Republican U.S. Senate candidate Mike Sapraicone speaks at the New...

Republican U.S. Senate candidate Mike Sapraicone speaks at the New York State GOP nominating convention in Binghamton on Feb. 22.  Credit: Newsday/Keshia Clukey

Despite securing the coveted endorsement of former President Donald Trump, Republican Mike Sapraicone is facing not one, but two Republican primary challengers in his race to unseat Democratic U.S. Sen. Kirsten Gillibrand.

In a rare, public intraparty dispute that arose the same day Sapraicone won the New York State Republican Party nomination by an overwhelming margin, moderate Republicans are pitted against die-hard Trump loyalists who say the former president may have been misled into backing Sapraicone.

Nassau County Republican Party leaders are at the center of the skirmish. The county party still is reeling after Democrat Tom Suozzi defeated Republican Mazi Melesa Pilip in a special election in the 3rd Congressional District on Feb. 13. The seat had been held by expelled GOP Rep. George Santos.

Sapraicone opponents, largely from the MAGA wing of the party, take issue with donations he and his company, Squad Security, made to Democrats such as Attorney General Letitia James, who received a $1,000 contribution from Squad in 2022. Later that year, James brought a civil fraud case against Trump and recently won a $450 million judgment against the former president and his business.

Political experts say the fight highlights the fear among many in the New York Republican Party of angering Trump and his MAGA base. 

Nassau and state party officials say they're worried MAGA candidates will run primaries not just against Sapraicone, but also against GOP congressional candidates such as first-term Rep. Anthony D'Esposito (R-Island Park), who would have to spend money and other resources he otherwise could use fighting Democrats.

Former Rep. Pete King (R-Seaford), who was involved in discussions about the Senate race, said he was concerned a Sapraicone candidacy could prompt primary challenges “up and down the ballot.”

King told Newsday, “It was felt that Mike’s support for Democrats such as Tish James could’ve caused President Trump to get involved in an unnecessary primary that would’ve weakened candidates down the line.”

Less than a week after Sapraicone, of Glen Head, secured the GOP nomination, King suddenly called on him to exit the race because of the donation to James.

Then, Trump surprised many involved in the discussions with his endorsement of Sapraicone in a posting on his social media site Truth Social last Saturday, according to a source who was directly involved in deliberations about Sapraicone's candidacy.

“I have political vertigo from all these moves. I’ve never seen anything like this since I registered to vote in 1972,” Curtis Sliwa, the Guardian Angels founder and conservative talk radio host, told Newsday.

But King said, “As far as I know, Nassau County recognized that Sapraicone is the nominee for the party and the fact that Trump has endorsed him takes away the threat of any serious primary.”

The first signs of trouble for Sapraicone's candidacy appeared in early February.

At that point, state party leaders were discussing several possible candidates to challenge Gillibrand, including Sapraicone.

Josh Eisen, a business owner who co-chairs the George Pataki Foundation and ran for Congress in 2020, and Cara Castronuova, a conservative journalist for Newsmax and a former Gold Gloves boxing champion and celebrity fitness trainer on “The Biggest Loser” reality show, also were under consideration.

On Feb. 7, Pataki, a Republican who served as New York governor from 1995 to 2007, endorsed Eisen.

On Feb. 16, Republican operative and Trump ally Roger Stone Jr. announced his endorsement of Castronuova on the social media platform X, formerly known as Twitter. Trump loyalist and former New York City Mayor Rudy Giuliani endorsed Castronuova the next day.

State GOP Chairman Ed Cox was Sapraicone's biggest backer, according to GOP sources familiar with internal party politics. Cox touted him as the ideal candidate given his experience as a former NYPD detective, party donor and former business owner, one of the sources said.

Then social media posts against Sapraicone raised concerns among GOP officials.

On Feb. 19, Paul Ingrassia, a conservative political commentator who serves on the New York Young Republican Club’s Board of Advisors, called out Sapraicone on X for donating to Suozzi and Democrats. The post was shared by others such as Newsmax host and right-wing commentator John Tabacco.

The next day, Ingrassia posted a blog on the Substack online platform: “The New York State GOP Poised To Repeat Mazi Pilip Debacle By Nominating Another RINO Candidate To Challenge Gillibrand In Senate Race.”

County Republican chairs gathered at a hotel in Binghamton on Feb. 22 to choose their U.S. Senate nominee. That day, New York Young Republican Club President Gavin Wax on X accused Cox of “rushing to coronate anti-Trump RINO @MikeSapraicone as the official NYGOP Senate candidate today. Sapraicone was a donor to James’ 2022 campaign. Pathetic.”

