Taylor Swift’s many celebrity exes include actors Tom Hiddleston and Jake Gyllenhaal. Photos: AFP, BFA, Reuters

In October, Taylor Swift made history by becoming a billionaire. Her notable entry into the ranks of the super-wealthy is particularly impressive because her net worth is derived largely from her music and not other side hustles (think Rihanna with Fenty or Jay-Z with his various businesses).

Taylor Swift performs last month during night two of her Eras Tour, in Rio de Janeiro, Brazil. Photo: Getty Images
While Swift’s relationship with NFL star Travis Kelce appears to be going strong, it’s certainly not the first time she has been linked to a well-known partner. And, of course, with fame comes wealth. So just who is the richest man Taylor has dated? We take a look with the help of Celebrity Net Worth and other reports …

9. Conor Kennedy, US$10 million

Conor Kennedy dated Taylor Swift for less than three months. Photo: Getty Images
The American socialite, who is the eldest child of Robert F. Kennedy Jr and Mary Kennedy, briefly dated Swift in 2012. The pair were linked in July of that year but split up in September, per US magazine. It’s been widely reported that Swift was there for the family after Mary Kennedy died by suicide.

He’s worth an estimated US$10 million.

8. Travis Kelce, US$30 million-US$40 million

Travis Kelce models his brand Tru Kolors’ Klassics premium hoodie, T-shirt and sweatpant set. Photo: Instagram/@trukolorsbrand

In September, Swift was spotted cheering on NFL player Kelce on at one of his games. By October, they were holding hands at a Saturday Night Live after-party. Then, in November, Kelce flew to Argentina to support Swift during her Eras Tour, per People, with a kiss between the couple solidifying relationship rumours.
Kelce has amassed a wealth portfolio of US$30 million-US$40 million, per Parade and Celebrity Net Worth, and might extend it with his recent foray into fashion through his brand Tru Kolors.

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7. Tom Hiddleston, US$40 million

Tom Hiddleston’s relationship with the world’s biggest pop star lasted just three months. Photo: BFA.com
Tom Hiddleston made his fortune from roles in the MCU’s first pair of Thor films, The Avengers film series, and TV series Loki. He’s worth US$40 million, per various reports.

After just three months of dating in 2016, Swift and her actor beau called it quits. According to US Weekly, the romance fizzled because Hiddleston wanted the relationship to be more public than Swift was comfortable with.

6. Taylor Lautner, US$40 million

Taylor Lautner became the subject of an apology ballad by Taylor Swift. Photo: @taylorlautner/Instagram
Best known for portraying Jacob Black in the Twilight series, the actor, model and martial artist has a net worth of US$40 million.

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Lautner’s relationship with Swift reportedly inspired her apology ballad “Back to December”. “I was really careless with him,” Swift said, per InStyle. The pair were linked from July 2009, but the romance was over by the end of the year.

5. Joe Jonas, US$50-55 million

Taylor Swift revealed on Ellen DeGeneres’ show that Joe Jonas had broken up with her in the briefest of phone calls. Photo: Instagram/@joejonas

Joe Jonas is no stranger to the limelight, so when he briefly dated Swift in 2008, the teen couple were never going to fly below the radar. The singer-songwriter and actor, who shot to fame on the Disney Channel, has a net worth of US$50 million-US$60 million, according to sources such as Celebrity Net Worth and Cosmopolitan.
Swift spoke about their split on The Ellen DeGeneres Show, saying Jonas broke up with her in a 25-second phone call. Clearly there are no hard feelings though, as the two have openly supported each other’s careers since.

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4. John Mayer, US$70 million

John Mayer was so offended by the song Taylor Swift penned in the wake of their relationship that he called it “cheap songwriting” and an “abuse of talent”. Photo: @johnmayer/Instagram
The Grammy award-winning singer-songwriter and guitarist has a net worth of US$70 million.

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His relationship with Swift made headlines both for their 2009 duet “Half of My Heart” and the break-up anthem that followed their 2010 split. Per US Weekly, the musicians got together after Swift accepted Mayer’s invitation to collaborate on a single for his next album.

Fast-forward to the October 2010 release of Swift’s album Speak Now though, and the song “Dear John” was clearly aimed at Mayer. It was a track unflattering enough that, per Rolling Stone, Mayer called it “cheap songwriting” and an “abuse of talent”.

3. Jake Gyllenhaal, US$80 million

Jake Gyllenhaal, pictured in December 2010. The actor and Taylor Swift went their separate ways after the songstress celebrated her 21st birthday without him. Photo: Reuters
Jake Gyllenhaal began acting as a child before successfully transitioning to grown-up roles, beginning with the 1999 film October Sky. With a net worth of US$80 million, Gyllenhaal is widely considered one of Hollywood’s most talented stars.

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Per People magazine, he and Swift were linked from October 2010, but had split by the end of the year after the songstress celebrated her 21st birthday without the actor.

2. Harry Styles, US$120 million

Harry Styles holds his 2023 Grammy Awards for Album of the Year and Best Pop Vocal Album, both for the album Harry’s House, in February, in Los Angeles, California. Photo: AP Photo

With an estimated net worth of US$120 million, per Cosmopolitan, megastar Harry Styles had the biggest-selling album in the UK last year, Harry’s House, and his global tour has certainly added to his wealth.

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Swifties will remember that Styles and Swift got together in 2012, forming what many called a pop icon power couple. According to People, their relationship ended in January 2013. Since then, songs written and released by both have been linked to each other by eager fans.

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1. Calvin Harris, US$240 million-US320 million

Calvin Harris at the MTV Video Music Awards in August 2017, in California. His split from Taylor Swift was the most publicly acrimonious of her break-ups to date. Photo: Invision/AP
The relationship between Swift and Calvin Harris – who topped Forbes’ list of the world’s highest paid DJs from 2013 to 2018 – probably generated the most headlines because of their bitter split. Per InStyle, the pair met backstage at the Elle Style Awards in February 2015. They co-wrote the song “This is What You Came For” while dating.

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But they split in June 2016 after 15 months, with both parties keeping mum until Harris penned a series of tweets, which he deleted soon after. “I know you’re off tour and you need someone new to try and bury like Katy [Perry] etc, but I’m not that guy, sorry. I won’t allow it,” he wrote. Harris later said he regretted going public about the split and acknowledged fuelling the media frenzy that ensued.

Still one of the wealthiest DJs in the world after being unseated from the top spot by The Chainsmokers, Harris’ net worth is estimated at US$240 million to US$320 million, per various reports.