Will Rollins was dismissed in 2022. Now, he might secure a Democratic majority.
Democratic organizations are investing millions in support of his rematch against Republican Rep. Ken Calvert in the district encompassing Palm Springs.
TroibNews 
**PALM SPRINGS, California** — Will Rollins faced off against the longest-serving California Republican in Congress two years ago, with many in the Democratic Party establishment viewing him as a longshot candidate who had to navigate the race independently.
Fast forward two years, and the Democratic Party is now actively supporting Rollins as a rising star.
The substantial financial support flooding into his rematch against Republican Rep. Ken Calvert highlights the Democrats' determination to flip the inland Southern California district as they seek to regain a House majority. Over $6 million has been poured into TV advertising by the party and its allies. Rollins, a former federal prosecutor, has raised an impressive $11.5 million, greatly surpassing the approximately $4.6 million spent by Democrats in the previous cycle.
Current polling indicates that Calvert and Rollins are neck-and-neck in what has become one of the nation's most closely watched and expensive battlegrounds, as both campaigns inundate the district with advertisements and teams of canvassers.
House Democratic Caucus Chair Rep. Pete Aguilar acknowledged that, while the district is one of the “toughest races on the board” for Democrats, Rollins is a valuable asset. “Will Rollins, I tell folks, I think is the best candidate we have in the country,” Aguilar stated.
Excitement around Rollins has grown since he came within about four percentage points of defeating Calvert as a first-time candidate in 2022. Elle Kurpiewski, political director for the Democratic Headquarters of the Desert, noted that volunteers are inspired by the idea that a Democratic majority could hinge on outcomes in the Coachella Valley desert. “This is no longer a possible, this is a very possible. He’s got name recognition now,” Kurpiewski remarked while taking a phone break at a volunteer operation in Cathedral City.
In response to Rollins' impressive fundraising, Republicans have ramped up their spending, with Calvert's vulnerability becoming a growing concern. During a rally in the Southern California desert, former President Donald Trump encouraged the audience to support Calvert: "Everybody needs to get out and vote for Ken."
As Rollins' fundraising efforts have gained traction, Republican PACs, including the Congressional Leadership Fund, have increased their investments. Calvert now benefits from approximately $9.5 million more in resources from outside groups compared to 2022, aided by a new super PAC established by former Speaker Kevin McCarthy, which has allocated $300,000 to attack Rollins.
Republican advertisements characterize Rollins as an “extreme” and “dangerous” progressive, attributing the state’s high living costs and crime rates to him and the Democrats. Conversely, Democratic ads depict Calvert as a self-serving ally of Trump who opposes abortion and LGBTQ+ rights.
Although Democrats have excelled in fundraising, the Republicans hold certain advantages. The GOP has about a 4,900-voter registration edge, and this is the only competitive swing seat in California that Trump won in the 2020 election, albeit by a slim margin. Traditionally, the party also enjoys stronger turnout in the Inland Empire region.
However, the district is no longer the solidly red bastion it once was, having been reconfigured into a purple battleground during California's last redistricting. This newly drawn district includes the progressive, LGBTQ-friendly Palm Springs alongside the more conservative suburbs of Riverside County, east of Los Angeles.
In 2022, Rollins, a former assistant U.S. attorney focused on national security, received little external support during his campaign. At that time, national Democratic groups withdrew from the costly Los Angeles media market, leaving candidates like Rollins without needed advertising resources.
Reflecting on his previous solitary campaign effort, Rollins made a lighthearted comment while meeting with firefighters' union leaders. “I was listening to a lot of Enya afterwards,” he joked.
The recent influx of funds for both Rollins and Calvert has manifested in advertising across the competitive Los Angeles media market. This financial boost has also enabled a more robust grassroots campaign; the California Democratic Party opened an additional field office aiming to enhance voter turnout in the Palm Desert area, and Calvert has set up an office nearby.
Earlier this year, First Lady Jill Biden visited the Palm Springs area for a fundraiser to bolster Rollins and other Democratic candidates, an upscale event co-hosted by former California Sen. Barbara Boxer and singer Barry Manilow.
While the Democratic Party aims to increase turnout in the district's more liberal areas, Rollins is actively courting independent and conservative-leaning voters in the district's western side, situated in Calvert's traditional stronghold. His campaign headquarters is localized in Corona, a suburban area defined as red-leaning.
