Who is Dan 'Razin' Caine, Trump's 'favorite' general who destroyed ISIS and now leads Operation Southern Spear against Maduro?

As the pressure against Nicolás Maduro reaches its peak in diplomatic, military and legal terms, Gen. Dan 'Razin' Caine, chairman of the Joint Chiefs of Staff, arrived Monday in the Caribbean Sea to directly oversee Operation Southern Spear, which seeks to dismantle the region's major cartels, including the Chavista Cartel de los Soles.

Caine, known to be Trump's "favorite" general, was the man who convinced the Republican president that it was possible to destroy ISIS in just weeks in 2018, during his first term.

During separate public speeches, Trump described his first meeting with Caine, a renowned F-16 fighter pilot, as "wonderful," recalling that he went to Iraq to bring a Christmas message to the troops and hear from the men on the ground. At the time, Trump spoke frankly with Caine and other senior military officers, and asked for their opinion on how long it might take to destroy ISIS. Caine told him that a few weeks would be enough and even plenty of time. That dialogue came just days after U.S. generals told the president that such an operation could take years.

"'We're only hitting them from a temporary base in Syria,'" Trump asserted, quoting Caine's words directly. "'But if you gave us permission, we could hit them from the back, from the side, from all over – from the base that you're right on, right now, sir. They won't know what the hell hit them.'"

Since then, Caine became an exceptional military man for Trump and, since February, following his nomination to chairman of the Joint Chiefs of Staff, his most highly regarded general.

Caine's track record is particularly unblemished. He was one of the pilots tasked with protecting Washington during the Sept. 11, 2001, attacks, when hijackers from Al Qaeda crashed commercial airliners into the Pentagon and the World Trade Center in New York, in the worst terrorist attack in the country's history. He also held several positions in Washington. He served as the associate director of military affairs for the CIA from 2021 to 2024 and was a member of the White House in the Department of Agriculture. He is also a counterterrorism specialist in the White House National Security Council.

According to AP, despite Trump's recurring claims that Caine is a fan of his, his military peers describe him as an apolitical professional.

During this second Trump administration, Caine was already a key part of the design and execution of Operation "Midnight Hammer," with which the U.S. struck Iran by surprise, leaving its nuclear facilities heavily affected.

Now, Caine is directly overseeing Operation Southern Spear, and this Tuesday, Nov. 25, he will visit Trinidad and Tobago, where he will meet with Prime Minister Kamla Persad-Bissessar. On Monday, he was in Puerto Rico.

"The visit will focus on the strong bilateral relationship between the two nations, strengthening regional stability and unity around the vital importance of combating illicit trafficking and transnational criminal organizations," the U.S. Embassy in Trinidad and Tobago described. 

Caine's presence in the Caribbean, miles from Venezuela, raises expectations of potential U.S. attacks on Venezuelan territory aimed at hitting the infrastructure of Cartel de los Soles and putting direct pressure on Maduro, who faces a U.S. drug trafficking indictment and a $50,000,000 reward, the highest in the country's history.

Cartel de los Soles, an officially designated terrorist organization, is led by Maduro, his second-in-command, Diosdado Cabello, and a network of Venezuelan generals who collaborate with major cartels in the hemisphere. According to U.S. security agencies, about 24% of the cocaine trafficked globally passes through Venezuela.

According to Pentagon chief Pete Hegseth, the designation of Cartel de los Soles as a narco-terrorist organization allows the Trump administration a broadening of options to combat narcotics trafficking and Maduro.

According to the New York Times, Trump has already approved clandestine CIA missions in Venezuela at various levels, up to and including potential special operations to assassinate the ringleaders of the Cartel de los Soles, including Maduro.

With Caine at the helm of the "Southern Spear," the largest US military deployment in the Caribbean since the 1960s, the pressure against Maduro is at its highest point so far, and some analysts already consider attacks against Venezuela and its key infrastructure to be "imminent."

In this context, Axios reported that Trump is ready for talks with Maduro. However, according to White House officials, the difference is that, on this occasion, Washington is not interested in giving more time to the Chavista dictator, who, on several occasions, managed to survive outside pressure to perpetuate himself in power with an iron fist.