Kayleigh McEnany highlights Hillsborough GOP Lincoln Day dinner

McEnany, daughter of a prosperous South Tampa family and graduate of Academy of the Holy Names, is a former pro-Trump CNN commentator who joined the Trump campaign as press secretary in February.
Kayleigh McEnany, National Press Secretary for Donald J. Trump for President, speaks to supporters in Houston in September.
Kayleigh McEnany, National Press Secretary for Donald J. Trump for President, speaks to supporters in Houston in September. [ JUAN DELEON | ]
Published Oct. 31, 2019

A Tampa woman who’s had a meteoric rise in politics and punditry, currently national press secretary for Donald Trump’s re-election campaign, will headline a Hillsborough County Republican Party fundraiser next month, the party has announced.

Kayleigh McEnany, 31, daughter of a prosperous South Tampa family and graduate of Academy of the Holy Names, joined the campaign in February after working as spokeswoman for the Republican National Committee and as a pro-Trump CNN commentator.

Tickets for the Nov. 23 Lincoln Day dinner at The Event Factory will start at $100.

“She will deliver the REAL news concerning the President and his campaign that the ‘Fake News’ will never report!” said the party’s announcement.

McEnany became known for what Business Insider called “her combative style and polished demeanor” during the 2016 presidential race and has vociferously attacked “the fake news media” and the House impeachment process.

“Democrats KNOW they can’t beat @realDonaldTrump so they seek to remove him through an ILLEGAL COUP!” she tweeted last week.

She made headlines in August saying during a heated exchange with CNN’s Chris Cuomo that Trump has never lied to the public.

“He doesn’t lie. Guess who lies, the press lies,” she said.

McEnany graduated from Georgetown University and Harvard Law School and interned for Rep. Adam Putnam and Tom Gallagher’s 2006 gubernatorial campaign.

She has written a book on Trump’s political rise, The New American Revolution: The Making of a Populist Movement.

McEnany is the daughter of commercial roofing company owner Michael McEnany and Leanne McEnany. She’s married to Sean Gilmartin, a former All-American Florida State University pitcher who has played with the New York Mets and is now a free agent.

One potential complication to the plans: McEnany told a Republican women’s group in a Sept. 28 speech that she was 7½ months pregnant.

She didn’t respond to email and social media messages seeking an interview, nor did local GOP officials.

Toledo kicks off re-elect

State Rep. Jackie Toledo, R-Tampa, kicked off her re-election campaign this week with a fundraiser featuring dozens of prominent local Republicans and GOP legislative leaders.

Jackie Toledo
Jackie Toledo

The big-time kickoff, plus a substantial campaign fund Toledo has already raised, looks like an attempt to stave off a possible Democratic challenger.

Toledo doesn’t yet have a filed or announced opponent, but Democratic insiders are seeking to recruit one, focusing on philanthropic fundraiser and civic activist Julie Jenkins, a former Tampa City Council candidate.

Spend your days with Hayes

Subscribe to our free Stephinitely newsletter

Columnist Stephanie Hayes will share thoughts, feelings and funny business with you every Monday.

You’re all signed up!

Want more of our free, weekly newsletters in your inbox? Let’s get started.

Explore all your options

Toledo has already raised $106,157 and garnered substantial favorable publicity from being House sponsor of a popular texting-while-driving ban. Her South Tampa-based District 60 leans Republican.

But she may not feel entirely safe. Trump won the district by less than 1.5 percent in 2016. In 2018, Toledo held off a challenge from first-time candidate Debra Bellanti by just under than 5 percent, after outspending Bellanti 4-1.

Further down the ballot, D60 is more reliably Republican, prosperous and business-oriented, said Democratic consultant Barry Edwards.

Cruz, Valdes breach healed

State Rep. Susan Valdes, D-Tampa, held her re-election campaign kickoff this week with a long list of prominent Democratic backers headed by state Sen. Janet Cruz, D-Tampa.

But the two have had differences in the recent past.

In 2018, Cruz publicly withdrew her endorsement of Valdes just before a contested primary because of support Valdes received from charter and private school interests, which also previously backed Valdes as a school board member. Cruz has sought to champion of public education.

Sen. Janet Cruz, D-Tampa, on the floor of the Florida Senate. [SCOTT KEELER   |   Times]
Sen. Janet Cruz, D-Tampa, on the floor of the Florida Senate. [SCOTT KEELER | Times]

The two are longtime friends, but, “I can't stand by her decision to accept support from the voucher industry,” Cruz tweeted at the time. Valdes still won easily.

Valdes, meanwhile, apparently maintains her favorable attitude toward charter and private school interests. She is continuing to receive substantial campaign contributions from those interests, and was one of the few House Democrats to vote last spring for hotly debated legislation expanding the voucher program.

Rep. Susan Valdes, D-Tampa. [The Florida Channel]
Rep. Susan Valdes, D-Tampa. [The Florida Channel]

Valdes is so far unopposed, but public school exceptional education teacher Laurie Rodriguez-Person of Tampa, a Democrat, has said she plans to file.

Cruz didn’t return messages to discuss the change.

Besides Cruz, Valdes’s kickoff cohosts include the entire Tampa City Council, all six Hillsborough Democratic legislators and a dozen or so other prominent local Dems.

Chronister PAC has splashy kickoff

Friends of Chad Chronister, the PAC supporting the Hillsborough sheriff, will hold a fundraiser Friday night at Eddie V’s Prime Seafood, including Boyz II Men and Chronister’s father-in-law, former San Francisco 49ers owner Eddie DeBartolo and his five Super Bowl trophies.

Hillsborough County Sheriff Chad Chronister. [MONICA HERNDON   |   Times]
Hillsborough County Sheriff Chad Chronister. [MONICA HERNDON | Times] [ Times 2019 ]

Admission ranges from $2,500 per couple to $50,000 for VIP access, 12 dinner tickets and photos with the singers and DeBartolo.

Chronister, a Republican, has little opposition but looks to be playing safe in a blue-trending county. He has courted and even contributed to the local Democratic Party, which isn’t supporting his Democratic opponent, Gary Pruitt.

Chronister hasn’t yet filed, but the PAC had raised $135,301 as of September.

Contact William March at