Healdsburg woman brings presidential candidates to Sonoma County

Iron Horse Vineyards CEO Joy Sterling can remember a time when the sight of a presidential candidate schmoozing in Sonoma County didn't necessarily turn heads.

This would have been in the 1980s, when former U.S. Rep. Doug Bosco was hosting the likes of Dick Gephardt and Walter Mondale, when, in Bosco's words, “it was a lot easier to get together 50 of my best friends.”

Sterling's parents, Barry and Audrey Sterling, went to Stanford University with William Rehnquist, the former chief justice of the U.S. Supreme Court who died in 2005, and retired associate justice Sandra Day O'Connor, and were later regular hosts of big-name political figures, Joy said.

Despite hosting O'Connor in 2014, the elderly Sterlings don't entertain as much as they once did. Neither does Bosco, leaving a vacuum for the type of power and perseverance necessary to attract big-name candidates to a spot that's not quite San Francisco and not quite Napa.

In the past couple of years, Sonoma County has experienced a revival as a fundraising springboard for presidential candidates thanks to Healdsburg's Barbara Grasseschi. Three 2020 hopefuls have made, or plan to make, stops in Sonoma County this year. A fourth could come by the end of the year, and each visit has been arranged by Grasseschi, who owns Puma Springs Vineyards with her husband, Tony Crabb, who also donates to candidates.

“There was no one organizing people up here,” Grasseschi said. “If (residents) ever wanted to see them to ask a question, they'd have to drive to San Francisco. Now there's a chance to do that here.”

This week, presidential candidate Julian Castro, the secretary of Housing and Urban Development from 2014 to 2017, will make a fundraising stop in Windsor. Before the year is out, Grasseschi wants to bring South Bend, Indiana, Mayor Pete Buttigieg to the area.

“If you look back historically, on the one hand, it's new; on the other hand, it's a little bit of a throwback to my parents' generation,” Sterling said.

Why Sonoma County?

Sterling, the chairwoman of the California Democratic Party Rural Caucus, said the visits are important to put Sonoma County - and the issues important to its residents - on the map.

She's partial to rural topics, and said despite outside appearances, Sonoma County - particularly the western half - embodies that rural lifestyle.

“The prevailing wisdom is that the road to victory is through the rural communities of the nation,” Sterling said. “It's great for Sonoma County to be a voice and a representative for those specific interests and concerns. That gives us the opportunity, once (the candidates) come talk to us, we get to hold them to account.”

You have to look back three decades to get to such a rash of visits from presidential hopefuls, including former Senator and Vice President Mondale, former House Majority Leader Gephardt and President Ronald Reagan, who also announced his candidacy for California governor in Healdsburg. The Sterlings, who settled in Wine Country in the late 1970s, had a hand in many of the visits.

Bosco was involved, too, Sonoma County Supervisor James Gore said.

Crabb said via text message that Grasseschi is the key driver of the couple's political work, and Grasseschi said her husband's role is purely as a donor. In that case, she is responsible for the resurgence, including what Gore called a growing number of visits from all levels of government.

“It's not just about fundraising; it's about organization,” Gore said. “Somebody has to call campaigns and give them a reason to care about your area. Do they care about the North Bay and the North Coast? It's not on their radar unless we put it on their radar.”

Then, as now, money is a big draw.

President Donald Trump wasn't in San Francisco or Los Angeles last week because he agrees with the politics, after all. He raised $15 million in his two-day trip through the state, according to CNN.

And former Vice President Joe Biden, who's scheduled to be in San Francisco on Oct. 3 for a fundraiser hosted by Sen. Dianne Feinstein and her husband, Richard Blum, will likely see donations from Sonoma County residents. But pulling strings to host him in Sonoma County would mean raising more than the $500,000-plus he's likely to pocket in San Francisco.

“(At this point in the race), you'd have to raise substantially more money to get their attention,” said Bosco, who's an investor in Sonoma Media Investments, which owns The Press Democrat. “They're campaigning all over the country - primarily raising money all over the country. Time is literally money for them.”

The exception is candidates lower in the standings. Castro is polling at 1%, and will be in Windsor on Thursday for a two-hour fundraising appearance.

Bosco put it less charitably.

“If they don't stand a chance, they're easier to attract,” he said.

But before Castro, Grasseschi and Crabb hosted Sens. Kirsten Gillibrand, D-New York, and Kamala Harris, D-California, with Harris being near her best polling position when she came to Hotel Healdsburg in July for a fundraiser. Just two weeks before her visit, Harris was the No. 2 candidate, according to Gore, who helped with that visit, said they raised about $150,000 for Harris.

That Harris is also a California senator could have served as a motivation for her visit and for her local donors, Bosco said.

They hosted Sen. Elizabeth Warren, D-Massachusetts, a little more than a year ago, but that was part of a fundraiser for Democratic women candidates and Warren hadn't yet announced, Sonoma County Supervisor Shirlee Zane said. Grasseschi said they hosted Gillibrand twice.

Four 2020 candidates already is pretty good, said Gore, who has received donations from Grasseschi and Crabb. And there's more to come: Work is underway to bring in Buttigieg, Grasseschi said.

Herman J. Hernandez, who is part of the host committee for Castro, credited the couple for Sonoma County's growing spotlight.

“They have been the movers and shakers of being able to get the North Bay recognized to get these candidates to come across the Golden Gate Bridge to the North Bay and into Sonoma County,” Hernandez said.

Credit where due

Sonoma County Democratic Party Chairwoman Pat Sabo pointed to the pair as being instrumental in that growing recognition. Ditto for Bosco and even Republican John Jordan, owner of Jordan Winery and a longtime GOP power broker.

