Jay Michael (Mike) Callaway passed away at his home in Boynton Beach, Florida at the age of 69 on Thursday, June 12, 2025.

A native of Delray Beach, he was born on August 18, 1955 to J. Major and Bunny Callaway and was a brother to J. Major Callaway, Jr. and Kathleen Mann. He is survived by his loving and devoted wife, Linda; four children, Jennifer Callaway Lackey (Michael), Jay Michael Callaway, Jr. (Sarah), Bailey Callaway Dimke (Tate), and Nicholas Martin Callaway; and five grandchildren, Brianna & Alexa Lackey, Emily & Elizabeth Callaway, and Jay Dean Dimke.

Mike graduated from Atlantic High School in 1973 as the Senior Class President and was voted the Most Likely to Succeed by his classmates. He attended Georgia Southern University prior to founding the Callaway Insurance Agency in Delray Beach at the age of 22. In 1985, he and his lifelong friend, Lee Weekes, became business partners at Weekes & Callaway, Inc., a Property and Casualty insurance agency. With hard work and dedication, they had over three decades of unprecedented success, growing to become one of the largest and most reputable independent insurance agencies in the state of Florida. One of Mike's crowning achievements was his partnership with the Florida Club Managers Association of America, positioning Weekes & Callaway to represent over 100 private golf clubs in Florida.  Weekes & Callaway, Inc. sold to CBIZ Insurance Services on November 1st, 2014. Mike joined CBIZ as President, Property & Casualty of Florida, and continued his insurance career following the merger. He was extremely proud to bring his son, Nick into the business in 2019 as his eventual succession plan.

Throughout his career, Mike was involved in many charitable endeavors, including serving as President and Board of Director of South County Mental Health Center; Board of Director of Gulf Stream Business Bank from 2005-2014; and Board of Director of the Delray Beach Chamber of Commerce. For over 25 years, he was a working member of the Delray Dunes-Bethesda Pro-Am committee and co-chaired the Bethesda Hospital Ball with his wife, Linda, and their partners, Lee and Sheri Weekes in 2002.

Mike, whose self-proclaimed nickname was The American Dream, had a gregarious personality filled with charisma, kindness, and generosity. His family and many friendships brought him immense joy. He beamed with pride to say that all four of his children are University of Florida graduates. In 1992, he created the Big Bertha Invitational (BBI) - a weekend long golf and gambling trip that continued for 25 years. It was an honor to be invited, and many lifelong friendships were made through the BBI fraternity. The legacy of Mike Callaway has left a lasting impact on those who had the pleasure of knowing him.

A Visitation will be held on Thursday, June 26, 2025, from 4pm to 7pm at Lorne & Sons Funeral Home, 745 NE 6th Avenue, Delray Beach, FL 33483. A Funeral Service will be held on Friday, June 27, 2025, at 11am at Unity of Delray Beach, 101 NW 22nd Street, Delray Beach, FL 33444. A Private Family Burial will follow at the Boynton Beach Mausoleum. And finally – in the true spirit of The American Dream – a Celebration of Life will be held on Friday, June 27, 2025, from 12:30pm to 3:30pm at Delray Dunes Golf & Country Club, 12005 Dunes Road, Boynton Beach, FL 33436. We encourage friends & family to attend and share their stories.

Mike was very fond of flowers however, donations may also be made to the Delray Dunes Foundation, Inc., 12005 Dunes Road, Boynton Beach, FL 33436, a charitable organization benefiting the employees of Delray Dunes Golf & Country Club.