Taylor Swift's Early Years: Exploring the Pop Star's Surprisingly Controversial Pennsylvania Origins

These days, Taylor Swift is mostly associated with Nashville and New York City, but she and her family actually hail from the suburbs west of Reading, Pennsylvania. That's where the pop star lived until the age of 14.

Taylor is a hometown hero to some locals. "My grandkids love her," said Kathy Reedy, the retired former owner of Penn Avenue Music in Springmont. "They know that she came from around here."

Still, the singer's Pennsylvania roots aren't a big part of her public image. Neither are Andrew Orth and Ronnie Cremer, who told Q they played an integral role in launching Taylor's career. Orth began taking professional-grade photos of the star when she was just a toddler. Cremer taught Taylor the mechanics of songwriting and used to manage her website.

While the men have many warm memories of Taylor, they both have bones to pick with the Swifts. The pair believe the family and its publicists have worked hard to understate their impact on Taylor's career. That's been a hard pill for Orth and Cremer to swallow, especially now that Taylor is a billionaire and arguably the most famous woman in the country.

It should be noted that both men have been very eager to associate themselves with Taylor's success. Orth has an entire page dedicated to photos of her on his professional website. Cremer has a website of his own called itaughttaylorswift.com. This led to a cease and desist order from the singer's legal team in 2015, which he ignored.

Taylor's publicity team didn't respond to Q's requests for comment. It's not clear how she and her family feel about Cremer and Orth or their recollections of Taylor's early years in Pennsylvania.

Taylor's father Scott has deep roots in the Keystone State. One of the singer's third great-grandfathers migrated there from Connecticut in the early 19th century. A different branch of Scott's family can be traced back to Charles Baldi, an industrious Italian immigrant who made his fortune as a banker, newspaper publisher and coal baron in Philadelphia.

Reading was a vital railroad hub in Baldi's era. The city's economy was centered on the Reading Railroad, which was once the crown jewel of the world's largest company. These days Reading is deindustrialized and depressed, but things are very different in the bedroom communities on the western side of the Schuylkill River.

There are intensely suburban areas like Wyomissing, a relatively wealthy town where the Swifts lived for a few years ahead of their move to Nashville. But Taylor's earliest years were spent in a rural area outside the nearby town of Shillington. The neighborhood is defined by its dense forests, working farms and stables. Horses are an important part of the culture in the area, which is in the heart of Pennsylvania's Amish country. Orth said Taylor's mother Andrea was an avid rider who owned several horses. This area may not be Appalachia or the Mississippi Delta, but it's certainly the kind of rustic landscape that could inspire a timeless country anthem.

Orth met the Swifts through his mother Dolly, who lived next door to the family when Taylor was little. Scott bought the property before he met Andrea, who originally hails from Texas. The homestead was a functional Christmas tree farm, but Orth said that was never an important part of the family's income. Scott and Andrea both had lucrative finance jobs. The photographer also claimed that Andrea came from a wealthy family. Taylor's maternal grandmother Marjorie Finlay was an acclaimed opera singer and TV personality. She was also living nearby when she died at age 74 in 2003. Finlay was the inspiration for the track "Marjorie" off Taylor's 2020 album Evermore.

Orth claims Andrea inherited a significant sum of money at some point in Taylor's childhood. But before then the photographer recalled her returning to work shortly after the singer was born. That's why his mother Dolly was recruited to babysit. She also looked after Taylor's brother Austin, who's three years younger.

Orth was living in Los Angeles and working as a celebrity portrait photographer at the time, but he would regularly return to Pennsylvania to visit his mother. He started taking pictures of Taylor when she was just 3. Orth doesn't know how the toddler understood that he was a photographer, but she did, and she desperately wanted to be in front of the camera. Whenever Orth returned, he would never have to wait more than an hour for the little girl with white hair to come bounding across the field to request a photo shoot. He described Taylor as incredibly photogenic and easy to direct and style. Orth added that the kind of untrained comfort she had in front of the lens is rare, especially for young children.

"All you had to do was compose a photograph and put her in the middle of it," he said.

Many of these early sessions were free, but the Swifts sometimes paid Orth for his work. The photographer also recalled Taylor's expressive melodic speech pattern and hearing her imitate songs she listened to on the radio.

The Swifts were financially secure and managed to send Taylor to private Catholic schools, but that didn't mean everything was perfect for the family. Orth and Cremer said there was significant tension beneath the surface. Both men recalled Scott and Andrea having a troubled marriage. They ultimately divorced around 2011. Andrea stopped working at some point in Taylor's childhood. Scott was deeply supportive of Taylor's career, but Cremer said it was mostly Andrea's project.

