Below Deck Captains Ranked by Sass Level

Captain Lee Rosbach Below Deck
Virginia Sherwood/Bravo/NBCU Photo Bank/NBCUniversal via Getty Images

Below Deck and its various spin-offs have seen many great Captains, although some are more beloved than others. Captain Lee Rosbach led the crew on the OG Below Deck show for ten seasons, before ultimately retiring. After Captain Lee, Captain Sandy Yawn from Below Deck Mediterranean has been in the franchise the longest, who has now filmed seven seasons of the spin-off.

Captain Glenn Shephard has also held the Below Deck Sailing Yacht crew down for four seasons, despite numerous challenges. The recent Below Deck Adventure featured Captain Kerry Titheradge, who is set to replace Captain Lee on Below Deck Season 11. Finally, Captain Jason Chambers quickly became a fan favorite, despite only being featured on two seasons of Below Deck Down Under so far.

When it comes to the five Below Deck captains, some are certainly sassier than others. Here is our official ranking of the captains, from the least sassy to the absolute sassiest!

Captain Kerry – Least Sassy

Kerry Titheradge/Instagram

When it comes to the Below Deck captains, there is no doubt that Captain Kerry ranks last in terms of sassiness, although we still love him! While viewers have only seen Captain Kerry on the first season of Below Deck Adventure, it is already clear that he is a team player who avoids conflict at all costs.

Captain Kerry was very easygoing with his crew, unlike some of the other Captains. Instead of criticizing the crew when making mistakes, Captain Kerry went out of the way to help his team whenever necessary, particularly Chef Jessica Condy. While we are certainly excited to see Captain Kerry take over on Below Deck Season 11, we are not confident that he will match Captain Lee’s level of sass.

Captain Glenn – A Little Sassy

Glenn Shephard/Instagram

In terms of sassiness, Captain Glenn is not much more sassy than Captain Kerry, although he can be at times. Like Captain Kerry, Captain Glenn is known for being one of the more compassionate and understanding Below Deck captains. As a result, he is usually not sassy with his team, especially when charter guests are around.

However, Captain Glenn has had some sassy moments on Below Deck Sailing Yacht, particularly with Chief Stew Daisy Kelliher. Captain Glenn is particularly hard on Daisy and the interior team at times, and tends to micromanage them more than the exterior team. On the other hand, he seems to have a soft spot for controversial cast member Gary King, which frustrates some viewers.

Captain Jason – Somewhat Sassy

Jason Chambers/Instagram

Out of all the Below Deck captains, Captain Jason falls in the middle of the sass meter. Captain Jason is a fan favorite, and recently received praise from Bravo fans after he fired two cast members on Below Deck Down Under for sexual misconduct. While there is no doubt that Captain Jason cares for his crew, he can also be sassy with them on occasion.

Captain Jason tends to micromanage at times, and can get frustrated with his crew when things do not go as planned. On Below Deck Down Under Season 2, Captain Jason has been particularly sassy with Chef Tzarina Mace-Ralph, who has been problematic. There is no doubt that fans love Captain Jason, however, even if he has a sassy side.

Captain Sandy – Second Most Sassy

Sandy Yawn/Instagram

While some Below Deck fans adore Captain Sandy, there are also a good number of viewers who cannot stand her. Captain Sandy maintains a no-nonsense attitude with her crew on Below Deck Mediterranean, which has made her one of the more controversial Below Deck captains.

There is no question that Captain Sandy isn’t the easiest to get along with, which viewers witnessed throughout her tense relationship with Chief Stew Hannah Ferrier. Captain Sandy eventually fired Hannah after working with her for several seasons, to the dismay of many fans. At the end of the day it is clear that Captain Sandy cares about her crew and guests, but she is not afraid to pull out some sass to get her way.

Captain Lee – The King Of Sass

Lee Rosbach/Instagram

Captain Lee is the ultimate definition of sass, when it comes to the Below Deck franchise. Throughout his ten years on the OG show, Captain Lee had more sassy moments than anyone could possibly count. Throughout all of the Below Deck shows, Captain Lee was the hardest on his team, although this ultimately worked out for them in the long run.

Captain Lee was not only sassy with his crew, but also with the guests. No one can forget Captain Lee’s reaction to Dolores, the charter guest who infamously decided to take a drunk swim in the ocean. Many Below Deck fans are sad to see Captain Lee finally leave the franchise, as it is unlikely any other Captain will ever match his humor and sass.