He won the 1990 Republican primary as a write-in candidate then defeated Democratic incumbent John P. Houston by 782 votes in the general election.
In 1998 he ran for the United States House of Representatives seat in Massachusetts's 3rd congressional district, but lost to incumbent Jim McGovern 56.9% to 41.5%.
[6] In 2002, acting governor Jane Swift appointed Amorello to the Massachusetts Turnpike Authority chairmanship, which put him in charge of the Big Dig, a project that was billions of dollars over budget and years past its completion date.
In 2004, Romney asked Amorello to resign after The Boston Globe reported that turnpike authority officials were aware of hundreds of leaks in Big Dig tunnels, but did not take action to repair them.
[11] After the collapse of a portion of the roof of the I-90 Connector Tunnel on July 10, 2006, in which 38-year-old Milena Del Valle, of Jamaica Plain, was killed, Romney and all but one of the candidates in that year's gubernatorial election called for Amorello's resignation.
[14] On July 27, 2006, Amorello agreed to resign, effective August 15, after the Massachusetts Supreme Judicial Court ruled that he could not block a hearing on whether or not he should be removed from office.
[7] On Monday August 9, 2010, a judge issued a warrant for Amorello's arrest when he failed to show up in court to face a drunken driving charge.