As a student, nothing good ever happens in the dean’s office. Nobody ever likes being sent there. But, in truth, the people you will meet there are kind and always want to help. This year, there is a new smiling face in there: Coach Boswell. 

This school year marks Boswell’s 25th anniversary of being at Bolles.  Before his time here, Boswell taught Health and Biology at Englewood High School in Jacksonville while also coaching their baseball team. Since he started working here, he has held various job titles such as Head of Security, Dean of Residential Life, and Administrative Assistant. Now, he holds two: Dean of Students and head baseball coach. 

Though Boswell has been here for a while, he still has much to learn about being a dean. “I’m still trying to learn everything there is to know, really on the Internet part of our system, such as Veracross,” he said. 

When Boswell isn’t at school, there is a very good chance that he is outside. Boswell loves all things outdoors like fishing, golfing, and baseball. In 1987, Boswell was selected by the Chicago Cubs in the 31st round and played two years in their organization. 

Here at Bolles, Boswell is most known for his astounding career as being the head baseball coach, a role he has filled for 21 years. Boswell has contributed to five State championships and recently recorded his 500th career win in 2023. He has coached three players here at Bolles who have made it to the major leagues: Austin Slater ‘11, DJ Stewart ‘12, and Hunter Barco ‘19.  

Something that people might not know about Boswell at first glance is that he is a grandpa. “I love it. I have two grandchildren today, and I’ll have three by Christmas.” 

Boswell explained that there is a big difference between being Dean of Residential Life and Dean of Students. “I have 800 students instead of having 100 up in the dorm… so it’s a bit more difficult.” The only hiccup that Boswell has experienced so far has been the lack of downtime.  

One goal for Boswell this year is to learn every student’s name. “It’s been very easy learning all the baseball players and a lot of the athletes by watching, and being up in the dorm and getting to know all of them. But now I want to learn everybody’s name.” 

In a sense, being a dean and a baseball coach have some similarities. “When I’m in their lives on a daily basis, it’s so much better,” Boswell said.

If there is one thing that Boswell wants students to know about him, it is that he is approachable. “I’ve been there. I’ve been in their shoes. I’ve had three kids in their shoes who have gone through Bolles. I know where they’re at, I know where they’ve gone, and I know what they’ve done.”