Firebrand commentator Michael Knowles delivers politics, a dose of scholarly wisdom – and a cigar brand heralding America’s early settlers
Michael Knowles began his college career with a thumb in the eye to the establishment. His application essay to Yale University detailed his infatuation with cigars, using the Cuban communists and the Sandinistas as a backdrop.
“I got in,” says Knowles, who had no legacy to rely on. “But later the admissions officer said one person had been unsure of admitting me, with the tobacco as a red flag.”
Tobacco, even as he applied in 2007, was already taboo. The state of Connecticut, home of Yale, has public smoking prohibitions dating back to 1979.
Knowles employed his considerable intellectual heft to tweak the established order. Uptight about the leaf? He had no interest in heeding the status quo.
Four years later, with a degree in history and Italian, Knowles graduated as an esteemed member of his class. And he got his classmates talking about cigars.
As a podcaster, social media maven and radio talk show host, Knowles, 35 years old in March, is a conservative ruckus raiser who is riding the crest of today’s political revolution.
His role as a part of the Daily Wire brand since 2016 helps him brandish formidable influence in the world of political debate. His podcast, “The Michael Knowles Show,” flexes his current events commentary and on occasion features guests including U.S. Sen. Marsha Blackburn and actor Kirk Cameron.
His podcast “Michael &” features interviews with spies, occultists and leftist political commentators. His monthly podcast, “The Book Club,” carried by PragerU, features a discussion of select classic literary works.
To relax from the sometimes dire world of politics and Western civilization, Daily Wire and Knowles in November 2023 released Mayflower Cigars, a line featuring two blends – Dawn, mild to medium, and Dusk, full bodied – in six sizes. The first production run of 50,000 cigars sold out immediately.
“The idea was of something patriotic, but also I didn’t want to be just a guns and cowboy boots kind of brand,” he says. His descendants on his father’s side of the family came to the U.S. from England on the Mayflower.
“The Mayflower wasn’t just pilgrims but also strangers,” he says. “There were aristocrats but also farmers, this mix of down-to-earth people and aristocracy. And that’s what cigars bring together.”
It was the realization of a dream for Knowles, who has pursued all his endeavors with a blend of insouciance, humor and determination, beginning at an early age.
“It was acting and politics that were my passions early on,” Knowles says. “Both of them have people who are egotistical and liars. But the good ones care about the truth and they require you to love and to study people. I like both of those things.”
He combines a Renaissance man style – erudite, sometimes profound, neat bordering on fastidious – with a fondness for the hoi polloi.
The father of three boys married his high school sweetheart, smoked his first premium cigar at age 15, a gift from a family friend, converted from atheism to Catholicism in his college days, and studied at the esteemed Stella Adler Studio of Acting in New York.
After that first cigar, the teenaged Knowles sought to learn all he could about cigars, heading to the Bronx where he found places where cigar rollers toiled, using Connecticut Shade wrapper.
Despite running a low wallet, he kept up his pursuit of cigars. While his parents split when he was young, Knowles was an only child who lived with his mom and saw his father daily.
It was the former who helped him pursue his cigar love.
“The year after my first cigar, my mom asked me what I wanted for Christmas, and I told her some Oliva Serie O,” he says. “Money was tight, but she got me a box of the Robustos, the cheapest. But they were great.”
The box joined his growing collection of accessories and his beloved Frank Sinatra humidor.
Knowles’ four years at Fox Lane High School in Bedford, New York gave him room to engage in his politics, and he was elected class president while also acting in whatever production he could find.
Once at Yale, he quickly sought to spread his love of premium cigars, forming the Society for Intellectual Growth and Reinvigoration, or SIGAR, which was essentially a cigar club.
But he also needed cigars.
So he wrote a cigar column for the Yale Daily News, the student newspaper, which allowed him some promotional freebies.
Photo credit: Courtesy of Michael Knowles
“My mom died nine days after I got into Yale, and I had no money,” says Knowles, who was attending as a needs-based student. “And I had an expensive hobby, cigars.”
Using his column reviewing cigars as leverage, “I went to the Owl Shop in New Haven, and they really helped me out,” he says.
Knowles’ works were a blend of review, lifestyle and politics, all dashed with a mischievous sense of humor.
“Last week, as I sat watching the Glenn Beck show with a fat maduro between my teeth, I discovered that the United States was on the verge of a communist insurrection,” he began one column.
In another he took on a smoking prohibitionist group on campus.
“The Tobacco Free Yale Workgroup is free to make whatever decision it likes. Regardless, the smokers and cigar enthusiasts will continue to enjoy one of life’s most basic pleasures, and the malcontent faculty members behind the ban will be welcome to peer down at reality from their small, petty, ivory offices and frown,” he wrote.
Knowles also appeared in 14 plays while at Yale – including a turn as Satan in “The Last Days of Judas Iscariot” – while stirring up debate and discussion through his political activities.
He graduated from Yale in 2012. He loved the East Coast, where he grew up. But his love of acting eventually drove him to Hollywood where he scored several roles, including spots in reenacted true crime shows and commercials.
“A Toyota commercial paid my rent for a year,” he says.
His career grew with a role in a feature film, “Hollyweird,” in which “I was a fake Cuban.”
