Can a Wine King Buy a Maryland Senate Seat?

In the last 37 years, there have only been two Senate vacancies in the solidly blue state of Maryland.

So when Sen. Ben Cardin (D-MD) announced his retirement earlier this month, he instantly set off a scramble among ambitious Democrats.

The race was always going to be a blockbuster, considering a safe Senate seat is one of the ultimate prizes in politics. But the cast of characters who have entered the race, or are considering a run, could make Maryland an unlikely center of drama in the 2024 Senate battle royale.

There’s Angela Alsobrooks, the chief executive of populous Prince George’s County, who has already racked up endorsements and would attract national support as a rare Black woman frontrunner for a Senate seat.

There’s Will Jawando, a progressive councilman in Montgomery County, positioning himself as the underdog favorite of the activist left.

Maryland Senator Retires, Setting Stage for Competitive Race‘IT IS TIME’

Erik Uebelacker

There’s Rep. Jamie Raskin (D-MD), a figure beloved by liberals nationally for his tenacious opposition to Donald Trump and his GOP allies, who is mulling a run.

And then there’s Rep. David Trone (D-MD), a deep-pocketed booze baron who has pledged to pour millions of his own money into the campaign—and has already won tough races by doing just that.

As the owner of Total Wine & More, Trone’s presence will almost certainly elevate the amount of money any candidate hoping to win the nomination will have to spend, and he’s already putting it to use in early advertising and travel around the state.

Whoever wins the May 2024 primary is all but a lock to win the seat in November, with the GOP’s only viable candidate, former Gov. Larry Hogan, passing on the race.

That means the Democrat-on-Democrat race will be intense, expensive, and potentially nasty—something that party leaders surely aren’t relishing as they try to defend their Senate majority amid a brutal 2024 outlook.

Still, Democrats in Maryland and Washington may be excited about the prospect of injecting some fresh energy into their long-running Senate representation.

Maryland Democratic operatives who spoke with The Daily Beast said Alsobrooks has some advantages off the bat. In many states, someone from the county level wouldn’t necessarily play well in a statewide race. But in Maryland, a smaller constituency, they’re relative power players. Her seat has given Alsobrooks a following in Prince George County, a Black-majority county that is very influential on the state level.

“Alsobrooks would have to be considered the front runner,” said Maryland Democratic strategist Len Foxwell, who cautioned it’s still early. “Because of her established name recognition… And you’re seeing the pillars of the Democratic establishment come out for her.”

“Her diversity both as a woman and a woman of color, plus her geographic diversity and in the state being from Prince George’s County, she can put together the coalition that can win. It’s not easy, but she has the profile to do it,” said Andrew Feldman, a Democratic strategist with experience in Maryland politics.

There are currently no Black women in the Senate. Alsobrooks could potentially leverage that fact to appeal to national donors and Democratic voters in the state.

But in the same beat, Democrats cautioned not to count Trone out, for his sheer spending advantage alone.

“David Trone is willing to spend whatever it takes, regardless of what that number is, to win this race. And that is not to be taken lightly,” Foxwell said.

Trone doesn’t have the same name ID as Alsobrooks—but he’s already up on the air with advertising. He doesn’t have to spend time fundraising like other candidates. And he’s working to counter the rich-guy persona by playing to his upbringing, with ads focusing on his childhood and family’s economic struggles. He’s also highlighted his work on the opioid crisis in his district and criminal justice reforms.

In an emailed statement to The Daily Beast, Trone touted his success of getting bills on mental health, opioid treatment, and criminal justice. “I’m willing to do the work, and right now we’re spending an incredible amount of time in every corner of the state, from Western Maryland to the Eastern Shore, Baltimore and everywhere in between talking about our state’s future,” Trone said.

For Trone’s opponents, it’s a daunting thing to be so out-raised from the get-go. But they insist they’re undeterred.

After all, being the owner of a business empire with millions to blow can come with baggage. The Spectator this week unveiled a police report in which Trone allegedly told a Total Wine employee he would “execute” and “fucking end” them during an argument over merchandise.

Gina Ford, a spokesperson for Alsobrooks, told The Daily Beast the campaign is “confident she will raise the necessary resources to be competitive in this race.”

Jawando, who’s running on a platform he dubbed as “pragmatic progressivism,” exuded the same confidence.

“I expect [Trone] to spend a lot of money. I don’t think that’s what’s going to win this race,” Jawando said in an interview with The Daily Beast.

“I ran in 2016,” Jawando continued. “Congress when I was elected, at that time, was the most expensive primary in the history of the country. And David Trone was in that race and he didn’t win.”

That part is true. Trone lost to Raskin in 2016 after the wine impresario poured $12 million into his candidacy. Raskin remains the major question in the race. He’s a strong fundraiser, beloved within the party, and has built widespread recognition in the state and nationally.

“He completely disrupts the chessboard. One-hundred percent,” Foxwell said of a potential Raskin run. “Jamie Raskin is a progressive darling, and in many circles within the Democratic Party, he’s an American hero… It’s impossible to overstate how much his entry into this race would disrupt the dynamic.”

Rep. Jamie Raskin Is in Remission From Cancer‘GRATITUDE AND LOVE’

AJ McDougall, Rachel Olding, Mathew Murphy

Raskin says he intends to make a decision in the next few weeks. His candidacy is by no means a shoo-in. He’s been battling cancer for months and just entered remission, making the challenge of a statewide campaign more complicated than it might be for other candidates. He’s also already positioned himself as a leader in the House and earned the top Democratic spot on the Oversight Committee, a coveted gig.

In other words: he doesn’t necessarily need the Senate to wield more power.

“He has such an important role right now on oversight, right?” said one Democratic operative with experience in Maryland politics.

The operative continued that Raskin is the “‘what’s going to happen’ factor here that will definitely shape the race.”

Republicans are not expected to make a major play in Maryland. Hogan, the last statewide Republican to be elected in Maryland, has already ruled out a run. And Maryland went to President Biden over former President Trump by more than 33 points.

The Democratic primary field isn’t necessarily closed off yet though. Democrats insist there’s specifically an opening for someone from Baltimore to jump in. But Baltimore County Executive Johnny Olszewski—one of the rumored names—has already bowed out and endorsed Alsbrooks instead.

Coincidentally, Trone has popped some not-so-subtle Baltimore imagery into his early ads, like literally sitting on a bench that says “Baltimore.”

“There’s so many dynamics at play here. And I think it’s gonna get tense and expensive, and you’ll probably have people jump in and then jump out,” said Feldman.

“And probably finally narrow to a final two or three by the end,” he said.