307 Howell Ave.

Herbert Smithson: Brooksville’s Unsolved Tragedy in the National Spotlight

A Town in the Shadows of Prohibition

Brooksville, Florida, a quiet town nestled in Hernando County, is known for its historic charm and tight-knit community. In 1931, however, it was thrust into the national spotlight by a shocking crime that exposed the underbelly of Prohibition-era lawlessness. The murder of City Attorney Herbert Smithson on October 12, 1931, outside the Tangerine Hotel remains one of Brooksville’s most enduring mysteries. This unsolved case, tied to the illegal alcohol trade, highlighted the tensions between law enforcement and bootleggers, drawing attention to the small town’s role in a national struggle.

Smithson’s death was more than a local tragedy—it was a stark reminder of the violence that Prohibition unleashed across rural America. His story, rooted in Brooksville’s fields and forests, captured headlines and continues to fascinate historians and locals alike, cementing the town’s place in the narrative of America’s Prohibition era.

Brooksville’s Fallen Advocate

Herbert Smithson was a pillar of Brooksville’s community. As City Attorney, he played a pivotal role in upholding the law during a tumultuous period. A seven-to-eight-year resident, he was deeply embedded in the town’s fabric, serving as commander of the local American Legion post. His leadership in this veterans’ organization reflected his commitment to civic duty, making him a respected figure in a town of fewer than 3,000 residents at the time.

On October 12, 1931, Smithson’s life was cut short in a brazen attack. After meeting with Judge Bird and Prosecuting Attorney J.R. Kelly at the Tangerine Hotel on Howell Avenue, he stepped outside and was gunned down by three men in a small sedan. Witnesses reported seeing two Ford cars—one without a license plate—speeding away, suggesting a carefully planned ambush. The attack was widely believed to be retaliation for Smithson’s alleged cooperation with federal agents to crack down on Hernando County’s thriving illegal alcohol trade, a lifeline for many during the Great Depression.

“Whiskey was made in nearly every other house,” wrote historian Richard Cofer, describing Hernando County’s bootlegging culture. Smithson’s efforts to disrupt this trade likely made him a target in a community where moonshining was a way of life.

A Case Shrouded in Mystery

The murder sparked an immediate and intense investigation. Sheriff W.D. Cobb, aware of the case’s complexity, requested that Governor Carlton appoint a special prosecutor, signaling the need for external oversight. Judge Whitehurst, one of four lawyer brothers in Brooksville, oversaw the inquest, while the American Legion, led by Smithson, assisted in gathering leads. Despite these efforts, the investigation faced significant hurdles.

Three men, including a deputy sheriff, were indicted for the murder, raising questions about corruption within local law enforcement. However, the charges were dropped due to strong alibis, leaving the case unresolved. Smithson’s family offered a $1,900 reward—equivalent to over $30,000 today—for information leading to convictions, but no one was ever brought to justice. Herbert’s body was taken to Talladega, Alabama, by his wife, marking a somber end to his time in Brooksville.

The involvement of a deputy sheriff among the suspects was a shocking twist, hinting at the deep ties between local authorities and the bootlegging trade. Sheriff Cobb himself, who was voted out of office in 1932 after other violent incidents, was rumored to have sympathies with moonshiners, further complicating the pursuit of justice.

Brooksville in the National Spotlight

The murder of Herbert Smithson brought unprecedented attention to Brooksville, as newspapers across Florida and beyond reported on the sensational crime. The case highlighted the challenges of enforcing Prohibition in rural areas, where bootlegging was not just a crime but a cultural and economic cornerstone. Hernando County’s vast forests and marshes provided ideal cover for stills, and its proximity to Tampa made it a hub for smuggling. Smithson’s death exposed these dynamics, drawing scrutiny to the town’s role in the national battle against illegal alcohol.

