With Election Day on Nov. 3, 2026, less than two weeks away, the Massachusetts governor’s race absorbed three jolts in one week: the Republican ticket lost its lieutenant governor candidate to a drunken-driving arrest, the House killed a gas tax holiday that both major candidates had endorsed, and a new poll put Gov. Maura Healey ahead by 22 points.

A running mate exits after a New Bedford crash

Shawn Oliver, the Republican nominee for lieutenant governor, suspended his campaign on Sunday, Oct. 18, a day after a late-night crash in New Bedford. Police said Oliver’s vehicle struck multiple parked vehicles before overturning on Dartmouth Street, and he was taken to a hospital with injuries, according to the Associated Press. Boston 25 News reported that officers arrived around 11:40 p.m. on Saturday, Oct. 17, and found five vehicles involved.

Oliver, 42, a New Bedford city councilor first elected in 2023 and a state corrections officer, was charged with operating under the influence of liquor, negligent operation of a motor vehicle, a marked lanes violation and speeding. The New Bedford Light first reported the arrest. He pleaded not guilty on Monday, Oct. 19, was released on personal recognizance and was barred from driving, with a next court date in November, Boston 25 reported.

In a post on X announcing his exit, Oliver wrote that “the election is too important to be overshadowed by personal matters,” the AP reported. The state Department of Correction placed him on restricted duty at the Massachusetts Treatment Center while it reviews the case, spokesperson Lindsay Corcoran told the AP. New Bedford Mayor Jon Mitchell, a Democrat, called the allegations deeply concerning and said the public deserved to hear from Oliver directly.

Minogue’s ballot problem

Republican gubernatorial nominee Mike Minogue, a businessman and military veteran, said he had asked Oliver to step aside and would formally request his resignation if elected. Because ballots were already printed, Oliver’s name remains on them. At a Monday press conference, Minogue asked supporters to vote the ticket as printed, warning that crossing out Oliver’s name or writing in another candidate could void the vote, according to Boston 25 News.

Minogue said he would leave the lieutenant governor’s post vacant if he wins, relying on the state’s existing succession order, and his campaign estimated that would save more than $300,000 in salary and security costs. Healey, speaking the same day, described the Minogue campaign as showing “chaos,” noting that Oliver was the second running mate the campaign has lost, Boston 25 reported. The lieutenant governor’s duties are largely ceremonial, but the officeholder is first in line if a governor resigns or dies. Healey’s running mate is incumbent Lt. Gov. Kim Driscoll.

Where the polls stand

A Suffolk University/Boston Globe poll released Tuesday, Oct. 20, found Healey with more than 58 percent support to Minogue’s 36 percent among 500 registered voters surveyed Oct. 14-17, with a margin of error of 4.4 percentage points, according to State House News Service reporting carried by WGBH. A UMass Amherst/WCVB poll released a day earlier put the race at 56-31.

The same Suffolk survey found a more complicated mood beneath the horse race. More than 42 percent of respondents said Massachusetts has gotten worse over the past four years, roughly 40 percent said it has stayed the same, and just over 52 percent said the state is headed in the right direction. About 21 percent said they had never heard of Minogue. Asked what strains their finances most, respondents most often named utility and heating bills (almost 23 percent) and gas prices (11 percent).

Down the ballot, the poll showed U.S. Sen. Ed Markey leading Republican John Deaton 60 percent to about 31 percent, and Attorney General Andrea Campbell leading Michael Walsh 54 percent to roughly 28 percent. Among the nine statewide ballot questions, Question 1, which would extend the public records law to the governor’s office and Legislature, drew the strongest support at more than 62 percent, while Question 8, which would repeal the recreational marijuana laws, drew about 21 percent.

The gas tax holiday dies in the House

The one policy both candidates agreed on did not survive the week. Healey had proposed a two-month suspension of the state’s 24-cent-per-gallon gas tax, a measure estimated to cost about $120 million, as part of a supplemental budget to close the books on fiscal 2026. The House Ways and Means Committee, chaired by Rep. Aaron Michlewitz, left the holiday out of its $2.35 billion redraft, WBUR reported, with Michlewitz citing the loss of transportation revenue and doubts that savings would reach drivers.

