Big money, attacks punctuate hyper-local judge race with major statewide implications

As Joe Bilby tells it, he grew frustrated. So frustrated that he decided to run for judge.

In early 2021, Franklin Circuit Chief Judge Philip Shepherd issued an opinion temporarily blocking the GOP-controlled General Assembly’s effort to change state emergency laws to circumvent Democratic Gov. Andy Beshear’s office and allow for more schools and businesses to stay open.

Bilby, who is Republican Commissioner of Agriculture Ryan Quarles’ top staff attorney, said that he then decided to give Shepherd a run for his money. The Franklin Circuit Court post, which runs on eight-year terms, is one of the most important for matters of state government – often the first courtroom where disputes with statewide implications are adjudicated.

“When I read it, I thought two things: one, he’s going to get reversed by the Supreme Court. Two: any judge who would issue an opinion like that, with statewide effect on the lives and liberties of every Kentuckian, should not remain in office,” Bilby recalled. “It’s never easy to take on an incumbent, especially in a judicial race. They almost never lose, in fact. But somebody had to do it and I thought, ‘well, I’ll do it.’”

Now Bilby says he has knocked on well over 10,000 doors and feels good about his odds of beating Shepherd, an established community figure who’s held the bench for 16 years, despite Bilby only having lived in the community for the past six years.

If campaign spending is any indicator, Bilby may be within striking distance. Not only has he raised a lot of money for a judge race, but Shepherd has amassed more than twice as much in response - a sign that the campaign takes Bilby’s challenge seriously. The race has attracted hundreds of thousands of dollars on both sides in what some say is the most expensive race Franklin County has ever seen, and is the most expensive race, in proportion to the voting population, this election cycle. One out-of-state Super PAC has spent an extra $200,000 in attack ads against Shepherd in the hopes of boosting Bilby.

Bilby is not alone in his frustration with Shepherd. Much of the state’s Republican establishment has expressed a similar sentiment – with former GOP governor Matt Bevin and the state Republican party taking aim at him – particularly after they’ve gained full control of the state legislature, and many of them are backing Bilby’s effort. That includes a PAC aligned with Senate Minority Leader Mitch McConnell.

Though the post is local, Franklin Circuit – as the court presiding over the capital in Frankfort – oversees many cases dealing with challenges to legislation as well as other state government matters.

Senate President Robert Stivers even hosted a fundraiser for Bilby in Frankfort during the General Assembly’s legislative session.

Franklin County is traditionally a Democratic stronghold. There are 25,266 registered Democrats and just 12,440 Republicans there as of earlier this month. Democrats largely dominate local elected office, but Republicans have seen some good news higher up the ballot: Trump won there by slim margins in 2016 and 2020, making Franklin County the most “purple” county in Kentucky, and U.S. Rep. Andy Barr carried it by seven percentage points.

Bilby is a registered Republican and Shepherd is a registered Democrat – both of their donor lists reflect this to some extent – but Bilby has been more vocal about politically branding his campaign, in his case as a “constitutional conservative.” He has also touted endorsements from socially conservative groups like Kentucky Right to Life.

The last time Shepherd ran in a contested race, in 2006, just over 15,000 Franklin Countians voted and he beat former county attorney Jim Boyd 72% to 28%.

While incumbent judges have an already baked-in advantage, as Bilby acknowledged, knocking off Shepherd in particular is no easy task. As Frankfort insiders will tell you: Shepherd is a household name.

Phillip Shepherd has been on the bench for nearly 16 years, and was entrenched in the Frankfort community before then. He grew up in town, where his father was a prominent Methodist minister. That kind of connection still matters a lot in a county of just 51,541 people, according to former Frankfort Mayor Bill May, who lays claim to the longest tenure of any Frankfort mayor in history.

“There’s some truth that if people run only once every eight years, their names aren’t out in front of the public as much, but he is someone who’s grown up and lived here, went to school here,” May said. “I think there’s a lot of people who recognize that and that is something that has always been important in Franklin County politics.”

And as a judge, Shepherd’s name has been in the local paper “virtually every week,” according to Frankfort State-Journal Publisher Steve Stewart.

He’s also widely respected in Kentucky’s legal circles, at least according to former Kentucky Supreme Court Justice Bill Cunningham.

“Phil Shepherd has a great reputation among all judges – whether they be conservative judges or progressive judges. He’s done good work,” Cunningham said.

