Couple Tanya and Leila Bailey-Stewart share their experience on “The Briefcase”


Tanya and Leila Bailey-Stewart are a Boston couple who work hard to provide for the two boys they take care of (Leila’s nephews) while also hoping to have a child of their own in the next few years. Tomorrow on the CBS series The Briefcase, they are given the opportunity to keep $101,000 or divide it between themselves and another family in need.

The Briefcase

At the exact same time in rural Texas, The Wylies are struggling with the same decision. They, too, have received a briefcase with $101,000 and must figure out how much they should keep, and how much to give away. The drama comes in when each family finds out just a little more about the other, it is painfully clear the Wylies are not supporters of equal marriage. It’s kind of maddening to watch. 

Tomorrow night, Leila and Tanya will make an important decision, and we spoke with them about their experience on the show. How did you get involved with the show? What were your initial thoughts?

Leila and Tanya: One day a friend called us and suggested that we consider being part of a documentary featuring a diverse group of hardworking American families trying their best to achieve the American Dream. We were hesitant, but she was convinced that our family should be a part of the show. She said that we were interesting and that people loved us so “why not?” We became more interested when considering the unique opportunity to showcase our family qualities and values. Never in a million years did we think it was actually for a BIG reality series on a major network.

We are a semi-private family so for us there were nerves, but also excitement to be sharing a different perspective with America. Our feelings quickly changed to surprise and shock when we saw the $101,000—the rest you get to see on the show.


AE: How did your thoughts about the other family change as you found out about more about them? Did it bother you that they were Republican conservatives?

L&T: What we knew right away was that any family is more complex than a basic description and we could not wait to learn more about them and find out who they were as a family and as people. We didn’t dwell on the information we initially got, we needed to understand the best we could who they were and what values they prioritized as a family.

Going through the journey we became more excited about the family and encouraged by the values that they displayed. There was nothing that we learned about them during the show that bothered us, in fact, we discovered more about our commonalities.


AE: How did you feel about the outcome? Do you feel like you made the right decision?

L&T: We are proud of our decision. We made the best decision we knew how to make as a family. We face each challenge we encounter as a team and try to live up to our values so that we don’t spend our lives looking back with regrets. This was an emotional rollercoaster. We didn’t always know what kind of drop or turn was coming next but we had faith and supported each other through the ride.


AE: What would you have changed about the experience if you had to do it all over again?

L&T: We would have asked more questions and insisted that we be able to phone a friend/family member. We haven’t had the opportunity to make a decision about $101,000 before. This experience was humbling and full of lessons that we will keep with us for the rest of our lives.

The Bailey-Stewart family episode of The Briefcase airs Wednesday, 8/7 central on CBS.

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