Anna Cladakis: The Woman Behind Golf Legend John Daly

Anna Cladakis has supported professional golfer John Daly through many stages of his career and life.

Her journey from working in hospitality to becoming his longtime partner and caddie shows dedication, teamwork, and steady commitment.

This biography shares factual details about her background, career, and role in Daly’s life.

Personal Details and Quick Facts

Detail	Information
Full Name	Anna Crissy Cladakis
Date of Birth	January 7, 1969
Age (2025)	56 years old
Birthplace	Florida, USA
Parents	Bill and Harriet Cladakis
Education	Tarpon Springs High School
Children	Charitsa (born July 2004)
Relationship Status	Engaged to John Daly (since 2014)
Instagram	@jdace (private account)
Business	Co-owner of The Bridge Lounge

Anna Cladakis Early Life and Background

Anna Crissy Cladakis was born on January 7, 1969, in Florida, making her 56 years old as of 2025. Growing up as the daughter of Bill and Harriet Cladakis, she learned early on about hard work and family loyalty. Her Greek heritage instilled strong values that would later serve her well in navigating the challenging world of professional sports.

After graduating from Tarpon Springs High School, Anna dove into the hospitality industry where she discovered her natural talent for connecting with people. You know that person who can make anyone feel comfortable? That’s Anna – and this skill would become crucial in her future role supporting one of golf’s most unpredictable personalities.

Her career in promotional work taught her organizational skills and people management abilities. These talents would prove invaluable when she later stepped into the complex world of professional golf, where managing personalities and logistics can make or break a career.

Anna Cladakis Meeting John Daly

In 2007, while working as a promotional director for Hooters, Anna met professional golfer John Daly during one of his endorsement events. At first glance, Their meeting in 2007 began a long partnership built on shared goals and understanding.

Daly was going through a rough patch, separated from his fourth wife Sherrie Miller, and dealing with the usual chaos that seemed to follow him everywhere. She saw something in him that others missed – not just the talented golfer, but the person who needed genuine support and understanding.

Their professional connection soon grew into a lasting personal relationship. Anna’s calm and steady nature helped Daly find balance during a challenging period in his career.

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Multifaceted Role in Daly’s Life

Here’s where her story gets really interesting – she’s not just John Daly’s fiancee. She wears more hats than you can imagine, and trust me, each one requires serious skills. As she puts it herself: “I’m Anna Cladakis, I’m John Daly’s fiance, caddy, mental coach, fashion designer, homeschool teacher for the kids and entertainment director for him.” (sportskeeda)

Anna stepped up as Daly’s caddie when his regular caddie had knee problems, giving Daly just eight hours to find a replacement. Most people would panic, but she saw an opportunity to support her partner even more directly. She’s been walking every hole and providing mental coaching during tournaments ever since.

She enjoys caddying at St. Andrews in Scotland, known as the ‘home of golf.’ Daly once expressed concern about the weight of the bag, but Anna showed determination by completing the round successfully.

Key Responsibilities Anna Handles:

• Tournament logistics and travel coordination
• Mental coaching during crucial golf moments
• Fashion coordination (yes, those matching outfits are planned!)
• Business partnership decisions and planning
• Family management and homeschooling duties
• Media relations and public appearances

Anna Personal Life and Family Dynamics

Anna’s personal life adds complexity to her already busy world. She has a daughter named Charitsa, born in July 2004, from her previous relationship with Chris T. Sullivan, the founder and chairman of Outback Steakhouse.

Anna went through a custody process with her former partner, businessman Chris T. Sullivan. They reached an agreement regarding the care and support of their daughter. Anna handled these complex financial discussions while building her relationship with Daly.

Anna has helped create a supportive blended family environment with Daly and their children. She’s taken on the role of homeschool teacher for Daly’s kids, showing that her commitment extends far beyond just being his romantic partner. She’s genuinely invested in the entire family’s well-being.

Legal Challenges and Controversies

Let’s be real – dating someone like John Daly comes with legal complications. In 2014, Daly’s former spouse filed a legal claim involving Anna, which was later addressed through the courts (Essentially Sports). Details of the case were publicly reported at the time. The situation involved complex legal matters that attracted public attention at the time.

The case went all the way to the Mississippi Supreme Court because Mississippi is one of the few states where you can actually sue someone for stealing your spouse’s affections. The U.S. Supreme Court declined to hear Anna’s appeal in 2015, allowing the case to proceed.

Anna experienced some personal and legal challenges earlier in life, which she has since moved past while focusing on her family and career. But here’s what I respect about her story – she didn’t let these setbacks define her future. Instead, she used these experiences to grow stronger and more resilient.

Professional Impact on Daly’s Career

Since Anna’s been in Daly’s life, his career has stabilized dramatically. She was right there caddying for him during the 2017 Insperity Invitational on the PGA Tour Champions – one of his most significant recent victories. She assists Daly during tournaments by handling caddie duties and offering steady support.

The couple is often seen wearing coordinated outfits at tournaments, which has become part of Daly’s recognizable image. Their coordinated outfits have become a unique feature of Daly’s public image. Anna understands that Daly’s flamboyant fashion and personality are part of his appeal, so she embraces it completely.

Her business partner role extends beyond the golf course. Anna co-owns The Bridge Lounge bar in Tarpon Springs, Florida, with her siblings. When the bar was struggling and losing $4,000 per month (partly due to the BP oil spill impact), she had the smart idea to get help from Spike TV’s Bar Rescue in 2016.

Anna’s Professional Contributions:

• Caddying expertise at major tournaments including walking every hole.
• Brand management and coordination of their distinctive public image.
• Business development through The Bridge Lounge and other ventures.
• Strategic planning for Daly’s transition to the senior tour.
• Event coordination for charity tournaments and public appearances.