The unsolved nature of the case amplified its impact, as it underscored the lawlessness that Prohibition fostered. Stories of the Tangerine Hotel, once a respectable establishment but later rumored to have become a bordello, added to Brooksville’s notoriety. The murder became a touchstone in local history, preserved in accounts like Richard Cofer’s “Bootleggers in the Backwoods” and articles in the Tampa Bay Times and Hernando Sun, ensuring that Smithson’s story—and Brooksville’s—remained in the public consciousness.

The murder of Herbert Smithson remains a poignant chapter in Brooksville’s past, a reminder of the town’s resilience in the face of adversity. The Tangerine Hotel, now Elevated Estates Brooksville, an assisted living facility, stands as a quiet testament to that turbulent era.

Smithson’s story continues to captivate, drawing historians, locals, and visitors to explore Brooksville’s Prohibition-era legacy. His sacrifice as a public servant who stood against corruption and crime underscores the town’s enduring spirit—a spirit that shines through its history, from unsolved mysteries to the achievements of its people. Brooksville, where the echoes of Herbert Smithson’s story remind us that even in the darkest times, a small town can leave a lasting mark on the national stage.

Citations

“Hernando County Goes Wet.” Tampa Bay Times, December 26, 1999. https://www.tampabay.com/archive/1999/12/26/hernando-county-goes-wet/.

“Hernando’s 100-Year-Old Courthouse Part of Long, Slow Journey to Justice.” Tampa Bay Times, October 4, 2013. https://www.tampabay.com/news/courts/hernandos-100-year-old-courthouse-part-of-long-slow-journey-to-justice/2145517/.

“Prohibition Era Murder at the Tangerine Hotel.” Hernando Sun, May 27, 2016. https://www.hernandosun.com/tangerine_hotel_5_27_16.

“Tour of Historic Brooksville, Florida.” FloridaHistory.org. https://floridahistory.org/brooksville.htm.

307 Howell Ave – The Tangerine Hotel

Welcome, folks, to one of Brooksville’s most storied spots, the Tangerine Hotel! Standing here at 307 Howell Avenue, you’re looking at a place that’s been the heart of this community since 1925, when it opened its doors during Florida’s big economic boom. Named for Brooksville’s proud title, “Home of the Tangerine,” this hotel was built to welcome tourists and seasonal travelers chasing the Sunshine State’s promise. Picture it: seventy-five cozy guest rooms, a bustling dining hall, and rates as low as 40 cents a bed—quite the deal back then!

As you take in this handsome building, imagine the lively scene it once hosted. The Tangerine wasn’t just a place to rest your head—it was Brooksville’s social hub. The dining room rang with laughter and chatter during American Legion meetings, Kiwanis gatherings, and even the Brooksville Garden Club’s first-ever flower show in 1930. Folks from all walks of life came together here, making it a true cornerstone of our town’s spirit. Fun fact: the hotel’s owners were so proud of it that they invited King George of England to recuperate here in 1925! He politely declined for a Mediterranean cruise, but that bold invite shows just how special this place was.

Now, let’s add a dash of intrigue to our tale. In 1931, the Tangerine Hotel found itself at the center of a real-life drama—a murder mystery, no less! City Attorney Herbert Smithson was gunned down right at this entrance while meeting with a judge and a prosecutor. Rumor spread quickly, even by the Sheriff, that Herbert was helping Federal Prohibition agents crack down on illegal bootlegging during Prohibition, a risky business in those days. Prohibition officials denied this, and, not having any faith in the gossiping Sheriff, asked Governor Carlton to take over the investigation. Eventually, three men were arrested, two of them were Sheriff’s deputies. The case went cold when a key witness vanished. Standing here, you can almost feel the echoes of that fateful night, a reminder of how even quiet Brooksville wasn’t immune to the tensions of the era.

Like many grand dreams, the Tangerine hit hard times during the Great Depression, facing a bankruptcy sale in 1936. But it soldiered on as a hotel for years, adapting to the changing tides. By 1983, it transformed into Tangerine Cove, an assisted living facility, breathing new life into these historic walls. Today, known as Elevated Estates Brooksville, it continues to care for residents who enjoy strolls along Howell Avenue, tying the past to the present.

