Captain Glenn Shephard, who leads the cast of Below Deck Sailing Yacht, has tarnished his reputation due to a series of questionable decisions.
Captain Glenn Shephard, who leads the cast of Below Deck Sailing Yacht, has tarnished his reputation due to a series of questionable decisions. His damaged reputation could pave the way for a new captain in future seasons. As season 5 of the show airs, Captain Glenn–who has spent over two decades in the yachting industry–returns alongside First Officer Gary King and Chief Stew Daisy Kelliher.
Gary returns for his fourth season of the Below Deck spin-off, known for his lack of responsibility and womanizing ways. Not only does Gary approach his deck crew in ways that many think to be harsh, but he has also been the subject of a sexual misconduct allegation dating back to the summer of 2022. A Below Deck makeup artist accused Gary of inappropriate behavior, adding to his already controversial reputation. These issues have reflected poorly on Gary and Captain Glenn, who has continuously overlooked the First Officer’s behavior.
Below Deck Sailing Yacht’s Captain Glenn’s A Womanizer
The Age Gap In His Relationship Has Drawn Backlash
Captain Glenn has been in a relationship for almost six years. Despite their foundation, many viewers still cannot get over how much older he is than his girlfriend, Danelis “Dani” Jimenez. The leader of Below Deck Sailing Yacht season 5 is in his 60s, while Dani is 43. On her birthday in 2023, Glenn took to Instagram to fire back at all the naysayers.
“I knew this apparent age difference would be an issue for some, but my feeling is when you find someone who you click with that is perfect in every other way, when it comes to love and happiness, I can think of no other best time to throw caution to the wind,” Captain Glenn shared about his partner. “Like I always say, life is short and you only die once and when you do, you stay that way for a very long time.”
Captain Glenn concluded his post by telling everyone to keep their thoughts to themselves. He insisted their love is solid despite the large age gap. Still, some viewers continue to comment on his posts, saying Dani looks young enough to be his daughter, which isn’t great for his reputation.
Below Deck Sailing Yacht’s Captain Glenn’s Lets Gary King Act Out
Their Friendship Is A Threat To Captain Glenn’s Likability
Despite everyone else seeing his problematic behavior, Captain Glenn is good friends with Gary. The pair not only spend time together during work hours but also hang out outside of work, with Gary giving his boss the nickname “Glenjamin.” Their friendship has never been a secret, which isn’t a good look for the Captain, who continues to turn a blind eye to all of Gary’s indiscretions. He even publicly supported Gary on social media amid the sexual misconduct allegations, raising even more eyebrows.
A lot of fans still view Captain Glenn as a sweet 63-year-old man, but his reputation is suffering because of his friendship with Gary. If he wants to continue being the face of Below Deck Sailing Yacht, he needs to pay more attention to all of the backlash Gary is getting. Captain Glenn needs to keep that in mind when it comes to their buddy-buddy relationship.
Below Deck Sailing Yacht’s Captain Glenn’s A “One Note” Captain
His Presence Has Become Quite Predictable
In addition to Captain Glenn’s questionable decisions involving some of the crew, it seems there’s not much more he can give as the leader of Below Deck Sailing Yacht. Nobody wants to watch a predictable character, especially in reality TV, and viewers already know exactly what they’re going to get from Captain Glenn in each episode. The other Below Deck captains have become fan favorites because of their over-the-top personalities, such as Captain Jason Chambers and Captain Sandy Yawn.
Captain Glenn is a lot more laid-back and likes to let his crew do their own thing, which has led to several blunders throughout the series. A more versatile captain joining the show would be a huge benefit to not only viewers but the crew themselves. His laid-back leadership has caused a lot of issues, and beyond that, his presence on the show has become stale. While Below Deck Sailing Yacht could benefit from a fresh captain, there are no signs that will happen any time soon.
