2019 Honoree

Honoring Lee Clyne

Lee Clyne, 92, passed away Monday, November 19, 2018.  Lee was born, on a farm, in Belview, Minnesota, July 27, 1926, the middle of three children. From her birth to her death she always provided a sunny disposition and helping hand to those around her. 

After graduating from high school, she attended the Augsburg College, achieving a degree in Education and then earning her Masters from Western Michigan University. Lee pursued opportunities in education, first in North Dakota, then Quincy, MI and finally in Coldwater, MI. She taught 4th grade for 29 years, loving every minute.  Her favorite causes were the prevention of child abuse and selecting talented high school students for scholarships. After retirement, Lee split her time between Coldwater and Key West, FL, where she made many friends. 

Lee loved to go out for dinner and a margarita. She was an avid reader, enjoyed crossword puzzles, playing bingo, attending movies, plays and concerts. Lee touched many lives and will always be remembered as a bright, shining, ray of light. We miss her.

Honoring Jason Shields

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Jason Yarrow Shields passed away on Wednesday, May 27th. 

A Gainesville, 4th generation Floridian - born on the Solstice - water child, you always knew where he was, hearing him joyously laughing at any moment, or seen climbing the giant live oaks, swaying and singing in the branches, or swimming in the Florida springs and rivers, and Atlantic Ocean. His love for being on the water was a constant.

He attended the Dayspring Waldorf School, Gainesville, FL, before moving to the Green Meadow Waldorf School, Chestnut Ridge, NY, Class of 1994, where he was athletic, excelling in baseball, basketball, and soccer, played the trombone, and performed in school theater productions. He was always fun and a joy to be with, a sensitive and soulful, caring person, and his presence will continue on in the lives of those many hearts he touched.

He lived and worked in Key West, managing the Java Lounge, and also became an accomplished and skilled film projectionist, at the Tropic Cinema, knowledgeable in cinema and film history. His great heart continues to circulate love in the world.


Honoring Robert Smith

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Robert Joseph Smith (8/17/87 - 10/31/16)

Rob was taken from us much too early in a tragic accident in October 2016. He was born in Walnut Creek, CA in 1987 and was a true sports fan. He played both soccer and baseball (pitcher, catcher & shortstop) and started skiing at an early age and loved to snowboard as well. Rob always enjoyed getting out of town and going on vacation - camping, swimming, boating, canoeing and kayaking – he loved to spend time with friends and family. Rob was a good young man, a wonderful friend and a great brother. Rest In Peace, dearest Rob.

Honoring Louie Cruz

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Louie Cruz passed from this life on August 9th, 2018.  He was a beloved husband, father, grand-father, and great-grandfather.  Born on 11 September 1935, nine days after his father was swept out to sea in the Great Hurricane of 1935, he grew up in Key West.  After a stint in the United States Air Force, and another 17 years in Hialeah, Florida, he and his wife, the former Mary Harris, (also a Conch) brought their four children back to their beloved Island home.  They made their home on Peacon Lane. And so it was there, on the Lane, that Louie was born, lived, and died, a true rarity in today’s world.

In later years, he learned to Scuba dive and he, along with sisters and brothers in law, spent their time chasing the “viz” in the Virgin Islands and the Bahamas.  In their 60 year long marriage, he and Mary also traveled to Japan and Europe, as well as marveling at the wonders of the great American West.

A 1954 graduate of Key West High School and a 1974 graduate of Florida International University, he spent many years in Law Enforcement.  He also learned to appreciate the beauty of his surroundings. An accomplished photographer, he has left us with an amazing collection of images that reflect that beauty.

This photo was taken in St. Mark’s Square, in Venice on our last international trip in 2014.  This image reflects the joy of someone who has realized his dream of seeing the world!

Honoring Joe Cummings

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Rolland "Joe" Cummings aka Joe Daddy 

June 27th 1942 to Sept 11th 2018 

What a man , what a life ! Thank you to this beautiful soul who became by father not because he had to but because he chose to . The years with him will never be enough. An angel walked among us for so many years , giving love and providing laughter ,  an avid cook , gardner, teller of tales with a smile that would light up the room . He chose to take his life this year and I will never understand why. Maybe it's not for me to understand but I will never forget who he was to us all and will be grateful for the years we had. I hope you have found peace Joe Daddy , with love for you always ...Chrissy Diane , the baconhead of you 

Honoring Walter Lepperd

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Walter William Lepperd Jr., 81, passed away on June 12, 2018 in Miami VA Hospital. 
Beloved husband of Fiona (Molloy) Lepperd, father of Christopher, Susan, Matthew, and Andrew Lepperd, and stepfather of Christopher Crespo. Grandfather of Caitlin, Zachary, Jared, Hannah, and Scarlett Vandervelde, and Dakota, Liam, Paige, and Carson Lepperd. He is preceded in death by his first wife, Phyllis A. Baker, and grandson Ethan.
Born in Amboy, Illinois, Walter graduated from Dixon Illinois High School in 1954. He was a proud veteran of the U.S. Navy, and served as an Engineman during the Korean War. He was a longtime employee of General Motors in Lordstown, Ohio, and Miller Brewing in Milwaukee, Wisconsin, where he lived in the village of Egal, Wisconsin.
He wintered for 10 years in the Florida Keys before moving permanently to Key West with Fiona and Sammi, their Jack Russell Terrier, in 2012, where he managed El Mar RV Resort in Stock Island and assisted Fiona in her ongoing musical career. Walter was always a welcome presence at Fiona’s concerts, making everyone feel warm and at home while he proudly relished in her performance, allowing the love their relationship to be brought to the evening, always adding to the evening’s enchantment. Walter will always be with us in the beauty of Fiona’s music. 

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Honoring Trumpet Bob

This Photo was taken during the Crooks Second Line by Ralph De Palma

This Photo was taken during the Crooks Second Line by Ralph De Palma

Trumpet Bob was a KW Legend. He passed away on August 7, 2018. He loved leading the New Orleans Style Street Funerals with his tuxedo, top hat and trumpet. Bob played on the patio of the Cafe Tropical in front of the Mel Fisher's Museum for over fifteen years. He played in many places all over Key West.
He loved to sit in with the Love Lane Gang. He first arrived in KW in 1952 while still in the Navy. Trumpet Bob was a world traveler and loved everyone. He had many friends here in Key West and will be missed by everyone who knew and loved him. Bob loved to play in musical groups with Richard Crooks and was a good friend to Richard. Bob also loved to get children involved in music and it will be an honor to be included in the January 30th, 2022 Crooks Second Line March.

Honoring David Wolkowski

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David Wolkowsky, a real estate developer, arts patron and unflagging supporter of a classy Key West, died in September at age 99. Known as “Mr. Key West,” Wolkowsky once owned the Pier House Resort, socialized with Tennessee Williams and was an important contributor – of art and funding – to the Key West Art & Historical Society.

David Wolkowski is one of our Community Honorees for the 2019 second line. If you would like to donate in his honor, please click the link below and choose “Sponsor a Placard”