In his advertisements, Rollins positions himself as a moderate and highlights his connections to the Republican Party, mentioning that his grandparents were Republicans and that he had worked for former GOP Governor Arnold Schwarzenegger, despite being a lifelong Democrat. He frequently showcases his law enforcement background and advocates for increased local funding for fire and police services.
Calvert works to challenge this moderate branding by labeling Rollins as a liberal who is “soft on crime.” His television ads attempt to connect Rollins with crime rates and California's high living costs, issues that resonate with voters, framing Rollins as a puppet for Democrats like Governor Gavin Newsom and former House Speaker Nancy Pelosi. “The California dream has turned into a nightmare,” Calvert said at an October rally with Trump, pointing to high gas prices and housing costs.
Calvert aims to leverage his seniority within California’s GOP House delegation, emphasizing how he has utilized his role on the House Appropriations Committee to secure funding for critical projects in the rapidly growing district.
Rollins, however, has turned Calvert’s lengthy tenure into a critique. Now 40, Rollins has highlighted the age difference by sharing childhood photos from 1992—the year Calvert first entered Congress—and has cast Calvert, 71, as a career politician who has leveraged his position for personal gain.
LGBTQ+ rights feature prominently in this election, particularly as Calvert seeks support from conservative-leaning older men in the LGBTQ+ haven of Palm Springs. Throughout much of his career, Calvert opposed marriage equality and other pro-LGBTQ+ measures, including hate crime protections and transgender rights. Although he claims his views have changed, Rollins, who is gay, argues that Calvert's transformation is a strategic move to gain votes after Palm Springs was included in his district.
“The people in Riverside County want somebody who is not focused on culture war bullshit,” Rollins stated in an address to supporters at a Palm Desert door-knocking event.
Alongside Rollins were Lisa Middleton, a trans woman campaigning for the state Senate, and Christy Holstege, a bisexual Assembly candidate. Their campaigns have garnered support from national LGBTQ+ organizations and affluent LGBTQ+ retirees in Palm Springs.
Calvert has sought to compensate for Rollins' advantage on the eastern side of the district by establishing a campaign office in Palm Desert and highlighting endorsements from the Log Cabin Republicans, the largest organization of gay Republicans in the U.S.
In interviews, Calvert has dismissed Democratic critiques of his LGBTQ+ record and opposition to abortion rights as distractions from more pressing issues. “Those are settled issues in California,” he asserted. “Those things aren’t going anywhere in a state like ours.”
Melanie Mason and Jessica Piper contributed to this report.
Olivia Brown contributed to this report for TROIB News
Fast forward two years, and the Democratic Party is now actively supporting Rollins as a rising star.
The substantial financial support flooding into his rematch against Republican Rep. Ken Calvert highlights the Democrats' determination to flip the inland Southern California district as they seek to regain a House majority. Over $6 million has been poured into TV advertising by the party and its allies. Rollins, a former federal prosecutor, has raised an impressive $11.5 million, greatly surpassing the approximately $4.6 million spent by Democrats in the previous cycle.
Current polling indicates that Calvert and Rollins are neck-and-neck in what has become one of the nation's most closely watched and expensive battlegrounds, as both campaigns inundate the district with advertisements and teams of canvassers.
House Democratic Caucus Chair Rep. Pete Aguilar acknowledged that, while the district is one of the “toughest races on the board” for Democrats, Rollins is a valuable asset. “Will Rollins, I tell folks, I think is the best candidate we have in the country,” Aguilar stated.
Excitement around Rollins has grown since he came within about four percentage points of defeating Calvert as a first-time candidate in 2022. Elle Kurpiewski, political director for the Democratic Headquarters of the Desert, noted that volunteers are inspired by the idea that a Democratic majority could hinge on outcomes in the Coachella Valley desert. “This is no longer a possible, this is a very possible. He’s got name recognition now,” Kurpiewski remarked while taking a phone break at a volunteer operation in Cathedral City.
In response to Rollins' impressive fundraising, Republicans have ramped up their spending, with Calvert's vulnerability becoming a growing concern. During a rally in the Southern California desert, former President Donald Trump encouraged the audience to support Calvert: "Everybody needs to get out and vote for Ken."
As Rollins' fundraising efforts have gained traction, Republican PACs, including the Congressional Leadership Fund, have increased their investments. Calvert now benefits from approximately $9.5 million more in resources from outside groups compared to 2022, aided by a new super PAC established by former Speaker Kevin McCarthy, which has allocated $300,000 to attack Rollins.