On the House floor on Wednesday, Oct. 21, Rep. Todd Smola of Warren offered an amendment to restore the suspension with the backing of the full Republican caucus. It failed 30-121, and the underlying bill passed 152-0, the Daily Hampshire Gazette reported. House Speaker Ron Mariano dismissed the idea as gimmickry, and Rep. James Arciero, co-chair of the Transportation Committee, estimated the average driver would save about $25.

Healey’s office pushed back. “There is nothing gimmicky about a proposal to give gas tax relief to people,” a spokesperson said, according to the Gazette. Minogue, who has pledged to suspend the tax whenever prices reach $4 a gallon, called the House vote “a political stunt, pure and simple,” NBC Boston reported. The statewide average stood at about $4.28 a gallon, according to AAA figures cited by NBC Boston.

What else is in the $2.35 billion bill

The House package directs roughly $1.8 billion in gross spending to MassHealth, about $160 million to snow and ice removal paid from surtax revenue, $79 million toward unemployment insurance interest repayments, and $10 million to the Massachusetts Life Sciences Center, according to NBC Boston. It also adds disclosure requirements for AI-generated political ads and bars constitutional officers from using public money for ads featuring their own name, voice or likeness. The Senate, which did not hold a formal session this week, will write its own version; Michlewitz told WBUR he hopes to send a compromise to the governor by Nov. 15.

The Newsroom Take

Each of this week’s developments cuts against the Republican ticket, but the poll numbers suggest the race was not close before Oliver’s arrest and the gas tax fight. What the week did change is the shape of the closing argument. Minogue’s message of affordability now has to compete with questions about his own vetting, and his gas tax pledge collides with a Democratic House that just voted it down 121-30. Healey, meanwhile, finds herself on the same side of the gas tax question as her opponent and opposed by her party’s legislative leadership, a split that will matter more for the Senate negotiation in November than for the election itself. The number worth watching is not the 22-point margin but the 42 percent who say the state has gotten worse: that is the electorate the next governor, almost certainly Healey, will have to answer to on heating bills and housing in January.

What it means for you

• Early voting and mail ballots are already in circulation; a vote for the Minogue ticket counts as printed, and voters should not alter the lieutenant governor line.
• Do not expect pump prices to drop from a state tax holiday before Election Day. The House has rejected it, and the Senate is not in formal session this week.
• Nine ballot questions appear on the Nov. 3 ballot, including measures on public records, same-day registration, an all-party primary and the 2024 gun law. Read them before you vote.
• Business owners should watch the Senate’s version of the supplemental budget, which could still change the unemployment insurance and political advertising provisions.

BOSTON — Twenty years ago today, a 16-year-old from Pennsylvania who had moved to Nashville to write songs released an album with her own name on the cover. It came out on October 24, 2006, on a brand-new independent label called Big Machine Records. It opened with a song named after somebody else’s husband.

It did not sound like the start of the most successful songwriting career of a generation. It sounded like a kid with a guitar who had a lot to say about high school, pickup trucks and the boy who never noticed her. That turned out to be exactly the point.

A songwriter first

The detail that matters most about the debut is in the credits. Taylor has a writing credit on every song. She co-wrote seven of them with Nashville songwriter Liz Rose, and she wrote three entirely on her own: “The Outside,” “Should’ve Said No” and “Our Song.” Producer Nathan Chapman, then a little-known demo producer, handled every track except “The Outside.”

That was rare for a teenage artist in 2006, and it set the template for everything that followed. Twenty years and twelve studio albums later, the songs are still hers in every sense of the word.

The singles that built a fan base

• “Tim McGraw” (June 2006) reached No. 6 on Hot Country Songs and No. 40 on the Hot 100, and introduced a voice that wrote in specific, cinematic details.
• “Teardrops on My Guitar” (2007) crossed over to pop radio and became the album’s biggest Hot 100 hit at No. 13.
• “Our Song” (2007) went to No. 1 on Hot Country Songs. Taylor wrote it alone for a ninth-grade talent show.
• “Picture to Burn” (2008) reached the country Top 10.
• “Should’ve Said No” (2008) became her second country No. 1, again written by Taylor alone.

