From ‘1989’ through ‘The Tortured Poets Department,’ she has fiercely guarded Swift’s reputation: ‘The devil works hard, but Tree Paine works harder’
8 min
Taylor Swift was celebrating the end of the Australian leg of her Eras Tour in late February when a bit of unpleasantness sailed out from Down Under and landed on the home page of TMZ. The New South Wales Police Force was investigating a 71-year-old man for allegedly assaulting a 51-year-old man at a wharf north of the city, according to their media unit. Per TMZ, the septuagenarian was Scott Swift, Taylor’s father and a key member of her management team, and the younger man was a photographer.
The story had all the makings of a public relations nightmare: (1) Celebrity family member allegedly behaves badly while (2) disembarking from a luxury yacht, resulting in (3) a police investigation. To make matters more complicated, Taylor was reportedly present for the alleged altercation—hiding under an umbrella, TMZ said. Though the man didn’t require medical treatment, the police said, there was video footage. Would this be the end of the pop star’s marathon run of fawning press?
Not if Tree Paine could help it.
Swift’s longtime publicist first released a statement that did not refute TMZ’s story, exactly, but offered some exculpatory evidence: “Two individuals were aggressively pushing their way towards Taylor, grabbing at her security personnel, and threatening to throw a female staff member into the water.” Subtext: Scott Swift was simply protecting his daughter and another defenceless woman from a couple of rogue aggressors. He was not charged.
Around the same time, as if by magic, People found a video of Scott passing out sandwiches to young female fans at one of the Sydney shows and published it along with fan commentary. “Isn’t he the sweetest and cutest,” one cooed.
Online, Swifties clocked the People story as good old-fashioned damage control. As a chorus of fan posts put it: “The devil works hard, but Tree Paine works harder.” (In late March, the New South Wales Police Force media unit said that the North Shore Police Area Command finished its investigation and that it is taking no further action.)
The average celebrity publicist does not have fans. But Paine, the 52-year-old redhead seen trailing Swift at awards shows and rubbing shoulders with Gayle King in the Eras Tour VIP area, has become a Swiftverse cult figure in her own right. Fans post reverently about her PR machinations and share videos of her expertly attending to Swift’s needs: smoothing out Swift’s dress on the red carpet, leading Swift right past a scrum of reporters whose questions have not been approved, subtly offering Swift what appeared to be water at the Video Music Awards—a night when the star was filmed dancing in a manner that suggested inebriation.
Swift has trained her followers to look for meaning in her every gesture, outfit and Instagram caption. Paine’s own work—the stories she chooses to respond to, the narrative she puts forward in the media—has become part of that lore.
And Swift and Paine are creating a lot of lore lately. Swift spent the fall cheering on her new boyfriend, Kansas City Chiefs tight end Travis Kelce , as he sailed to Super Bowl victory , and dropped by the Grammys to pick up album of the year for Midnights and announce her new album in an acceptance speech for yet another award . The Tortured Poets Department , which fans speculate is at least partly inspired by her breakup with the British actor Joe Alwyn , drops this month, and Swift will promote it while balancing her public relationship, continuing her sold-out international Eras Tour amid growing criticism of her private jet usage and brushing off baseless conspiracy theories that she is secretly working as a Democratic operative to swing the 2024 election for President Joe Biden.
In a long career of riding high, Swift has hit the stratosphere. It’s Paine’s job to keep her there.
Back in 2014, Swift’s world domination was not yet assured. That March, trade publications reported that the pop star’s publicist of seven years, Paula Erickson, had submitted her resignation. Fairly or not, during Erickson’s tenure, Swift developed a reputation for being both boy-crazy and unwilling to joke about it. See: Swift’s string of high-profile relationships with Joe Jonas, Taylor Lautner , Jake Gyllenhaal and Harry Styles ; her alleged wedding-crashing with Conor Kennedy; her humourless response to Tina Fey and Amy Poehler’s joke at the 2013 Golden Globes about her dating life. (“There’s a special place in hell for women who don’t help other women,” she told Vanity Fair when asked about the incident.) Erickson declined to comment for this story.