The guitar teacher and computer technician first crossed paths with the family in 2001 through his brother, who directed shows for the Berks Youth Theater Academy. That year, 11-year-old Taylor starred in a production of Bye Bye Birdie which also included two of Cremer's stepchildren. He described the Swifts as big fishes in a small pond. Taylor always got the lead roles in the theater's plays. Scott would buy out any un-purchased tickets so the shows would officially be sold out. Taylor's Bye Bye Birdie co-star was a 14-year-old named Cody Derespina who later became a Fox News reporter. In 2016, he claimed that the pop star hated sharing the spotlight and ripped down photos of him hanging in the theater during a fit of jealousy.

Taylor was more of an actress than a singer at this point, Cremer said. Andrea was friends with Cremer's mother, who he claims was responsible for getting the Swifts interested in turning Taylor into a country star. Cremer's mom realized that there was a gap in the market when it came to solo teen country performers. Cremer's brother put the Swifts in touch with him after they asked about taping a demo. He recalled being paid around $200 to help Taylor track covers of three songs: "There’s Your Trouble" by the Dixie Chicks, "Here You Come Again" by Dolly Parton and Olivia Newton-John's rendition of "Hopelessly Devoted to You" from the Grease soundtrack.

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The Swifts then turned to Cremer to help mold Taylor into a professional-grade musician in June 2002. This came just a few weeks after she performed the National Anthem at a Philadelphia 76ers game.

By this point, Cremer said the family was living in a rented home in Wyomissing. He would stop by twice a week after his day job to give Taylor a three hour lesson. Sometimes he would stay longer or provide extra sessions. Cremer stressed that he was not a traditional guitar teacher or a fan of country music. The first song he taught Taylor was "I Want You to Want Me" by Cheap Trick, which she performed live as recently as 2011. Some of the lessons focused on simple chords, vocal projection and confidently strumming catchy pop tracks. But Cremer also taught Taylor how to compose her own songs. The pair spent a lot of time working in the digital audio workspace Ableton Live. When it was time for Taylor to delve deeper into the mechanics of the guitar, Cremer sent her to another local musician named Joe Piecora, who's since passed away.

Cremer and Orth described Taylor as a golden child and Austin as often struggling for parental attention. Still, Orth recalled him receiving a $90,000 Land Rover for his 16th birthday. Cremer also claims that Andrea could be harsh on her daughter, recalling one incident where Andrea went to Taco Bell and brought something back for Austin, but didn't get anything for Taylor. Cremer claims Andrea told her that "nobody wants to see a fat pop star."

"I can hear it like it was yesterday," he said. "It’s the first thing that really struck me as odd."

Cremer and Orth said the Swifts treated them like family for years. They had a lot of good times together. Andrea and Orth regularly played tennis. Cremer considered Scott a friend. They spent time together outside of his lessons with Taylor. The Swifts' relationship with Cremer and Orth began to shift after the clan relocated to the Nashville suburb of Hendersonville in January 2004. Taylor had secured an artist development deal with RCA, which she quickly backed out of. The label wanted the singer to wait until she was 18 to release her first album, but she was eager to get started.

Reedy remembers Scott bringing two guitars to Penn Avenue Music shortly before the move. One was a six string and the other was a twelve string. Beth Boone, the store's tech at the time, said the instruments were in poor shape. Reedy said Scott was polite but demanding. He needed the guitars back as soon as possible because the family's move to Tennessee was imminent. This was stressful for Boone, but nothing the seasoned tech couldn't handle, Reedy said.

"Back then, nobody knew who Taylor was," she added. "It was a cool thing that they brought her guitars here. I tell a lot of people."

Orth and Cremer remained in the Swifts' good graces for a time after the move. They were both invited to stay with the family in their new home. Cremer was still in charge of Taylor's website and Orth continued to take pictures of the pop star. His images were even used for the cover of her 2006 self-titled studio debut. But it didn't take long for a series of business disputes to roil Orth and Cremer's relationships with Taylor's parents.

Orth said Taylor's fame had a big impact on Andrea, who became angrier and more demanding. Cremer says he experienced this firsthand on one summer day in 2004. He was trying to get in the car with his family to leave for a beach trip when Andrea called him. She said the conversation would take five minutes, but Cremer claims he was stuck on the phone with her for a full two hours. His marriage was already on the rocks at that point due to the amount of time he spent working for Taylor and the Swifts. "It was like a tug of war between my wife at the time and Andrea," Cremer said. "I was spending a lot of time with Andrea’s kids and not so much with my wife’s." When Cremer got back into the car, he realized the delay had been a grave blow to his marriage. He ended his professional relationship with the Swifts shortly thereafter. Cremer referred Andrea to a different web designer, but said she didn't take the news well: "She was really ugly about it."

