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The Illustrious Life of Shuggy

October 25, 2026
Shuggy with his new found passion: Sargassum! 

Sunday, 25 October 2026
Noon Position: 22° 51.5’ N x 058° 59.3’ W
Ship Heading: 210°
Ship Speed: 7.1 kn
Log: 1740.5 nm
Weather / Wind / Sail Plan:  S x E winds Beaufort Force 4,  with bright, tropical sun and scattered cumulus clouds.  
Location: We are approximately 400nm from the nearest Caribbean island.

Shuggy of the esteemed B Watch!: Hello Proctor, family, and future sailors. You have come to read this blog to hear tales of adventure, glory but alas I have no such myths or fables. You might think I have been battling 60 foot waves as I stand lookout at the bow as the wrath and fury of the oceans and heavens crash against our hull. But surprisingly for a man of my attributes, this has yet to happen. Our pro crew has kept us far away from any storms. They won’t even let us sniff this small gust called Josephine. Honestly all of the exciting things that have happened have been assimilated into one memory. Ocean Classroom. I think we’ve all lost count of days at sea. Which sounds insane, I mean this has been the coolest experience of my life. How could I have it all mesh together into one memory? With how the watch system works, you don’t really have regular “days.” You kind of just eat, sleep, watch, repeat. Which sounds like a bad t-shirt yet it’s true. Without the typical end of night before bed breakdown of the day, everything cool that happens just gets added to the “Ocean” file in my brain (right next to meaningless sports and history knowledge). That is not to say cool stuff hasn’t transpired. First off I had the day I got struck with the bubonic plague. It was still really fun being sea sick though because misery has company and Tim and I make great company. Then after I had three rounds in the ring with sea sickness, I got to see Dolphins dancing at the bow as the sun set around us.

Shuggy and Tim at the leeward rail coping with seasickness.

When I say the bad T-shirt saying it sounds like we just work, but cool moments like these are the ultimate constant while we’re at sea. There are still so many things to do and enjoy aboard the mighty Corwith Cramer. My favorite being late night talks with the far wiser men and women around me, as we de-compile our lives and Proctor experiences. Lots of people have been reading too. I read a lot on shore. I thought after reading The Prince on land that “wow I’m going to have the time of the life on the boat and become educated.” Now every time I have free time I’m too tired and lacking in neuron density to read Critique of Pure Reason. Much like me saying, “I don’t get sea sick on land” I too have been humbled by Kant.  Then another activity I have grown to love is music. Nothing is better than being on lookout, stewing in your thoughts singing “River of Dreams” (by the greatest musician of all time Billy Joel). One of the closest connections I’ve made has been singing with Ando. I think everyone is sick of hearing us serenade them with the chorus of “Don’t Look Back in Anger” by Oasis. We do not know any other lyrics other than, “So Sally can wait…” and the ensuing chorus. Even though I threaten to give hearing loss to those on this endeavor through my repeated singing of the Billy Joel catalogue, we have all grown remarkably close. It truly is a privilege to be among them as it is to be with all of you back on land. One of the reasons I went on Ocean Classroom was to come closer to grasping the full Proctor experience. So while I will miss commentating sports games, assembly, and Holderness Day, I know all of that will be waiting for me when I get back. This will most likely be the only time in my life that I will sail the seven seas on a tall ship with 21 of my closest friends.

Shuggy and Cian sweat up the jib halyard while Piper minds the working sheet. 

Many people say one of the best parts of being at sea is being disconnected with the outside world and being away from your phone. This is true, what is not true is them saying that everything will become a lot clearer. My dreams have been so vivid, but very confusing. One of the two such dreams I will share is of me sleeping on the quarterdeck, waking up (in the dream while also sleeping), and panicking I’ve been sleeping on watch (not good you have 38 lives on board to take care of). The other dream (which is much closer to a nightmare) is of when we get to St John, civilization, and more importantly to this dream Wi-Fi, I get handed a phone. So naturally instead of doing the ethical and right thing of calling my mom and dad I check the NFL standings. I read that the Steelers are 4 and 7 and the browns 11-2. I kid you not when I read this in the dream I jolt awake in real life. It was very spooky. As much as I’ve enjoyed my life on the big blue, the Steelers are just one of the familiar things I miss so dearly. When on shore before we left for Ocean we got twenty minutes of phone time. Boy enough to do it, man enough to admit it, my eyes watered a little bit at the fact I got to call my twin sister Alex who was having a time similar to mine on Proctors Segovia trip. My phone time with her was some of the best and meaningful of the trip. Knowing me I might shed a tear when I see everyone reading this at Proctor, November 19th. (Be there or be square!)

Shuggy, B-Watch

PS – Hey Mom, Dad, Annie, Alex, Boo, Avery. I miss all of you, and I have so many funny stories to tell all of you. I miss watching football with you Dad, and I miss talking about lore with my sisters. Mom you were right, I do get sea sick, and thank you for worrying about me or I’d be in worse shape. Alex, as much as I might potentially complain about you sometimes, I miss you more than you know. The other twins on here have been keeping me company. Chuck and Lela have also been missing their twins so I’m not alone. To the boys at Proctor, Colin Gall, I know you are succeeding a great deal at school. Last I saw the Raiders were doing good too. Keep the room in shape and I know we’re going to have the best time this winter! To James and Jack, I cannot wait to hop on a call with you fine lads after this and laugh for hours. MOST IMPORTANTLY, Jonny you beauty hit 225. The last two things to say on my needlessly long blog are, Pittsburgh Steelers, here we go and Roast the Bulls. I love you all!