Below Deck season 11’s Captain Kerry Titheradge has struggled with Bosun Ben Willoughby’s attitude all season, and after having his leadership undermined, the Captain is coming for his former employee. While Below Deck season 11 ended without a reunion, Captain Kerry and the rest of the cast have been doing their best to update viewers on what happened in the aftermath of the charter season. Having nearly a year to ruminate on their Below Deck experiences, the Captain and the rest of the crew have been speaking openly about their feelings about each other, as well as the season.

“Biggest disappointment was the lead deckhand.”

Captain Kerry’s struggles with Ben were prevalent throughout Below Deck season 11, and though he entrusted the former Lead Deckhand with the responsibility of being the Bosun of the vessel, the Captain may have some regrets about his choice after watching Below Deck season 11. In a shocking post on X (formerly Twitter), Captain Kerry explained that he wasn’t happy with the fact that Ben had undermined former Bosun Jared Woodin and, after getting promoted, had undermined him.

“Much of the crew’s personal drama surprised me,” Captain Kerry shared. “Biggest disappointment was the lead deckhand undermining his bosun and chief stew, then once becoming bosun doing the same to me.” The Captain was shocked to see that Ben tried to undermine authority before he had any power and, once he did, continued to try to undermine the highest authority figure on the vessel.

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As Below Deck season 11 continued, it became clear that Ben was struggling aboard the St. David. After getting shut down for interfering in drama during his time as Lead Deckhand, Ben was put in a position of power that afforded him more power than he’d ever had before. While his work didn’t suffer, Ben clearly had the power of becoming Bosun go to his head a bit. Throughout the second half of the charter season, Ben felt that he knew better than Captain Kerry at every turn, questioning his decisions and criticizing the way he managed the Below Deck crew.

Outside of the series, Ben shared that there was more than met the eye about his disdain for the Captain, criticizing his behavior off camera and his treatment of the Below Deck production team. Ben has come out and shared that he won’t work under Captain Kerry again in the future, though he would be interested in working with Below Deck Med‘s Captain Sandy Yawn if it’s possible. Regardless of his prowess as a Bosun, Ben’s inability to listen to people in positions of power was tough to watch. Ben would need to work on his insubordination if he were to work with Captain Sandy.

In the future, Ben’s role on Below Deck may look a bit different if he decides to return to the series. Though he’s good at what he does, his job as Bosun is to report to the Captain of the vessel, and undermining their power isn’t something most Captains will take lightly. Ben may be great at working as a Bosun, but he needs to be able to humble himself and submit to the hierarchy of a superyacht crew if he wants to continue in his career in general, even outside of Below Deck.

Source: Captain Kerry/X