A Complete Timeline Of Ron And Casey DeSantis' Relationship

With the 2024 presidential election looming, things are starting to heat up in the world of politics. It appears it'll be a showdown between President Joe Biden and former President Donald Trump once again, but there's a wildcard this time — Florida Governor Ron DeSantis. There's widespread speculation that Ron has a real chance of winning the Republican presidential nomination, which means the 2024 election might well see DeSantis facing off against Biden.

Ron and Trump used to be buddies, but lately, it's clear that their relationship has soured. Ron is trying to recruit Trump's supporters, and the Financial Times even went as far as to call him "Donald Trump with brains." Whether that will be a good thing remains to be seen. Political strategist Myra Adams told BBC that Ron "doesn't have an easy-going personality," but that's something his wife, Casey DeSantis, seems to be able to handle just fine. The couple has been married since 2009, and Casey has been a steady presence throughout her husband's political career. 

Before she was Florida's First Lady, Casey was a TV reporter, and many cite her early career experience as one of the reasons Ron's political career thrived. "She knows how the media works. She knows how to capitalize on things. And she has done an excellent job so far of guiding him on these kinds of ways to get national attention," political analyst Jim Clark told Click Orlando. Intrigued? Read on for a complete timeline of the couple's relationship.

During his presidency, Donald Trump reportedly spent the equivalent of almost a year on the golf course, and even the global pandemic did not keep him from engaging in this leisurely activity. Clearly, the golf course is a great place to ignore your problems, but it's also an excellent place to meet new people because this is where Ron DeSantis met his wife, Casey DeSantis way back in 2006.

The day Casey met her future husband, she barely noticed him at first. She was hellbent on bettering her swing, and she noticed a bucket of balls close to Ron that would help her do just that. "As I'm looking over behind me, Ron is over there. He thinks I'm looking at him. I was really looking at the balls. Long story short we started to talk and that's how we met," Casey told First Coast News. In an interview with Piers Morgan for the New York Post, Ron admitted that he genuinely thought Casey was checking him out at first, but then admitted, "I think in fact she was looking at the balls. I do think I was wrong!"

During an interview with SiriusXM's Patriot, the couple revealed that they technically went on their first date right after they met on the golf course. They really hit it off, and Casey even admitted that she thought Ron looked like Tom Cruise's doppelganger at the time.

After the fated golf course meet-up, Ron DeSantis and Casey DeSantis started dating, and he knew early into the relationship that he'd met the woman he wanted to marry. "I was like 'This is different' and I made sure to court her," he told the New York Post.

During a chat with Governor Kim Reynolds for the Freedom Blueprint, Ron revealed that he was in the Navy while he and Casey were dating and that he got deployed to Iraq shortly after they started their courtship. It was during his time away that he got clarity about their relationship. "I told myself, as soon as I get back from Iraq, I'm proposing," he said. "And if you know my wife, that wasn't a very difficult judgment for me to make," he added. Ron got down on one knee six months after they first met, and Casey said yes without hesitation.

There wasn't a lot of fanfare surrounding the proposal. Ron told the New York Post that he proposed the old-fashioned way. "I took her to a nice little resort in Florida and we were out on the balcony, and I had a nice ring, and I just dropped to the knee and asked her," he revealed. A friend of Casey's told Insider that Ron was a perfect match for her because he treated her as an equal. "I think he was the type of person she was waiting for," they added.

Yup, Ron and Casey DeSantis really got married at Disney World, and according to Ron, it was all his wife's idea. Her family are Disney enthusiasts, and Ron just kind of rolled with it. During his chat with Governor Kim Reynolds for the Freedom Blueprint, Ron revealed that he left all the planning for the wedding up to Casey. He told her, "I'll show up, you do what makes you happy."

