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More Than a Mentor, Forever Family

By Match Stories

At just 11 years old, Jacob had already learned that life could ask a lot of a kid. With his parents absent from his life and his grandparents serving as his primary guardians, he often had to grow up faster than he should have. He needed someone to help carry some of that weight, someone who would show up, offer guidance, and remind him he was still a kid who deserved to have fun.

His grandmother knew how important it was for Jacob to have a positive male role model, so she turned to Big Brothers Big Sisters of Tampa Bay. After nearly two years of waiting, Jacob was matched with Buddy, a 60-year-old retired veteran and pilot. What began as a mentoring match grew into a lifelong bond neither of them could have anticipated.

Shortly after their match, Jacob experienced a profound loss when his grandfather passed away. During this difficult time, Buddy became more than a mentor. He became a steady, trusted presence in Jacob’s life. As their bond grew, Jacob asked if he could call Buddy “Dad,” a reflection of the deep connection they had built and the place Buddy had come to hold in his family.

Looking back, Jacob says Buddy gave him back his childhood. After growing up quickly in his household, he finally had someone who encouraged him to enjoy being a kid. Together, they made memories through fishing trips, baseball games, and learning to play golf. These seemingly simple outings became some of the most meaningful moments of Jacob’s childhood.

But Buddy’s impact didn’t stop when Jacob grew up.

The two were formally matched through Big Brothers Big Sisters of Tampa Bay for seven years, until Jacob aged out of the program. Throughout every new chapter, Buddy remained in his corner. He cheered Jacob on as he graduated, served four years in the Marines, started a family, and began pursuing a career in teaching.

For Jacob, Buddy’s presence has been a constant reminder that he doesn’t have to navigate life’s challenges alone. For Buddy, watching Jacob grow into the man he is today has been a rewarding part of their journey together.

Their story is a powerful reminder that mentoring is about so much more than spending time together. It’s about showing up consistently, building trust, creating lasting memories, and becoming someone a young person can count on for years to come.

At Big Brothers Big Sisters of Tampa Bay, we believe every child deserves a caring adult in their corner. Buddy and Jacob’s relationship shows what can happen when someone chooses to make that commitment: a mentor becomes a role model, a role model becomes family, and a relationship changes a life forever.

Kindness in Action, Potential in Motion

By Networking, Uncategorized

Big Brothers Big Sisters of Tampa Bay is honored to be selected as one of just 12 nonprofit organizations for Strikes of Kindness. Strikes of Kindness is an annual community partnership between the Tampa Bay Lightning and Benchmark International that awards grant funds and organizes joint volunteer services.

Through this opportunity, our organization is joining a select group of nonprofits recognized for their impact and commitment to serving others. Being chosen provides an exciting opportunity to introduce our mission to new audiences, build community awareness, and inspire more people to get involved in creating brighter futures for local youth.

At Big Brothers Big Sisters of Tampa Bay, we believe every child has incredible potential, and having one caring adult in their corner can make all the difference. Across our nine-county service area, we connect young people with caring mentors through professionally supported, one-to-one mentoring relationships that help them build confidence, navigate challenges, and reach their full potential.

With more than 600 children waiting for a mentor across our service area, opportunities like Strikes of Kindness are especially meaningful. They help highlight the growing need for mentors and show how community partnerships can create lasting, positive change.

Whether you become a mentor, make a gift, or share our story, every act of kindness can help a young person realize their potential.

That’s a Wrap on Mission: Possible!

By Fundraising Events, Uncategorized

The mission was clear, the stakes were BIG, and our community proved that changing a young person’s future is always possible.

On October 10, Big Brothers Big Sisters of Tampa Bay brought Mission: Possible to life at the Motor Enclave for an unforgettable evening celebrating the mentors, supporters, and community partners who make life-changing relationships possible. From inspiring stories to well-deserved recognition, the 2026 BIG Gala reminded us that when we show up for our youth, incredible things happen.

Want to relive the magic? Watch the BIG Gala video and view photos from the evening to revisit the special moments, inspiring stories, and incredible people who made the night unforgettable.

A highlight of the evening was recognizing Celeste Roberts, Founder and CEO of the Skill Center, as the 2026 Rays Up Award recipient for her impact and commitment to the community.

The evening also celebrated the extraordinary relationships at the heart of Big Brothers Big Sisters. Russell Nelson and his Little Brother, Yulon, were recognized as Big Brother of the Year, celebrating a match that began when Yulon was just 10 years old. Sandra Tidd and her Little Sister, Allyson, received Big Sister of the Year honors, recognizing the meaningful difference their relationship has made in Allyson’s life. Crystal L. Lauderdale and Peter Masa were honored as Big Couple of the Year alongside their Little Brother, Jorge.