Orth had a similar blowout with Scott around this time. Taylor quickly courted millions of followers on MySpace, then the hottest social media channel around. Orth said super fans were furiously downloading official pictures to create their own websites. The trend alarmed Scott. Orth claims the father accused him of selling the photos to the fan sites without the Swifts' permission. The photographer denied this, but the parents were still angry. Orth also claimed that there were instances where his photos of Taylor were used without proper attribution. His relationship with the Swifts ended for good while Scott was driving him to the airport after his final visit to Tennessee. The photographer claims Scott threw a lengthy contract in his lap and demanded that it be signed immediately. Orth refused. When they arrived at the airport, Scott threw his bags out of the vehicle and drove off.

"All I could think of was how her father probably tarnished my reputation in Taylor's eyes," Orth said.

As Taylor's notoriety grew, the family began relying on a team of professionals to manage her public image. Cremer and Orth said many of the narratives these publicists spun around the budding pop star were embellished or false. An anti-bullying message was a key part of Taylor's public persona at the time. Cremer believes this was meant to fit in with an anti-bullying initiative then-First Lady Laura Bush was pushing in that era. The narrative was bolstered by Taylor's claims that she suffered bullying during her school years. But Cremer said that was false, and that the singer was actually one of the most popular girls in her class.

He also claims that the publicists minimized his role in Taylor's early career. He alleges this was because he could refute the bullying claims, but also part of an effort to portray the singer as a more of a self-made upstart than she actually was.

Cremer remained loyal to the Swifts throughout the late 2000s. He was regularly approached by tabloids, but didn't spill any potentially unflattering details about Taylor's early career. He was still in touch with Scott at this point, but their relationship was very different. The father would occasionally call Cremer, but they didn't have normal conversations. These were allegedly one-sided speeches where Scott would brag about Taylor's success before jumping off the phone. He sent Cremer a platinum record in 2007 following the massive success of Taylor's debut album.

Scott had a big request for Cremer in 2009. One of the first guitars Taylor ever played was her teacher's 12 string Ovation acoustic. Scott asked Cremer if he was interested in selling it so he could give it to Taylor as a 20th birthday present. They ended up bartering instead. Cremer received a $5,000 instrument from Taylor Guitars, which sponsored the singer at the time. He also received a brief call from Taylor after the Swifts received the guitar. Cremer hasn't spoken to her since.

His relationship with Scott ended for good in 2010. Cremer alleges that he received an angry call after an internet user who claimed to be the daughter of Taylor's guitar teacher made unflattering comments about the pop star. Cremer said he only has one biological child, a son who was just 3 months old at the time. But Scott was still livid.

"He laid into me," Cremer said. "I’m thinking, 'How dare you? … I’ve been defending your family for years.'"

That's why when a New York Daily News reporter showed up at Cremer's shop in 2015, he had no qualms about speaking out. He didn't consider anything he said for the story particularly salacious, but it did make waves at the time. Orth was also interviewed for the article.

Taylor returned to the Reading area in 2016 for her childhood friend Britany Maack Lamanna's wedding. The pop star was the maid of honor. She also visited one of her childhood homes in the region while on tour in 2018. The singer shared a picture of her and some friends sitting on the floor of her old bedroom. Taylor's May 2023 concerts at Philadelphia's Lincoln Financial Field were billed as hometown shows.

"Philly was a dream, honestly," she said in a tweet at the time. "Playing three nights in the stadium I used to see on tv when my dad watched Eagles games every Sunday. The most magical 3 hometown shows a girl could hope for."

Just a few months later, the singer started dating NFL player Travis Kelce. His brother Jason Kelce recently retired from his career playing for the Philadelphia Eagles. Jason recently promised fans that he and his family won't be leaving the Philly area when he retires. If things get more serious between Taylor and Travis, maybe she'll buy a home in Pennsylvania to stay close to his relatives.

Cremer and Orth both stressed that the financial resources Taylor's parents provided were a huge part of her success.

"Do I think as her teacher that she is uniquely talented? No," Cremer said. "Taylor will never understand the plight of a musician trying to make it in this business."

That's not unique to Taylor, though. The children of wealthy, powerful parents are overrepresented in the music industry and the upper echelons of the American economy at large. Still, it wouldn't be a bad thing if Taylor did more to acknowledge her Reading roots.

"My mom's never gotten so much as a Christmas card from them, and it hurts her feelings," Orth said of Dolly, who's now 96. "They're telling everybody (Taylor's) now officially a billionaire… What would it take for that girl to write my mom a note?"