As we linger here, think about the layers of history in this spot—the travelers who rested, the locals who celebrated, the drama that unfolded, and the community it still serves. The Tangerine Hotel isn’t just a building; it’s a story of Brooksville’s resilience, heart, and zest for life, just like the fruit it’s named for. Ready to keep exploring? Let’s head to our next stop and uncover more of Brooksville’s charm!

Citations:

“Historic Brooksville Walking Driving Tour 307 Howell Avenue.” Tour Brooksville. https://www.tourbvl.com/307-howell-avenue.

“Prohibition Era Murder at the Tangerine Hotel.” Hernando Sun, May 27, 2016. https://www.hernandosun.com/tangerine_hotel_5_27_16.

“Tangerine Hotel, Bright Spot of Brooksville, Is Indicator of Town’s Future Development, Tampa Sunday Tribune, May 31, 1925, pg. 1.

“King’s Reply to Brooksville,” Tampa Sunday Tribune, March 8, 1925, pg. 11-G.

“Garden Club News,” Tampa Sunday Tribune, April 27, 1930, pg. 20.

Classifieds, Tampa Daily Tribune, October 12, 1926, pg. 19.

“Business Girls Call Conference,” St. Petersburg Times, January 28, 1929, pg. 3.

“Sale of Tangerine Hotel is Approved,” Tampa Daily Times, April 18, 1936, pg. 2.

307 Howell Ave – The Tangerine Hotel

Welcome, folks, to one of Brooksville’s most storied spots, the Tangerine Hotel! Standing here at 307 Howell Avenue, you’re looking at a place that’s been the heart of this community since 1925, when it opened its doors during Florida’s big economic boom. Named for Brooksville’s proud title, “Home of the Tangerine,” this hotel was built to welcome tourists and seasonal travelers chasing the Sunshine State’s promise. Picture it: seventy-five cozy guest rooms, a bustling dining hall, and rates as low as 40 cents a bed—quite the deal back then!

As you take in this handsome building, imagine the lively scene it once hosted. The Tangerine wasn’t just a place to rest your head—it was Brooksville’s social hub. The dining room rang with laughter and chatter during American Legion meetings, Kiwanis gatherings, and even the Brooksville Garden Club’s first-ever flower show in 1930. Folks from all walks of life came together here, making it a true cornerstone of our town’s spirit. Fun fact: the hotel’s owners were so proud of it that they invited King George of England to recuperate here in 1925! He politely declined for a Mediterranean cruise, but that bold invite shows just how special this place was.

Now, let’s add a dash of intrigue to our tale. In 1931, the Tangerine Hotel found itself at the center of a real-life drama—a murder mystery, no less! City Attorney Herbert Smithson was gunned down right at this entrance while meeting with a judge and a prosecutor. Rumor spread quickly, even by the Sheriff, that Herbert was helping Federal Prohibition agents crack down on illegal bootlegging during Prohibition, a risky business in those days. Prohibition officials denied this, and, not having any faith in the gossiping Sheriff, asked Governor Carlton to take over the investigation. Eventually, three men were arrested, two of them were Sheriff’s deputies. The case went cold when a key witness vanished. Standing here, you can almost feel the echoes of that fateful night, a reminder of how even quiet Brooksville wasn’t immune to the tensions of the era.

Like many grand dreams, the Tangerine hit hard times during the Great Depression, facing a bankruptcy sale in 1936. But it soldiered on as a hotel for years, adapting to the changing tides. By 1983, it transformed into Tangerine Cove, an assisted living facility, breathing new life into these historic walls. Today, known as Elevated Estates Brooksville, it continues to care for residents who enjoy strolls along Howell Avenue, tying the past to the present.

As we linger here, think about the layers of history in this spot—the travelers who rested, the locals who celebrated, the drama that unfolded, and the community it still serves. The Tangerine Hotel isn’t just a building; it’s a story of Brooksville’s resilience, heart, and zest for life, just like the fruit it’s named for. Ready to keep exploring? Let’s head to our next stop and uncover more of Brooksville’s charm!

