“Title Guy on the Fly”: Unveiling Anthony McDonald's Journey

In the warm and inviting atmosphere of The Local Motive, our table awaited us for a meaningful discussion over an array of carefully chosen mocktails and cocktails. It was here that Mayor Stacy Link and I had the honor of engaging with Anthony McDonald, the owner of Freestate Title Consultants, LLC, and the sole Black entrepreneur on Sykesville’s Main Street.

Anthony's partner in life and business, Debbie, joined us with her radiant smile, melting Anthony's heart even after three decades of marriage. 

There's a particularly amusing anecdote about the bobblehead named "The Title Guy on the Fly," which Debbie takes everywhere she goes, but that's a tale for Debbie to share, ideally from their Suite 305 located at 7566 Main Street.

Our focus; however, shifts to the remarkable narrative of Anthony McDonald - an extraordinary individual whose personality and laughter fill the room, matched by his gentle and kind nature.

To truly immerse you into Anthony's story, envision the resonant, deep tenor voice of Anthony, a distinctive trait of his 6’1” stature, which exudes warmth and depth.  A voice that envelops you, resonating with kindness and honesty - the voice of a man who has risen from the grips of uncertainty and poverty and has navigated life's many challenges to become a business owner renowned for his excellence and cherished for his community contributions.

Picture each quote being delivered in that profound voice. And when you imagine Debbie's laughter punctuating the conversation, think of the musical, infectious joy of a French woman, her loving glances at her husband a constant throughout our interview with Mayor Link. There's no need to signal when her adoration was evident throughout the hours we spent uncovering the story of Anthony McDonald.

How has your heritage influenced your business philosophy and practices? 

“So, I moved here from West Virginia.  Well, let's go back so from Charles Town, WV, like Debbie said, my dad passed when I was 13 years old.  My mom raised six of us, three boys and three girls.  I'm the youngest boy and Sabrina is the youngest girl. My dad was a horse trainer at the Charles Town racetrack. So you know, growing up as a young guy, I would get up every day at 4:30am and go to the racetrack with my dad.  My dad had it set-up, during the school week, that the school bus would pick me up in front of the guard’s shack of the racetrack and then, when school was out, the school bus would drop me back off at the racetrack in the afternoon, to feed the horses in the evening with my dad.  Then we’d go home, we’d have dinner, I'd do my homework, then bedtime and the next day at 4:30 am, we’d do it all over again. So when Dad passed, you know, just growing up, going to school and I was asked to play football since that sport starts in August, but I wanted to continue to spend my Summer working at the racetrack.”

During Anthony's teenage years, a fervent passion for horse racing pulsed through his veins, shaping his early experiences. He would dash to the grocery store on errands for Miss Lucille’s cigarettes, help his mom any way he could and prepare to reach his dream: to play basketball in high school. 

“Okay, so in high school, I played basketball. That was my heart, my dream and everything.  So Coach Taylor passed away in 2021.  He was the track coach at Jefferson High School.  I went to school and he always begged me - “Anthony, please come out and run track for me, please.”   So I ran track for my last two years in high school, and I was good at it, right?  I ran the 400-meter and stuff like that.  So, after my Senior year, I got a full ride to Marshall University to run track.  So that Summer, before I went to Marshall, I worked at Shepherd University, well it was known as Shepherd College at the time, then it turned into a university because the population got bigger. So that Summer, again before I went to Marshall, I worked as a maintenance guy cutting the grass, hedges and stuff like that.  So when lunchtime rolled around, which was from 12 to 1 pm, Monday through Friday, I was going to the gymnasium. That’s where I’d eat my lunch and just watch the guys out there shooting.   So one day, they only had nine guys and they could not run games since they needed teams of five.  So they looked up at me, in the bleachers, and said “Hey boy, can you play ball?”  I said, “Yeah, I can, I can run, but I got my boots on and I need some shoes.” 

From a player's locker, a pair of shoes appeared, subtly altering the course of Anthony's journey.

“I have a t-shirt on and my dirty jeans, and I'm shooting hoops. I'm holding my own because that's my passion. So we ran a couple of games, and all of a sudden, you see the doors open in the gym, okay.” 

