Maryland's Senate race reopens old wounds

BALTIMORE — On a crisp fall afternoon in late October, dozens of people sat at the edge of their seats in Baltimore Unity Hall, eager to hear from the day’s marquee draw: Yusef Salaam.

A member of the exonerated “Central Park Five,” Salaam, who is Black, spent seven years wrongfully imprisoned and even targeted for the death penalty by Donald Trump in 1989. Now a rising star in Democratic politics since his election to the New York City Council, Salaam was an obvious lure for an audience interested in criminal justice reform.

The other speaker taking the stage with him was considerably less obvious: Rep. David Trone, the magnate of the nation’s largest alcohol retailer Total Wine and More who is running for Maryland's open Senate seat.

Trone, 68, stood out as one of the only white men in a nearly all-Black room. But as he spoke, he began recounting an arrest for white collar crimes decades ago, an anecdote he punctuated with adding that he and Salaam “traveled down roads that weren’t that dissimilar.” The Democratic congressman later added: “I was also justice-impacted,” a reference to this decades-old brush with the law, for which he served no prison time.

Winning a Senate race in a state like Maryland, one of the most diverse in the nation, requires coalition building with groups of voters that may not be natural or obvious fits for their campaigns. But few are attempting to execute an effort as ambitious as what Trone is attempting to pull off.

As he embarks in the final weeks of one of the toughest Democratic Senate primary fights in the nation, the man who routinely finds himself on listicles touting the wealthiest members of Congress, is pitching himself to voters as a champion of criminal justice reform and advocate of giving second chances to those who’ve transition out of the penal system, while using his fortune to forge alliances among Black activists and local politicians. He’s also leaned on his connections to people like Salaam to assure audiences that his intentions are genuine.

“I’ve got to give props to David for what he’s doing,” Salaam said at the event. He thanked Trone for his commitment to this issue, including hiring more than 1,400 formerly incarcerated people in his stores. He is “putting his money where his mouth is,” said Salaam.

The biggest Democratic Senate primary in the country

Having well-respected surrogates is key for Trone if he is going to get past his chief rival for the nomination, Angela Alsobrooks, the top executive from a powerful and wealthy county. She aims to make history as the state's first African-American senator and bring some much-needed gender diversity to Maryland’s federal delegation, which is currently made up entirely by men. Alsobrooks also has the backing of virtually every Democrat on the state and federal level.

Both campaigns have placed a premium on winning over voters in Baltimore, a city marred by decades of violent crime. Whoever wins Baltimore will likely win the nomination and face off against Larry Hogan, the state’s popular former Republican governor, who recently announced that he too would be seeking the seat of retiring Sen. Ben Cardin (D-Md.).

In a hypothetical matchup against Hogan, Trone is tied with the former governor and Alsobrooks trails Hogan by 7 points, according to an Emerson College poll released last month. Trone's campaign also shared internal polling with POLITICO that showed him leading Alsobrooks by 21 points, with solid leads among Black and white Democratic voters in the Baltimore area.

That Alsobrooks has so far struggled to gain traction with Black voters in Baltimore does not come as a surprise to state Sen. Jill Carter, who represents parts of the city.

“She’s taking for granted that every Black woman is just going to support her. And she's also feeling like, ‘What do I need you for? I got [Maryland Gov.] Wes Moore,'” said Carter, who backs Trone because she said Alsobrooks never reached out to her.

The Alsobrooks campaign counters that she not only has the backing of Moore, the nation's only Black governor who made the rare choice to endorse in the primary, but also has the backing of Maryland’s House Speaker Adrienne Jones, the first Black woman to hold the post.

Hanging over the entire primary fight — and the more narrow debate over who has more appeal to the state’s Black voters — are the deep intraparty fissures that erupted the last time the state had an open Senate seat.

In 2016, then-Reps. Chris Van Hollen, who is white, and Donna Edwards, who is Black, were vying for the nomination to replace retiring Democratic Sen. Barbara Mikulski. The party establishment backed Van Hollen, long considered a Democratic golden boy, breaking what had been a dead heat in the race. Edwards lost the primary by 19 points.