Then Casey presented the idea of a Disney World wedding to a dumbstruck Ron. "Does Disney do weddings?" he recalled asking her, wondering if the wedding was supposed to happen at Cinderella's castle. But as it turns out, Disney World actually has a chapel available to rent for weddings, so Casey went ahead and did just that. "One of the other great things was the fact that they did a lot of the planning for you. So it was a – I could just show up, sort of thing," Casey told SiriusXM's "Patriot" (via Daily Mail).

While Ron was fine with having his wedding at the theme park, he did have one condition — he didn't want any Disney characters present at the ceremony. "[I just drew] one line in the sand — no Mickey or Donald Duck at our wedding," Ron told the crowd at the Freedom Blueprint. He wanted the wedding to still look like a traditional one, and Casey was good with that. " [I]t was really a lot of fun," she told "Patriot."

In 2011, Ron DeSantis released his first book, titled, "Dreams from Our Founding Fathers: First Principles in the Age of Obama." The title was technically a rip-off of former President Barack Obama's memoir, which was titled "Dreams from My Father: A Story of Race and Inheritance." To add insult to injury, the cover of Ron's book was almost an exact replica of Obama's. Needless to say, Ron's book was a critical look at the Obama administration and all it stood for.

Ron dedicated the book to his wife, Casey DeSantis, but that's the only personal touch readers will find inside its pages. While many thought the book might read like a memoir, it was anything but a personal look into Ron's life. Instead, it gave readers a very clear idea of his political views and ideals. Within its pages, he accuses Obama of "redistributing wealth" and criticizes the Democratic Party for being "[inclined] to spend other people's money, a lust to control the lives of their fellow citizens and desire to perpetuate oneself in office." He also called Obama cocky and claimed that the former president "made outlandish claims about his own significance as an individual."

Needless to say, the book was nothing short of controversial and probably left many Democrats seething.

While former President Donald Trump and Hillary Clinton were battling it out for the presidency in 2016, Ron and Casey DeSantis were readying themselves for the birth of their first child. Their baby girl, Madison, was born in late November, likely a few weeks after Trump won the election.

Ron took to Facebook to share the big news on November 24, 2016. "Casey and I are so happy to welcome our daughter Madison, who was born 7 lbs, 7 ounces and very healthy," he wrote, adding, "Mom and baby are doing great. What a blessing!" The post was accompanied by pictures of their sleeping newborn wrapped in blankets with a beanie decorated with a massive bow on her head. Ron also added two pictures of him and Casey with Madison. Both parents were beaming in the snaps.

The comment section was a mixture of congratulations and angry comments from people who were enraged that Ron and Casey backed Trump's attempts to abolish the Affordable Care Act (ACA), on which millions of Americans depend for their healthcare needs. Many voiced their anger at the couple for receiving the best medical care available, while other working-class citizens would have to suffer from sub-par care once the ACA was abolished. "Hope to hell your daughter grows up to be a hell of a lot smarter than you are!" one enraged person commented.

In January 2018, Casey DeSantis was seven months pregnant with her and Ron DeSantis' second child. This did not, however, deter her from showing up at his campaign's kickoff rally to put in a good word before her husband took to the stage. She presented her husband as a man who is running for governor because he really cares about people. "Nowadays we see so many people who run for the wrong reasons," Casey said, adding, "They're not running for the people." She continued to assure the crowd that Ron is running for the right reasons and "to do great things, not to be someone." Casey also said that she has infinite respect for her husband and that he is "a man of integrity and honor." She also expressed her pride in being able to be by his side.

Two months after her speech, Casey gave birth to a baby boy. Ron excitedly took to Twitter to announce the news, posting snaps of him and his wife with their newborn. "Casey and I are blessed to welcome our son Mason Joseph DeSantis. 8lbs, 4oz and very strong! Both baby and mom are doing great," Ron wrote.

If you saw Ron DeSantis' 2018 endorsement ad (the one that was practically an ad for Donald Trump too), it's probably still seared into your mind. For those not in the know, the ad featured Ron's whole family, but Casey did most of the talking, informing the audience of the stand-up man her husband is while footage of Ron playing with his kids flashed across the screen.