Guests also heard the inspiring story of Ari and her Big Sister, Deen, who have been matched for nearly eight years. Their relationship shows how showing up consistently can create lasting memories, build confidence, and help young people imagine a bright future.

The Gala was more than a celebration. It was a chance to invest in the future of children across the nine counties Big Brothers Big Sisters of Tampa Bay serves. With nearly 600 children waiting for a mentor, community support is essential to creating more life-changing matches.

Be part of what’s possible. Become a Big Brother, Big Sister, or Big Couple and help a young person discover their potential. If mentoring isn’t the right fit for you, you can still make a BIG difference by donating, connecting us with a community partner, or sharing our mission with your network.

From the CEO – October Letter

By Uncategorized

Dear Friends,

Our BIG Gala, Mission: Possible, was a tremendous success! From the incredible venue and mission-inspired theme to the inspiring stories shared throughout the evening, it reminded us of what we can accomplish when our community comes together. I am incredibly grateful to everyone who helped make the night possible and to all who continue to show up BIG for the children and families we serve.

One highlight of the evening was celebrating our 2026 Rays Up Award recipient, Celeste Roberts, Founder and CEO of the Skill Center, along with our outstanding Bigs and Littles of the Year. Their stories remind us of the lasting impact a caring, consistent mentor can have on a young person’s life. Click here to read our Gala blog post and relive the incredible evening!

We’re also building exciting momentum as we launch the Hillsborough Big League chapter. Our growing community of young professionals is committed to making a difference through mentorship, leadership, and philanthropy. I’m excited to see this initiative create new opportunities for our community to get involved and help more young people reach their full potential. Look out for more information as we launch our next chapter in Pinellas in early 2027.

On a personal note, I was honored to be recognized by the Tampa Bay Buccaneers and AdventHealth’s Goal Getters program earlier this month. I’m grateful for the chance to share my passion for our mission and highlight the importance of mentoring. Every day, I’m reminded that it takes a community of dedicated individuals to help ignite the power and promise of youth, and I’m proud to be part of that effort.

Thank you for continuing to believe in our mission and for being part of the BIG difference we’re making together. With your support, we can create more meaningful mentoring relationships and help even more young people discover what’s possible for their futures.

With gratitude, 

Robyn  

Marion County Goes BIG for Mentorship

By Fundraising Events, Networking

What an incredible Give4Marion!  

Big Brothers Big Sisters of Tampa Bay was proud to participate in this year’s community-wide giving celebration on September 15–16, bringing together generous supporters, community partners, and advocates who believe in the power of mentorship. 

Throughout the two-day event, our team had the opportunity to connect with supporters across Marion County, share the impact of professionally supported one-to-one mentoring relationships, and highlight the BIG difference caring adults make in the lives of youth. 

From the #CogentPowerHour to community conversations and social media shoutouts, Give4Marion was filled with opportunities to raise awareness and rally support for local young people.  

Robyn Ostrem, CEO at Big Brothers Big Sisters of Tampa Bay shares, “I am incredibly grateful to Susan Alexander, our Partnership Manager in Marion County, for leading us through another successful Give4Marion. It’s exciting to see the incredible work happening in Marion County and the continued support from our community. We are fortunate to have such a large footprint across nine counties, allowing us to serve so many deserving young people.”  

We are so grateful to everyone who shared our mission, made a gift, encouraged a friend to get involved, or helped spread the word. 

While Give4Marion may be over, the need for mentorship continues. There are still young people in Marion County waiting for a Big of their own. To learn more about becoming a Big Brother, Big Sister or Big Couple, click here!  

A Double Play for BIG Impact

By Match Stories

Some moments are about more than a game. For Nate, his Big Jeff, and Nate’s Little, Asher, a trip to the ballpark became a memory they will all treasure, and a powerful reminder of how mentorship can shape a life. 

On September 19, the trio took to the field at a Tampa Bay Rays game as part of the TD SYNNEX Double Play initiative, which selected Big Brothers Big Sisters of Tampa Bay as its charity of choice. Following a special check presentation, Asher stepped onto the field to throw out the first pitch, right to his Big, Nate. 

For Nate, the moment carried an extra layer of meaning. Early in his own mentoring relationship with Jeff, Nate had the opportunity to stand on that same field and throw the first pitch to his Big. Jeff was there for Nate through the years, offering encouragement, support, guidance, and, most importantly, the consistency of having a caring adult in his corner. Nate knows firsthand the difference a Big can make in a young person’s life. 

Now, years later, Nate has the opportunity to provide that same kind of support for Asher. Sharing the experience with his Little created a full-circle moment, one that reflects how the impact of a mentoring relationship can extend far beyond the time a Big and Little spend together. Nate experienced the power of having someone believe in him, and today, he gets to be that person for Asher. 