Alexandra Acker-Lyons, political director for Electing Women Bay Area, the group behind the Gillibrand visit - at least publicly - directed any questions about presidential visits to Grasseschi.

Grasseschi said it started with the Wine Country chapter of Electing Women Bay Area, a group dedicated to raising money for female candidates for state and national office. The organization has grown in the past couple of years, and includes men and women, Grasseschi said.

“Two years ago, there's no way we would have been able to do this, and raise the money we have,” Grasseschi said.

Grasseschi and Crabb bought Puma Springs Vineyards in 2000. Grasseschi was a sales and marketing executive most recently with Cisco Systems. Crabb, an engineer born in England, has spent time in South Africa, Scotland and Silicon Valley. On campaign finance reports, each has the same occupation listed: “farmer.”

“When we moved here, we had pretty active careers,” Grasseschi said. “We weren't exactly going to sit on the front porch and knit. We love being engaged.”

Grasseschi and Crabb were big bundlers for President Barack Obama, raising up to $500,000 for his 2012 reelection, according to, and they continue to spend about a quarter million or more individually on national races - presidents and political action committees - today.

Individual donations to presidential campaigns are limited to $2,800. So Grasseschi has donated $2,800 to Gillibrand and another $2,800 to Harris. She also donated $600 to climate hawk and Washington Gov. Jay Inslee, $750 to Buttigieg and $2,000 to Rep. Eric Swalwell, D-Castro Valley. Crabb has donated $2,800 to Gillibrand, too. But he donated $300 to Swalwell. Of those, only Harris and Buttigieg remain candidates for the Democratic nomination.

Making it rain donations fits in with an overarching pattern Sterling gave voice to, saying donors are getting involved because of Trump, and that involvement is attracting candidates.

“There are Sonomans who are engaged in wanting to mark the end of an error, and I mean E-R-R-O-R,” Sterling said, spelling it out.

Without that motivation - or without Grasseschi - Sonoma might be back in another lull, watching Napa County play host, as it did for Hillary Clinton during her run for president in 2016.

There's some disagreement among people with money, power and influence as to why that is.

Bosco thinks there's plenty of money in Sonoma County to bring in big-name candidates, including Biden.

“Sonoma is still somewhat unsophisticated in the fundraising scheme of things,” Bosco said. “Considering there's a tremendous amount of wealth in Sonoma and Napa counties, I don't think you have people that routinely raise money for major national candidates.”

Jordan would disagree about the “tremendous amount of wealth” part, saying Sonoma County is no Palm Beach, Florida, Atherton or Palo Alto.

“In many ways, Sonoma County is really a backwater,” Jordan said.

Putting money on it

Grasseschi agreed that Sonoma County can be a bigger player. She has visions of potentially hosting the eventual Democratic nominee, saying she's hopeful, and, “You never know.”

“I think there's potential here,” Grasseschi said. “I think we're gradually moving in the direction of raising our economic support for really great candidates. But it's a process. Somebody needs to organize and make it happen.”

Bosco and Jordan talk of attracting candidates to Sonoma County - or anywhere - in practical terms.

“Six to eight months ago, almost any of the candidates would have been willing to show up in Sonoma County for a brief period of time if you could raise them $100,000,” Bosco said. “The closer people are to looking like they might win, the more they demand and the more you have to raise to get them to come to an event locally.”

As the stakes get higher, and the field narrows, the amount of money needed to compete on a national level grows dramatically, forcing candidates to more carefully guard their time.

Jordan said Sonoma County is more likely to get Democratic presidential candidates, although Sen. Marco Rubio visited in the run-up to 2016. In either case, though, candidates will stay closer to San Francisco if they can, Jordan said.

“The true heavyweights look at it the same way,” said Jordan, who is also a Fox News contributor with a studio at his house. “They have a dollar figure that they need to pull down for them to spend X number of hours.”

To date, Sonoma County has given a little more than $400,000 to presidential candidates, giving Harris more than a quarter of that total. Sen. Bernie Sanders, I-Vermont, who made a campaign stop in Cloverdale in 2016 - more rally than fundraiser - sits in second place county-wide, according to Federal Election Commission data through June 30, the latest available report.

Castro has just five donations from four Sonoma County residents totaling $980.80, a number that's bound to increase in the coming days following his fundraising stop in Windsor.

Grasseschi said she would vote for a different campaign finance system if she could.

“In the meantime, we'll work to support (candidates) in the system we live in,” Grasseschi said.

If there's a less cynical silver lining to Grasseschi's efforts, there are Sonoma County residents willing to highlight it. Hernandez said it's inspiring to see national candidates here. He knows Castro isn't likely to win, but he said he's excited to hear Castro's story, which Hernandez said speaks to the Latino community.

Gore said it was cool taking his 7-year-old daughter to meet Harris, a senator, presidential candidate and powerful woman. The fundraisers, too, give donors an opportunity to look candidates in the eye and judge candidates' authenticity and integrity, Gore said.

Sabo said the visits inject excitement for volunteers - the grassroots people who aren't writing $2,800 checks, the ones who “do what they can.”

“When you see a presidential candidate, somebody who has been on that debate stage, somebody who is delivering a strong message that they believe in, it gives you hope,” Sabo said. “It gives you something to believe in.”

You can reach Staff Writer Tyler Silvy at 707-526-8667 or at On Twitter @tylersilvy.

Editor's note: This article has been updated to clarify Barbara Grasseschi's leading role in bringing candidates to Sonoma County. Additionally, information about Dianne Feinstein's political title and Bernie Sanders' 2016 visit to Sonoma County has been corrected.

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