The ad shows Ron playing with his daughter while encouraging her to "build the wall." Next, footage of Ron reading Trump's "The Art of the Deal" to his baby son flashes across the screen with the words "Pitbull Trump Defender" appearing at the bottom. Then, we see him trying to teach his youngest to speak by teaching him Trump's catchphrase "Make America Great Again." The clip closes with footage of their son in a onesie sporting the same slogan. The ad made heads turn on both ends of the spectrum. The Guardian called it "surprisingly (and disturbingly) funny," while Rolling Stone pointed out that it can come across as "pretty damn creepy." During an interview with News4Jax, Casey said that the ad was humorous and that they had fun making it. "I think a lot of people got the joke," she said. It also seems that a lot of people... didn't?

The ad didn't age well. With Ron and Trump at loggerheads, Trump pivoted, calling Ron "average" and disloyal, dubbing him "Ron DeSanctimonious."

By the time Ron and Casey DeSantis welcomed their third child into the world, the global pandemic was in full swing. Ron had kept the media in the loop regarding how his wife was doing during this time, and tongues started wagging that Florida's First Lady was about to give birth when Ron forfeited a COVID-19 press briefing that was scheduled for March 26.

All the speculation surrounding the new baby's possible arrival might well have been correct, because Casey took to Twitter on March 30 to share the good news. "Ron and I are beyond blessed to welcome our new baby girl, Mamie to the world. At 7 lbs 4 oz she was the smallest of the bunch, but she is already holding her own. Madison and Mason are so excited for their new baby sister!" Casey wrote. The post was accompanied by two pictures — one of newborn Mamie, and another snap featuring their new family of five.

On October 4, 2021, Ron DeSantis released a shocking statement: His wife, Casey DeSantis, had been diagnosed with breast cancer. The statement was largely positive, with Ron making it clear that Casey had his full support and that he believed she would make it through to the other side. While it might have appeared as if they were handling the whole situation pretty admirably, Ron admitted to the New York Post that it was one of the most difficult things he and his wife ever had to live through.

Casey was diagnosed early because she insisted on getting a mammogram, even after her doctor told her she had nothing to worry about. Ron admitted that even he thought she'd be fine, but then the test results came back, and they were positive. He described it as the most difficult moment of the whole journey. "That was really, really difficult. It totally changes your life, changes your family's trajectory," he said. Ron remained positive that his wife would make a full recovery, and he told her that. "I knew it wouldn't be easy, but I absolutely thought she was gonna beat it," he said. But it wasn't an easy journey. He accompanied Casey to all her chemotherapy appointments, and it was hard to watch her go through the excruciating treatment. But, just as he'd hoped, Casey's treatment was successful.

Five months after Ron DeSantis released a statement to announce his wife's cancer diagnosis, he released another statement, this time to inform the public that Casey DeSantis had been declared cancer-free. "She still has more to do, but I'm confident she's going to make a full recovery," Ron said. He went on to thank everyone who prayed for Casey and encouraged those in the midst of their cancer battles to keep holding on to hope. "I know it's very difficult, but my wife is proof positive," he said.

The statement also contained some quotes from Casey, who expressed her joy at winning the battle against the disease. "There are no words to express how truly blessed, grateful, and humbled I am to hear the words cancer free," she said. She also offered hope and encouragement to those in the midst of their own cancer battle, saying, "Have faith and stay strong."

As soon as Casey DeSantis was back on her feet after her battle with cancer, she got right back to supporting Ron DeSantis' gubernatorial reelection campaign, and she did so by filming a heartfelt message detailing her husband's support during the most difficult time of her life when she was battling breast cancer. "He was the dad who took care of my children when I couldn't. He was there to pick me off the ground when I literally couldn't stand," Casey said tearfully, adding, "He was there to fight for me when I didn't have the strength to fight for myself."