Citations:

“Historic Brooksville Walking Driving Tour 307 Howell Avenue.” Tour Brooksville. https://www.tourbvl.com/307-howell-avenue.

“Prohibition Era Murder at the Tangerine Hotel.” Hernando Sun, May 27, 2016. https://www.hernandosun.com/tangerine_hotel_5_27_16.

“Tangerine Hotel, Bright Spot of Brooksville, Is Indicator of Town’s Future Development, Tampa Sunday Tribune, May 31, 1925, pg. 1.

“King’s Reply to Brooksville,” Tampa Sunday Tribune, March 8, 1925, pg. 11-G.

“Garden Club News,” Tampa Sunday Tribune, April 27, 1930, pg. 20.

Classifieds, Tampa Daily Tribune, October 12, 1926, pg. 19.

“Business Girls Call Conference,” St. Petersburg Times, January 28, 1929, pg. 3.

“Sale of Tangerine Hotel is Approved,” Tampa Daily Times, April 18, 1936, pg. 2.

307 Howell Ave – The Tangerine Hotel

Welcome, folks, to one of Brooksville’s most storied spots, the Tangerine Hotel! Standing here at 307 Howell Avenue, you’re looking at a place that’s been the heart of this community since 1925, when it opened its doors during Florida’s big economic boom. Named for Brooksville’s proud title, “Home of the Tangerine,” this hotel was built to welcome tourists and seasonal travelers chasing the Sunshine State’s promise. Picture it: seventy-five cozy guest rooms, a bustling dining hall, and rates as low as 40 cents a bed—quite the deal back then!

As you take in this handsome building, imagine the lively scene it once hosted. The Tangerine wasn’t just a place to rest your head—it was Brooksville’s social hub. The dining room rang with laughter and chatter during American Legion meetings, Kiwanis gatherings, and even the Brooksville Garden Club’s first-ever flower show in 1930. Folks from all walks of life came together here, making it a true cornerstone of our town’s spirit. Fun fact: the hotel’s owners were so proud of it that they invited King George of England to recuperate here in 1925! He politely declined for a Mediterranean cruise, but that bold invite shows just how special this place was.

Now, let’s add a dash of intrigue to our tale. In 1931, the Tangerine Hotel found itself at the center of a real-life drama—a murder mystery, no less! City Attorney Herbert Smithson was gunned down right at this entrance while meeting with a judge and a prosecutor. Rumor spread quickly, even by the Sheriff, that Herbert was helping Federal Prohibition agents crack down on illegal bootlegging during Prohibition, a risky business in those days. Prohibition officials denied this, and, not having any faith in the gossiping Sheriff, asked Governor Carlton to take over the investigation. Eventually, three men were arrested, two of them were Sheriff’s deputies. The case went cold when a key witness vanished. Standing here, you can almost feel the echoes of that fateful night, a reminder of how even quiet Brooksville wasn’t immune to the tensions of the era.

Like many grand dreams, the Tangerine hit hard times during the Great Depression, facing a bankruptcy sale in 1936. But it soldiered on as a hotel for years, adapting to the changing tides. By 1983, it transformed into Tangerine Cove, an assisted living facility, breathing new life into these historic walls. Today, known as Elevated Estates Brooksville, it continues to care for residents who enjoy strolls along Howell Avenue, tying the past to the present.

As we linger here, think about the layers of history in this spot—the travelers who rested, the locals who celebrated, the drama that unfolded, and the community it still serves. The Tangerine Hotel isn’t just a building; it’s a story of Brooksville’s resilience, heart, and zest for life, just like the fruit it’s named for. Ready to keep exploring? Let’s head to our next stop and uncover more of Brooksville’s charm!

Citations:

“Historic Brooksville Walking Driving Tour 307 Howell Avenue.” Tour Brooksville. https://www.tourbvl.com/307-howell-avenue.

“Prohibition Era Murder at the Tangerine Hotel.” Hernando Sun, May 27, 2016. https://www.hernandosun.com/tangerine_hotel_5_27_16.

