In a Bay State Conference championship basketball game, a ball he inbounded with two seconds left on the clock was tipped away by a player from Dedham High School, causing Needham to lose by one point.

[26][27] According to a 2007 blue-ribbon panel, the cost overruns of the Big Dig, combined with Baker's plan for financing them, ultimately left the state transportation system underfunded by $1 billion a year.

[26] Baker defended his plan as responsible, effective, and based on previous government officials' good-faith assurances that the Big Dig would be built on time and on budget.

[30] Baker responded by cutting the workforce by 90 people, increasing premiums, establishing new contracts with Massachusetts physicians, reassessing the company's financial structure, and outsourcing its information technology.

[28][31] During his tenure as CEO, the company had 24 profitable quarters in a row and earned recognition from the National Committee for Quality Assurance as its choice for America's Best Health Plan for five consecutive years.

[43] Baker ran as a social liberal (in favor of gay marriage and abortion rights) and a fiscal conservative, stressing job creation as his primary focus.

[39][40] He reinforced his socially liberal position by selecting as his running mate Richard Tisei, an openly gay Republican who had supported same-sex marriage legalization efforts in Massachusetts.

Patrick, facing low approval ratings, criticized Baker for his role in the Big Dig financing plan, and for raising health premiums while head of Harvard Pilgrim.

In July 2014, Democrats criticized Baker for refusing to say whether he supported a provision in the new gun control law that gave police chiefs discretion to deny firearms identification cards, which are required to purchase shotguns and rifles.

[64] In the general election, Baker faced Jay Gonzalez, a private health insurance executive who also served under Governor Deval Patrick as the state's secretary of administration and finance.

[67][68] At the end of Walsh's governorship, Sean Cronin (deputy commissioner of the Massachusetts Division of Local Services) claimed that his Community Compact Cabinet had distributed 1,400 grants amounting to $65 million.

[76] In April 2018, Baker submitted a request to the U.S. Treasury Department that 138 census tracts in Massachusetts be designated as "opportunity zones" under the Tax Cuts and Jobs Act of 2017.

[98] In April 2017, the Massachusetts Department of Public Utilities released data showing that more than 8,000 of the 70,000 drivers for transportation network companies who applied failed to pass the state background check requirement signed into law by Baker the previous August.

[123] In February 2017, Baker's administration announced $35 million in capital grants for life science facilities at 14 colleges, graduate schools, and research institutes in the state.

[134] In February 2016, Baker launched a $15 million initiative creating an inter-secretariat working group between state agencies to write a report identifying better means of allocating funding to low- and middle-income residents to access clean energy.

[153] In September 2016, following the record breaking snowfall in Boston from the 2014–15 North American winter and during a severe drought,[154] Baker signed an executive order directing various state cabinet offices to develop and implement a statewide, comprehensive climate change adaptation plan.

[157] In February 2017, Baker joined a bipartisan coalition of governors that sent an open letter to President Donald Trump, calling on his administration to support renewable energy.

[167] The same month, the Massachusetts Department of Energy Resources released a comprehensive energy plan in accordance with an executive order Baker issued in September 2016 for state agencies to develop a statewide adaptation plan for climate change,[143] and Massachusetts, along with eight other states and the District of Columbia, announced that it would participate in the interstate Transportation and Climate Initiative to reduce greenhouse gas emissions from the transportation sector;[168] he withdrew from the TCI, in part, because it was "no longer necessary.

"[184] In November 2016, Baker's administration received approval from the Centers for Medicare and Medicaid Services to implement a five-year waiver authorizing a $52.4 billion restructuring of MassHealth.

[186] In January 2017, in an open letter to U.S. House Majority Leader Kevin McCarthy, Baker defended certain provisions of the ACA and urged the 115th U.S. Congress not to repeal the law too quickly and disrupt insurance markets.

[216][217][218] Baker's lack of transparency about infections and death rates has been criticized by the media and public health researchers have urged him to follow the lead of the CDC and many other states and provide accurate and complete data.

The bill also extended the time frame for abortions beyond 24 weeks in cases in which the fetus cannot survive or the pregnancy would impose a substantial risk of grave impairment of the person's physical or mental health.

[238] After the final opinion was issued in June 2022, officially overturning Roe v. Wade, Baker signed an executive order protecting abortion rights in Massachusetts.

[241] In the wake of the November 2015 Paris attacks, Baker opposed allowing additional Syrian refugees into the state until he knew more about the federal government's process for vetting them.

[243] After Donald Trump became president in January 2017, Baker opposed the Trump administration's original and revised travel bans,[244][245] arguing that "focusing on countries' predominant religions will not make the country safer", and wrote an open letter to then U.S. Secretary of Homeland Security John F. Kelly highlighting concerns with the effects of the travel ban on Massachusetts businesses, colleges and universities, and academic medical centers.

"[255] In November 2017, Baker wrote an open letter to acting U.S. Secretary of Homeland Security Elaine Duke urging the Trump administration to continue to allow citizens of El Salvador, Haiti, and Honduras to stay in the U.S. under temporary protected status,[256] and the next month, Baker and a bipartisan group of 11 other governors wrote an open letter to the leadership of the 115th U.S. Congress urging it to allow DACA recipients to stay in the U.S. as well.

"[260] In December 2018, Baker called for the suspension of a state district court judge who allegedly assisted an illegal immigrant from being detained by an ICE agent during a legal proceeding from hearing further criminal cases until the federal investigation of the incident is concluded.

[266] In February 2015, Baker announced the formation of a working group to write a report formulating a statewide strategy to address the opioid epidemic in Massachusetts,[267] which was released in June 2015.

[283] In May 2016, Baker and Massachusetts Attorney General Maura Healey launched a statewide campaign to promote awareness of protection for people calling in drug overdoses under Good Samaritan laws.

[318] On December 17, 2024, in a US Senate hearing on sports betting, Baker got into a heated exchange about transgender athletes on college teams and in locker rooms with Sen. Josh Hawley (R-Mo.)