It was a striking message, and Ron told the New York Post that he didn't actually see the ad before it hit the airwaves. "I didn't know what she was going to say, I just said, 'Don't worry about my filter, don't listen to anyone else, you just speak from your heart,'" he told the outlet, adding that, in the end, Casey did the whole ad without a script. "To have her thank me publicly like that was very heartwarming," Ron admitted, adding that Casey was determined to beat cancer so she could be there for him and their young kids.

On May 24, 2023, Casey DeSantis posted a video on Twitter showing Ron DeSantis stepping onto a stage, the American flag in front of him, with a voiceover declaring that "America is worth the fight." This showed her support for her husband's upcoming presidential bid, but what stood out most, perhaps, was the voiceover by someone who appears to have a British-sounding accent, which caused some widespread confusion. "[I'm] confused by the British accent in the voiceover. Seems out of touch for any political campaign in the US," one Twitter user said. "Folks, let's be fair to DeSantis. Maybe his species doesn't know what a British accent sounds like? It could be new to them — like all other human interaction," another quipped.

To no one's surprise, Ron officially announced his 2024 presidential bid later that day. Depending on who you ask, this was either good or very bad news. It's no secret that the governor has signed several anti-LGBTQ+ bills in 2023 alone, along with a bill that allows doctors to refuse to treat patients based on their own religious, moral, or ethical beliefs. All these legislations have been publicly backed by his wife. "The past few years have given me a new appreciation for the fragility of our freedoms," Ron states on his official website. The minority groups gravely affected by all the governor's discriminatory bills would likely point out that it's really their freedom hanging in the balance, but we'll digress.

When you ask people in the know how Ron DeSantis managed to get where he is, they'll tell you his wife, Casey DeSantis, had a lot to do with it — and still does. "She is every bit as involved in Ron's rise as Ron is himself," former GOP Florida congressperson David Jolly told Politico.

It's clear that Casey is a force to be reckoned with, but even those who support Ron have raised concerns about whether Casey perhaps has too much power and influence when it comes to her husband. "He's a leader who makes political decisions with the assistance of his wife, who was elected by nobody, who's blindly ambitious," one of Ron's former administration staffers revealed, adding, "And she sees ghosts in every corner." The unnamed staffer isn't the only one who made this observation. Some of Ron's supporters told the outlet that it would be a grave mistake to keep Casey on as Ron's primary advisor during his presidential campaign. Instead, they say, he needs experienced individuals who know how to play the game at this level. They simply don't think Casey is up to it.

A DeSantis donor and supporter, Dan Eberhart, observed that Casey is Ron's "biggest asset and his biggest liability." Another big wig on the DeSantis campaign didn't hold back at all. "He's a vindictive motherf**ker. She's twice that. She's the scorekeeper" they told the outlet.

Some argue that Ron DeSantis' successful gubernatorial reelection campaign in 2022 was all thanks to Casey DeSantis' "Mamas for DeSantis" initiative. Now, she's set to turn it into a national movement to garner support for her husband's 2024 presidential campaign. In Casey's own words, "Mamas for DeSantis" will be "the largest mobilization of moms and grandmothers across the United States of America to protect the innocence of our children and to protect the rights of parents."

Casey did a voiceover for an ad promoting this initiative, which, among other things, criticizes the mask mandate President Joe Biden instated after he was elected president. The ad also accuses the leftwing of corrupting innocent children, with Casey saying, "We will not allow you to exploit the innocence of our children to advance your agenda." The ad also throws some serious shade at the LGBTQ+ community. Finally, Casey introduces Ron DeSantis as "our fighter."

There's no arguing that Casey is her husband's biggest supporter, but while her "Mamas for DeSantis" movement has connected with several people, others found it downright insulting. "Protecting the rights of parents ... apparently excludes immigrant parents, parents fighting to prevent gun violence in schools, parents who want their children to have a truthful understanding of U.S. history, parents of transgender kids seeking gender-affirming care,[and] parents who want their kids to become more empathetic and understanding of their own emotions," MSNBC reporter Ja'han Jones wrote.