Donald Trump’s favored military advisor, who he asserts wore a MAGA hat to win his favor, has orchestrated two jaw-dropping operations this year, defying expectations and silencing even the fiercest critics of the White House.

General Dan ‘Raizin’ Caine, a four-star general and chair of the Joint Chiefs, transitioned from an F-16 pilot to a venture capitalist before Trump recalled him from retirement to serve again at the Pentagon. Recently, he made headlines as he recounted the astonishing mission where U.S. forces captured former Venezuelan leader Nicolas Maduro.

“This mission demanded the full might of our joint forces, involving soldiers, sailors, airmen, marines, and guardians, seamlessly collaborating with intelligence agencies and law enforcement in an historic endeavor,” Caine explained at a Mar-a-Lago briefing, unveiling the intricacies of ‘Operation Absolute Resolve.’

Exuding professionalism, Caine provided a meticulous breakdown of the operation while Trump and his key Cabinet members observed, with the nation eagerly absorbing every riveting moment.

Caine’s steadfast integrity was evident during his Senate confirmation hearing in March, where he refuted Trump’s anecdote about him wearing a MAGA hat and expressing unwavering loyalty during a presidential visit to Iraq in 2018.

“I believe the president was referring to someone else, as I have never donned political gear or made such statements,” the general clarified to senators questioning Trump’s account.

Pictures taken at Mar-a-Lago during the height of the weekend’s high-stakes operation show Caine coolly looking at monitors displaying feeds of the mission as the president, CIA Director John Ratcliffe, Secretary of War Pete Hegseth and top Trump lieutenant Stephen Miller watch with nervous looks. 

During the press conference, Caine, who worked for the CIA from 2021 – 2024, detailed how America had a mole inside Venezuela, and a spy team had been on the ground for months. 

Chairman of the Joint Chiefs of Staff Gen. Dan Caine speaks during a press conference with President Trump at Mar-a-Lago club on Saturday

Caine donning civilian clothes gestures as Secretary of War Pete Hegseth watches monitors displaying live feeds of ‘Operation Absolute Resolve’ in the early hours of Saturday morning

Caine served as an F-16 pilot for years, racking up over 2,800 flight hours – over 116 days in the air. He served two tours in Iraq before overseeing special forces operations and joining the CIA as the associate director of military affairs

They knew where Maduro and his wife Cilia Flores were living, when and where they traveled, what clothes they wore, what food they ate, even what pets they had, ‘Raizin’ revealed. 

After months of planning and weeks of monitoring weather conditions for the perfect time to strike, the president authorized the operation at 10:46 pm ET, and thus a chain of events began that would hours later prove that American military might is still the engine for the world’s greatest superpower. 

Over 150 aircraft at 20 US bases across the western hemisphere were tasked and ready. After receiving the greenlight, the aircraft were fitted with ordinance, special operators and pilots loaded in, rotors began whirring and jet engines screamed to life.

Maduro, the strongman socialist dictator who had an iron grip on the oil-rich nation, would soon come face-to-face with all the president’s most deadly men. 

The massive operation was to include F-22 Raptors, F-35s, F/A-18 Hornets, EA-18 electronic warfare aircraft, E-2 command and control planes, B-1 bombers, helicopters, refueling aircraft and numerous remotely piloted drones.

The youngest crew member on board was 20, the oldest 49.

Helicopters took off with the extraction force that would capture Maduro, including members of Delta Force, the Army’s elite direct action unit, and law enforcement officers who would serve the warrant for his arrest on drug charges.

The helicopters flew in across the water at just 100 feet while Space Command and Cyber Command took up the baton.

Venezuelan President Nicolas Maduro and wife Cilia were both seized by a US military unit in the early hours of Caracas, with Maduro now set to face drug and gun charges in the United States  

It is believed that they were involved in taking out lights on the ground in Venezuela, while aircraft disabled air defense systems to allow the helicopters into the target area.

Before reaching the target, the extraction force – the exact size of which remains unclear – flew behind one last area of high terrain, and it was only when they emerged that they were finally spotted, according to Caine.

They had successfully maintained the element of surprise.

Despite his futile attempt to flee into a steel safe room in his compound, Maduro was captured. Though he made it inside, American forces were able to apprehend the dictator and his wife before they could close the door. 

Within hours, after a short helicopter ride with the Delta Force, Maduro was aboard the USS Iwo Jima, where he was pictured handcuffed and blindfolded. 

After a few additional hours, he was in New York, still handcuffed, and being perp walked for the nation to see the outcome of the death-defying raid. 

Despite videos of widespread bombing and gunfire, not a single American was injured. Not a single aircraft was lost. Just one helicopter was hit by some ground fire, though it was still operational.  

It would prove to be the chairman of the Joint Chiefs’ second spectacular attack on a primary US rival in about six months. 

The US used seven B-2 bombers to attack the Iranian sties

‘Operation Midnight Hammer,’ the shock-and-awe bombing of Iran’s most sophisticated nuclear facilities, was Caine’s debut on the world stage, letting America’s enemies know that the US, under Trump, is back in the bad-guy breaking business.

During that dangerous mission, Caine and Hegseth coordinated the largest stealth bombing run ever in history. 

The June 21 – 22 surprise attack utilized seven B-2 stealth bombers that dropped 14 30,000-pound ‘bunker buster’ bombs on Iran’s primary nuclear enrichment facility at Fordow.

Over 125 US aircraft participated in the mission, including bombers, fighters, and refueling tankers, Caine said at the time. 

Approximately 75 precision-guided weapons were employed in the attacks, including Tomahawk missiles fired from submarines.

Trump holds a meeting with White House Chief of Staff Susie Wiles, Caine and other cabinet members in the Situation Room as ‘Operation Midnight Hammer’ unfolded

Caine sits close to Trump at a meeting with Ukrainian President Volodymyr Zelensky on December 28

Caine’s plan included misdirection and multiple refueling stops.  

‘As part of a plan to maintain tactical surprise, part of the package proceeded to the west and into the Pacific as a decoy. This deception effort was known only to an extremely small number of planners and key leaders here in Washington DC and in Tampa [the headquarters of US Central Command],’ Caine detailed at a press conference after his first successful strike, when he was just over two months into the job.

‘The main strike package proceeded quietly to the east with minimal communications,’ he added. ‘Throughout the 18-hour flight into the target area, the aircraft completed multiple in-flight refuelings.’

That mission, Trump said, was a ‘spectacular military success’ that ‘completely and totally obliterated’ Iran’s nuclear ambitions. 

Serving in the military since being commissioned in 1990 after graduating from the Virginia Military Institute, Caine’s military career has sent him careening – and soaring – across the globe. 

Potentially his most important military success to date: securing the complete trust of the president who has long been skeptical of his top military brass. 

‘Caine, he’s a fantastic man,’ Trump said on Saturday. 

‘I’ve worked with a lot of generals, I worked with some I didn’t like, I worked with some I didn’t respect, I worked with some that just weren’t good, but this guy is fantastic.’