For Asher, getting to throw the first pitch was a moment he won’t soon forget. 

“It was really special to throw the first pitch,” Asher shared. “I’m excited I got to keep the ball I threw. This is my fifth collectible ball, and I’m really excited to add it to my collection.” 

But the significance of the day went far beyond stepping onto a Major League field or adding a new ball to a collection. It was about creating a BIG memory with someone Asher knows will show up for him, someone who listens, encourages him, celebrates his accomplishments, and makes time for the moments that matter. 

Thanks to the generosity of TD SYNNEX and the Tampa Bay Rays, the Double Play initiative is helping Big Brothers Big Sisters of Tampa Bay create more opportunities for young people across our nine-county service area. Their support helps make moments like Nate and Asher’s possible, while giving more youth the opportunity to experience the lasting impact of having a Big in their corner. 

Interested in becoming a Big? Click here to learn more. 

 

Introducing The Big League: A BIG New Way to Get Involved

By Fundraising Events, Networking

Big things are happening at Big Brothers Big Sisters of Tampa Bay, and we’re excited to introduce The Big League. The Big League is a new community for Bigs, Alumni Bigs, and young-to-mid-career professionals who believe in the power of mentorship and want to make a lasting impact. 

James Bremis, RMR Wealth Builders, Inc., and Board Member at Big Brothers Big Sisters of Tampa Bay, along with Chad Mitchell, Vice President of Mission Partnerships & Advocacy at Big Brothers Big Sisters of Tampa Bay, are championing this new initiative.  

Launching first in Hillsborough County in the fall of 2026, The Big League will bring together individuals who share a passion for giving back, building meaningful connections, and investing in the future of our youth. The Big League will offer opportunities to connect, network, grow, and make a BIG difference. 

We’re looking for our first 50 Founding Members to help shape this new community from the ground up. Founding Members will play an important role in setting the stage for what The Big League can become across our nine-county service area. 

Membership is about more than attending events. It’s about joining a community of like-minded individuals who want to make an impact while growing personally and professionally. Members will have opportunities to attend networking mixers, participate in professional development experiences, and connect with our Executive Leadership Team and Board of Directors. 

The Big League will also offer signature event discounts, holiday gatherings, and opportunities to deepen your connection to the mission of Big Brothers Big Sisters of Tampa Bay. 

Membership is $300 annually, or a minimum monthly payment of $25. Captains and Co-Captains can also help lead the community through a $1,000 give/get commitment. 

As we prepare to launch in Hillsborough County and expand across our nine-county service area in 2027, we invite you to be part of this exciting new chapter. 

Register now for an upcoming info session, or if you’re ready to become an official member, click here!  

A Brother by Choice, Family by Heart

By Match Stories

When Joe Donaldson first met Et Winzer, he was just six years old and unsure of what to expect from the Big Brothers Big Sisters program. His grandmother had enrolled him in the program, hoping to provide him with a positive influence and trusted adult in his life.

Et had recently moved to Tampa from the Washington, D.C. area when the Big Brothers Big Sisters of Tampa Bay team came to his office in the late 1990s to recruit volunteers.

He agreed to become a Big and initially planned to meet his Little at school during the lunch hour. Et was told his Little might be shy and distant. Instead, Joe walked into the room with a big smile.

That first meeting marked the beginning of a relationship that would shape both of their lives.

What started with school lunches, Oreo cookies, milk, and games of Connect Four soon grew into something much deeper. Et eventually transitioned from school-based visits to a traditional community-based match, picking Joe up almost every weekend. They explored new places, took road trips, attended activities, and simply spent time together.

For Joe, those experiences opened his eyes to possibilities he hadn’t known existed.

Growing up without his mother and father, Joe was raised by his grandmother, Agnes, who gave him a strong foundation of love, honesty, morals, and faith. But Et introduced Joe to another kind of possibility: seeing a man who looked like him living a life Joe hadn’t imagined for himself.

“He showed me what was possible,” Joe recalls.

Et taught Joe how to carry himself, how to communicate, how to take responsibility and, perhaps most importantly, how to believe in himself. One lesson in particular has stayed with Joe throughout his life.

As a child, Joe once tried to explain away trouble he had gotten into by blaming the people around him. Et challenged him to take accountability for the choices he made and the company he kept.

Joe didn’t like hearing it at first. But eventually, he realized Et was right. That lesson became a foundation for the man Joe would become.

Over the years, their relationship grew far beyond the traditional definition of a mentoring match. Joe became part of Et’s family and Et became part of Joe’s Village. Et attended Joe’s school and activities. Joe visited Et’s office during school breaks and even ushered at Et’s wedding.

