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Captain Lee Rosbach has always begrudgingly said that Below Deck guest Timothy Sykes delivered the highest tip ever.

Sykes tipped the Below Deck Season 5 crew $35,000 after initially appearing on Below Deck Season 2. And while the Below Deck Season 10 crew has seen a few tips at $30,000 this season, Jake Clopton and guests set a new record, leaving a $40,000 tip.

The ‘Below Deck’ crew earned that $40,000 tip

Clopton and friends definitely made the crew work for their tip, but the crew and Captain Lee Rosbach had a blast with them too. When Clopton’s friend Angel fell asleep on one of the large floats, Rosbach and the other charter guests decided to prank him and allow the float to drag several additional feet behind the superyacht.

Captain Lee Rosbach from 'Below Deck' talks to Baker Manning
Captain Lee Rosbach, Baker Manning |Virginia Sherwood/Bravo/NBCU Photo Bank/NBCUniversal via Getty Images

Angel was a good sport about the prank and the rest of the guests had a good laugh. The crew met and seemed to exceed the guests’ requests and it certainly showed in the tip.

“Thank you so much, everything was fantastic,” Clopton said as he departed the yacht. He handed Rosbach, not one, but two fat envelopes of cash, which the crew noted.

“That’s two envelopes!” stew Hayley De Sola Pinto exclaimed in a confessional. “One could be filled with just Monopoly money though as a sick joke.”

Each ‘Below Deck’ crew member received $3,076

But the tip was no joke. “That’s a fat little f***er isn’t it?” Rosbach told the Below Deck crew during the tip meeting. “Job well done, I can’t thank you enough.”

Rosbach first reviewed the docking and got to the tip. “It’s more than I thought it was gonna be,” he said. “This is [$] 40 [000].”

The crew cheered when they learned they got a $40,000 tip. The breakdown was $3,076 per crew member.

“$40,000 of payoff money for literally having to deal with Angel,” De Sola Pinto said. “That’s a lot of money. He probably has to do it wherever he goes, to be honest. Every time he goes to a restaurant, ‘This one’s for him. You know, I’m sorry about him.'”

“Well done and well earned,” Rosbach told the crew.

The former ‘biggest tip’ was from ‘Below Deck’ guest Timothy Sykes

Rosbach seemed to enjoy this charter far more having the former king of the big tip on board. Rosbach was shocked when, during Sykes’ first charter, he removed some of the tip money from the envelope. Sykes said his girlfriend, who preferred quesadillas, didn’t get what she wanted on charter.

Despite Sykes delivering the biggest Below Deck tip until now, he was one of Rosbach’s least favorite guests. “I think the biggest tip in history we got, it was $35,000,” Rosbach said on the Side Piece with Melissa Pfeiste‪r podcast. “And from the most unlikely source. Timothy Sykes!”

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“He did it on his second trip,” Rosbach recalled. “Because his first trip, remember he took back five grand. Because you screwed up my 19-year-old date’s dinner.”

“He wanted uni and all this exotic stuff, which [chef] Ben [Robinson] did a great job for him,” Rosbach recalled. “In fact, he had to be segregated from the rest of his guests. He didn’t want his guests, or peasants eating with him. So we segregated him. Ben prepared this lavish, extravagant meal. And she [wanted] chicken fingers and quesadillas.” 

Thankfully, the crew had a better time with Clopton and guests and have one more charter left. The Below Deck Season 10 finale airs on Monday, March 20 at 8 pm ET.