The Maryland primary has obvious long-term implications for the Senate too.

Never before has the Senate had more than one Black woman at a time. Sen. Laphonza Butler (D-Calif.), the only Black woman in the Senate now, is holding the seat that will likely eventually go to Rep. Adam Schiff (D-Calif.). That leaves Democrats with two potential options, Alsobrooks, and Delaware Rep. Lisa Blunt Rochester, who is the heavy favorite to win in the fall.

Alsobrooks, who currently holds the job of Prince George's County executive, has fundraised well. She has $3 million on hand according to her latest campaign finance report, but she is being overrun by Trone, who has already dropped more than $34 million of his own money into the race.

Because of her financial disadvantage, Alsobrooks has leaned on a strategy that paints Trone as out of touch.

In her first campaign ad of the cycle, she railed that the average age of a U.S. senator is 64 with a net worth of $16 million. “That’s not me,” she said, casting herself as a member of the so-called sandwich generation — juggling the challenges of providing for her college-aged daughter and her aging parents.

At a campaign event in February at a hotel rooftop bar overlooking the East Baltimore skyline, Alsobrooks took a not-so-subtle stab at Trone’s core message, suggesting he might not be self-aware. “I believe in the second chance,” she said. “But it is so disturbing to me … when this country has never given so many of us even the first chance at success.”

Trone, a three-term congressman who represents one of the whitest and westernmost districts in the state, was born in Cheverly, Maryland, in the county that his opponent represents. By age 11, his father moved the family to a farm near the state line with Pennsylvania, but the family fell on hard times and lost it. Trone eventually got into Wharton business school and built up his beer and wine business with his brother Robert. Total Wine and More now operates in 28 states and has become the largest wine retailer in America.

Eventually, Trone got the itch to enter politics, though he lost his first run for Congress to Rep. Jamie Raskin (D-Md.) in 2016. He dropped $12 million of his own money into the effort. He ran again in 2018, replacing Rep. John Delaney, a Democrat, who was, like Trone, one of the richest members of Congress during his tenure.

Trone learned to become a crafty campaigner and says he “loves to fight.” And it’s clear that his game plan is to try and drive a wedge between Alsobrooks and the Black community. He has counterpunched the attacks she has made against him by turning her previous role as a state prosecutor into a political liability. His goal is simple: raise concerns among voters in Maryland, which ranks fourth in the nation for prisoners convicted as children, and tie that dubious statistic to someone who comes from the world of locking people up.

“There's not a chance that I'm not going to win over someone who is a prosecutor with all the things that prosecutors do,” Trone said in an interview.

Trone’s disdain for prosecutors is still deep and festering. It stems from the early 1990s when he, his wife and his brother faced a bevy of charges that included tampering and criminal solicitation that would have amounted to over 100 years of incarceration if convicted.

He insists the charges were an effort from overzealous prosecutors trying to put pressure on him to take a plea deal. At the time, Trone was trying to use the purchase power of multiple business locations to bring down retail prices for alcohol purchases. He would then offer those discounts to customers. But owning more than one liquor store was illegal at the time. So Trone had his wife own one store, his brother another and the rest he was looking to buy would be owned by friends and associates.

The Pennsylvania state attorney general didn’t buy the workaround and went after him for trying to undercut his competitors.

Trone eventually shook the charges rather than taking that plea deal. But he acknowledges it cost him millions in legal fees. He concedes he never could have fought them if he weren’t white and had access to money and credit.

“I also had the education to understand what I was charged with, which is wrong, and I was going to win,” Trone told POLITICO. “So I will talk about my privilege all the time. And that's one of the reasons why we're so driven on this [issue].”

Since being elected to Congress, Trone has pushed for legislation that would help citizens returning home from prison to find gainful employment and restore health care benefits — including a month of mental health services after a return to civilian life.

Trone’s has gone on to partner with the ACLU, which named its criminal justice center after him — following a $15 million donation he and wife gave in 2015 to study recidivism and sentencing reform. He’s also a founding member of the Second Chance Task Force in Congress, which pushes bipartisan solutions to improving employment access to people returning from the justice system.