Wax comes from the extreme right. In 2018, he wrote an article titled “We Are All Proud Boys Now,” and in 2022 he hosted white nationalists at the club's annual gala in Manhattan, according to news reports.

Sapraicone received 84% of the weighted convention vote, with Castronuova and Eisen each winning about 8%.

Also on Feb. 22, Giuliani on his WABC radio show and podcast noted Sapraicone's contributions to Democrats such as former State Sen. Todd Kaminsky (D-Long Beach).

“Didn’t we learn our lesson with Mazi?” Giuliani said. “You do not nominate for the Senate and expect to win, a guy who donated $1,000 to Letitia James in 2022.”

Sapraicone has donated to Republicans and Democrats in recent years, according to campaign filings. 

Sapraicone last year donated $5,000 to the National Republican Congressional Committee and more than $100,000 to the Nassau County Republican Committee between 2022 and 2023.

Sapraicone donated $2,500 to Kaminsky in 2018 and 2019 and more than $22,000 to Suozzi’s congressional campaign between 2021 and 2022. Suozzi represented the 3rd Congressional district from 2017 to 2023, before winning the seat again this year.

Sapraicone defends his political contributions to both parties.

“To be successful in business, you need to make sure that you take care of both sides of the aisle,” he told Newsday, adding “you need to understand the way politics are played.”

King laid out his case against Sapraicone on the WABC radio show “Sid and Friends in the Morning,” on Feb. 28.

“I think the right thing for him to do would be to withdraw from the race and if he doesn’t, I would ask President Trump to ask him to withdraw. There’s a real tipping point with Tish James who is launching a vendetta against President Trump … ,” King said.

Hank Sheinkopf, Manhattan-based political strategist who has worked for Republicans and Democrats, said he believes King's and Nassau Republican officials' move to distance themselves from Sapraicone was “all about offending Trump.”

“They [Nassau GOP] see Trump as being very vindictive and he is,” Sheinkopf said. “They want to play it safe to hold onto what they have and their game on the local level. But Trump’s intervention wouldn’t change that.” Sapraicone is “an Italian American, ex-cop — he fits the profile. He’ll still a win on Long Island no matter what.”

Nassau GOP Chairman Joseph Cairo did not respond to Newsday's requests for an interview.

Cox told Newsday he never asked Sapraicone to step down because of the donations to Democrats. “He’s the designated candidate of the party and the party has been behind him,” Cox said.

With Sapraicone fighting off criticism from his own party, Cox sought the endorsement of Trump, said GOP sources familiar with the matter.

Cox was “very influential in getting us on the same page with the president,” along with other Republican leaders, Sapraicone said. “It’s his job keeping the party together.”

Late last Saturday night, Trump posted on Truth Social: 

“Mike is a strong and successful person, and I look forward to working with him to take New York State away from the people who have destroyed it with hundreds of thousands of Migrants flowing in, and ruining our Schools, Hospitals, Parks, and increasing Crime many fold,” Trump wrote. “Good luck to Mike — He has my Complete and Total Endorsement!”

Not all party members are ready to rally around Sapraicone, however.

The day after Trump's announcement, Giuliani said on his radio show: “I do not believe that this Sapraicone guy was vetted properly before the president of the United States to get his endorsement.”

Rudy's son, Andrew Giuliani, a political commentator who ran unsuccessfully for New York governor in 2022, said “maybe [Trump] didn’t get the full information while making this endorsement.” Trump may not have been aware of Sapraicone’s donations to Democrats, particularly James, Andrew Giuliani told Newsday.

Officials with Trump's presidential campaign couldn't immediately be reached for comment.

Rudy and Andrew Giuliani’s are backing Castronuova in the GOP Senate primary on June 25.

Even with Trump's endorsement of Sapraicone, Castronuova told Newsday in an email her plans to run a primary “have not changed … I have had tremendous grassroots outreach from the base to help me with signatures because they know I am the only candidate that can beat Gillibrand. Maybe once President Trump sees more of me he will support me.”

Eisen could not be reached for comment, but he has posted campaign events on his social media since Trump's endorsement of Sapraicone.

Longtime Republican political consultant Dave Catalfamo said he thought Trump’s endorsement would have put the issue to bed.

“In this case, the author of MAGA has endorsed the party’s candidate,” Catalfamo said. “It’s kind of bizarre that we have a divide in the party over who’s more MAGA.”

Correction: Gavin Wax is president of the New York Young Republican Club. A previous version of this story misstated his title. 

Despite securing the coveted endorsement of former President Donald Trump, Republican Mike Sapraicone is facing not one, but two Republican primary challengers in his race to unseat Democratic U.S. Sen. Kirsten Gillibrand.

