The Butterfield Bermuda Championship returns to the Port Royal Golf Course in Southampton for the eighth consecutive season. Adam Schenk won for the first time in 243 Tour starts at this event in 2025, continuing the trend of longshot champions at the tournament. If selecting longshots in the middle of the Atlantic Ocean does not float your boat, DraftKings Sportsbook offers plenty of other angles to attack. Let’s dive in!

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Digging deeper, Pendrith returns to Bermuda for the first time since a T8 in 2023. On debut, in 2021, the Canadian shot 61 in the second round and owned the 54-hole lead by three shots. He faded on Sunday and finished T5. He lost a playoff at the ISCO Championship in July.

In a field limited in depth, I am relying on two of the best ball-strikers around to do the business. James has been scalding hot since June, and the only remaining space on his bingo card is a win. He began the FedExCup Fall with a solo second at the Biltmore Championship Asheville after finishing solo third at the Wyndham Championship to wrap the regular season. He earned T5 money at the Bank of Utah Championship in his last start, once again stalking the lead.

Conners, who can grind out fairways and greens in any conditions, is not here for vacation. The Canadian, twice a winner at the Valero Texas Open, should be able to navigate his golf ball in the breeze off the Atlantic. Making his first appearance at the event and his first start after the Presidents Cup, this event fits his strengths. Before the Presidents Cup, he closed with 64 in the final round at the Biltmore Championship Asheville, another course he had never seen before in competition.

I’m not sure how many putts this duo will hole, but they should hit most of the fairways and greens in regulation. Both rank inside the top 55 in Strokes-Gained: Tee-to-Green in 2026, and are racking up weekend tee times. Hoey has made seven consecutive cuts, including his best 2026 result, a T10 at the Bank of Utah Championship. Parry owns four consecutive paydays and collected a check in six of his previous seven events. The Englishman has not missed a start in the FedExCup Fall and hit the top 25 (T22, T23) in two of three outings.

Digging deeper, I found a pair of plus-money horses for courses. Whaley, who missed qualifying for the weekend in his debut in 2020, returned to cash in the top 10 in his next four visits, including his career-best finish, a T3, in 2025. After he closed 68-65 at the Biltmore Championship Asheville, he withdrew from the Bank of Utah Championship with a rib injury.

If a recent injury scares you off, turn to Lower. His streak of four consecutive paydays at T20 or better at Port Royal crashed with a missed cut in 2025. His streak included top-10 finishes of T5 in 2024 and T8 in 2022. Lower enters the week on the island off T33 and T21 paydays in his last two starts, with his previous seven rounds in the 60s.

The bold can combine this pair as a Same Game Parlay for Top 30 (or Top 20).

The wind is always a factor at this event. I will rely on another pair of journeymen ball-strikers who are comfortable in the conditions on the island of Bermuda. Neither has missed the cut in nine combined appearances. Wu made the cut in both of his FedExCup Fall starts, but Sigg is making his first start since April. Interestingly, Sigg (+114) is shorter than Wu (+120) in this market.

In the seven previous editions, there has been only one event requiring extra holes. The 2020 edition saw veteran Brian Gay knock off a younger Wyndham Clark to earn his first win since 2013. In three of the next five editions, the margin of victory was one shot, including tough scoring conditions in 2021 and 2025. If the forecast for 2026 is on point, a wet, windy Sunday could bunch up the field at the finish line. Let’s gamble!