The original Below Deck series recently recorded the largest tip money a group of charter guests have ever given a crew on the Bravo yachtie flagship franchise. Commercial real estate business owner Jake Clopton proved he’s uber successful when he tipped the Below Deck season 10 crew members $40,000, the record for the highest tip given in Below Deck‘s decade-long history, including all spinoff shows. However, there’s been a lot of other generous tippers over the years, so let’s do a rundown of Below Deck‘s biggest tips and which charter guests made it rain cash for the reality TV yachties in the original series. We’ll also answer what these charter guests’ jobs and business are that they attained enough wealth to afford paying to charter a Below Deck yacht.
Below Deck Season 1’s Biggest Tip Was From A Professional Hypnotist Primary Charter Guest
The total tip money for Below Deck season 1’s cast was pretty pathetic. It didn’t help that Captain Lee Rosbach and his crew had to kick off the inaugural group of gay LA photographer charter guests for suspected cocaine use. Further reducing the tip money total in the first charter season, another group of charter guests canceled their trip. Add in the conflict between Chief Stewardess Adrienne Gang and her insubordinate third stew Sam Orme, it’s little surprise this was one of the worst seasons for tip money.
However, renowned hypnotist Steve G. Jones gave a very generous tip of $15,000, instead of using his Jedi mind tricks to get out of paying a tip at all. For those curious, the first season filmed in late 2011, so factoring in inflation the $15,000 tip equates to just over $20,100 USD in 2023’s value of money.
In total, Below Deck season 1‘s crew made a paltry $46,000 in tip money. Thankfully Below Deck cast members make Bravo and Yacht salaries on top of their tips.
Below Deck Season 2’s Highest Tip Given By Investment Banker
Below Deck season 2’s crew didn’t get any outlandishly high tips either. It didn’t help that stews and ex friends Kat Held and Amy Johnson had an unresolved feud over a guy. The boat’s harmony took on further discord when Chief Stew Kate Chastain bickered with Chef Ben Robinson.
Nevertheless, Primary Charter Guest and investment banker Christopher Davies, age 45 at the time, and his wife Shana Weiner, then 28, enjoyed their time aboard motor yacht Ohana. Although the crew judged the New Jersey accents, Christopher and the rest of the charter guests tipped a very generous $20,000.
Below Deck Season 3’s Top Tip From Restaurateur
Tahoe and Reno restaurateur and Primary Charter Guest Kevin Johnson’s trip didn’t start off on the right foot. He was thoroughly disappointed Kate didn’t stock Don Julio 1942 tequila. Kate rectified the situation, getting a bottle of Don Julio delivered to the superyacht by tender. And blonde siren Rocky Dakota entertained the charter guests with her theatrics. Kevin tipped the biggest on season 3 with $25,000 large.
Below Deck Season 4’s Returning Primary Dean Slover Finally Gives Biggest Tip
Recurrent Below Deck Primary Charter Guest Dean Slover finally forked out the highest tip on his third charter on Below Deck. The previous season he gave the second highest tip of $20,000. Foodie Dean, a restaurant and club owner, raved about Chef Ben’s food and tipped the crew a jaw-dropping $26,000.
Below Deck Season 5’s Primary Timothy Sykes Gives Crew Lots Of Benjamins
Returning Primary Charter Guest and financial investor guru Timothy Sykes got accused of being a cheapskate the previous season he was on Below Deck. He reduced the first tip he gave a previous due to lack of internet connection and some other hiccups. This time around, Timothy didn’t get disappointed and didn’t skimp on his largesse. He gave the crew at-the-time record-setting biggest tip of $30,000. He could afford to give out the tip after turning $12,000 into $7 million by largely investing in penny stocks.
The Blind Side-based Sandra Bullock character Leigh Anne Tuohy and husband Sean Co-Primary Charter Guests as well as Co-Primaries Bradley and Summer Smith both deserve honorable mentions for each group tipping $21,000 on their respective charters.
Below Deck Season 6’s Entrepreneur Couple Give Highest Tip
Co-Primary Charter Guests and couple Alan Miller (racecar driver) and Danyelle Rabine raved about Chef Adrian Martin’s exceptional cooking. They joked to Captain Lee they were stealing him at the end of charter and giving him the entire tip. Luckily for the rest of the crew they got to split a decent $22,000 tip from the Blue Marble Cocktails owners.
Below Deck Season 7’s Two Groups Tied For The Top Tip
Avid Below Deck fans won’t be surprised to here the poor attitude and arrogance from Chef Kevin Dobson and his fellow despised Bru Crew (Bosun Ashton Pienaar and his deckhands Tanner Sterback and Brian de Saint Pern) causing major friction with the interior crew didn’t bode well for the tips from charter guests.
The highest tips, $20,000 apiece, came from Sports Journalist and Primary Jemele Hill‘s charter and Co-Primaries Helen Hoey (lingerie designer) and Richard Fiore.
Below Deck Season 8’s Crew Had Lots Of Big Tips
Ahoy big spenders! Tip money rained down on Below Deck season 8’s crew. Primary and CEO of CW3 Public Relations Charley Walters got the party started. Although his charter started off poorly with disorganized stews Elizabeth Frankini and Isablle “Izzy” Wouters and he was disappointed Kate was replaced by Chief Stew Francesca Rubi, Charley still obviously thought the crew did very well. He tied for the largest tip of the season at $25,000. Matching his generous gift to the crew, Primary and North Carolina’s hotshot realtor Bryan Guarnieri wouldn’t be outdone, dropping twenty-five grand, too.
Despite Chef Rachel Hargrove getting absurdly drunk on nights off out with crew, she clearly delivered the goods when it came to her five-star food.
Trial lawyer Tim Scott and wife Beth Fegan’s group deserve an honorable mention for tipping a respectable $20,000, too.
Below Deck Season 9’s Charter Guest Tip Big, Too
Although the n-word controversy between Chief Stewardess Heather Chase and deckhand Rayna Lindsey overshadowed much of Below Deck season 9, the charter guests remained happy judging by tips. Below Deck season 9’s crew struggled, especially the deck crew, but they still managed to make some major tip money. Self-made real estate entrepreneur Ronnie Weiss celebrated his 75th birthday with family. He tipped $25,000, tying for the top tip of the season.
Retired naval officer and tech entrepreneur Tony Thornton renewed his wedding vows with his wife Porscha while aboard the superyacht. His group of charter guests matched Ronnie’s highest tip of the season.
Below Deck Season 10’s $40,000 Tip Makes New Record
On Below Deck season 10 Chief Stew Fraser Olender bad-mouthed a primary and his wife’s best friend, suggesting they were having an affair. Olender sure changed his tune after he and the rest of the crew received a $40,000 tip from commercial real estate tycoon Jake Clopton and his friends.
Clopton’s group weren’t the only ones tipping very high in season 10. The second highest tip came from power sports couple retired tennis star Gigi Fernandez and retired golf pro Jane Geddes, at a $31,000 tip.
The crew made $222,300 in tip money for the charter season — nearly half a million dollars! Split between the crew who were there the entire season, each one got $17,000.
Below Deck season 11 just wrapped up filming in Grenada, so we’ll have to wait a year to see if any charter guests from the latest season will beat the record for highest Below Deck tip ever.