In a rare, public intraparty dispute that arose the same day Sapraicone won the New York State Republican Party nomination by an overwhelming margin, moderate Republicans are pitted against die-hard Trump loyalists who say the former president may have been misled into backing Sapraicone.

Nassau County Republican Party leaders are at the center of the skirmish. The county party still is reeling after Democrat Tom Suozzi defeated Republican Mazi Melesa Pilip in a special election in the 3rd Congressional District on Feb. 13. The seat had been held by expelled GOP Rep. George Santos.

Sapraicone opponents, largely from the MAGA wing of the party, take issue with donations he and his company, Squad Security, made to Democrats such as Attorney General Letitia James, who received a $1,000 contribution from Squad in 2022. Later that year, James brought a civil fraud case against Trump and recently won a $450 million judgment against the former president and his business.

WHAT TO KNOW

  • Despite former President Donald Trump's endorsement, Republican Mike Sapraicone is facing two GOP primary challengers in his race to unseat Democratic U.S. Sen. Kirsten Gillibrand.
  • In a rare, public intraparty dispute, moderate Republicans are pitted against die-hard Trump loyalists who say the former president may have been misled into backing Sapraicone.
  • Nassau GOP leaders are at the center of the skirmish. They still are reeling after their candidate Mazi Melesa Pilip lost to Democrat Tom Suozzi in 3rd Congressional District special election.

Political experts say the fight highlights the fear among many in the New York Republican Party of angering Trump and his MAGA base. 

Nassau and state party officials say they're worried MAGA candidates will run primaries not just against Sapraicone, but also against GOP congressional candidates such as first-term Rep. Anthony D'Esposito (R-Island Park), who would have to spend money and other resources he otherwise could use fighting Democrats.

Former Rep. Pete King (R-Seaford), who was involved in discussions about the Senate race, said he was concerned a Sapraicone candidacy could prompt primary challenges “up and down the ballot.”

King told Newsday, “It was felt that Mike’s support for Democrats such as Tish James could’ve caused President Trump to get involved in an unnecessary primary that would’ve weakened candidates down the line.”

Less than a week after Sapraicone, of Glen Head, secured the GOP nomination, King suddenly called on him to exit the race because of the donation to James.

Then, Trump surprised many involved in the discussions with his endorsement of Sapraicone in a posting on his social media site Truth Social last Saturday, according to a source who was directly involved in deliberations about Sapraicone's candidacy.

“I have political vertigo from all these moves. I’ve never seen anything like this since I registered to vote in 1972,” Curtis Sliwa, the Guardian Angels founder and conservative talk radio host, told Newsday.

But King said, “As far as I know, Nassau County recognized that Sapraicone is the nominee for the party and the fact that Trump has endorsed him takes away the threat of any serious primary.”

Signs of trouble

The first signs of trouble for Sapraicone's candidacy appeared in early February.

At that point, state party leaders were discussing several possible candidates to challenge Gillibrand, including Sapraicone.

Josh Eisen, a business owner who co-chairs the George Pataki Foundation and ran for Congress in 2020, and Cara Castronuova, a conservative journalist for Newsmax and a former Gold Gloves boxing champion and celebrity fitness trainer on “The Biggest Loser” reality show, also were under consideration.

On Feb. 7, Pataki, a Republican who served as New York governor from 1995 to 2007, endorsed Eisen.

On Feb. 16, Republican operative and Trump ally Roger Stone Jr. announced his endorsement of Castronuova on the social media platform X, formerly known as Twitter. Trump loyalist and former New York City Mayor Rudy Giuliani endorsed Castronuova the next day.

State GOP Chairman Ed Cox was Sapraicone's biggest backer, according to GOP sources familiar with internal party politics. Cox touted him as the ideal candidate given his experience as a former NYPD detective, party donor and former business owner, one of the sources said.

Then social media posts against Sapraicone raised concerns among GOP officials.

On Feb. 19, Paul Ingrassia, a conservative political commentator who serves on the New York Young Republican Club’s Board of Advisors, called out Sapraicone on X for donating to Suozzi and Democrats. The post was shared by others such as Newsmax host and right-wing commentator John Tabacco.

The next day, Ingrassia posted a blog on the Substack online platform: “The New York State GOP Poised To Repeat Mazi Pilip Debacle By Nominating Another RINO Candidate To Challenge Gillibrand In Senate Race.”

County Republican chairs gathered at a hotel in Binghamton on Feb. 22 to choose their U.S. Senate nominee. That day, New York Young Republican Club President Gavin Wax on X accused Cox of “rushing to coronate anti-Trump RINO @MikeSapraicone as the official NYGOP Senate candidate today. Sapraicone was a donor to James’ 2022 campaign. Pathetic.”

