May 31, 2026
My alarm sounded at 4:30 AM and I gladly jumped out of bed. Any other day, I might lay in bed for a few minutes, but not today. Ben Young, Paul Puckett, and I were set to leave at 6 AM for a twelve hour drive down to the Keys. It is Paul’s annual birthday tarpon trip and I couldn’t be more excited to spend time with friends chasing the Silver King, which are my current obsession.
We made our first pit stop at Dodge’s Chicken just south of Charleston for some breakfast biscuits, cranked up Lionel Richie’s All Night Long and hit the road. The vibes were high, we had good tunes, and some ridiculous conversation about the correct ratio of sausage to shrimp in a Lowcountry Boil, and I brought along some Parrott hats for good measure.
Making a twelve hour drive solo would have been pretty miserable, but splitting it three ways, good tunes, and some Mill House podcast, the trek down was easy. I have made this drive a few times, and there is something magical that happens once you get south of Miami, so we cranked up Jimmy Buffett’s A1A album, made a pit stop for some cold beers and stared out the windows admiring the green and blue waters of the Florida Keys.
June 1, 2026
We are staying at Paul’s buddy’s place, Jeff, who is a gracious host. Another college buddy of Paul’s, Ryan and his wife and daughter are staying there as well, and everyone is super down to earth, tarpon obsessed, and great people.
We are not fishing today, so we decide to head to Key West to spend the day checking out the sites and playing tourist. Paul, Ben and I headed to The Angling Company, which is a wonderful fly shop in Key West with friendly staff and I could have spent all day in there getting the latest fishing reports. The palola worm hatch had apparently gone off last night around Sugarloaf Key, which could be really bad news for us if the tarpon had gorged themselves and didn’t want to eat, or really good if they were fired up. We hoped for the latter.
“I went down to Captain Tony’s to get out of the heat
Then I heard a voice call out to me, “Son, come have a seat”
I had to search my memory as I looked into those eyes
Our lives change like the weather, but a legend never dies”
Our next stop was The Green Parrott, then to Captain Tony’s, where Jimmy Buffett wrote Last Mango in Paris, and the paper and original lyrics are hanging in the bathroom. We then popped into a local book store, where I insisted that Paul and Ben buy a copy of Mile Marker Zero: The Moveable Feast of Key West, which tells the story of how these writers and artists (Jimmy Buffett, Tom McGuane, Jim Harrison, etc.) found their identities in Key West and maintained their friendships over the decades, despite oceans of booze and boatloads of pot, through serial marriages and sexual escapades, in that dangerous paradise.
There is something special about all old port cities, such as Charleston, Savannah, Key West, New Orleans, etc. due to their history, but as a tarpon angler and Parrot Head, Key West is special because of the nostalgia associated with the aforementioned legends, add Hemingway, Cuban influence, historic architecture, being in the tropics, and oh yeah, tarpon, bonefish, and permit, and you have all the correct ingredients for a mighty fine time. We met Jeff, Ryan and their families for lunch, then headed to Rick’s Bar to cap off a fun day in Key West.
June 2, 2026
Ben and I were paired up to fish together on day one with Captain Mike O’Dell. The air was heavy with tropical heat, it was partly cloudy with a light breeze, and we immediately saw tarpon rolling once we got the first flat we were to fish. A good sign.
I was way too excited on the first tarpon eat I got and set the strip set the absolute shit out of the hook and the fly broke off the line. Next, Ben lands a little 10-15 pounder who had several jumps and was successfully landed. The tarpon were very spread out on this flat, so we decided to change positions from ocean side to mangroves for some smaller tarpon, which was incredible!
There were schools of tarpon weaving in and out of the mangroves, water visibility was clear and we had a damn blast jumping and landing smaller tarpon all day. I have never fished for tarpon who were so willing to eat a fly! Probably because they were younger, but it was my personal best day of tarpon fishing and Ben and Mike were great company. I ended up landing three tarpon that day and jumping a half dozen more with sizes ranging from 20-30 pounds and was an absolutely epic day, all back in the mangroves. Ben ended up landing 3 and jumping another half dozen as well. Ben’s biggest was probably 30-40 pounds and can’t say enough about how fun it was. Truly epic day.
Paul ended up landing a 30 pounder fishing with Jeff and we spent the evening over cold drinks and reliving the day with stories of eats, misses, and landed tarpon. Life is good!