While in Los Angeles, he encountered the political monolith of show biz, meaning “I was invited to some Bernie [Sanders] fundraisers. But I didn’t go.”
While his fellow aspiring actors tended bar and drove delivery trucks between roles, Knowles’ side hustle was politics. As a principal of Red Pillar Consulting, a boutique house of strategists and advisors that helped run political campaigns, he served as a spokesman and/or director for local and national candidates.
He met the leadership of the Daily Wire at a dinner party in Los Angeles, a chance meeting of like-minded red people awash in a sea of blue politics. He joined the fledgling conservative news brand as a social media expert before being asked to host a podcast.
In early 2017, Knowles self-published a spoofy book, “Reasons to Vote for Democrats: A Comprehensive Guide,” which featured only blank pages, page headings and a bibliography. The book was a viral hit, picked up by Simon & Schuster and lauded on social media by President Donald Trump.
Daily Wire moved to more politically friendly Nashville in 2020, and Knowles moved his family and embraced the South. As Daily Wire expanded its influence, Knowles broadened his audience, setting the table for what came next.
He’d written a review of Foundation Cigar’s Co.’s Tabernacle cigar for the Daily Wire at one point, “but they didn’t run it because they don’t run cigar reviews,” Knowles says. But he had planted the cigar idea, although Knowles was the accomplished cigar expert on the team. He took it a step further a couple years later.
“When I was a kid, I thought how cool it would be to have my own cigar brand,” Knowles says. He outlined what would become Mayflower Cigars.
The search for a manufacturer was underway when Knowles appeared on a talk show with U.S. Congressman Guy Reschenthaler, a fellow cigar lover who was part of the 30-member Congressional Cigar Caucus, an informal collective supporting the cigar industry. He loved Oliva and suggested the brand to Knowles. Connection made, samples began arriving.
It took seven to eight months to get the blends right, Knowles says, “because I was really annoying about it.” His experienced palate allowed him to discern what he wanted.
The successful launch emboldened Knowles and Daily Wire to expand the line. Accessories, including a 100-count humidor, triple flame lighter and cutter, came next. And then the smoking jacket.
High-end menswear brand Shepherd’s was making suits for some of the Daily Wire talent. The Kansas City-based brand was co-founded by Kansas City Chiefs kicker Harrison Butker. Shepherd’s made Knowles a “killer suit…then I found out Harrison Butker and his team were going to be in [Nashville], so we had a cigar and kicked around ideas.”
And they landed on a smoking jacket.
“I had this Paul Stewart smoking jacket that I have had since I was 19,” Knowles says. “But that jacket was $1,200 in 2010. I didn’t want that.”
The result was a sleek jacket that came out in October for $895. Like the first run of the Mayflower, it sold out quickly. It hasn’t gone back into production, but Knowles said it would likely return as a special drop.
While Mayflower had fielded offers to be carried in retail shops on its entry into the market, Knowles found the various laws made it difficult to do so. In September, Mayflower made its brick-and-mortar debut atHouse of Ferruzza, a barber shop/cigar lounge in Bethel Park, Penn., outside of Pittsburgh.
In April, Knowles and Mayflower are heading to the Premium Cigar Association’s annual conference, this year in New Orleans, in hopes of broadening the base.
“Cigar retail shops are the last mom and pops in America,” Knowles says. He gives numerous speeches every year in cities across the U.S., “and the first thing I do when I get someplace is look for a cigar shop.”
Knowles leaned into the merits of cigars as a teen, and his early conclusions resonate now more than ever.
“There is no finer equalizer than the hand-rolled, long-filler cigar,” he wrote in a column for the Yale Daily News in early 2011. “Some of the most important conversations in my life have taken place with friends, family and complete strangers in a warm bath of smoke
The Standard, Nashville
The aged grill of The Standard, a relic of the Antebellum Era, sits two blocks off the sticky, fetid tourist thoroughfare that is Broadway aka Honky Tonk Highway. It is a subtle, aesthetic beacon. It is a townhouse, simple enough, that cloaks a historic, regal interior.
Up a flight of stairs inside the doorway of The Standard is a bevy of cozy, well-tended rooms that form a private smoking and dining club. Creaky wooden floors, velvet curtains, private rooms, dignified service and jovial attitudes are part of The Standard experience.
“It’s the place where you can have a steak and smoke a cigar at the same time,” says Michael Knowles, who has struck deals and entertained guests at what he says is his favorite smoking place in the city.
The Standard was built in the 1840s as a boarding house and during the Civil War was occupied by Union soldiers. The years saw it change ownership but not appearance, and it still looks out of place in the middle of Nashville, tucked between an empty retail storefront and what appears to have once been a bank.
The cigar menu is a limited, greatest-hits affair including offerings from Drew Estate, Crowned Heads, La Aurora, Davidoff and Padron, with a selection of roughly 40 smokes.
The food and drink are predictably fine – the Standard Filet, a plate of calamari and generous pours of red wine make for an excellent culinary experience – but the Old South vibe is what makes The Standard a destination.
A smoke, a little vino and red meat – it all tastes like freedom.
Click here to watch our interview with Michael Knowles at The Great Smoke 2025