The slow-burn chart run

The album debuted modestly, at No. 19 on the Billboard 200 with about 40,000 copies. Then it just kept going. It reached its peak, No. 5, in January 2008, more than a year after release. It spent 24 weeks at No. 1 on Top Country Albums, and by October 2009 it had logged 157 weeks on the Billboard 200, the longest chart run of any album released in the 2000s. In September 2025, the RIAA certified it 8× Platinum.

The era brought a CMA Horizon Award in 2007 and a Grammy nomination for Best New Artist in 2008. In 2022, Rolling Stone ranked it among the 100 best debut albums of all time.

1. June 19, 2006“Tim McGraw” is released as the first single.
2. October 24, 2006Taylor Swift is released on Big Machine Records. It debuts at No. 19 on the Billboard 200 with about 40,000 copies.
3. 2007“Teardrops on My Guitar” crosses over to pop and reaches No. 13 on the Hot 100. Taylor wins the CMA Horizon Award.
4. Late 2007 and 2008“Our Song” and “Should’ve Said No,” both written by Taylor alone, hit No. 1 on Hot Country Songs. She’s nominated for Best New Artist at the Grammys.
5. January 2008More than a year after release, the album reaches its Billboard 200 peak at No. 5.
6. October 2009157 weeks on the Billboard 200, the longest-charting album of the 2000s.
7. May 30, 2025Taylor buys back the masters of her first six albums, including this one, and says her debut re-recording is finished.
8. September 2025The RIAA certifies the album 8× Platinum.
9. October 24, 2026Twenty years.

Owning the beginning

For years, the debut was part of the catalog Taylor did not own. When Big Machine was sold in 2019, her masters went with it, and she spent the following years re-recording her albums as “Taylor’s Versions.” On May 30, 2025, she announced she had bought back the master recordings of her first six albums, including this one. In the same letter she said her debut re-recording was finished and that it could still “re-emerge when the time is right.”

Fans have circled this anniversary as a likely moment. As of our deadline, no release date for Taylor Swift (Taylor’s Version) had been announced. If that changes, this story will be updated.

From a debut to a dynasty

It is a long road from a debut at No. 19 to The Life of a Showgirl, which opened in October 2025 with more than 4 million album-equivalent units in its first week in the US, the biggest debut week on record. A deluxe edition, The Encore, followed in late September 2026. The craft that runs through all of it was already there on the first record: honest lyrics, sharp details and a writer who refused to let anybody else tell her story.

Keep celebrating

Catch up on every chapter in our field guide to the Eras of Taylor Swift, and follow the newsroom’s ongoing coverage in the Boston Made Reader.

Sources

• Wikipedia: Taylor Swift (album)), including chart, certification and credits data
• WAMC / NPR: Taylor Swift buys back the rights to her first six albums (May 30, 2025)
• Wikipedia: The Life of a Showgirl

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.

BOSTON — Two days to go. We have told the story of how the debut was made, walked through every song and followed the radio tour. Now it is your turn. Eleven songs, head-to-head, until only one is left.

How to play

Every matchup is between two songs from the standard edition of Taylor Swift. Pick the one you would rather hear right now. Winners move on, and if a round has an odd number of songs, one gets a bye. The order is shuffled every time, so play twice and see if your champion holds up.

Taylor’s Version watch

The other question fans are asking this week is whether a re-recorded debut is on the way. Here is what is on the record:

• 2019: Big Machine Records was sold, and the master recordings of her first six albums, including the debut, went with it.
• 2020 onward: Taylor began re-recording those albums as “Taylor’s Versions,” releasing four of them.
• May 30, 2025: She announced she had bought back the masters of all six albums. In the same letter she said the debut re-recording was finished, and that it could still re-emerge when the time is right.

As of our deadline, no release date for Taylor Swift (Taylor’s Version) had been announced. We will be watching on October 24, and so will everyone else.

Sources

• Wikipedia: Taylor Swift (album))
• WAMC / NPR: Taylor Swift buys back the rights to her first six albums (May 30, 2025)

Boston Made is not affiliated with or endorsed by Taylor Swift or her record labels. Photos are freely licensed from Wikimedia Commons and credited under each image.