While battling its insurers over funds to cover hurricane damage, Daytona Beach, Fla.-based hotelier Bray & Gillespie Management LLC consulted with Juridica Investments Ltd., which invests in lawsuits for a share of the recovery. The investment never happened, according to court documents—but the conversations were not forgotten by the parties the hotel owner was suing.

In a 2008 deposition, their lawyers asked about the discussions. The conversations, they believed, might reveal weaknesses in Bray’s case. Bray’s counsel at Reed Smith immediately objected, arguing that the discussions were covered by attorney-client privilege.

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