Join us for our weekly “Rock Reflections,” a series celebrating Trinity alumni. From all 50 states to countries worldwide, our graduates are making an impact, and we'll share their stories on Trinity's website and social media.
This week's profile is about Jesse Ryan '90
The Ryan family attended Catholic schools and knew the value of parochial education. Jesse Ryan came to Trinity from Ascension Catholic School. His brothers, John ’89, Keith ’92 and Charles ’96, are Trinity alumni. His sister, Debbie, graduated from Assumption High School in 2008. Jesse’s mother, Doris, attended Presentation Academy. His father, David, attended Flaget High School and coached for more than 20 years in the Catholic School Athletic Association, mostly at St. Pius X and Ascension schools.
Jesse immersed himself in life as a Trinity student. He earned multiple Shamrock Awards, was a Trinity Scholar and on the Honor Roll all four years. He ranked in the top 10% of his class. He was a natural leader, serving on the Student Council and in the National Honor Society and Spanish Club.
An outstanding student-athlete, Jesse earned All-State and Academic All-State honors in football. He played safety on the 1988 and 1989 undefeated football state championship teams that started a state-record winning streak of 50 consecutive games under Coach Dennis Lampley H’92. He also was a member of the track team.
‘They truly cared for their students’
Jesse recalls the life lessons taught by some of Trinity’s most legendary teachers – Tom Zehnder ’63, Gene Eckert ’62, Dennis H’01 and John H’05 Esterle, Rich Rostel H’93, Brother Charles Cully, Greg Sysol H’03, and Sister Jane Hall.
“They had such unique and dynamic personalities,” Jesse said. “They were great teachers who could relate class subject matter to real life. They could also give you tough love when you needed it. They truly cared for their students.”
Few high school students may say it, but Jesse recalls those four years as fun.
“You wanted to be at school,” Jesse said. “We worked hard and it was challenging, but it was a fun challenging time with your friends.”
After graduating in 1990, Jesse attended the University of Kentucky. Thanks to college placement credits he earned at Trinity, he started at UK with 48 hours in the books.
“The education I received at Trinity and the discipline and structure I learned there made college just a lesson in time management,” he said. “Trinity instills in you to keep up with all facets of your life – academics, clubs, sports, activities, jobs, relationships – and be responsible.”
Jesse earned a bachelor’s degree in accounting in 1994. While at UK, he was a member of Sigma Alpha Epsilon fraternity and was honored with the “True Gentleman” Award in 1994.
‘It takes alumni to be able to help fill the gaps’
After graduating, Jesse spent six years in public accounting at Ernst & Young and Carpenter, Mountjoy, and Bressler, PLLC. He worked primarily in audit and tax during the dotcom era of the late 1990s, as well as performing due diligence audits during much of the merger and acquisition activity that occurred at the time.
In the early 2000s, Jesse left public accounting and joined one of his clients, Service Net, as general manager of risk management. Jesse and his ownership group would go on to sell the company. Following the acquisition and around the time of the birth of his son, Nate, he joined Parker + Lynch as the managing director.
After more than 10 years with Parker + Lynch, Jesse joined Hilliard Lyons as an associate financial advisor. Established in 1854, Hilliard Lyons is one of the nation’s oldest financial services firms. The company employs more than 500 people in Kentucky, more than 5,000 internationally and manages over $400 billion in private client wealth. Jesse is currently a vice president of the firm.
In 2019, Hilliard Lyons and Hilliard Lyons Trust Company became wholly owned subsidiaries of Baird, an employee-owned, international wealth management, asset management, investment banking/capital markets and private equity firm. Jesse and his team focus on financial and retirement planning, tax and estate planning, IRA rollover guidance, education funding, and annuity and insurance services. Jesse holds Series 7, 66 and life and health insurance licenses.
Jesse has been involved with the Alumni Association for decades. He is currently secretary for the Alumni Board of Directors, a Class Agent and an Alumni Phonathon volunteer. Additionally, he has served on his class reunion planning committees and the Annual Fund Committee.
“I’m one of five children, and we all went to Catholic school,” Jesse said. “My family received financial aid. Someone gave me the opportunity to go to Trinity so it’s a no-brainer to participate in fundraising to help today’s students. It takes alumni to be able to help fill the gaps. I encourage all alumni to consider giving to the Annual Fund at whatever level they can. Every dollar adds up.”
Jesse and Amanda Ryan, a Mississippi native and Ole Miss graduate, have a son, Nate, who is a Trinity senior. Nate is a three-time Shamrock Award winner and is a member of the football and track teams. They are members of Holy Trinity Catholic Church.
Share an alumni story!
Do you know a Trinity alumnus with a compelling story? Please reach out to Travis Wagoner '90, Alumni Relations & Communications Director, at 502-736-2122 or wagoner@trinityrocks.com.
A History of Greatness
Since 1953, Trinity has benefitted from great teachers, resources, and activities to shape and guide promising boys into great men. The 106 students from our first graduating class have been followed by a legacy of academic, personal and cultural achievement. To learn more about our proud heritage, visit https://www.trinityrocks.com/o/trinityfoundation/page/about-us.
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