Coach Starkey walks into the gym. He strides confidently onto the floor during the game, capturing the moment with his presence. As the game concludes, Anthony retreats up the bleachers to finish his lunch, observing from afar, as Coach Starkey is warmly introducing Coach Ron Gerlufsen to his players. The players glow with pride, fortunate to be under his guidance.  Anthony then returns to his work.

“So probably about a week later, I got my headphones on, I'm trimming you some hedges and I got a tap on my shoulder, and it was Assistant Coach E.J. Schodzinski.  He introduced himself and said “Coach wants to talk to you.  He saw you playing with his boys in the gym the other day.”  He gave me directions across campus to get to Coach Gerlufsen’s office and I went there at five o'clock, once I was finished with my work.  Once there, I asked “You want me to take my boots off?”  “Come on in here,” he said, and I sat down.  “What's your deal?” he asked, “I saw you in the gym playing with my boys and you were holding your own out there, right, just doing well.”   So I told you my whole story which I repeated to him.  “You know, Coach, I got a full ride and I am leaving in two weeks to go to Marshall University on a track scholarship. My dad died when I was 13 years old and my mom is getting by working three to four jobs to make ends meet for herself and us kids.  “Is this why you didn't pursue basketball?” he asked.  I said “Coach, basketball is my heart and my dream. I didn't get any money to be able to go to Shepherd so I gotta go where the money is to get more education.”  “That's a shame because I really think you can make this team,” said Coach.  Bells went off in my head since staying home with my Mama would be great as I was a Mama’s boy, right?!  “Go talk to your mom and get back to me” Coach said.

So that is exactly what Anthony did.  Anthony and his mother had that conversation over dinner. She recognized the gravity of his decision, acknowledging the rare opportunity at Marshall but also understanding Anthony's unwavering dedication to basketball. She knew her boy, a hard-working young man, mature beyond his years.  Anthony’s mom said “With your work ethic in basketball if anyone can bridge this gap, it's you."

Taking her words to heart, Anthony approached the situation with resolve. Despite the financial security offered by a full ride for track at Marshall, he chose to pursue his passion for basketball at Shepherd, knowing well the financial hurdles this entailed. He explained to his Coach, "I've managed to save enough to cover my first year's tuition."  Aware of the challenge, he was told, "All scholarship funds are allocated, but next year opens new possibilities.  Make the team and things can change."

Determined, Anthony took on the challenge. With the cost of attendance manageable through his savings, he prepared for the tryouts. The gym was filled with hopefuls, about 16, including Anthony, and his friend Raymond, who also aspired to join the basketball team while on a football scholarship.

The tryouts were intense, a three-day ordeal that tested every athlete's mettle. In the end, Anthony and Raymond earned their spots on the team. As the season progressed, Anthony's moment to shine arrived when a Senior player's injury opened up a spot in the starting line-up. With his name listed in the crucial second slot on the chalkboard, Anthony's dedication and hard work had paid off, cementing his place on the team and marking the beginning of a significant chapter in his college basketball career. 

The player who was injured never reclaimed his position, a testament to Anthony's relentless work ethic. His training regimen was intense, always pushing himself to be at the forefront, whether it was during five-mile runs or sprint drills. This dedication was born from his upbringing in Charles Town.

Transitioning to college basketball presented a new challenge with Anthony facing opponents who towered over him. Initially, not an outside shooter, but capable of impressive jumps and ball handling, his game had to evolve. The Assistant Coach E.J., saw potential in him and dedicated hours to refining Anthony's shooting skills. This hard work paid off, especially in his Junior and Senior years, where his performance on the court was nothing short of remarkable.

Reflecting on his journey, Anthony acknowledges the paths not taken and the life lessons learned along the way. He muses on the notion that if he had pursued a different path, his life might have diverged significantly, possibly not for the better, in Charles Town, grappling with the challenges of rampant drug activity.. 

This reflection brings him back to his high school days, particularly a memorable experience, when he was taken to the McDonald Classic, a prestigious high school basketball event, where the best high school players participate in an All-Star game. There, amidst the excitement and talent, Anthony found himself sitting next to the legendary Lefty Driesell. This moment, further marked by Anthony meeting Lien Bias, HIS all-time favorite basketball player, and shaking Len’s hand - a hand so large it seemed capable of holding two basketballs, illuminated the inspiring and unpredictable path of his basketball odyssey.