Though the Fair Courts America Super PAC spent $200,000 in an effort to boost Bilby, Shepherd has significantly outraised his opponent. He’s brought in more than $500,000 compared to Bilby’s total of about $190,000. He’s also got some help from an in-state PAC called Liberty & Justice For Kentucky, which is largely boosting incumbent Kentucky Supreme Court Justice Michelle Keller against GOP Rep. Joe Fischer, but has chipped in about $80,000 in digital and radio ads for Shepherd. That group is funded by the oftentimes Democrat-aligned Kentucky Educators’ PAC as well as Christy Brown of the Brown-Forman fortune.

So how can Bilby, who moved to Frankfort only six years ago, make up the difference? He says hard work, as evidenced by his door-knocking operation. Some of his campaign materials and tactics indicate that a strong offense attacking Shepherd’s record is the way to go.

Attacks, defenses and texts

Just a month before the Nov. 8 election, many Franklin County voters got a text.

“It’s true… as reported by the Frankfort State Journal… Judge Phillip Shepherd sent a child sex offender back into our community,” the text read.

The conversational tone of the text was accompanied with a video critical of Shepherd’s sentencing in the case of Martin Klemens. Klemens was caught by undercover investigators attempting to have sex with a 15 year-old girl in Frankfort. To the chagrin of a prosecutor working the case, Shepherd sentenced the man to just under two years of home incarceration.

The text and ad came from Fair Courts America, a Super PAC that published plans to fund the Franklin Circuit race, as well as two challengers in Kentucky’s 2nd and 6th Supreme Court Districts, with a total of more than $1.6 million. Fair Courts America is run by a former Republican candidate for Senate in Illinois, Doug Truax. Of late, the bulk of its funding has come from another Super PAC called Restoration PAC. Restoration PAC’s recent cash infusions have come from Illinois logistics businessman, and heir to the Schlitz brewing fortune, Richard Uihlein who’s given them well over $10 million since May 2021.

The Bilby campaign had been beating the drum on the Klemens case as well. They featured details of the case on a website they created called firephilshpeherd.com.

“As a result (of Shepherd’s sentencing) Martin Klemens served his sentence in home incarceration, on the couch with full access to the internet. When I tell that to voters, they immediately grasp the problem of a judge who doesn’t follow the law,” Bilby said.

Central to the ad, and Bilby’s negative messaging on Shepherd, is that the incumbent judge has failed to “follow the law.”

This phrasing has gotten under the craw of many Shepherd supporters. It also got some serious pushback from Larry Cleveland, longtime Franklin County Commonwealth’s Attorney, who penned an opinion piece in the Frankfort State Journal calling the ad “false, misleading information.”

“It is easy, and at election time convenient, for a judicial candidate to claim he will follow the law. It is often difficult, however, to properly apply the law in a practical, sensible, justice-serving manner, as was done in this case,” Cleveland wrote, adding that the Department for Probation and Parole stated that Klemens’ risk of re-offending was zero.

Shepherd, when asked to respond to the Bilby camp’s criticisms over the Klemens case, referred to Cleveland’s op-ed. Days after the op-ed was published, the Shepherd campaign bought a half-page ad republishing the piece in the State Journal. It also aired television commercials countering the ad.

Though Franklin Circuit Court is best known in the state for its effect on public policy, Stewart said that the focus on a criminal case – as opposed to the civil case that launched Bilby’s interest in running for the seat – makes sense given that many Franklin County voters are more interested in local matters.

“I really thought they would go pretty hard after Shepherd on what some say is a bias toward Democrats, though I never thought that was a particularly fair criticism,” Stewart said. “But not everyone is a political junkie and many voters are not tuned into the power struggle between Republicans in state government and Judge Shepherd.”

As for Shepherd himself, he finds the criticism that he doesn’t “follow the law” – that includes reference to his being overturned on the emergency laws case – to be disingenuous.

“I think the record speaks for itself. I’ve presided over approximately 12,000 cases. They have found a handful that they are criticizing me about. I think that’s a line of criticism that simply has no substance. You can repeat it a thousand times, but that simply doesn’t make it true,” Shepherd said.

Though the Klemens ad certainly drew attention across the county, Bilby has been the target of a fair share of attacks, too.

