Family Trees at Tiffany & Bosco

February 12, 2019

Practicing Law is a Family Affair at Tiffany & Bosco

Unique among law firms, Tiffany & Bosco, P.A. has multiple familial relationships among its 60+ attorneys. These relationships include:

To learn more about their family dynamics, we asked these attorneys about their experiences practicing law with family members, why they chose to work together, and, of course, who in the family is the better or best bocce ball player (as displayed at the firm’s annual competition).

Was it always the plan to work with one another?


Father and son Mark and Michael Bosco

Mark S. Bosco: From the time I was in grade school, I wanted to be a lawyer and practice law with my father. I did not have any reservations about practicing together and doing so has provided many fond memories and wonderful opportunities. I was very fortunate.

As a father of two children and given the history of practicing law with my father, starting early on, I always hoped one or both of my children would want to attend law school and possibly practice law together. We are fortunate to have had both our children graduate from University of Notre Dame Law School. Currently, our son Michael practices law as a member of Tiffany & Bosco. Our daughter Abbey recently graduated and passed her Michigan bar exam.

Michael F. Bosco: Yes. Once I quit playing ice hockey, my goal was to become a lawyer and join the firm.

Father and son David and Darren Case

David L. Case: I always had hoped one of our children could practice in the same firm with me. When Darren became interested and was excelling in the same areas of law, we both really knew we wanted to do so, which evolved into my joining Tiffany & Bosco to make it happen.

Darren T. Case: As both of our law practices continued to grow, Ashley and I realized quickly that teaming up would be mutually beneficial for our careers.

Alisa Gray practices with her husband James Fassold

Alisa J. Gray: Jim and I never even planned to go to law school, let alone get married and practice together.

Did you have any reservations about working together?

AJG: I maybe hesitated for about five minutes. Jim jumped at the option.

Has the family dynamic changed?

DTC: Ashley and I have been working together side by side for 16 years through college and law school, so not much has changed now with both of us being at Tiffany & Bosco.

AJG: We’ve been doing it for 21 years, so I don’t really have a memory of how it was before.

How do you make it work?

MSB: Initially it takes some getting used to, but the key is to focus on the positives surrounding the unique opportunity of working and spending so much time with family. Over time, the opportunity creates a unique bond. I witness this bond between each family working together at Tiffany & Bosco.

AJG: We have utmost respect for each other’s skill, judgment, etc. We routinely use each other as a sounding board, especially when dealing with difficult clients, counsel, or knotty areas of the law. I can’t imagine not having Jim’s perspective to rely on. Finally, we occasionally spend time teaching mindfulness and time management to lawyers. Those seminars always bring us closer together.

Ashley Case practices with her husband Darren Case and father-in-law David Case

Ashley L. Case: Communication.

DTC: Communication.

What are the biggest challenges of working with family members?

DLC: There will always be some challenges when helping launch another career, but with family, the communication, love and desire for success make it all work well.

James Fassold practices with his wife Alisa Gray

James A. Fassold: To stop being colleagues and return to being spouses and parents.

AJG: Taking time to break away from the business and just be “Alisa and Jim.”

What are the advantages of working with family members?

MFB: You get the opportunity to spend more time with your family members.

DLC: Seeing your son and his wife succeed in the practice is extremely rewarding.

ALC: I no longer have to worry about attorney-client privilege. I can give Darren all of the details of a matter I’m working on.

AJG: We don’t have to worry about sharing confidential or privileged information so we can discuss difficult situations, problematic cases, etc. without any of those concerns.

Where is the strangest place you have talked about work outside of the office?

MFB: The middle of a lake.

ALC: On a playground in Whistler, Canada.

JAF: On the top of Mount Haleakala, Maui.

Why did you become a lawyer?

MFB: I wanted to follow in my dad’s and grandpa’s footsteps.

DTC: Interestingly, I went to law school with the goal of becoming a sports agent, having previously worked in Major League Baseball. However, after getting the top grade in my tax law course and receiving a scholarship to obtain my masters in the laws of taxation, I knew then I wanted to be a tax and estate planning attorney.

What has it been like to have two or three generations practicing at the same law firm?

DLC: This has been a very rewarding experience for a father, both from the standpoint of having the opportunity to pass on knowledge and skills to the next generation, but even more so to see Darren excel at such a high level.

Is it difficult to separate legal and personal matters?

DLC: Though it would be impossible to completely separate family aspects, in the long run, that is what is most important.

DTC: It is important to flip the “work switch” off when you leave the office.

JAF: We talk about cases and firm matters when we have to, but we try to decompress before we get together at home, either with meditation, yoga, or exercise.

What advice would you give to others thinking about working with family members?

MSB: Be patient. Understand developing a strong, positive working relationship is a process that takes time. It doesn’t happen overnight. If successful, the end result is well worth the effort. Some of the most rewarding moments and memories arise from the years working with my father and now my son.

AJG: Be wary of any people or situations that seem to drive any wedge between you. Develop good communication skills and the ability to say things such as: “I don’t want to talk shop right now. Can we set a time to do this later?”  

DLC: Embrace it, enjoy it, and appreciate the opportunity.

DTC: Really, working with family should be no different than working with non-family members.

ALC: Communicate. Have I said that enough yet?

What accomplishments of your family members give you the most pride?

MSB: My father’s more than 50 years of dedicated, passionate commitment to the practice of law. The work ethic and commitment to our clients my father passed to me and I will pass to my son.

Our families’ charitable giving to help others that are less fortunate and often so badly need assistance. We now have three generations dedicating significant time and resources to help make a difference in the community where we live and work.

Michael A. Bosco, Jr.: Having my son and two grandchildren carry their generations into the practice of law, and, of course, my grandson Michael’s choosing Tiffany & Bosco to do so.

JAF: 50 Most Influential Women; national recognition as an expert on yoga and mindfulness; recognition as perhaps the premier probate litigator in the state.

AJG: People routinely call Jim for his wisdom and experience.

Did you have any choice in joining the firm with your other family members?

MFB: Yes, but Tiffany & Bosco was where I wanted to be.

Who is the most competitive?

DLC: Not sure what Darren would say, but I think it is about equal. You have to be somewhat competitive to succeed in life, but it has to have balance.

Who is the best bocce ball player in the family?

MSB: I have been to the Tiffany & Bosco finals at least once, losing a close match to Mike Tiffany and Rob Royal at the Broadmoor, and on several occasions lost in the late rounds to teams that went on to win the Tiffany & Bosco annual tournament.

DTC: I think my two championships speak for themselves.

AJG: We both suck.

Learn More About Life at Tiffany & Bosco

Although Tiffany & Bosco has several family members working together, our firm is built on equality, transparency, camaraderie, mutual respect, growth, and an entrepreneurial spirit. If you’re interested in learning more about life at Tiffany & Bosco, visit our Careers page. For industry news and insights provided by our attorney’s, visit our Insights page.

Compiled by Robert A. Royal

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