During this period, the casino industry was flourishing in Charles Town, transforming the social fabric and drawing in a surge of low-cost drug tourism. This shift presented a perilous allure to the local youth. Faced with the dual pressures of easy money within arm's reach and the heightened risk of confrontations with law enforcement, Anthony made the decisive choice to pack his belongings and relocate to Maryland to seek a safer and more stable environment.  

But before his permanent move to Maryland, Anthony was to put Shepherd University on the map.

“We were the last seed, okay, as the 16th seed, we played the 3rd seed because the 1st and 2nd seeds receive first round byes.  We won and the next night we got to play the 1st seed.  Of course, we knocked them off and you are talking about a Cinderella story, right?  Now, you got buses and buses of fans coming from Shepherd down to Charleston Civic Center.  We won the whole thing!” “So, if you go to Shepherd University’s gymnasium and to the trophy cases, there appear lots of football stuff because that is what they are known for, but there is only one for basketball.”

With a picture of Anthony and his team, this is where this picture can be found!

Anthony’s life has revolved around sports.  Today, Anthony has assisted his stepson, also named Anthony, in coaching travel baseball through Howard County Youth Program since their boys were 9 years old and now 16 and 17 years old. His stepson has recently been appointed as the Head Coach of the JV baseball team, with Hammond High School, where his stepson will face the bittersweet reality of transitioning from coaching younger boys to taking on more significant challenges. This move marks a substantial shift, especially considering the profound impact his stepson has had on his players during crucial years of growth and change.  Both Anthony's coaching journey is notable not just for their strategic skill but also for the deep connections they form with their players.  Despite the racial diversity of their teams, both navigate these dynamics with grace, emphasizing unity and personal growth over mere victory on the field. Their approach to coaching extends beyond the game as it's about mentoring young lives and providing a space for open communication and trust.

Anthony shares a particularly touching aspect of his role - the ability to be a confidant for his players, helping them navigate personal challenges they might feel unable to discuss with anyone else. This aspect of coaching transcends the sport, touching on the profound impact a Coach can have on a young person's life.

As Anthony reflects on his coaching philosophy, it's clear that his motivation stems from a desire to fill the void of mentorship he perceived in his own youth. Even as his stepson moves on, Anthony's passion for coaching remains undiminished, with plans to return to coaching basketball, a sport that will always hold a special place in his heart.

The respect and admiration Anthony commands, not just in his immediate community, but also in Charles Town, his hometown, underscore the lasting influence of his commitment to youth and sports. As he contemplates his future in coaching, Anthony's legacy is evident in the lives he's touched and the community he's helped build - a testament to the power of dedicated mentorship.

We asked Anthony about his visits to his hometown. He revealed that his trips have become infrequent. Tragically, Anthony's mother passed away just over a year ago.

Delving into Anthony's career journey presented us with yet another fascinating story, full of unexpected twists and revelations.

“I worked at a nursing home, when I got out of college, since that is what I went to school for therapeutic recreation but horse racing was still in my blood.  So once I  moved here, I went to the Laurel racetrack and I got a job working with Tim Ritchie, a local trainer.”

One Friday evening, Anthony chose to venture out to a club with his sister, Deborah, who moved here when she turned 18, and he coincidentally crossed paths with Debbie, who was also enjoying a night out with her girlfriend. Amidst the lively atmosphere and the expanse of a long bar, Anthony's attention was swiftly captured by Debbie.  Eager to connect, he attempted to engage with her beyond the confines of the dance floor.  Despite receiving only a dance in return and despite Debbie's friend encouraging her to open up to the possibility of more, that night marked the beginning of their unique journey together.

In a moment that could have ended their story before it began, Debbie expresses that she is not interested in Anthony. This was quickly overcome by the unfolding reality of their connection. Anthony, with a mix of humor and grace, pointed out the flaw in her assumption. This exchange led to laughter and a shared understanding that paved the way for their relationship. They met in 1995 and were married in 2005, living a fairy tale type of love and parenting Debbie’s son from a previous marriage. This journey, marked by growth and understanding, showcases the depth of their bond.

“So fast forward, and I am working at the racetrack with Tim Ritchie, who is from Delaware.  So he has 80 horses that he trains in Laurel Park, but one year, Tim decided to relocate all of his horses to Delaware Park and wanted me to relocate with him.”

