Party-recruited candidates seek seats currently held by members who defied GOP demands, despite lack of voter signal for changes
In 2023, David DiCarlo lost his Douglas County school board race with just 23% of the vote. Two years later, he’s heading a Republican party committee that recruited four hand-picked candidates for November’s election. All are running to replace sitting conservative board members who defied GOP demands not to support placing tax measures on the ballot.
How the Douglas County GOP responded to electoral defeat by seizing control of candidate recruitment reveals a three-year power struggle over which candidates are willing to toe the party line.
The confrontation began in November 2022 when conservative board members Mike Peterson, Christy Williams, Becky Myers, and Kaylee Winegar joined with their more progressive colleagues to unanimously place a mill levy override [MLO] and a $450 million bond on the ballot.
The four board members represented a majority on the seven-member board and could have blocked the measures. Both failed by roughly nine percentage points.
The following year, the entire board again placed tax measures on the ballot, including a $66 million MLO and a revised $484 million bond. Voters approved the MLO with 54% support while again rejecting the bond, albeit by just four points. The approved measure funded 7-9% average teacher raises, security staffing, and pay parity for educational assistants and bus drivers.
But 2023 also exposed a deeper problem for GOP leadership. Conservatives were running for school board without party permission. While David DiCarlo ran as the only GOP-endorsed candidate, three other conservatives formed the “BEST slate” and ran without the party’s blessing. Andy Jones, Jason Page, and Maria Sumnicht ran independently. In one race, both DiCarlo and Page faced progressive candidate Braid Gieger, splitting the conservative vote. Meek won. DiCarlo received just 23% of the vote, and Jones received 29%
The messy outcome triggered finger-pointing on both sides. According to a November 2023 column in Complete Colorado, the party had voted earlier that year to oppose any tax increases. After BEST slate candidates supported the tax measures, one candidate renounced her party’s endorsement after being accused of misleading the party, while another withdrew his endorsement request after being told he would never receive one.
A $490 Million Ultimatum
On July 16, 2024, weeks before the board would vote to once again ask voters to approve a proposed bond measure, the Douglas County GOP formally condemned the school board in a public resolution for even considering it.
The resolution criticized the board for placing “a nearly $500 million bond on the ballot” and alleged that “pro-taxation groups, such as Invest in DCSD, that rely on underhanded allegiances with Democrats and far-left Teacher Union allies” were supporting the tax measures through developer donations.
The resolution also demanded the board reject any tax measures “that would result in such taxes being added to the ballot” or face the consequences.
When board members Christy Williams, Tim Moore (who replaced Mike Peterson after he resigned in late 2023), Kaylee Winegar and Becky Myers defied the ultimatum and endorsed the bond measure, voters approved it with 59.54% support in a county where registered Republicans outnumber Democrats more than two-to-one.
After these defeats, party leaders established their own centralized candidate selection process for the 2025 school board race, when four incumbent board members would be up for reelection. Williams, Moore, Winegar, and Myers were all eligible to run again, but minutes from Douglas County GOP meetings show the party began recruiting new candidates as early as May 2025.
The process included formal interviews, video recordings and confidentiality agreements for party officials. It featured 45-minute conversations designed to “identify candidates who demonstrate integrity and follow-through, not those who shift positions post-election.”
Executive Committee members who wanted to observe interviews were required to sign a Code of Conduct prohibiting them from recording sessions or sharing information outside the committee.
As chair of the Non-Partisan Committee, DiCarlo described the 2025 process in a public Facebook post. Responding to a commenter’s critique that “this was not about endorsing candidates, it was about choosing them,” DiCarlo replied in part that “we interview Republicans. Not Democrats. Not the unaffiliated. Republicans. We interviewed every Republican to put their name forward. Your problem is what? That the party endorsed candidates? Get used to it we will be involved in every race from dog catcher on up.”
DiCarlo also promised to fire and publicly humiliate whomever leaked the private executive committee notes
To be clear, the party’s description of its “selection” process did not prevent other candidates from running, but made clear from the outset that only party-approved Republicans would receive endorsements and with them access to campaign resources.
In fact, two of the four GOP-endorsed candidates, Matt Smith and Dede Kramer, registered as Republicans during the recruitment process, apparently in response to the party’s requirement that only registered Republicans would be considered.
Smith registered as a Republican on April 2, 2025, just before the Non-Partisan Committee began conducting interviews. He said he changed his party affiliation “several months before I knew about the DCGOP endorsement process” because “it is difficult to run in Colorado as an unaffiliated candidate.”
Dede Kramer registered as a Republican on July 9, 2025, one day before the Executive Committee endorsed her campaign. She said party registration was not required “that I know of” and that she found out about the interview process “from the other candidates” just days before deciding to participate. “That interview was the first day I met anyone from the DCGOP,” said Kramer. Steve Vail and Keaton Gambill were registered Republicans throughout the period.
