Obituary of James Carlos Castillo

We celebrate the life of James "Jimmy" Carlos Castillo, whose 73 years were filled with joy, creativity, and laughter, touching everyone he met with his humor and warmth.

Born on December 4, 1950, Jimmy was celebrated equally for his professional achievements, as well as his larger-than-life personality and his uncanny ability to fill any room with laughter. A proud graduate of Georgetown University with a Bachelor of Science in Foreign Service, he was a respected brother of the Delta Phi Epsilon Professional Foreign Service Fraternity. Throughout his commercial real estate development career, Jimmy’s intellectual drive and determination shaped skylines and communities across the country, with projects in Puerto Rico, Florida, Texas, Mississippi, Arizona, Colorado, New Jersey, Virginia, Washington D.C., and beyond. 

Whether running down the racquetball court or behind the camera capturing life's unscripted moments, he found joy in being in the present. As a mentor, he lent his wisdom to those around him, as seen in his role as the coach of his son's basketball team, where he shared lessons, always with a dose of humor.

Jimmy's adventurous spirit was evident in the family's frequent travels, exploring new places and creating lifelong memories. This spirit extended beyond just his family and friends, touching lives internationally through his volunteer work in Haiti. His efforts helped rebuild a local pastor’s home and school, leaving a lasting impact on the community of Saut d’Eau.

He leaves behind a loving family with whom he shared countless adventures and memories— his wife of 34 years, Helen Jacoby Castillo (and her sisters Ashley Jacoby and Jennifer Trippeer), his son, Taylor Castillo (and his wife Emma Merrill), his sister, Margaret Rodenberg (and her husband Bert Helfinstein), and his brother E. Christopher Castillo (and his wife Susan Castillo). Additionally, he was the beloved uncle of nieces Erin Metz and Caitlin Lazo and their families, of nephews Kevin Castillo, Richard Trippeer and Michael Trippeer, and their families, and of step-nieces and nephews Sarah Helfinsiegel, Amy Buono, Benjamin Helfinstein, and their extended families.

Jimmy's life will be celebrated at St. Mary’s Episcopal Church in Arlington, VA, this Saturday, March 16th, at 2 pm. In lieu of flowers, the family invites donations to the mission where Jimmy volunteered in Haiti, Dallas Plemmons Ministries in Saut d'Eau, continuing his legacy of service to others. If you do donate, please mention in the comment section that it is in Jimmy’s memory. 

As we remember Jimmy, we are reminded of the love he shared and the lives he touched. He lived life with enthusiasm and positivity. We invite you to join us in celebrating his life and legacy.