Anthony, despite deeply valuing his job, observes the unfair treatment of Tim's horses and decides to address this concern. Understanding the potential repercussions, he still chooses to speak the truth to the owner. Anthony is someone who values honesty above all. The owner, upset by the situation, decides to move his horses back to Delaware, hoping Anthony will relocate to continue training them. However, Anthony's heart now lies with Maryland, more specifically with Debbie, leading him to decline the offer in favor of seeking employment elsewhere.

Anthony continues on a professional path deeply intertwined with the equine world. After he declined to leave Maryland, Anthony began working a horse farm in the Woodbine area. This connection led him to encounter August Riggs, a notable figure whose great-granddaughter was the acclaimed actress Glenn Close. Anthony's meeting with Close occurred under somber circumstances, at the funeral of Mrs. Riggs, a woman of significant stature linked to Riggs National Bank and even Kellogg's Corn Flakes empire.

Mrs. Riggs, in her later years, was in a vegetative state, with her only interaction with the world being the occasional moments when she was wheeled out to see the horses on her farm. Anthony described these poignant moments, reflecting on the impact she had on those around her, even in silence.

As the narrative unfolded, Anthony detailed how life's changes led him and Debbie to live on the Riggs’ property, taking residence in a small gatehouse. This arrangement was made possible through negotiations with Mike, the farm manager, who eventually moved to Kentucky, leaving Anthony to seek new employment once again.

The story took another turn as Anthony transitioned from farm life to learning about Debbie's professional world at a title company. He humorously recounted attempts to fit into the corporate environment, including changing his voice to suit his new role as a receptionist.

“I fell in love doing it (title work). You do all the back end after the settlements and stuff like that, right? Yep and a lot of trouble solving.”  I loved it, so I did that and then working with lawyers and stuff like that, then I got a job with a company called Mid-Atlantic Title Consultants, LLC, where I was the President. There came a time when Mid-Atlantic closed their doors, at which time I decided to open up my own company.”

Taking a significant step forward, Anthony decided it was time to venture out on his own. He discussed the idea with Debbie, who offered unwavering support, saying, "Whatever you decide, I'm behind you." Motivated by her encouragement, Anthony embraced the opportunity. Together, they brainstormed a name for the new endeavor, marking the beginning of their journey.  Initially, Anthony set up a home office, where he worked for the first two years.

During this time, Debbie continued her work with another title company in Eldersburg, pursuing her professional path. Yet, Anthony saw potential in Sykesville, a place he frequented and felt connected to. He envisioned establishing a physical presence in downtown Sykesville, believing it would be an ideal location for his growing business, further entwining his professional aspirations with the fabric of the community.

Following the departure of a therapist from the Greenberg Building, now known as The William Gossage Sr. Arcade Building, Anthony seized the opportunity to relocate his business into the vacated small office space.

“So we opened Freestate Title Consultants, LLC, and there were many long hours that come with managing and operating a business.”

The initial fear of taking the leap was swiftly overcome by the fruits of Debbie and Anthony’s hard work, deep knowledge of the field, strong referrals from partnerships, and a reputation cultivated through years of dedication.

For over a decade now, they have successfully completed settlements. Their unique business model, which emphasizes a comprehensive A to Z approach, has positioned them as the go-to company in their field. This strategy has not only allowed them to build a solid customer base but has also enabled them to establish numerous partnerships within the community, further solidifying their reputation and presence in the industry.

When inquired about how his identity as a Black business owner has influenced his experience in Sykesville, Anthony asserts that relationships in this community transcend color and they are rooted in personal connections. Having gotten to know Anthony more closely, it's clear he has captivated both the market and the hearts of many through his exceptional talents and unique charm.  Indeed, "The Title Guy on the Fly" has made a significant and memorable impact on Main Street!

Through our conversation with an individual celebrated for his impressive 42-inch vertical leap, culinary expertise, and a life filled with diverse experiences, including 29 years of devoted love for his wife, which is evident in the sparkle of his eyes, we have come to recognize that Anthony possesses a genuinely remarkable essence. His capacity to transcend and connect across racial divides is founded on a profound love for others, a sincere interest in their lives and challenges, and innate inclusiveness. With Anthony and Debbie's presence, “our downtown is fuller” as said by Mayor Link, a testament to the unique and positive impact they bring to our community.