Ashley Estrada has the unique perspective of experiencing the professional baseball life as a nanny and girlfriend. Estrada’s joined us to share her experiences challenges and future plans.
Estrada was working at a trampoline park when she met brothers Jon and Stewy. The three of them would connect and eventually she was offered a babysitting job by their parents. That door ended up opening another door when the brothers no longer needed a babysitter.
“About 4 years ago I worked at a trampoline park where I met Jon and Stewy. Jon was 9 at the time and Stewy was 11. When I first met the boys we immediately connected. They would talk to me about their friends, school, and of course… baseball; Oakland Athletics baseball to be exact.
If you are in Major League Baseball or affiliated with baseball, you know Mike Thalblum. Mike Thalblum is Oakland Athletic’s Visiting Clubhouse Manager. He is also Jon and Stewy’s dad. I grew so close to the boys that I started to babysit them outside of my job, they became like a second family to me. I started taking the boys to A’s games, where we could enjoy the game and they could also spend time with their dad. As Jon and Stewy got older I started to babysit them less and less. They were just getting too old for a “babysitter.” Their mom connected me with Kaycee Sogard, her husband Eric played for the A’s. She thought I would be a good fit for their family and she was totally right!
2017 would be a year of change and growth for Estrada. She accepted an offer to be a live-in nanny for the Sogards, which required her to leave her hometown of Livermore, California. Estrada began expanding her horizons, traveling and meeting new people.
“This 2017 season was the first year I moved with the Sogards to be their live-in nanny. The first couple years I was with them I lived close enough to where I could work and still live at my house. Throughout most of my life I never really left my hometown. My first time on an airplane was in 2013, I was 18 years old. I had such an insane fear of flying, but this job has forced me out of my comfort zone and helped me grow as a person. This season we traveled all over the country and I met a lot of new people. I have been able to connect with other player’s wives and girlfriends, which has become a nice safety net for me.”
Being a nanny carries immense responsibility for decisions are made that affects children’s lives. The baseball offseason brings a transition from the children and families until the spring, when the regular season routine begins again.
“A lot of the time it is just you and the mom watching the kids because the guys are on the road so often. It is a huge responsibility to help co-parent and make decisions that affect the kid’s lives. Because you play a role in helping with the kids and building such a special relationship with them, the times apart from them make everything that much harder.
Three years ago when I started working for the Sogards their oldest, Saydee, was only six months. Kids grow a lot in those six months leading up to 1 year. Baseball is a tough business to nanny in because you get so attached to the kids and then just like that September comes and they leave to their offseason homes.
The following year Kaycee came back to Oakland pregnant! With her second, Knix, it was challenging in the opposite way because I missed the first six months of his life. Regardless of the challenges, watching the kids grow and learn has been the most rewarding part of my job.”
Her career as a nanny would intersect with her personal life in a way that she hadn’t envisioned possible. She promised herself that she wouldn’t date a baseball player, but life threw her curveball in the form of Brewers prospect Nathan Orf.
“When I became a nanny in baseball I promised myself I would never date a baseball player. There is just so much more to the baseball world that you do not understand until you are a part of it. At the end of the 2016 season, Eric got picked up by the Milwaukee Brewers and started the year in Triple-A with the Sky Sox. I met my boyfriend Nathan Orf, who was on the Sky Sox with Eric.
Working in the baseball world it is hard to find people that understand the hectic schedule and lifestyle. I think we bonded so well because we are both a part of it. During this season it was hard to make time to see each other because our schedules were both so demanding. I was very fortunate that the Sogards were supportive and understood that I had to work, but also had to make time to see my boyfriend. Throughout the season I made a couple trips out to visit Nate and watched some of his games. The key to maintaining our relationship in the baseball world is constant communication and understanding. Even though a huge majority of our relationship has been long distance, we continue to grow as a couple every day.”
With an eye towards her future, Estrada is currently working towards her Bachelor’s degree in Child Development, as she follows her passion for working with kids.
“I have always had a passion for working with kids. It has been a dream of mine to have my own family and be a stay at home mom. After being in the baseball world for a couple of years now, I have learned that it is hard to plan ahead and think too much about the future. In this lifestyle, it is so important to live in the present moment.”