“Tangerine Hotel, Bright Spot of Brooksville, Is Indicator of Town’s Future Development, Tampa Sunday Tribune, May 31, 1925, pg. 1.

“King’s Reply to Brooksville,” Tampa Sunday Tribune, March 8, 1925, pg. 11-G.

“Garden Club News,” Tampa Sunday Tribune, April 27, 1930, pg. 20.

Classifieds, Tampa Daily Tribune, October 12, 1926, pg. 19.

“Business Girls Call Conference,” St. Petersburg Times, January 28, 1929, pg. 3.

“Sale of Tangerine Hotel is Approved,” Tampa Daily Times, April 18, 1936, pg. 2.

307 Howell Ave – The Tangerine Hotel

Welcome, folks, to one of Brooksville’s most storied spots, the Tangerine Hotel! Standing here at 307 Howell Avenue, you’re looking at a place that’s been the heart of this community since 1925, when it opened its doors during Florida’s big economic boom. Named for Brooksville’s proud title, “Home of the Tangerine,” this hotel was built to welcome tourists and seasonal travelers chasing the Sunshine State’s promise. Picture it: seventy-five cozy guest rooms, a bustling dining hall, and rates as low as 40 cents a bed—quite the deal back then!

As you take in this handsome building, imagine the lively scene it once hosted. The Tangerine wasn’t just a place to rest your head—it was Brooksville’s social hub. The dining room rang with laughter and chatter during American Legion meetings, Kiwanis gatherings, and even the Brooksville Garden Club’s first-ever flower show in 1930. Folks from all walks of life came together here, making it a true cornerstone of our town’s spirit. Fun fact: the hotel’s owners were so proud of it that they invited King George of England to recuperate here in 1925! He politely declined for a Mediterranean cruise, but that bold invite shows just how special this place was.

Now, let’s add a dash of intrigue to our tale. In 1931, the Tangerine Hotel found itself at the center of a real-life drama—a murder mystery, no less! City Attorney Herbert Smithson was gunned down right at this entrance while meeting with a judge and a prosecutor. Rumor spread quickly, even by the Sheriff, that Herbert was helping Federal Prohibition agents crack down on illegal bootlegging during Prohibition, a risky business in those days. Prohibition officials denied this, and, not having any faith in the gossiping Sheriff, asked Governor Carlton to take over the investigation. Eventually, three men were arrested, two of them were Sheriff’s deputies. The case went cold when a key witness vanished. Standing here, you can almost feel the echoes of that fateful night, a reminder of how even quiet Brooksville wasn’t immune to the tensions of the era.

Like many grand dreams, the Tangerine hit hard times during the Great Depression, facing a bankruptcy sale in 1936. But it soldiered on as a hotel for years, adapting to the changing tides. By 1983, it transformed into Tangerine Cove, an assisted living facility, breathing new life into these historic walls. Today, known as Elevated Estates Brooksville, it continues to care for residents who enjoy strolls along Howell Avenue, tying the past to the present.

As we linger here, think about the layers of history in this spot—the travelers who rested, the locals who celebrated, the drama that unfolded, and the community it still serves. The Tangerine Hotel isn’t just a building; it’s a story of Brooksville’s resilience, heart, and zest for life, just like the fruit it’s named for. Ready to keep exploring? Let’s head to our next stop and uncover more of Brooksville’s charm!

Citations:

“Historic Brooksville Walking Driving Tour 307 Howell Avenue.” Tour Brooksville. https://www.tourbvl.com/307-howell-avenue.

“Prohibition Era Murder at the Tangerine Hotel.” Hernando Sun, May 27, 2016. https://www.hernandosun.com/tangerine_hotel_5_27_16.

“Tangerine Hotel, Bright Spot of Brooksville, Is Indicator of Town’s Future Development, Tampa Sunday Tribune, May 31, 1925, pg. 1.

“King’s Reply to Brooksville,” Tampa Sunday Tribune, March 8, 1925, pg. 11-G.

“Garden Club News,” Tampa Sunday Tribune, April 27, 1930, pg. 20.

