There have been several memorable captains throughout the Below Deck franchise, but while some cast members have succeeded in viewers' expectations, others have unfortunately missed the mark. Since Below Deck premiered in 2013, the popular series has expanded to include spin-offs like Below Deck Mediterranean, Below Deck Sailing Yacht, Below Deck Down Under, and Below Deck Adventure. With plenty of drama and conflict to go around, the Below Deck franchise has retained its large fan-base due to showing the usually-undiscussed extravagant yachting business, where luxury is a necessity and tips can reach astronomical numbers.
While dozens of deckhands, chefs, and polarizing chief stewards like Kate Chastain have helped make Below Deck one of Bravo's biggest franchises, Below Deck and its spin-offs would be nothing without its captains at the helm. As the sole leaders of each yacht, the captains featured on Below Deck have to run a tight ship for every charter to be successful while still being entertaining enough to win fans over at home and keep them coming back for more. On Below Deck, it's imperative to balance having a strong work ethic with a dazzling personality, and while some Below Deck captains have gone down as the best, others are, unfortunately, thought of as the worst.
Best: Captain Lee Rosbach (Below Deck)
Longtime Below Deck fans know Captain Lee Rosbach is widely considered one of the best cast members across the franchise and with good reason. Captain Lee took the wheel for Below Deck season 1 almost ten years ago, and since then, he has continued to run a tight brigade. Although Captain Lee has a generally hands-off approach to how his crew operates each charter, he isn't afraid to assert his authority with his crew or clients. An example of this is when an unruly guest caused Lee to angrily end her charter early on Below Deck season 8. Despite his tough persona, Captain Lee is not only hilarious but empathetic, such as when Ashton Pienaar was dragged overboard on Below Deck season 6. Sadly, while Captain Lee returned to his post when Below Deck season 10 premiered in November, the fan favorite's days with Bravo have come to a temporary end due to reoccurring health issues.
Worst: Captain Sean Meagher (Below Deck)
To be fair, Below Deck's Captain Sean Meagher didn't have a lot of time to show off his skills on Bravo, as he was hired to temporarily replace Captain Lee on Below Deck season 9. Due to an unspecified medical condition at the time, Captain Lee was unable to join My Seanna for the first charter, and while Captain Sean stepped in to fill Captain Lee's shoes, he didn't make a strong impression among his crew or viewers at home. Captain Sean, who admitted that he had never watched Below Deck prior to being cast, was an obvious micromanager whose only goal was to provide great service to his guests. While bosun Eddie Lucas and the rest of the crew anxiously waited for "boat daddy" Captain Lee's return, Captain Sean's quirky personality was interesting to watch during his brief stint on Below Deck. In the end, Captain Sean's short Below Deck stint wasn't that impressive or memorable.
Best: Captain Glenn Shepard (Below Deck Sailing Yacht)
Captain Glenn Shepard quickly became a Below Deck fan favorite when Below Deck Sailing Yacht kicked off in 2020, and with strong leadership skills and a stellar personality to match, it's not hard to see why. While some Below Deck stars like Captain Lee are considered to be more hands-off when it comes to their crew, Canadian native Glenn has shown himself to be the opposite. When Captain Glenn isn't at the helm, he can be spotted helping bring provisions aboard, checking in on his subordinates, and even bonding with his charter guests. While Glenn has dealt with a few crashes on Below Deck Sailing Yacht, his passion, professionalism, and dedication to yachting bleed through every episode. There's no doubt that Below Deck Sailing Yacht would feel completely different without Captain Glenn at the wheel.
Worst: Captain Jason Chambers (Below Deck Down Under)
Captain Jason Chambers, known as "captain cutie," has one of the best Below Deck personalities, but when it comes to the actual job at hand, the Below Deck Down Under star hasn't appeared to be of the same caliber as Captain Lee or Captain Glenn. Jason, who is the youngest person to helm a yacht on Below Deck, became a fan favorite in the debut season of Below Deck Down Under due to his adventurous attitude and good looks. Many viewers also agreed that Jason made the right decision to fire Below Deck chef Ryan McKeown and third stew Magda Ziomek. That being said, Captain Jason's simultaneous laid-back and micromanaging management styles didn't make a strong impression, which was imperative as Captain Jason was already known for crashing into a marina in 2019. Despite his rough start, many Below Deck fans want Captain Jason to return if and when Bravo announces Below Deck Down Under season 2.
Best (So Far): Captain Kerry Titheradge (Below Deck Adventure)
Captain Kerry Titheradge is Below Deck's newest leader after Below Deck Adventure made its debut in early November, but so far, the Australian native is doing a great job directing the Mercury yacht and its crew around Norway. Like Captain Lee and the other Below Deck leaders, Kerry is a well-traveled individual with over 30 years of yachting experience, and it shows on Below Deck Adventure. Assertive and confident, Kerry is not afraid of confrontation or conflict, such as when he forced controversial deckhand Kyle Dickard to resign after Kyle made one too many early mistakes. When Captain Kerry finds a break from helming the Mercury, he has been shown to have a warm and affable personality with the crew and his charter guests. If Kerry's strong performance remains consistent throughout the rest of Below Deck Adventure, there's no doubt he'll be asked to return as captain.
Toss Up: Captain Sandy Yawn (Below Deck Mediterranean)
Captain Sandy Yawn is a staple figure on Below Deck Mediterranean, but while she holds the distinction of being Below Deck's first and only female captain, Sandy is also one of the franchise's most polarizing stars. When it comes to the job itself, Captain Sandy has excellent leadership skills, an extensive resume, and a hard work ethic. While her experience is impressive, Captain Sandy's interpersonal relationships and overall personality have been criticized for years, especially by some fans who recently tuned into Below Deck Mediterranean season 7. As captain, Sandy has made questionable decisions multiple times, such as when she fired Chef Hindrigo "Kiko" Lorran and fan favorite Hannah Ferrier on Below Deck Mediterranean season 5. In addition, while Sandy always makes sure to put her duties first, she has a bad habit of unnecessarily meddling in her crew's affairs. Depending on whether skills or personality are judged first, Sandy is either one of the best or worst captains to be on Below Deck.