Gambill disputed characterizations that the GOP recruited the candidates. “We have heard through the rumor mill that we were hand-selected by the GOP to run, which is false,” he said. “The four of us decided to run individually through community involvement and then applied for the endorsement.” However, Smith said the GOP “sent out emails to a community group I was involved in to see if anyone was interested in an endorsement.”
Clearing the Path
With the county party’s selection process underway, Tim Moore, Kaylee Winegar, Christy Williams, and Becky Myers all announced they wouldn’t seek reelection.
Moore said his decision was based on “work schedules and the fact that I am the primary caregiver for my mother and her needs require more time now.” He added, “The DC GOP and any position they had on me as a board member played no role in my decision not to re-run for the DC Board of Education. In fact, they were respectful and waited until I had made a decision before they proposed other candidates.”
Kaylee Winegar cited in her announcement “evening commitments” and a desire to “be more present for my family” after four years of service.
“I chose not to run because the amount of time I am gone in the evenings is more than my family had anticipated and they just want mom home. The GOP had nothing to do with my decision,” Williams said in response to inquiries. “Serving this community in this capacity has been a humbling experience. I am incredibly proud of this district,” she added.
Moore also reflected on his time on the board.
“I very much enjoyed my time serving the staff, students and parents of Douglas County. I learned a great deal about the inner workings and challenges in education and I’m very proud of our school district, staff, leaders, superintendent and students for what they have accomplished and continue to prioritize. It’s a special and strong school district and I will miss them.”
The departure of all four incumbents simultaneously is unusual. Nationally, school board incumbents win reelection at rates exceeding 80%.
Praising the Board They’re Replacing
The recruited candidates now publicly praise the board the party condemned.
“I want make sure that we continue the great momentum that the current conservative board and that Erin (Kane) is doing and that we can just keep that momentum going,” Vail said in an October radio interview he and Smith gave together to 630 KHOW.
“I’ve seen what happens when the school board does not listen to parents,” Smith said, without specifying which past actions he was referring to.
During the interview, both candidates outlined traditional Republican positions that echo the same conservative themes their predecessors had campaigned on unsuccessfully.
“This is about biological boys entering female-only sports in their spaces, and so we want to make sure that we protect them… we want to fight hard to keep the biologic boys out of their spaces, because it really makes women and girls uncomfortable to be forced into those spaces,” Smith said when addressing transgender policies.
“We are not voting for a CBA [collective bargaining agreement]… It’s going to create an adversarial relationship between the teachers and the administration… This will not be about students or outcomes,” Smith said on the topic of a potential teachers’ union.
All four GOP-endorsed candidates now express support for the bond and mill levy measures the party had opposed. “The taxpayers just passed a recent bond and MLO,” Smith said. “As a fiscal conservative I maintain that we should be good stewards of that money.” Vail said the measures “are providing a great deal of value to the school district.”
Neither candidate mentioned why the current board members are leaving office or referenced the GOP’s previous condemnation of their actions.
GOP Response
DiCarlo directed inquiries to Douglas County GOP Chairwoman Robin Webb. Webb stated that the party has endorsed in nonpartisan school board races since 2009 to help voters “know which candidate on their ballot is the Republican who most closely aligns with the Republican party platform.”
Webb said that “though the task of conducting interviews may be delegated to a committee, it is the entire Executive Committee that ultimately votes on whether or not to endorse in a race.”
Webb did not respond to questions about whether current board members were invited to interview for reelection, whether only registered Republicans were eligible for consideration by the Non-Partisan Committee, or whether the committee’s role was to recruit new candidates or endorse among existing candidates.
On Nov. 4, voters will choose between two competing slates for four open seats in what represents a test of the GOP’s strategy to replace board members who listened to voters rather than party demands.
The Common Sense DCSD slate, endorsed by the Douglas County GOP, includes Smith in District B, Gambill in District D, Kramer in District E and Vail in District G. The committee’s website emphasizes “parental rights,” “curriculum transparency,” and a promise to “fight to preserve girls-only teams, restrooms, and locker rooms.”
The Community’s Voice, Community’s Choice slate includes Kyrzia Parker in District B, Tony Ryan in District D, Clark Callahan in District E and Kelly Denzler in District G. This slate emphasizes candidates’ education experience and promises to make the district “accountable to the people, not politics.”
School board elections in Colorado are nonpartisan, with candidates appearing on the ballot without party affiliation listed. Voters will see only the candidates’ names, with no indication that two GOP-endorsed candidates registered as Republicans during the selection process, or that all four were chosen by party leaders whose candidates were rejected by voters just two years earlier.
The Douglas County School District serves approximately 68,000 students across Castle Rock, Parker, Highlands Ranch and surrounding communities.
