Below Deck Sailing YachtfigureheadCaptain Glenn ShephardmishandledGary King’s insubordination behavior in season 5, which is not a good reflection on Captain Glenn’s leadership. Captain Glenn has been the face ofBelow Deck Sailing Yachtsince its season 1 premiere in 2020. Having mostly fresh faces on the spinoff has given way to showcasing returning cast. Along with First Officer Gary being a part of the show since season 2, Chief Stew Daisy Kelliher has also been around the same amount of time.
Chief Engineer, Colin MacRae, was a returning crew member for three seasons, and Chase Lemacks has been a part of the latest two seasons. Gary is the most controversial cast member of the spinoff, and arguably the franchise. His disrespectful behavior, womanizing ways, poor leadership abilities, andoff-camera sexual misconduct allegationshave earned him the negative reputation he has. What’s worse, is that Captain Glenn is good friends with Gary and never draws the line with him, which is not what a good captain should do.

Gary Disrespected Captain Glenn In BDSY Season 5
Gary Got Drunk, Caused Chaos, & Lied
InBravo’sBelow Deck Sailing Yachtseason 5, Gary made several huge mistakes that weren’t taken as seriously by Captain Glenn as they should have been. Early in the season, Gary was flirting with a female talent act that performed for the guests while he was driving her back to shore. During the ride, Gary carelessly hit a rock. Fortunately, the tender was not badly damaged. When Gary brought it up to Captain Glenn,Captain Glenn largely brushed the incident offand did not come down on Gary like he should have.
Gary’s biggest disrespect came when the guests asked for the crew to go out drinking with them. Captain Glenn gave the strict rule that each crew member was only allowed two drinks.Gary had 10 drinks, and came back to the boat boasting about how he wasn’t drunk while stumbling around and refusing to go to bed. When Captain Glenn brought up the excessive rule-breaking drinking and announced he would take $500 each of their tip money, Gary threw a fit and insulted Glenn, saying that Captain Glenn"obviously"needed the money.

Captain Glenn Missed An Opportunity With Gary King
Gary Can Act With Impunity Around Captain Glenn
Captain Glenn allowed Gary to speak to him in the insolent way he did and show no remorse, which diminished Captain Glenn’s authority. When addressing the season as a whole on departing day, Captain Glenn chose to err on the side of friendship and nicety instead of being stern and creating a teachable moment.
“What a season, not withstanding the lollipop fiasco and the drag night drinking. In your position as First Officer, you’re one of the gang, but you kind of have to separate yourself a little bit. You know you need to start kind of rising above a little bit.”

Gary deserved a lot more of a talking to each step on the way inBDSYseason 5, especially considering Gary has an ambition to become a captain soon.
Captain Glenn demonstrated his poor leadership abilities by being too relaxed with Gary and condoning his impropriety.
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Captain Glenn Should Be Replaced As Captain
There Are Better Below Deck Captain Options
Outside of his lax demeanor and actions as a captain, Captain Glenn is boring compared to the other franchise captains. IfCaptain Glenn is not presenting as formidablenor creating entertaining reality TV, then he should be replaced onBelow Deck Sailing Yacht. Letting Gary act with impunity over setting an example by punishing him is not what a good captain should do. A new captain could enter the franchise, or a former First Officer or Bosun could take over.
Below Deck Down Underairs Tuesdays at 8 p.m. EST on Bravo.