Wax comes from the extreme right. In 2018, he wrote an article titled “We Are All Proud Boys Now,” and in 2022 he hosted white nationalists at the club's annual gala in Manhattan, according to news reports.

Sapraicone received 84% of the weighted convention vote, with Castronuova and Eisen each winning about 8%.

Also on Feb. 22, Giuliani on his WABC radio show and podcast noted Sapraicone's contributions to Democrats such as former State Sen. Todd Kaminsky (D-Long Beach).

“Didn’t we learn our lesson with Mazi?” Giuliani said. “You do not nominate for the Senate and expect to win, a guy who donated $1,000 to Letitia James in 2022.”

Sapraicone has donated to Republicans and Democrats in recent years, according to campaign filings. 

Sapraicone last year donated $5,000 to the National Republican Congressional Committee and more than $100,000 to the Nassau County Republican Committee between 2022 and 2023.

Sapraicone donated $2,500 to Kaminsky in 2018 and 2019 and more than $22,000 to Suozzi’s congressional campaign between 2021 and 2022. Suozzi represented the 3rd Congressional district from 2017 to 2023, before winning the seat again this year.

Sapraicone defends his political contributions to both parties.

“To be successful in business, you need to make sure that you take care of both sides of the aisle,” he told Newsday, adding “you need to understand the way politics are played.”

Tightrope with Trump

King laid out his case against Sapraicone on the WABC radio show “Sid and Friends in the Morning,” on Feb. 28.

“I think the right thing for him to do would be to withdraw from the race and if he doesn’t, I would ask President Trump to ask him to withdraw. There’s a real tipping point with Tish James who is launching a vendetta against President Trump … ,” King said.

Hank Sheinkopf, Manhattan-based political strategist who has worked for Republicans and Democrats, said he believes King's and Nassau Republican officials' move to distance themselves from Sapraicone was “all about offending Trump.”

“They [Nassau GOP] see Trump as being very vindictive and he is,” Sheinkopf said. “They want to play it safe to hold onto what they have and their game on the local level. But Trump’s intervention wouldn’t change that.” Sapraicone is “an Italian American, ex-cop — he fits the profile. He’ll still a win on Long Island no matter what.”

Nassau GOP Chairman Joseph Cairo did not respond to Newsday's requests for an interview.

Cox told Newsday he never asked Sapraicone to step down because of the donations to Democrats. “He’s the designated candidate of the party and the party has been behind him,” Cox said.

The endorsement

With Sapraicone fighting off criticism from his own party, Cox sought the endorsement of Trump, said GOP sources familiar with the matter.

Cox was “very influential in getting us on the same page with the president,” along with other Republican leaders, Sapraicone said. “It’s his job keeping the party together.”

Late last Saturday night, Trump posted on Truth Social: 

“Mike is a strong and successful person, and I look forward to working with him to take New York State away from the people who have destroyed it with hundreds of thousands of Migrants flowing in, and ruining our Schools, Hospitals, Parks, and increasing Crime many fold,” Trump wrote. “Good luck to Mike — He has my Complete and Total Endorsement!”

Not all party members are ready to rally around Sapraicone, however.

The day after Trump's announcement, Giuliani said on his radio show: “I do not believe that this Sapraicone guy was vetted properly before the president of the United States to get his endorsement.”

Rudy's son, Andrew Giuliani, a political commentator who ran unsuccessfully for New York governor in 2022, said “maybe [Trump] didn’t get the full information while making this endorsement.” Trump may not have been aware of Sapraicone’s donations to Democrats, particularly James, Andrew Giuliani told Newsday.

Officials with Trump's presidential campaign couldn't immediately be reached for comment.

Rudy and Andrew Giuliani’s are backing Castronuova in the GOP Senate primary on June 25.

Even with Trump's endorsement of Sapraicone, Castronuova told Newsday in an email her plans to run a primary “have not changed … I have had tremendous grassroots outreach from the base to help me with signatures because they know I am the only candidate that can beat Gillibrand. Maybe once President Trump sees more of me he will support me.”

Eisen could not be reached for comment, but he has posted campaign events on his social media since Trump's endorsement of Sapraicone.

Longtime Republican political consultant Dave Catalfamo said he thought Trump’s endorsement would have put the issue to bed.

“In this case, the author of MAGA has endorsed the party’s candidate,” Catalfamo said. “It’s kind of bizarre that we have a divide in the party over who’s more MAGA.”

Correction: Gavin Wax is president of the New York Young Republican Club. A previous version of this story misstated his title. 

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