Throughout its history, Sanford has been a town of full of colorful characters, even by Florida standards.

There’s W.J. Hill, an Englishman who lived in a packing crate on the banks of Lake Monroe when he moved to Sanford in 1872. He went on to build an empire in the hardware business.

Then there’s Jack Bolt, one of the greatest fighter pilots in US history; Drew “Bundini” Brown, who provided Muhammad Ali with some of his most famous quotes; and of course, Forest Lake, the 11-term Sanford mayor who created Seminole County and later wound up in prison for embezzlement.

Those names are familiar to locals who follow Sanford history. The name Sy Smith, on the other hand, probably won’t ring any bells.

What little history is known about Sy intrigues me because of his links with Forrest Lake. It wasn’t an association Sy chose. If he could have foreseen the future, he may have avoided Lake like the plague. Odd stuff happened to Sy when Lake was around.

Sanford native, business owner and Sanford Elks Chaplin David Doudney discovered Sy’s history when he was doing research for Lodge #1241’s 100th anniversary back in 2011.

Sy was the custodian at the Elks Lodge, a prestigious job because it was a paid position at an exclusive club that included free room and board at the lodge. That’s probably where Sy meet Lake, who was an Elk member and served as the 5th president of rhe Florida Elks Association.

According to David’s research, Sy first shows up in Sanford’s history in April 1913. Lake, thanks to his shenanigans in the Florida Legislature, had just successfully created Seminole County out of the northern part of Orange County. Such an event warranted a celebration, and what better way to rejoice than by firing a cannon. Sy was responsible for loading the cannon’s charge, but he packed too much gunpowder into the cannon, causing it to crack the barrel when it was fired.

A cannon exploding wasn’t Lake’s fault, of course, but it was his celebration. Sy’s next entry into the history books is a little less explosive.

In the early 1920s a traveling circus came to town, and Sy ended up with a monkey. How or why no one knows. That’s the thing about colorful characters. They end up with weird stuff, like a pet monkey, for no good reason. Sy kept it at the Elk’s Lodge for a while, but Lake and the other Elks brothers made him get rid of the primate. He did so by donating it to the Sanford Fire Department. That donation became the cornerstone of the Central Florida Zoo (“Sanford zoo began with a little monkey business downtown“).

Here’s where things take a turn for the worse.

It was the mid-1920s and Mayor Lake was going fullbore with public improvements throughout Sanford. He was also building the Hotel Forrest Lake. At the time, 1st Street ended at Sanford Avenue. Lake wanted to extend 1st Street to his hotel, using taxpayer money of course. But the mayor had a problem.

Doudney, who is a surveyor by trade (he owns Doudney Surveyors, started by his father in the 1950s), has studied old land records and determined the Elks Lodge was located near where the basketball courts are today in Fort Mellon Park. It was also directly in the path of where Lake wanted to extend 1st Street.

It was Sy who discovered how Lake resolved the issue.

One Sunday evening, Sy came home around midnight to find the lodge fully engulfed in flames. The lodge burned to the ground. Now there had been a fire at the Orlando Elk’s Lodge the week before, and the Gainesville Elk’s Lodge also burned within weeks after the Sanford fire. Doudney, a fan of Lake, is still suspicious.

“Circumstantially, it smells fishy to me,” he said.

Sy lost his home until the lodge relocated, but no matter – 1st Street got extended to the Hotel Forrest Lake.

A couple of years later, Sy and Lake would take center stage in one of the darkest times in Sanford history.

In 1927, Forrest Lake’s Seminole County Bank had closed and Lake was being investigated for embezzling bank and city funds. Among the hundreds of thousands of dollars unaccounted for at Lake’s bank was $5,700 in $50 bills (“Forrest Lake: crook or visionary?”). During the investigation, prosecutors interviewed Sy.

In the 1920s, a $50 bill was not the standard currency one used in the course of every-day transactions. Sy told investigators that Forrest Lake had recently been throwing around $50s at the Elks Lodge as if they were 50-cent coins. Whether he was buying drinks or playing cards, Sy said that Lake was paying with $50 bills.

At least, that’s what Sy said before Lake’s trial. Once on the stand, Sy claimed he had no knowledge of Lake using $50 bills at the Elks Lodge.

Why did Sy change his story? He was a black man with a good job working at an all-white club comprised of Sanford’s leading politicians and businessman. With Jim Crow segregation in full effect at the time in Sanford, it’s no wonder he changed his story.

Whether by choice or not, Sy Smith is at the center of some of Sanford’s more notorious moments. And that’s just the stories David Doudney has uncovered.

Unfortunately, that’s all we know about Sy. I have no idea, for example, where he was born, when he died or who his relatives are. I wish I knew.

Actually I wish I could’ve bought him a drink at the Elks Lodge. I bet he had some stories that would curl your toes.

– By Dan Ping

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