Bootleggers Bash Toasts Windsor’s Close Connection to US Prohibition

(Actors Eric Branget (left) and Rob Tymec sharing the role of gangster Baby Face Frankie during the inaugural Bootleggers Bash, a celebration of Windsor Ontario’s 100 year anniversary in connection to US Prohibition, at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.)

Friday night’s inaugural Bootleggers Bash, at the charming Water’s Edge Event Centre, gave Windsorites a true opportunity to dress up in their 1920s finery. And many did showing off their interpretations of what patrons of speakeasys would wear back in the day. Although most accessorized with fine items of jewelry or appropriate head gear from the era, others were seen carrying tommy guns.

Bootleggers Bash guests dressed in 1920's suits and flapper apparel

People wearing 1920’s prohibition era costumes during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

Rob Tymec in the role of Baby Face Frankie dancing with a guest of the inaugural Bootleggers Bash

Actor Rob Tymec in the role of Baby Face Frankie dancing with a guest of the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

At the time, America was entering a protracted period of alcohol prohibition, so the guns were actually de rigueur, given criminals were supplying the nation in violation of the Volstead Act. Enacted in 1919, making this its 100th Anniversary, the Act effectively ended the distilling and sale of alcoholic beverages anywhere in the United States.

Bootleggers Bash

A guest dressed in 1920’s era costume sporting a handlebar moustache during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

Karen Smallwood, organizer of Friday night’s event, told Eyes On Windsor, the Volstead Act was nothing if not good news for the Rose City and its prolific Hiram Walker whisky making operation. Some 80% of the spirits sold illegally south of the border, she says, originated in Windsor.

Bootleggers Bash: Alana Wallace, Tamara Tedeeva, Alexandra Fischer and Karen Smallwood

Alana Wallace, Tamara Tedeeva, Alexandra Fischer and Karen Smallwood enjoying the inaugural Bootleggers Bash in support of Windsor Family Respite Services at The Water’s Edge Event Centre on Friday, October 11, 2019. They helped organize and or are volunteering the event. Photo above by Robert Tuomi / Eyes On Windsor.

One of the leading state-side distributors of illicit liquor was the infamous Al Capone. He built a criminal empire in Chicago and apparently was not an uncommon visitor to the Walkerville facility. As can be expected, Capone was well represented at the Bash, particularly by its host the affable gangster “Baby Face Frankie.” Local actors Rob Tymec and Eric Branget played the Baby Face role to a perfection and were seen throughout the night interacting with guests.

Eric Branget, Miss Universe Canada Alyssa Boston, and Rob Tymec

Actors Eric Branget (left) and Rob Tymec, in character as gangster Baby Face Frankie, greeting Miss Universe Canada, Alyssa Boston, during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

Smallwood was more than grateful for a turnout that exceeded her expectations. The good news is the money collected by the one-night fundraiser will support the work of Family Respite Services of Windsor-Essex.

Those who attended were served up a taste of night life in a speakeasy where criminals and regular folk would mingle while sampling illicit whisky and other fancies. In the background the band played and the girls danced to the beat of burlesque music.

Bootleggers Bash Whisky Sampling

Guests at the Bootleggers Bash sampling Windsor, Ontario distilled J.P. Wiser whisky inside The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

Bootleggers Bash

People seated at tables enjoying food and libations during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

Sitting in the middle of the Music Makers Band, trumpet player Kevin Masterson was doing what he loved, playing the music he loves. Within a week he’ll celebrate his 86 birthday, proving you can’t keep a good musician down. Masterson told Eyes on Windsor the secret to the continuing popularity of tunes from the 1920s lies in their chords and melodies coming together as what he calls “happy music,” the kind that sets a mood with its rhythm and harmonies.

This was well evident in such songs as Babyface, Blue Moon, All of Me and When You’re Smiling to name a few on the group’s extensive period song list.

Kevin Masterson and Jackson Brobko

Trumpet player Kevin Masterson and Jackson Brobko on the electric upright bass performing during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

Music Makers Band at the Bootleggers Bash

Music Makers band members Dave Willick, Kevin Masterson, Owen Jones and Jackson Brobko performing during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

The happy music swung over to the risqué tunes common for the entertaining burlesque dancers, an attraction of many speakeasys. Windsor’s Win City Rose had six of its exquisite dancers take to the stage performing their brand of entertainment which included help from oversize fans and more than the occasional sultry glance.

Burlesque Win City Roses performers Rosalind St. Pixel and Dolly Diamond

Win City Roses burlesque and performance group members Rosalind St. Pixel (left) and Dolly Diamond during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

Win City Roses Burlesque Performers

Win City Roses burlesque and performance group members Develin Von Treat, Marjke, Charlotte Chartreuse, and Vivi the Vamp during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

Burlesque performer Vivi the Vamp

Vivi the Vamp of the Win City Roses burlesque and performance group sitting on steps during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

All of this right under the noses of both the clergy and the police. Dale Molnar, of CBC Windsor News, wore the uniform of the local constabulary, but cautioned that he wasn’t a real cop. While Biz X columnist Joe McParland, also in attendance, wore the appropriate trappings of a man of the cloth.

Dan Molnar and Joe McParland at the Bootleggers Bash

Dan Molnar in character as a 1920’s era police officer holding a baton, standing with Joe McParland who is playing the role of a prohibition era clergyman during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

And true to form, there were protesters. Well, one at least, in the form of Dona Stanley. Her sign reading “Lips That Touch Liquor Shall Not Touch Ours” was a sentiment common during the Prohibition period particularly by supporters of the ban on alcohol.

Dona Stanley holding a prohibition era protest sign during the Booteggers Bash

Dona Stanley holding a protest sign condeming those who oppose prohibition during the inaugural Bootleggers Bash at The Water’s Edge Event Centre on Friday, October 11, 2019. Photo above by Robert Tuomi / Eyes On Windsor.

All of this good time fun will mean more financial support for services provided to local families to help children under the age of 18 with intellectual, physical, or mental health challenges. Respite uses its funds to work with these families on in home or out of home programs.

For more about Family Respite Services Windsor – Essex visit http://www.familyrespite.org

For more about The Water’s Edge Event Centre including upcoming events and rental of the event venues space and services visit https://watersedgeeventcentre.ca

Robert Tuomi

Article by Robert Tuomi

For over a decade, Robert has covered local news and community events. Initially as a contributor to CBC Radio’s local morning show and then as the long-time producer and host of CJAM’s The Rest of the News and as a journalist at the Windsor Square. A graduate of the Nikon School of Photography he enjoys illustrating his reports with what he sees through his camera’s lens.