June 3, 2026
Today is Paul’s birthday and the reason we are down in the Keys this week (Happy Birthday, Hermano!). I am fishing with Keith, Paul’s father-in-law and Captain Brian Stilley. It is overcast and windy, and not ideal conditions. The day doesn’t get off to a great start. I always take my shoes off before getting on to a skiff, but for some reason did not this morning, and my flip flops have zero traction on the bottom. When I went to hop onto the skiff, I slipped and both my shins hit the underside of the skiff. I shrugged it off, but after a couple of minutes glanced down to my feet sitting in a small puddle of blood. Also, not ideal. After cleaning up the wounds, we headed out to fish ocean side and saw tarpon rolling. I was on the pointy end first and had a small tarpon eat my fly, but I missed him. Damn!
We hung out ocean side for a couple of hours posted up in front of white patches of sand because that was the only way we could see the tarpon due to the cloud cover. I had another follow and some additional shots, but no takers, so we decided to move to the backcountry. We were running from rain and even saw a pretty big water spout form and water visibility was really tough, but we finally were able to see a school coming from about 50 yards, waited and I made my cast as the school was swimming over a white patch of sand. A large tarpon broke off from the school and I watched her inhale my worm fly, came tight, and she then proceeded to kick my ass for the next fifty minutes!
She stayed with the school the vast majority of the fight and I leadered the fish five times before I finally really putting the screws to her. For context, I still consider myself a novice tarpon angler, and I learned a couple of extremely valuable lessons this day.
Lesson #1: 16 pound tippet is incredibly strong. If I would have let the 85 pound tarpon run, then put the screws to her like I did at the end, I would have landed the fish in half the time.
Lesson #2: Do not ever grab the rod above the cork while fighting a large tarpon.
It is towards the end of my tango with the tarpon. My fingers, hands, and forearms are on fire and I am fatigued, but I have the tarpon away from the school and she is next to the skiff. Brian is a great guide and is coaching me through the fight. Reel down, and slow and steady pull up on the fish as he puts on his gloves and tells me what will happen once he grabs the leader and then the tarpon. Something happens and the fish decides to make one last run, and I fear I am going to drop the rod because my arms are cooked. Then, I make the mistake Brian had told me repeatedly not make. I grabbed the rod above the cork, and the 1-piece Hardy exploded into four pieces and sounded like a mix between a lightning strike and a bomb going off! I frantically grab the line, recover the broken pieces of the rod and start handlining the fish, get her next to the skiff, and she breaks free.
I am gassed, but elated to have gotten a fish of this size to eat in tough conditions, but also embarrassed that I broke the rod. That said, I learned a ton fighting this tarpon and now know what to do the next time around. We fish for a couple more hours and see some tarpon but know more eats.
I have to fly back to Charleston that night and will miss Paul’s birthday party, and the rest of the guys have another day of fishing tomorrow that I will sadly miss, but I am grateful for the invite and the opportunity to become a better angler and chase a fish that has consumed me these last few years in a special place with great friends.
Conclusion
Tarpon have a unique ability to consume my mind, and for good reason. They are literal dinosaurs that you can sight fish, are incredibly powerful and acrobatic, and also live in beautiful places, like the Florida Keys. Combine tarpon fishing with great friends, Cuban sandwiches and coffee, a tropical locale, and the old stomping grounds of some of my hero’s like Jimmy Buffett, Tom McGuane and Jim Harrison, mix it all together and you have the makings of a highly addictive pursuit and a beautiful way to spend a few days celebrating life.
Grateful to get spend time with old friends and new one’s, making memories doing what we all love…tricking a dinosaur to eat some chicken feathers.
Being privileged to get to have experiences like this always bring me back to why I started Emerger Strategies in the first place: to protect what I love. Fishing and outdoor brands also have a responsibility to protect the resource their businesses are dependent upon. Protecting the resource should come in the form of advocacy, supporting conservation organizations like Bonefish & Tarpon Trust or Captain’s for Clean Water, and authenticating that they actually give a damn by reducing greenhouse gas emissions, going zero waste in their operations, switching to more sustainable packaging, and ensuring that their products are minimizing their environmental impact.
If you are a fishing or outdoor brand who wants to learn more about how Emerger Strategies can help you reduce costs, earn customer loyalty, and mitigate risks by measuring and improving your sustainability performance, check out our Sustainability Consulting Services and schedule a discovery call today!
P.S. Ole Ben Young landed the tarpon of the trip, a 100 pounder that he boated in 10 minutes, the next day. I am already daydreaming about next year and have been high on tarpon since I left!