Weld cultivated the wrong enemies. A vehement anti-privatization push by the T’s Carmen’s union did not work in Weld’s favor. In fact a strong case can be made that the opposition was the decisive factor. It was a lesson learned by Weld’s successor A. Paul Cellucci (R), who upon running for his own term in 1998, cut a deal with the unions. Cellucci, with significant support from conservative Democrats, went on to beat Attorney General Scott Harshbarger.