Tales of the Trail Boss, Pt 1: Meet The Trail Boss

Tales of the Trail Boss, is a multipart series about our initial push into Iraq and the young folks of our armed forces who made it happen. There is some excitement, some humor and underlying it all, initiative and leadership displayed at all levels by America’s finest. It happened something like this…

Back in the Spring of 2003, I was the Deputy Operations Officer of a 2-Star General Officer headquarters charged with all the logistical support for units in Southwest Asia. Elements of our headquarters had been on the ground in the area for the better part of 2 years, supporting the efforts to topple the Taliban in Afghanistan and prepping for regime change in Iraq. 

Our unit was responsible for not only getting our own assets into the Theater of Operations, but we were also responsible for receiving and staging all the combat units who would be doing (most of) the actual fighting. From Saddam Hussein’s point of view, imagine seeing over an 18 month period, this huge military fist being drawn further and further back—and wondering just when that right cross would put him on the mat.

The time was rapidly approaching for the Coalition Forces to uncork that right cross and put Saddam Hussein out for the count. One day, while I was taking a break outside, swilling down one of many daily cups of coffee and smoking one my even more countless death sticks, my Commanding General approached me and said “Mike, I’ve got a little something for you to do.” Uh oh. Every time The Big Boss had said something like that, I’d ended up someplace where the weather sucked and people would shoot at me. I didn’t much care for that.

The last time that happened, required a little jaunt over to Afghanistan. Although I must say, during that little foray, the weather was actually quite nice and I enjoyed standing on the airfield looking up at the mountains while watching the Special Forces guys skiing down them. But I digress.

What The Big Boss wanted, was for me to put together a small team of 20 or so folks who would go forward to be his eyes and ears so to speak and keep him apprised of the situation as it developed while we made our initial push into Iraq, which was expected any day now.

One of the folks I picked for the team, was a motivated young Captain. I’ll call him HM for now. HM was sharp, energetic and flat out knew how to get things done. So I made him my XO (Executive Officer) and put him in charge of gathering all the vehicles, equipment, arms, ammunition and other supplies we’d need for the trek Northward. He far exceeded my expectations, especially for hard-to-get stuff.

If you remember Peter-San, aka “The Scrounger” in John Wayne’s, “The Green Berets,” that’s HM…on steroids. If I mentioned we needed some esoteric item, he had it—and within 2 hours, 12 at the most…even some of the odd batteries that some of our electronics used and were chronically in short supply.

Then the day came—and we were ready. We departed Camp Arifjan Kuwait in the middle of a series of SCUD attacks, survived an ambush in Southern Iraq and a few days later grabbed Tallil Airbase from the Iraqis…well…OK. We rolled in the Southern part of the base as the Iraqis screamed out of the Northern end.

It was during the march up there that HM earned his moniker, “The Trail Boss.” For the march North, I had assigned him as “tail-end-Charlie,” the rear of our convoy, responsible for dealing with any stragglers and to keep equipment and personnel accountability. He went through a series of radio call signs until he managed to find the one he liked, going from: Gator-trail, to Gator-tail and even Gator’s a**, as suggested by some folks. Finally, he settled on, “The Trail Boss.” It seemed a good fit.

He was everywhere, staying on top of everything, for a convoy that had grown from 17 vehicles, to well over a hundred as we took on stragglers from other units and even one entire convoy that had gotten lost in the middle of the desert. The Trail Boss even helped extract our huge convoy from an Iraqi ambush on the way North, exhibiting a coolness under fire that displayed a maturity far in excess of his rank and experience. But it was once we got to and established ourselves at Tallil Airbase that he truly came into his own.

We had brought everything we thought we might need AND could stuff into every nook and cranny of our (initially) 17 vehicle convoy, expecting not to get resupplied for some time. Our mission was to help the Air Force detachment riding along with us, in evaluating the airbase and getting it ready to receive Coalition aircraft as soon as possible.

L-R: Trail Boss, MG K (the Big Boss), Author

The Trail Boss excelled in everything I threw at him. He was everywhere. Every unit on the installation knew him and when he gave suggestions to unit commanders, many (most) of which were senior to him, those suggestions were executed with alacrity. By the time the Air Force had fully taken over operation of the base and our element was preparing to depart, we (he) had come up with enough vehicles to fully equip a Combat Engineer Company. More people had heard of The Trail Boss than knew the Base Commander’s name. Pretty heady stuff for a young Captain.

One day after the Air Force had taken over security of the base, Trail Boss comes cruising up to the gate in his very “non-standard,” modified Humvee. The Airman pulling security there barked, “Halt! ID please.” This was quite understandable as Trail Boss, returning from some scrounging mission or other, was wearing his customary Trail Boss “uniform” of boots, camouflage pants, t-shirt & headband. He looked a lot like something out of a Francis Ford Coppola movie and almost nothing like a United States Army Captain. The young Airman repeated, “ID please!” Trail Boss slowly lounges back in his seat, fixes the youthful guard with his best steely eyed stare and drawls, “Don’t you know who I am?” The guard stammers, “Nnnno.” Trail Boss declares, “I’m The Trail Boss!” The guard immediately pops to attention, whips out a snappy salute and asks, “THE Trail Boss?” Followed by, “I’ve heard of YOU Sir. Pass!

Understand folks, this is a young Army Reserve Captain, who not all that many months prior, was relegated to the routine and often dreary administrative tasks delegated to his level in an army not quite at war. While in Iraq, like so many of our fine young warriors, The Trail Boss was making routine decisions that in peacetime, would ordinarily be made at the Colonel level. Heady stuff indeed.

Now that we have set the stage, tune in next time when The Trail Boss meets Tallil Tom, an Iraqi Turkey with a bad attitude.

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7 thoughts on “Tales of the Trail Boss, Pt 1: Meet The Trail Boss”

  1. The trail boss did a great job in sculling and probably threatening the quartermaster to obtain the necessary items needing for this important mission but I think that at least fifty percent of the credit should go to his commander that knows how to delegate authority. By delegating the commander was forming a succession of people to replace him on future missions and not spreading himself too thin. Who was this commander?🥇

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