Paine, who had been working as the senior vice president of publicity in the Christian and Country divisions of Warner Music Nashville, came on board and quickly flipped the script. She launched her own firm, Premium PR, and signed Swift as her first and only client. “There isn’t a publicist in NY, LA or Nashville that wouldn’t jump at an opportunity to work with someone as talented as Taylor Swift and her management team,” Paine told Page Six at the time.
That year, Swift moved from Nashville to New York, went full pop with the release of 1989 and began flaunting her friendships with a gaggle of famous women, known colloquially as The Squad. The public started to forget about the time Swift, age 22, allegedly bought a house across the street from the Kennedy compound in Hyannis Port, Massachusetts.
Throughout this transformation, Paine refused to let rumours about her client fester. The very week her hiring was announced, she began issuing public rebuttals to the tabloids. “Never believe the National Enquirer,” she tweeted about an apparently false story that Swift declined to record a duet with Randy Travis. Ten years later, the gossip about Swift has changed, but Paine’s approach has not: She recently called out the anonymous gossip account Deuxmoi for causing “pain and trauma” by posting false rumours about Swift secretly marrying Alwyn before the two broke up.
Paine became even more visible to fans in 2020, when she appeared in Swift’s Netflix documentary Miss Americana . Wearing white shorts and blue nail polish, she clinked white-wine glasses with Swift as the singer-songwriter anxiously prepared to post her first political statement on Instagram. Swifties have since turned Paine into something of a meme: Online, they joke that Swift’s “Out of the Woods” lyric “the monsters turned out to be just trees” is a reference to the publicist and that a redheaded Eras Tour backup dancer is Tree-coded. They have decided that in the inevitable Paine biopic, the publicist will be played by Amy Adams, and that she will win her first Oscar for it.
The fan obsession has been fuelled, in part, by how little Paine has shared publicly about herself. Her Instagram is private. The last time she sat for an interview was 2012, when she was a VP at Warner and appeared in Nashville Lifestyles ’ “Most Beautiful People” issue; she posed for a photo in front of a shiplap-covered wall wearing a peasant blouse and made the astonishing revelation that she was “trying to enjoy life.” I cannot report whether that is still true; Paine declined to be interviewed for this story.
Born Trina Snyder, Paine grew up in Costa Mesa, California. She was still going by Trina when she was initiated into Pi Beta Phi at the University of Southern California in 1990, according to the women’s fraternity’s official publication, The Arrow .
Like her client, Paine is a Nashville transplant. In her early career, she worked her way up at a variety of L.A. record labels—World Domination, Maverick and Interscope, whose roster included Snoop Dogg, No Doubt, Nine Inch Nails and Marilyn Manson. She launched her own guerrilla-marketing company, worked for the Academy of Country Music and eventually joined Warner Music in Tennessee.
In 1998, she married Lance Paine, a businessman and onetime president of the Nashville candy brand Goo Goo Cluster, in Las Vegas, according to public records. (Lance also served as president of the company owned by HGTV’s Property Brothers.) The Paines have one teenage daughter, and according to the society pages, they have spent some nights mixing with locals at Nashville charity galas.
But mostly, Paine works. She has built a fearsome reputation in media circles, closely guarding access to Swift and sending emails to journalists with surprising velocity whenever she disagrees with a story. “Once I started working in media, I would always hear about people getting emails from Tree Paine, or maybe, people being afraid of getting emails from Tree Paine,” says Hunter Harris, a self-described “Painiac” and the writer of the entertainment newsletter Hung Up , which regularly chronicles Paine’s engagement with the press. (Harris has also contributed to WSJ. Magazine .)
In the past 10 years, Paine has guided Swift through some of the more tumultuous moments of her career: her feud with Kim Kardashian and Kanye West; her trial accusing a former DJ of sexual assault; her battle against her former label , Scooter Braun and private-equity giants for the control of her master recordings. At almost every turn, Paine presents Swift—arguably the most famous woman on the planet, a billionaire with a private jet—as a relatable underdog fighting for her voice to be heard.
It has, for the most part, worked. In the process, Paine has become one of the most powerful people in the entertainment industry.
