Counterproductive pride: The story of how the US Army refused to adjust, ending the careers of two top brass

In September 2011, I was at the US Embassy in Baghdad, Iraq and we were in the middle of negotiating with the Iraqi government about extending the US military presence there. Brett McGurk, who negotiated the 2008 status of forces agreement, was back in the country as a senior adviser to Ambassador Jim Jeffrey and was working with the Iraqis to try to find a way to strike a deal.

Our plan was to keep about 10,000 troops in the country to provide a massive training and advice mission to Iraqi military commanders and their units. The plan placed all US forces in Iraq under Lieutenant General Robert Caslen, a former division commander of combat troops in Iraq in a previous assignment. Within that 10,000 would be an undisclosed number of special operations forces, which would be led by a two-star admiral named Ed Winters, a Navy SEAL and former commander of DEVGRU. And finally, there would be a large foreign military sales program led by an air force one-star general who was an expert in contracts, acquisitions, and military sales.

In mid-to-late September, Caslen and his staff arrived in the country, taking the reins of the US advising and training mission from LTG Michael Ferriter and waited for us at the embassy to do our work and get the status of forces agreement passed through the Iraqi government.

Prime Minister Nuri al-Maliki expressed to us on numerous occasions his desire to keep a large number of US troops in the country but repeatedly told us that he did not see how he could get the agreement passed through the Iraqi parliament. In short, Iraq found a lot of value in having the US military in the country, but it was just time to move on.

As September turned to October, General Lloyd Austin, the US military commander in Iraq, and other generals were growing concerned about their ability to get all of the military equipment and personnel out of the country before the end of the year when the agreement expired.

The clock kept ticking until October 18th and with no movement by the Iraqi government, we received the order from the White House: bring the troops home. There would be no new agreement. No 10,000 troops. No special operations forces. No training mission. The only thing that would remain would be a staff of about 150 senior military officers who would conduct the United States’ largest foreign military sales program in the world and be officially attached to the embassy as diplomatic personnel. It was called the Office of Security Cooperation-Iraq (OSC-I).

At this point, the Pentagon had a choice to make: keep LTG Caslen, RADM Winters, and the others in those positions, putting them in charge of the security cooperation mission or recall them and replace them with others who would be more fitting for these roles.

For context, most OSC programs, like the large ones in Saudi Arabia, Pakistan, Israel and other countries to whom we sell a lot of equipment, usually are run by one-star generals or perhaps even a colonel. In Iraq, we had, at this point, three officers with stars on their shoulders, plus even a few civilians of equivalent rank. And beneath them was a horde of colonels, lieutenant colonels, and majors. This was in addition to the official US defense attache, a US Army colonel.

As the US military began a two-month endeavor to move tens of thousands of people and tons and tons of equipment out of the country and across the border into Kuwait, every day I would receive a situation report from our military counterparts that showed fewer and fewer troops in the country.

While the US military is certainly the world’s greatest logistics machine, it was not the most flexible organization. It was a proud bunch who didn’t like to admit defeat or error, and they stuck to their guns regarding the team that would remain. And then the news came: the army held firm that Caslen and his team would lead the way for a successful security cooperation relationship between the US and Iraq. Caslen and Winters, the army said, were the right people for the job.

But even as a 27-year-old one-time diplomat and junior navy reserve intelligence officer, I knew their backgrounds didn’t align to their new mission, and I had a feeling this was going to be rough.

As the year turned, and LTG Caslen became the official head of the security cooperation mission, he continued to do things like he was leading a combat mission. He ran his joint operations briefings twice a day, getting updates from each of his joint staff section heads on the status of their operations. As the weeks passed, I could see the futility (and in many cases absurdity) of the entire situation.

One day, Caslen was being briefed by his J-6, the officer in charge of communications, who reported that US personnel who were located at one of the Iraqi military bases didn’t have enough cell phones. Then ensued a 15-minute discussion in front of the entire group about how to get them more cell phones. I just kept thinking: Caslen is a three-star general and he has to figure out how to get a few cell phones to a base in the middle of the desert? This should be handled by a sergeant. Caslen shouldn’t be involved in this. The army screwed him. Caslen, to his credit, was doing the best he could with the shit sandwich he was given.

It wasn’t any better for Winters. He was originally selected to lead special operations forces and continue the hunt for the handful of guys who were leading the suicide bombs and rocket attacks that still plagued the country. But he couldn’t. He was left to shake hands with Iraqi generals at dinner parties and visit some Iraqi army bases to view their tank training. For a guy who was the former commander of Naval Special Warfare Command and one who was awarded a Legion of Merit and not one, not two, but three Bronze Stars, the army screwed him, too. Winters never directly stated to me in any of our discussions that he was unhappy with how things turned out, but my gut told me otherwise.

Caslen and Winters were guys who had led thousands of people in combat and now they were relegated to selling military equipment, while their counterparts of equal rank had far more high-profile positions.

When I left Iraq in August 2012, Rear Admiral Winters had already departed the country. Caslen stayed another year until 2013, when he took an assignment as the Commandant of West Point, of which he was an alumnus.

And that ended up being Caslen’s swan song. He retired from West Point in 2018 with three stars, never earning his fourth, which I always felt was his ultimate goal. Caslen is now serving as the president of the University of South Carolina, a fitting assignment considering his recent experience. We recently connected on LinkedIn, and he offered the opportunity to catch up and show me around his campus if I ever visited the Columbia area.

Winters retired with two stars a year after returning from Baghdad. Interestingly, his official navy biography page doesn’t even list his assignment in Iraq. He settled on the Florida gulf coast, near where he grew up, with his wife and kids, and he began working a number of security-related consulting positions. As he wrote to me in an email: “Security and assessment missions are the best because you run into old friends.” I was just glad he was back doing what he did best.

And that’s the story of how the US military screwed two very capable flag officers out of further advancement. The Army had the chance to pivot, but it remained firm in its counterproductive pride. And that pride is what ended the careers of two very fine combat veterans.

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