1992

In 1992, incumbent Representative Marc Pacheco decided to run for Massachusetts Senate, leaving open his 3rd Bristol District seat in the Massachusetts House of Representatives. At the time, the 3rd Bristol district included all of wards 1, 2, 3, 4, 5, 7, and 8 in the city of Taunton.^[9]
Fagan ran in the Democratic Party primary for the seat, facing opponents Carol Doharty, Gail Tardo, Alfred Baptista Jr, and George Bertoldo. In a close race, Fagan won the nomination with 2,106 votes to Doharty's 2,024 and Tardo's 1,993.^[10]
Fagan faced Republican Audrey Zrebiec in the general election. He defeated her by a 35-point margin, garnering 10,870 votes to Zrebiec's 5,130 votes.^[9] This would prove to be Fagan's most competitive election for nearly two decades.

1994

Due to the results of the 1990 United States Census, the boundaries of Fagan's districts were altered slightly prior to the 1994 election. The newly drawn district, still wholly within the city of Taunton, now included all of wards 1, 2, 3, 4, and 5, as well as ward 7, precinct A; and ward 8, precinct B.^[11]
Running for re-election, Fagan faced no opposition in the Democratic primary or the general election, and thus secured a second term in the House.^[12][11]

1996

In 1996, Fagan again faced no opposition in the primary or general election, and was re-elected to a third term.^[13][14]

1998

Fagan's path to a fourth term was easy again in 1998, as he was re-elected without any opposition in the primary or general election for the third consecutive cycle.^[15][16]

2000

In 2000, Fagan again faced no opposition in the primary or general election, securing a fifth term with relative ease.^[17][18]

2002

As a result of the 2000 United States Census, the district boundaries were somewhat changed prior to the 2002 election. The new 3rd Bristol district, which was still completely within the city of Taunton, now included all of wards 2, 3, 5, 7, and 8, as well as ward 1, precinct B.^[19]
Fagan again faced no opposition in the primary election, and only minor opposition in the general. He received 7,809 votes compared to 45 votes for all other candidates, sending him to a sixth term in the House.^[20][19]

2004

Seeking a seventh term in 2004, Fagan faced only trivial opposition in both the primary and general elections, winning with over 99% of the vote in both contests.^[21][22]

2006

Fagan yet again faced only minor opposition in the 2006 primary and general campaigns, prevailing with over 99% of voters for both elections.^[23][24]

2008

In 2008, Fagan sought re-election to a ninth term in the House. He faced minor opposition in both the primary and general, and claimed victory with over 98% of votes in both elections.^[25][26]

2010

Fagan ran for re-election to a tenth term in the House in 2010. In the primary election, he faced no major opposition, and won with 97.9% of the votes cast.^[27] However, for the first time since his initial election in 1992, Fagan faced serious opposition in the general election. His Republican opponent was court reporter Shaunna O'Connell.
O'Connell cited comments that Fagan had made on the House floor in 2008 as her inspiration to challenge Fagan.^[28] During debate on Jessica's Law, a bill which would set mandatory 20-year prison sentences for child rapists, Fagan noted that the law would require the young victims to take the stand. As a defense attorney, Fagan argued, he would have no choice but to interrogate the victims, stating,

I'm gonna rip them apart. I'm going to make sure that the rest of their life is ruined, that when they’re 8 years old, they throw up; when they’re 12 years old, they won’t sleep; when they’re 19 years old, they’ll have nightmares and they’ll never have a relationship with anybody.^[29]

Fagan's comments drew national outrage, yet Fagan himself defended the comments as hyperbole intended to demonstrate the negative consequences of the bill.^[30] Nevertheless, O'Connell sought to make the issue central to her campaign; a mailer distributed to voters by her campaign included an audio clip of Fagan making the infamous remarks.^[2] O'Connell also questioned whether Fagan's job as a defense attorney was a conflict of interest, as Fagan would be defending people from laws he had a role in crafting.^[4] She referenced Fagan's previous support for tough-on-gun stances, yet noted the irony that Fagan would then request leniency for a client charged with illegal firearm possession.^[4] In the same interview, O'Connell went a step further, asserting that "intimidating, bullying and unnecessarily going after people is classic Jim Fagan,"^[4] a straightfoward and personal attack on Fagan's well-documented outspoken nature.
The contentious campaign came to a head when, during a debate between the candidates, Fagan questioned O'Connell's ability to count, a charge that was viewed by some as sexist.^[31] During the same debate, O'Connell refused to look at Fagan, and took her cell phone out while he made his closing remarks.^[31] The Taunton Gazette endorsed Fagan in the days prior to the election, citing his experience in the House and track record as a lifelong Tauntonian with deep ties to the community.^[31]
On election night, O'Connell narrowly defeated Fagan by a razor-thin 44 vote margin.^[28] Both candidates requested a recount,^[32] the results of which showed O'Connell indeed defeating Fagan, albeit by a slimmer margin of only 31 votes.^[33][34] With the victory, O'Connell became the first Republican to represent the 3rd Bristol district in at least 40 years.^[35]

Patrick Fagan shooting incident

In January 2002, Fagan's son Patrick was shot in the aftermath of a “feud.”^[1] Rather than defending his son as a victim, Fagan went on the record admonishing his son and criticizing him for being unemployed.^[1] Representative Fagan stated,

I have no bleeping tolerance for this group of morons, and morons is the politest term I could apply to them. The truth is still the truth. It doesn't matter if it's your child. I'll make no excuses for what I believe is intolerable behavior. ... I'm a citizen who's fed up with this bullbleep just like everybody else.”

Death of Kevin Fagan

In the early morning hours of 3 February 2008, Fagan's son Kevin was killed after accidentally slipping and falling from the Washington Bridge in East Providence, Rhode Island, which was under construction at the time.^[36][37] Representative Fagan lamented, “this is just an absolutely devastating loss to our family.”^[36]