Shepherd’s campaign recently released a video ad of a woman urging voters to “reject Joe Bilby” because of his anti-abortion stance, as detailed in an interview with the pastor of a local church best known for its refusal to close its doors during the height of the COVID-19 pandemic.

And, as in Shepherd’s case, an outside group is also chipping in on attacking Bilby. It’s not a Super PAC, though. It’s the Kentucky Democratic Party (KDP).

Since news broke of Stivers’ fundraiser for Bilby in March, the KDP has sent out six press releases critical of Bilby. Most recently, they have focused on his work hours – or lack thereof – during campaign season. An open records request by KDP staff showed that Bilby only worked two full days in April, three in March and five full days in May.

“While most Kentuckians have to actually show up and work hard to keep a job, Quarles gives Bilby special treatment to keep his six-figure job without showing up. No one can say they’re fiscally conservative when they pay a political appointee six figures in taxpayer funds to campaign instead of work,” KDP Chair Colmon Elridge said in a release.

Bilby defended the timesheets, saying that he had used up his accrued vacation time, and since then has been using leave without pay to campaign for judge.

“What these critics really object to is that I’m trying so hard to win this election,” Bilby said.

How much will partisan politics matter?

Bilby’s perceived partisanship is a point of criticism from the Shepherd campaign, which previously touted that it has accepted no donations from politicians - though after a complaint from the Bilby campaign, it refunded a few donations made by Democratic local elected officials.

Bilby is quick to point out that, for all of the hand-wringing about the GOP backing his campaign, many “professional Democrats” are throwing their support behind Shepherd.

It’s true. Some of the state’s most prominent former elected Democrats – ex-governor Brereton Jones, former lieutenant governor Crit Luallen and former Louisville mayor Jerry Abramson, among others – have all donated to Shepherd this cycle.

But Shepherd, in response to Bilby’s argument that such “professional Democrats” are aligning behind him as much as Republicans are backing Bilby, pointed out that many in the GOP are supporting him as well.

“The difference is that in my case, I’ve got bipartisan support. I’ve got contributions from prominent Republicans. Republican lawyers, Republican former public officials. That’s something he (Bilby) can’t point to,” Shepherd said.

That’s also true. Former Republican cabinet official and prominent businessman Jim Host, former GOP speaker of the house Jeff Hoover, longtime GOP state lawmaker Bob Heleringer, and Jim Deckard, general counsel for Republican governor Ernie Fletcher, all donated to Shepherd.

Bilby said in an interview that his campaign branding would not make his judicial tenure particularly partisan

“When I say I’m a constitutional conservative, I’m not promising to deliver conservative outcomes. I’m saying that I take seriously and wish to conserve our proper constitutional order, and how it regards judges. I’m not running to be a Republican version of Phillip Shepherd, and anyone who thinks that’s the case is going to be disappointed when I’m judge,” Bilby said.

Aside from blue and red, another divide that may play a role in the race is that between city and county.

Anna Marie Rosen, an outgoing Frankfort city commissioner who supports Shepherd, said that signs for his reelection dominate her downtown neighborhood. But out in the county, that’s not the case.

“(Shepherd) looks dominant in the city of Frankfort, but then when you go out in the country more and see the Bilby signs along with other Republican signs. I think that he’s going to have a problem in those areas, so I think it’s gonna be really close,” Rosen said.

Studler agreed, adding that he thinks that if Bilby’s “conservative” message gets out to the outer parts of the county enough, then he’s got a good shot at taking Shepherd down.

Stewart added that Shepherd’s likely constituency among Franklin Countians consisted of “Democratic partisans and apolitical people who vote based on name recognition,” as well as people of all political stripes “who just kinda like the guy” based on their run-ins with him over the 50-plus years Shepherd’s been in town.

Bilby’s base, Stewart said, is a combination of Republican loyalists – no longer an insignificant chunk of Franklin County – and those that are convinced by the campaign’s portrayal of Shepherd as “soft on crime.”

“If you step back and look at that objectively, you think the numbers favor Shepherd – but a lot of money is being spent and clearly ads can influence voters. So, which side is more motivated? That’s a great question,” Stewart said.

Stewart noted also that it’s possible that media and close observers of the race are exaggerating the extent to which partisan politics play into the race.

“Franklin County is no longer a place where you can put a ‘D’ by your name and count on 65% of the vote,” Stewart said. “Now, how many of those emerging conservative voters are as in tune with the party politics of this race? Probably not as many as we think.”