A daunting choice for Democrats

Even as Trone has positioned himself to the left of Alsobrooks on criminal justice and the Israel-Hamas conflict, there's very little policy daylight elsewhere between the two.

The major question facing Democrats, rather, is who do they believe is best suited to face off against Hogan: the wealthy, white self-funding congressman or the potentially history-making Black woman?

Hogan left office with a sky-high approval rating — including an 81 percent rating among African Americans in the state. And who the party thinks is best suited to tackle that challenge will provide a telling window into their values and priorities.

“It’s a serious threat,” said Will Jawando, a Democratic councilmember in Maryland’s Montgomery County who initially sought the nomination himself, regarding the general election matchup.

Jawando, who backs Alsobrooks, laments that Hogan has changed the Senate map. Every dollar Democrats spend defending the Senate seat in Maryland is one they won't spend to protect incumbents like Sens. Sherrod Brown in Ohio or Jon Tester in Montana.

“My old boss Sherrod Brown, you know, I’ve got to send my money to him,” he said. “I think that is obviously a concern for national Democrats and Chuck Schumer.”

For now, the DSCC is remaining neutral, though it did not shut the door to getting involved in the final stretch of the primary.

Trone knows Hogan's entry makes his wealth appealing. And his team hasn’t shied away from the fact that his deep pockets are a selling point.

“David is fully committed to doing whatever it takes to win the primary and the general,” a Trone spokesperson told POLITICO.

Alsobrooks, for her part, has leaned into the issue of abortion to distinguish herself— particularly after Hogan fumbled an answer on it during a CNN interview last month. She said she's the “only candidate in this race who's never compromised on abortion rights." And Emily’s List, which is backing her candidacy, has accused Trone of funding abortion bans by pointing to political donations his company has made to Republicans over the years, including in Texas and North Carolina where abortion is largely illegal.

Trone said donations to Republicans are just the cost of advancing his liquor business in red-leaning states. He also said it shows a willingness to work across the aisle.

“The establishment doesn’t want an outsider,” Trone told POLITICO. “The politicians pick winners and losers, they never picked me, so I don’t expect them to pick me here.”

Some of Trone’s biggest endorsements have come from out of state, including top House Minority Leader Hakeem Jeffries of New York. Trone even got the backing of Rep. Jonathan Jackson (D-Ill.), the son of a civil rights icon.

Perhaps the biggest endorsement Trone locked up was from the state's largest teachers union, which boasts a membership of 75,000. He’s also got the support of some officials from Alsobrooks’ own county, showcasing some political savvy to earn the backing of Latino leaders who took Alsobrooks to task for failing to hire anyone of Hispanic descent to a high-ranking position early on in her tenure as county executive.

But if he ultimately is going to win the primary, it won't just be through money and endorsements alone — it will be because he managed to convince voters that, despite his prodigious wealth, he best relates to them.

Trone leans into a campaign style that puts a premium on intimate, smaller meet-and-greets with voters as he has crisscrossed the state. His aim is to show, despite his wealth, he’s a relatable down-to-earth guy who grew up on a chicken and hog farm and the son of an alcoholic father.

During a recent visit to Mera Kitchen Collective, an eatery set up in a rowhouse along Calvert Street in Baltimore that adds a 20 percent livable wage fee to every order, Trone donned a black apron and took orders from a preset menu that included grilled chicken kielbasa, tacos de carne asada and lentil soup.

“All we know is that $3.63 is outrageous,” said Trone, nodding to Maryland’s current tipped worker minimum wage during his turn at the “server for an hour” event that was co-sponsored by the advocacy group One Fair Wage. He pledged to vote to raise the federal minimum wage to $20 an hour if elected.

But even as he ingratiates himself, Trone's wealth is always just below the surface.

Asked by one attendee if he had ever waited tables before, Trone flashed a wry smile, telling the man he never did, but he’s “a great cashier [and] a very good forklift driver," roles he has stepped into as the owner of his multimillion-dollar retail chain.