Cladakis Relationship Philosophy and Dynamics

After nearly 18 years together, Anna and Daly have figured out what works for them. They announced their engagement in December 2014 with Daly posting: “Today I asked my best friend, my soul mate & no one better to marry me and she said yes!” But they’re in no rush to actually tie the knot.

As Anna explains it, they “pushed it back a year at least just to get him on the senior tour” – showing how their personal decisions align with career strategy. “It’s eight years feels married it’s just the party you guys are all invited,” Anna said, showing their casual approach to formal ceremonies.

Anna’s philosophy about dating a golfer is refreshingly honest: “If anybody wants to date a golfer you got to have some patience not every day is a great day at all and you better be ready to handle that cool off period.” She gets that golf is an emotional rollercoaster.

Recent Activities and Charitable Work (2024-2025)

In April 2025, Anna organized John Daly’s Golf Invitational charity tournament at Old Hickory Country Club. This wasn’t just about golf – she incorporated wellness elements like yoga stretches and nutrition lessons, showing her interest in public health and community engagement.

Daly publicly acknowledged her contribution, posting: “To my amazing fiancé, thank you for your unwavering hard work & generous heart that made our charity event this week such a HUGE success!” (newsweek) The tournament, originally founded by Daly’s mother in 1991, raises funds for the Boys & Girls Club of the Arkansas River Valley.

The John Daly Charity Classic team spots cost $10,000 each, but She helped organize the event’s wellness activities, which included yoga and nutrition lessons for participants. Her charitable work goes beyond just showing up – she actively contributes program elements that make events more meaningful for attendees.

Social Media and Public Presence

Anna keeps a low profile on social media and shares occasional updates with friends and family. This controlled approach contrasts with Daly’s more public persona, which shows wisdom on her part given the legal scrutiny she’s faced. (sportskeeda)

Her social media presence focuses on family moments and behind-the-scenes glimpses rather than seeking personal attention. She understands that being supportive sometimes means staying in the background and letting your partner shine.

She limits her online presence to maintain her family’s privacy. Given all the legal drama and public attention over the years, this balanced approach makes perfect sense.

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Looking Forward: 2025 and Beyond

At 56 years old in 2025, Anna shows no signs of slowing down. With 19 tournaments scheduled for Daly on the PGA Tour Champions this year, she’ll continue as his constant companion and business partner. Their relationship represents the longest stable partnership in Daly’s personal life.

They may continue to explore new business and charitable projects together in the future. Anna’s entrepreneurial spirit and experience with wellness program planning suggest she might develop that side of their brand even further.

Their story continues to evolve, but one thing’s clear – Anna has created a modern supportive partnership that redefines traditional relationship roles. She’s proven that being supportive doesn’t mean being invisible or powerless.

Anna’s Multiple Roles:

• Professional caddie for PGA Tour Champions events
• Mental coach and emotional support system
• Business partner in various ventures
• Homeschool teacher for family children
• Charity event organizer and wellness coordinator
• Entertainment director managing Daly’s personal activities

Interesting Facts About Anna:

• She learned to caddy with just 8 hours notice
• Her favorite golf course to caddy is St. Andrews
• She coordinates their famous matching outfits including Loudmouth golf apparel
• Has Greek heritage from her parents’ background
• Survived a custody battle with Chris Sullivan, an Outback Steakhouse billionaire
• Helped save the family bar through Bar Rescue with Jon Taffer

Conclusion

Anna Cladakis represents something special in professional sports partnerships. She’s not just along for the ride – she’s actively driving success in ways most people never see. From caddying at St. Andrews to organizing charity tournaments with wellness education, she has redefined what supportive partnership looks like.

Anna’s story reflects resilience and consistent support through both personal and professional challenges. She’s faced legal challenges, family complications, and the intense pressure of being with one of golf’s most controversial figures. Through it all, she’s maintained her own identity while genuinely supporting Daly’s career and personal growth.

Their 18-year relationship proves that the best partnerships happen when two people complement each other’s strengths. Anna brought stability to Daly’s chaotic world, while he gave her a platform to showcase her organizational talents and business skills.

If you’re inspired by stories of people who create their own paths and refuse to be defined by others’ expectations, Anna’s journey offers plenty of lessons. She took a chance on love, built a modern supportive partnership, and continues to evolve both personally and professionally.

What do you think makes their partnership work after all these years? Share your thoughts – I’d love to hear your perspective on what creates lasting relationships in high-pressure situations like professional sports.

FAQs About Anna Cladakis

Q: How long have Anna Cladakis and John Daly been together? 

A: Anna and John have been together for nearly 18 years since meeting in 2007, making this Daly’s longest stable relationship.

Q: Does Anna Cladakis have children with John Daly? 

A: No, Anna and John don’t have children together. Anna has a daughter Charitsa from her previous relationship with Chris T. Sullivan.

Q: What business does Anna Cladakis own? 

A: Anna co-owns The Bridge Lounge bar in Tarpon Springs, Florida with her siblings, which was featured on Bar Rescue in 2016.

Q: How did Anna Cladakis become John Daly’s caddie? 

A: Anna started caddying when Daly’s regular caddie had knee problems, giving them just 8 hours to find a replacement for a tournament.

Q: When did Anna Cladakis and John Daly get engaged? 

A: They announced their engagement in December 2014 after seven years of dating, though they haven’t married yet.

Q: What legal issues has Anna Cladakis faced? 

A: Anna was sued for “alienation of affection” by Daly’s ex-wife Sherrie Miller in 2014, and has faced personal legal challenges including battery and shoplifting arrests.

Q: What role does Anna play in John Daly’s charity work? 

A: Anna actively organizes charity tournaments, including incorporating wellness programs like yoga stretches and nutrition lessons while managing logistics for events supporting the Boys & Girls Club.