Getting any kind of journalistic access to Swift has become a fool’s errand. The star sits for few magazine interviews, and in between, Paine does her best to ensure that no information about Swift that Swift has not expressly chosen to share with the public becomes available. One magazine writer recalls the slightly fraught process of interviewing another artist on one of Swift’s stadium tours a few years ago. As a condition of the interview, the writer had to agree that anything they witnessed or discovered about Swift while spending time with the other artist before a show would be off the record. Paine was clear: No journalist is going to catch Swift in her sweatpants backstage and write about it.
When writer Emily Kirkpatrick reached out last year to seek Swift’s comment for a profile of the actress and musician Suki Waterhouse for the fashion website Ssense, Paine surprisingly acquiesced, with the caveat that Swift’s quote be printed in full—no edits, no line breaks. (Kirkpatrick, annoyed, accepted the terms.)
This is an understandable sticking point for Paine. The Kardashian-West debacle revolved, in large part, around a truncated recording of Swift. Before the rapper released the single “Famous,” which contained lewd lyrics about Swift, they spoke by phone, where he asked her to promote the track on Twitter. For years, a snippet of the call released by Kardashian painted Swift as a liar who publicly rejected the lyrics but privately approved them. When someone released the full call online—a friendly heads-up but one in which West never shares the final lyric (“I made that bitch famous”)—Kardashian tried to save face. “To be clear, the only issue I ever had around the situation was that Taylor lied through her publicist who stated that ‘Kanye never called to ask for permission…,’ ” she tweeted. But Paine never said that exactly. She tweeted a rejoinder: “I’m Taylor’s publicist and this is my UNEDITED original statement. Btw, when you take parts out, that’s editing. P.S. who did you guys piss off to leak that video?”
The biggest year of Swift’s career has also been her most public yet. There’s the tour, the new album, the NFL boyfriend , the constant tabloid coverage of her relationship with the NFL boyfriend, the never-ending paparazzi strolls with her famous friends at sceney New York City restaurants. There have been stumbles: Swift forgot to thank Celine Dion, who presented the album of the year award, when accepting her Grammy. (A photo of the two singers hugging circulated online later.) She’s still taking heat for her private jet. She dated Matty Healy.
But the sheer volume of information about Swift that pours, ceaselessly, out of every tabloid and news outlet from the Daily Mail to the New York Times typically washes away negative stories as soon as they are published. There are fans who speculate that Paine sent Swift to Kelce’s regular-season game against the New York Jets in October so that internet searches for “Taylor Swift jets” would return cheery images of Swift dancing in a VIP suite with Blake Lively instead of stats about CO2 emissions.
Swift is at a point in her career, however, where she could completely disappear from view and still generate more headlines than just about any other person on earth. Scientists at Caltech and UCLA recently published research proving the existence of “Swift quakes” (seismic activity caused by fans dancing and jumping at concerts). Ancestry.com shared on social media that Swift is a sixth cousin, three times removed, of poet Emily Dickinson. The New York Post talked to experts to guesstimate how much Kelce has spent wooing Swift so far (more than $8 million, allegedly).
If Swift released The Tortured Poets Department with zero fanfare, it would probably still hit No. 1 on the Billboard charts. But she chooses to feed the beast—with black-and-white Instagram posts, snippets of possible lyrics, a pop-up poetry library, so many vinyl editions —and, with Paine’s help, make her own news.
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Strong family financial planning can help reduce taxes and support younger generations. From intrafamily loans and asset gifts to inheritance disclaimers, strategic cooperation can create meaningful financial benefits—when families have the trust and structure to make it work.
4 min
Happy is the family whose members—parents, grandparents and grown children—trust each other enough to cooperate on shared goals, especially financial ones. When that is truly the case, Uncle Sam’s tax rules can help as well.
This matters especially now that mortgage rates are above 7%, and many families are looking for ways to help younger members. If the elders have resources and are confident younger ones can cooperate, a family loan could make homeownership possible while providing the elders with a useful income stream.
Other strategies can actually lower taxes, such as when funding 529 plans or Roth IRAs, or when someone inherits a traditional IRA with required withdrawals larger than they will need.
Here are three strategies useful for functional families.
It is perfectly legal for families to lend money to a relative for a down payment or even a private mortgage.
