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Tyler left Gallagher Re earlier this year.
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The reinsurer confirmed its intention to reduce the K-Cession sidecar for 2025.
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Cheaper traditional reinsurance as of mid-year may have dampened deal pipeline.
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The failure of a Jamaica bond to pay out following Hurricane Beryl damage has brought focus onto the deals.
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Daniel Ineichen, former co-head of ILS, had been with the company for nearly two decades.
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The outgoing CEO will leave the company at the end of March 2025.
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The Florida carrier reported a 103.5% combined ratio in Q3.
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In other property, Helene and Milton will assure rates remain attractive, he added.
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The latest issuance signals the second time the sponsor has entered the cat bond market.
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The bond offers a midpoint multiple of 4.1x with an expected loss of 0.92%.
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The carrier said it expected its Milton losses to fall below its EUR500mn ($537mn) Helene loss.
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Stokes has been with Pillar for nearly four years.