Republican advertisements characterize Rollins as an “extreme” and “dangerous” progressive, attributing the state’s high living costs and crime rates to him and the Democrats. Conversely, Democratic ads depict Calvert as a self-serving ally of Trump who opposes abortion and LGBTQ+ rights.
Although Democrats have excelled in fundraising, the Republicans hold certain advantages. The GOP has about a 4,900-voter registration edge, and this is the only competitive swing seat in California that Trump won in the 2020 election, albeit by a slim margin. Traditionally, the party also enjoys stronger turnout in the Inland Empire region.
However, the district is no longer the solidly red bastion it once was, having been reconfigured into a purple battleground during California's last redistricting. This newly drawn district includes the progressive, LGBTQ-friendly Palm Springs alongside the more conservative suburbs of Riverside County, east of Los Angeles.
In 2022, Rollins, a former assistant U.S. attorney focused on national security, received little external support during his campaign. At that time, national Democratic groups withdrew from the costly Los Angeles media market, leaving candidates like Rollins without needed advertising resources.
Reflecting on his previous solitary campaign effort, Rollins made a lighthearted comment while meeting with firefighters' union leaders. “I was listening to a lot of Enya afterwards,” he joked.
The recent influx of funds for both Rollins and Calvert has manifested in advertising across the competitive Los Angeles media market. This financial boost has also enabled a more robust grassroots campaign; the California Democratic Party opened an additional field office aiming to enhance voter turnout in the Palm Desert area, and Calvert has set up an office nearby.
Earlier this year, First Lady Jill Biden visited the Palm Springs area for a fundraiser to bolster Rollins and other Democratic candidates, an upscale event co-hosted by former California Sen. Barbara Boxer and singer Barry Manilow.
While the Democratic Party aims to increase turnout in the district's more liberal areas, Rollins is actively courting independent and conservative-leaning voters in the district's western side, situated in Calvert's traditional stronghold. His campaign headquarters is localized in Corona, a suburban area defined as red-leaning.
In his advertisements, Rollins positions himself as a moderate and highlights his connections to the Republican Party, mentioning that his grandparents were Republicans and that he had worked for former GOP Governor Arnold Schwarzenegger, despite being a lifelong Democrat. He frequently showcases his law enforcement background and advocates for increased local funding for fire and police services.
Calvert works to challenge this moderate branding by labeling Rollins as a liberal who is “soft on crime.” His television ads attempt to connect Rollins with crime rates and California's high living costs, issues that resonate with voters, framing Rollins as a puppet for Democrats like Governor Gavin Newsom and former House Speaker Nancy Pelosi. “The California dream has turned into a nightmare,” Calvert said at an October rally with Trump, pointing to high gas prices and housing costs.
Calvert aims to leverage his seniority within California’s GOP House delegation, emphasizing how he has utilized his role on the House Appropriations Committee to secure funding for critical projects in the rapidly growing district.
Rollins, however, has turned Calvert’s lengthy tenure into a critique. Now 40, Rollins has highlighted the age difference by sharing childhood photos from 1992—the year Calvert first entered Congress—and has cast Calvert, 71, as a career politician who has leveraged his position for personal gain.
LGBTQ+ rights feature prominently in this election, particularly as Calvert seeks support from conservative-leaning older men in the LGBTQ+ haven of Palm Springs. Throughout much of his career, Calvert opposed marriage equality and other pro-LGBTQ+ measures, including hate crime protections and transgender rights. Although he claims his views have changed, Rollins, who is gay, argues that Calvert's transformation is a strategic move to gain votes after Palm Springs was included in his district.
“The people in Riverside County want somebody who is not focused on culture war bullshit,” Rollins stated in an address to supporters at a Palm Desert door-knocking event.
Alongside Rollins were Lisa Middleton, a trans woman campaigning for the state Senate, and Christy Holstege, a bisexual Assembly candidate. Their campaigns have garnered support from national LGBTQ+ organizations and affluent LGBTQ+ retirees in Palm Springs.
Calvert has sought to compensate for Rollins' advantage on the eastern side of the district by establishing a campaign office in Palm Desert and highlighting endorsements from the Log Cabin Republicans, the largest organization of gay Republicans in the U.S.
In interviews, Calvert has dismissed Democratic critiques of his LGBTQ+ record and opposition to abortion rights as distractions from more pressing issues. “Those are settled issues in California,” he asserted. “Those things aren’t going anywhere in a state like ours.”
Melanie Mason and Jessica Piper contributed to this report.
Olivia Brown contributed to this report for TROIB News