Classifieds, Tampa Daily Tribune, October 12, 1926, pg. 19.

“Business Girls Call Conference,” St. Petersburg Times, January 28, 1929, pg. 3.

“Sale of Tangerine Hotel is Approved,” Tampa Daily Times, April 18, 1936, pg. 2.

307 Howell Ave – The Tangerine Hotel

Welcome, folks, to one of Brooksville’s most storied spots, the Tangerine Hotel! Standing here at 307 Howell Avenue, you’re looking at a place that’s been the heart of this community since 1925, when it opened its doors during Florida’s big economic boom. Named for Brooksville’s proud title, “Home of the Tangerine,” this hotel was built to welcome tourists and seasonal travelers chasing the Sunshine State’s promise. Picture it: seventy-five cozy guest rooms, a bustling dining hall, and rates as low as 40 cents a bed—quite the deal back then!

As you take in this handsome building, imagine the lively scene it once hosted. The Tangerine wasn’t just a place to rest your head—it was Brooksville’s social hub. The dining room rang with laughter and chatter during American Legion meetings, Kiwanis gatherings, and even the Brooksville Garden Club’s first-ever flower show in 1930. Folks from all walks of life came together here, making it a true cornerstone of our town’s spirit. Fun fact: the hotel’s owners were so proud of it that they invited King George of England to recuperate here in 1925! He politely declined for a Mediterranean cruise, but that bold invite shows just how special this place was.

Now, let’s add a dash of intrigue to our tale. In 1931, the Tangerine Hotel found itself at the center of a real-life drama—a murder mystery, no less! City Attorney Herbert Smithson was gunned down right at this entrance while meeting with a judge and a prosecutor. Rumor spread quickly, even by the Sheriff, that Herbert was helping Federal Prohibition agents crack down on illegal bootlegging during Prohibition, a risky business in those days. Prohibition officials denied this, and, not having any faith in the gossiping Sheriff, asked Governor Carlton to take over the investigation. Eventually, three men were arrested, two of them were Sheriff’s deputies. The case went cold when a key witness vanished. Standing here, you can almost feel the echoes of that fateful night, a reminder of how even quiet Brooksville wasn’t immune to the tensions of the era.

Like many grand dreams, the Tangerine hit hard times during the Great Depression, facing a bankruptcy sale in 1936. But it soldiered on as a hotel for years, adapting to the changing tides. By 1983, it transformed into Tangerine Cove, an assisted living facility, breathing new life into these historic walls. Today, known as Elevated Estates Brooksville, it continues to care for residents who enjoy strolls along Howell Avenue, tying the past to the present.

As we linger here, think about the layers of history in this spot—the travelers who rested, the locals who celebrated, the drama that unfolded, and the community it still serves. The Tangerine Hotel isn’t just a building; it’s a story of Brooksville’s resilience, heart, and zest for life, just like the fruit it’s named for. Ready to keep exploring? Let’s head to our next stop and uncover more of Brooksville’s charm!

Citations:

“Historic Brooksville Walking Driving Tour 307 Howell Avenue.” Tour Brooksville. https://www.tourbvl.com/307-howell-avenue.

“Prohibition Era Murder at the Tangerine Hotel.” Hernando Sun, May 27, 2016. https://www.hernandosun.com/tangerine_hotel_5_27_16.

“Tangerine Hotel, Bright Spot of Brooksville, Is Indicator of Town’s Future Development, Tampa Sunday Tribune, May 31, 1925, pg. 1.

“King’s Reply to Brooksville,” Tampa Sunday Tribune, March 8, 1925, pg. 11-G.

“Garden Club News,” Tampa Sunday Tribune, April 27, 1930, pg. 20.

Classifieds, Tampa Daily Tribune, October 12, 1926, pg. 19.

“Business Girls Call Conference,” St. Petersburg Times, January 28, 1929, pg. 3.

“Sale of Tangerine Hotel is Approved,” Tampa Daily Times, April 18, 1936, pg. 2.