In 2010, Joe and Et were recognized as Big and Little of the year. But their story didn’t end there. Although their official match eventually concluded, their relationship continued for more than 15 years and counting.

Et is proud of the husband, father, and person Joe has become and Joe considers Et much more than a Big Brother.

“He is like a father to me,” Joe says. “They say you can’t choose your father or mother. That’s okay, because God chose mine.”

For Et, the relationship is a reminder that giving back doesn’t always feel like a grand gesture. Sometimes, it is simply showing up consistently, sharing your experiences, and helping a young person see a world of possibilities.

Joe and Et’s story is proof that a mentoring relationship can evolve, grow, and last a lifetime. Their match may have started with a school visit in Tampa, but it became something neither of them could have predicted: a lifelong bond.

Celebrating the People Behind the Mission

By Uncategorized

Recently our team and a handful of board members came together at the Florida Aquarium for an energizing and meaningful all-staff meeting focused on connection, collaboration, and our shared commitment to the mission of Big Brothers Big Sisters of Tampa Bay.

Surrounded by the aquarium’s incredible exhibits and marine life, staff had the opportunity to step away from their day-to-day responsibilities and spend time together as one team. The gathering was a chance to celebrate the work we’ve accomplished, align around the work ahead, and recognize the people who make our mission possible every day.

A special highlight of the meeting was celebrating Tiona Mosby, who was honored with the Sweet Alice Award for her ongoing dedication to our mission and the matches in her care.

Tiona shared, “I always look forward to our in-person meetings. It’s a great time to reconnect.” She adds, “I remember Robyn reading the nomination before she announced the winner and thought, wow this could be anyone in the room. Everyone at Big Brothers Big Sisters of Tampa Bay is to making a difference and it shows in everything we do. I am extremely humbled to receive this award and am still in shock! Thank you to everyone at the agency for seeing me!”

The Sweet Alice Award is a meaningful recognition of the people who consistently go above and beyond for our mission, and Tiona is incredibly deserving of this honor. Her dedication, compassion and commitment to the young people and volunteers she serves make a lasting difference in the lives of those around her.

Beyond the recognition and team updates, the day was an important reminder that our impact is powered by people from the staff working behind the scenes to the program teams supporting matches and, most importantly, the Bigs who show up for their Littles.

Our mission is big, but we accomplish it together.

Thank you to our entire team for the passion, creativity, and care you bring to Big Brothers Big Sisters of Tampa Bay each day. And congratulations again to Tiona on this well-deserved recognition!

 

Driven to Make a Difference: Thank You, Motor Enclave!

By Fundraising Events, Networking

What a weekend!

Big Brothers Big Sisters of Tampa Bay is incredibly grateful to everyone who came together at the Motor Enclave for Guys Night Out: Cars & Comedy and the 10th Annual Cars En Coffee, two unforgettable events that brought our community together while supporting the power of mentorship.

From incredible cars and high-energy experiences to plenty of laughs, the weekend was all about having a great time for an even greater cause.

Guys Night Out: Cars & Comedy kicked things off on Friday, August 28, with an evening filled with one-of-a-kind vehicles, motorsport experiences, luxury goods, great food and drinks, and plenty of laughs thanks to headliner Adam Carolla. Hosted by Brad Oleshansky and Jeff Gigante, the event gave guests an opportunity to experience the Motor Enclave while making a meaningful difference for local youth and an elevated dining experience from Next Level Brands Hospitality including a sneak peek at the new Matilde concept.

The fun continued the next morning with Cars En Coffee, where car enthusiasts and thousands of community members gathered to admire an incredible collection of vehicles, connect with one another, and learn more about the mission of Big Brothers Big Sisters of Tampa Bay. We were happy to show up BIG with our branding throughout the property and having a handful of Bigs and Littles connect with guests, and our staff promote our transformational programs.

We have a strong and ongoing need for Big Brothers in our community, and both events provided an incredible platform to elevate that need and introduce our mission to thousands of potential volunteer mentors. Every new conversation has the potential to become a life-changing mentoring relationship for a child who is waiting for someone to show up and be there for them.

Every dollar raised helps Big Brothers Big Sisters of Tampa Bay create and support life-changing mentoring relationships across our nine-county service area. With more than 1,000 children currently waiting for a mentor, partnerships like this are more important than ever.

We extend our heartfelt thanks to The Motor Enclave staff, Brad Oleshansky, Jeff Gigante, Adam Carolla, Karie MacFarlan, event sponsors, volunteers, vendors, attendees, and every member of our community who helped make the weekend possible.

Thank you for showing up, having fun and, most importantly, going BIG for kids in Tampa Bay.

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