But it is important not to cut corners, says Ryan McKeown, a CPA with Modern Wealth Enhancement in Minnesota. If the loan is for a down payment, be honest with the mortgage provider and have a formal agreement. The lender owes tax on the interest payments received.
If the loan is for a private mortgage, both sides should have legal representation with a formal written agreement, including payment terms. The lender owes tax on the interest, and the borrower often can deduct it if he or she itemizes.
To avoid IRS trouble, the interest rate shouldn’t be lower than the agency’s Applicable Federal Rate at the time of the loan. Currently that is about 5% for loans longer than nine years; about 4.5% for loans three to nine years; and about 4% for loans three years or less. Currently, traditional mortgage rates are generally above 7%.
In addition, the lender could use the $19,000 annual gift-tax exemption (described below) to forgive some or all of the interest or principal annually. If both lenders and borrowers are married, that is up to $76,000 a year. There is no tax for the borrower on such forgiveness, because it is from a gift.
If you’re going this route, McKeown advises against having a fixed plan to forgive the debt. Instead, do it in one-off letters specifying the amount—and keep careful records. Otherwise the IRS might try to treat the loan as a taxable gift.
Powerful tax-saving moves for families often use gift-tax provisions. Under current law, anyone can give anyone else up to $19,000 of assets annually, free of gift tax. That means a married couple with three grandchildren could give them a total of $114,000 in 2026.
The gifts can be cash or other assets, like stock. For noncash gifts, the cost basis—which is the starting point for measuring taxable gain after a sale—“carries over” to the recipient. So if someone buys $1,000 of stock and gives it away when it is worth $5,000, the recipient’s cost basis is $1,000. If the recipient later sells the shares for $8,000, the taxable gain is $7,000.
Here’s an example showing how gifts could save a family taxes. Grandma is a widow of modest means, while her child and spouse have prospered. The couple has two children, and they want to contribute $5,000 to a 529 college-savings plan for each—but they need to sell stock to do it. Their tax rate on the sale would be 18.8%, and they would need to sell about $11,000 of stock.
However, Grandma’s federal tax rate on the stock sale is 0%. If the couple gives $10,000 of shares to Grandma, she could sell them, pay no tax, and fund the grandchildren’s 529 plans. This saves about $1,000 of tax.
These moves are legal, and they could be used in other ways, such as to help a young person fund a Roth IRA.
But trust among family members is essential: Under the law, givers can’t put conditions on a gift. Grandma could use her stock proceeds to take a cruise, but she makes 529 contributions instead.
Mark Sellner, a retired tax attorney and CPA living in Sarasota, Fla., uses this strategy. His children sell stock he gives them and fund 529 plans for his grandchildren.
The family’s tax savings aren’t huge, but he likes other benefits. The sales by his children don’t boost his adjusted gross income, which in turn could raise his Medicare Irmaa premiums or his 3.8% surtax on net investment income.
Sellner doesn’t worry about his children using the funds for another purpose.
“There can’t be any strings attached to gifts. Of course, it is up to us to decide whether to make them in the future,” he says.
Two caveats: The “kiddie tax” applies to most children under age 24, and it is levied at the parents’ rate on investment income above $2,700 in 2026. Consider this before making gifts to a young person.
Investors who give away stock also forgo the step-up, an important provision that exempts assets held at death from capital-gains tax.
Sellner knows he’s losing a step-up, but says, “The children could use a little more now. Why should they wait 20 years to get it?”
A disclaimer is a highly useful strategy in which one heir renounces an inheritance in favor of another heir. Assuming family members cooperate, this can save taxes.
Here’s one example. Dad died and had a large traditional IRA that he left to Mom. She has enough assets and income to cover her expenses, and she lives in a state with a stiff estate tax. The inherited IRA would put her estate over the threshold.
Also surviving are three young-adult children. If Mom disclaims all or part of Dad’s IRA within nine months of his death, that amount could go directly to the children. They will have 10 years to empty the account, and the family as a whole will likely save estate and income taxes.
Disclaimers have many key details, especially regarding beneficiary documents. Although heirs have great freedom in choosing what assets to disclaim, the rules about who gets disclaimed property are rigid. It is best if the original owner names tiers of heirs so that if one disclaims, the next recipient is clear.
