James "Jim" Cavallo

Who was Jim Cavallo? To quote Jimmy Buffett, he had a “Caribbean soul he could barely control.” He loved traveling to the islands and brought his adventures (and many beach bars) to life at home through his imaginative “Jimsical Caribbean Art” paintings. He was a chocolate malt aficionado, always ready with a witty quip, and most importantly was a loving and devoted husband, father, grandfather, brother and family member. 

Jim was born in Milwaukee, WI to Joseph and Betty Cavallo. A graduate of Marquette University High School, he enjoyed playing sports, especially basketball. He went on to graduate from St. Norbert College before spending most of his career as an advertising executive where he managed accounts for major national brands. It was through his career that he met the love of his life, Barbara.

Jim and Barbara were married in 1986, had their daughter, Samantha, and headed south to get on island time. They traveled to and temporarily lived on many remote Caribbean islands, including Bequia and St. Vincent and the Grenadines, just to name a few. But Jim’s favorite place was always Grand Cayman in the Cayman Islands, where he proposed to Barbara, they celebrated their honeymoon, and then eventually spent much time and many years together as a family on Seven Mile Beach.

Jim and Barbara made their island life dreams permanent when they moved their family to Marathon in the Florida Keys and spent nearly a decade living in a condo on Coco Plum Beach.  

Jim is survived by his wife, Barbara; his daughter Samantha (Michael) Zimmerman; his grandson, Joseph, who Jim often referred to as “such a joy”; sisters Sharon Flynn, Kathy Kraemer and Betty Jo (Jerry) Zuba; brothers Bob (Mary Keskey) and Tom (JoAnn), as well as many nieces, nephews, cousins and other beloved family members and friends.

He is now reunited in heaven with his son, Joshua Cavallo; parents, Joseph and Betty Cavallo; mother-in-law, Jean Bornfleth; brother-in-law, Bob Flynn; and sister-in-law Dolores Cavallo. 

A visitation will be held on Saturday June 3, 2023, at the Becker Ritter Funeral Home, from 11 a.m. until the time of Jim’s Memorial Service at 1 p.m. In honor of Jim, please opt for bright and colorful attire at his service.

We hope in heaven Jim is sitting at one of the beach bars depicted in his paintings (he was particularly fond of Cosmic Ray’s) and enjoying a Mount Gay Rum and Diet Coke.

To quote one of his favorite songs, “I’ll tell you all about it when I see you again.”