Unlike the tennis tour all year round, where you can expect some predictability, the off-season brings its own surprises. Players reveal plans for next year. They announce engagements. Some even take a hiatus. You never know what to expect from the month off. But Jelena Ostapenko just made a bold move. She put her belongings up for sale on Instagram. This quirky decision left fans scratching their heads. Even Jessica Pegula couldn’t resist chiming in!

Taking to the Player’s Box Podcast, which Pegula hosts alongside Madison Keys, Jennifer Brady, and Desirae Krawczyk, the World No.6 delivered a lighthearted response. She said, “We have to give a shoutout to Jelena Ostapenko. Talking about utilising the most of your career, she is selling things on Instagram.” Although, this had some fans buzz with curiosity. Why would the 2017 French Open champion, who has earned over $18 million in prize money, sell items online?

For the unversed, the Latvian pro launched “Jelena’s Marketplace” online under the handle @j.o.clothes1997. She listed perfume samples, a Dyson vacuum cleaner, and even storage boxes starting at just £4. Whatever sparks this fun side hustle, Jessica Pegula loves it!

“I’m like flabbergasted by the fact that she does this,” she admitted, “But we also, I think, respect it because girl’s just trying to like get her bag and make her money. A little cash here and there, you know? Why not? It’s kind of awesome.”

This year alone, Jelena racked up a little over $2 million in prize money! She teamed up for doubles titles in Charleston with Erin Routliffe and Abu Dhabi with Ellen Perez. She also clinched a singles crown in Stuttgart, toppling Aryna Sabalenka in the final. Still, her season stayed mixed with ups and downs.

On the other hand, Jessica Pegula enjoyed a strong season. She reached the WTA Finals again as the fifth seed, proving her consistency among the elite. Riyadh tested her grit, and though she fell in the semifinals, the effort capped a year to remember. Titles in Bad Homburg, Charleston, and Austin boosted her trophy count and confidence. In total, Pegula earned over $5 million in prize money—a solid haul for a year of steady brilliance.

Although Jessica’s story stands apart. She comes from a family whose net worth reaches into the billions. For those who don’t know, she’s the daughter of Terry and Kim Pegula, owners of the Buffalo Bills (NFL) and the Buffalo Sabres (NHL). Yet the 31-year-old has made it clear she plays for something more personal. She’s been outspoken about creating her own legacy, one swing at a time.

Now she’s taking a breather, cooling down after the grind of 2025. But tennis never stays far from her mind. Jelena isn’t the only star Pegula is cheering for these days. The American tips her hat to her fellow countrywomen, celebrating as they reach a shiny new milestone.

Jessica Pegula cheers on new American tennis feat!

On November 24, the USTA hit a brought out some nostalgia and excitement on Instagram with a collage that made tennis fans smile. Across the top row stood four current stars: Pegula, Coco Gauff, Amanda Anisimova, and Madison Keys. Each closing out 2025 inside the WTA Top 10!

The best part? Below them were icons from two decades earlier: Lindsay Davenport, Serena Williams, Venus Williams, and Jennifer Capriati. For the first time since 2004, four American women had ended a season among the world’s top tier. It felt like the golden era had come full circle.

Jessica Pegula couldn’t hide her joy as she reposted the USTA collage to her Instagram story. Proudly cheering on the group’s success. For instance, Keys snagged the Australian Open title to start the season in style. Gauff owned the clay, conquering Roland Garros. Anisimova proved her comeback was real, blazing into consecutive finals at Wimbledon and the US Open. And Pegula? She checked off milestone after milestone, reinforcing her reputation as one of the tour’s most reliable forces.

Just last month, she etched her name into the record books again. She became the oldest player to qualify for four or more straight WTA Finals since Nathalie Tauziat between 1997 and 2001, and the oldest American to do it since Martina Navratilova’s streak from 1991 through 1994. Her run is proof of steady work and the kind of quiet drive that separates good seasons from great ones.

Speaking on an episode of the Player’s Box Podcast, Jessica Pegula reflected on the wild ride with a little wit: “Motto of the year – it’s not easy 😂.” Now, there’s one month till 2026 kicks off and the grind restarts. Will she snag more wins and milestones?