👋 Welcome back to The Daily Theory, our morning rundown to help you stay on top of your favorite sport. I’m Allen McDuffee, your guide to all things tennis.

On tap today: Jenson Brooksby takes home a first title, so does Flavio Cobolli, Jessie Pegula holds steady, Daniil Medvedev takes on Karen Khachanov, plus more in today’s tennis news.

Let’s tennis!

Five Points

🎾 The wait is over: Jenson Brooksby came back to professional tennis only three months ago after a few devastating factors kept him off the tour for two years. On Sunday, the 24-year-old came through qualifying in Houston to win the first title of his career, staving off multiple match points along the way. But it was the final against Frances Tiafoe that was the biggest test of nerves, which he passed with flying colors by taking out his fellow American 6-4, 6-2.

  • What he said: “Thank you to my team. All the way from qualifying, match point down,” Brooksby said during the trophy ceremony. “That’s pretty intense, so thanks for sticking with it, every match, every day here for me.”
  • More than a week: Brooksby may have been thanking them for his team’s effort in Houston, but there’s more packed in that expression of gratitude. It’s been an unbearable couple of years for Brooksby, who was suspended from the tour for missing doping tests, underwent double wrist surgery, and recently opened up about his life with autism spectrum disorder.
  • Now: Brooksby entered the Houston event ranked 507 in the world. With 250 points in his pocket, he jumped 335 spots to 172. That’s just in time to make qualifying at Roland-Garros — a tournament that notoriously doesn’t give wild cards to anyone unless they’re French.

🎾 Not the only one: Joining Jenson Brooksby in the first title club on Sunday was Flavio Cobolli. In Bucharest, the 22-year-old Italian took home the 250 title by defeating top-seeded Sebastian Baez in the final, 6-4, 6-4. What makes it particularly notable is that Cobolli hadn’t won a tour-level match since October last year.

  • What he said: “I feel great. I feel happy. It’s a big dream come true for my career,” Cobolli said after the match. “I always dreamed of winning an ATP tournament and it has happened today. I’m really happy to be here and to have reached my best result ever. I came from a tough moment. I had not won a match, before this tournament, this year, and I won the tournament. So I’m really happy about it.”

🎾 Holding steady: Jessie Pegula won the Charleston Open, defeating fellow American Sofia Kenin in the final. Clay isn’t exactly Pegula’s favorite surface, making the fast turnaround from Miami to Charleston that much more impressive. Add to that the fact that she was down 5-1 in the second set before taking the final, 6-3, 7-5.

  • What she said: To be able to come here this week after a long two weeks in Miami and take the title is just incredible...In the second set, I just wanted to hold, I just wanted to tell myself to get momentum for the third, because coming into a third like that never feels good. I honestly didn’t think I was going to break her twice, but luckily I could play some good tennis.

🎾 Following the money: As the Charleston tournament came to a close over the weekend, organizers made an important announcement: Charleston will offer equal prize money to the ATP 500 events beginning in 2026. That’s the first time a WTA 500 will offer that level of prize money to players. Once the ATP announces the prize money guidelines for 2026, the Charleston Open will match it.

  • What they said: “The Credit One Charleston Open has always been at the forefront of promoting women in sports, and we’re incredibly proud of our legacy. We’ve broken attendance records year after year, drawing more than 90,000 attendees and 26 million international television viewers,” Ben Navarro, Credit One Charleston Open tournament owner, said in a statement. “As North America’s largest women’s-only tennis tournament and one of the longest-running women’s-only events in professional sports, we’re not just celebrating the past - we’re actively shaping the future.”
  • In other words: As tournaments do better, so should the players. If that line of thinking sounds familiar, it’s because that’s the argument at the heart of the PTPA lawsuit and the letter the top 20 players sent to the majors.

🎾 ICYMI: In what amounted to a Friday afternoon news dump, the ATP released a statement that Massimo Calvelli will step down in June from his role as the organization’s chief executive officer. No reason was given for Calvelli’s departure other than “new opportunities ahead.” ATP Chairman Andrea Gaudenzi will step into the role and do double duty while a search for Calvelli’s successor is completed.