Legal action by a New York investment bank has coincided with a pause in the expansion plans of distressed asset player Tiptree Marine.

The Stefanos Kasselakis-headed company is a subsidiary of Nasdaq-listed insurance underwriter Tiptree Inc and is the controlling shareholder in SwiftBulk Holding and SwiftTanker Holding.

In a series of legal actions in US federal and New York state courts, Silver Leaf Partners has alleged it was never paid for its work in putting together Tiptree Marine and originally demanded up to $22m in actual and punitive damages based on allegations of fraud.

But the bankers have subsequently withdrawn their fraud allegations and cut back their demand to $4m.

Tiptree Marine's lawyers have countered that Tiptree was not a party to Silver Leaf's contract with a Kasselakis-controlled entity, and have forced Silver Leaf to take its complaint back to the drawing board.

Extensive legal filings — viewed by TradeWinds — include confidential investor briefings, as well as email and text exchanges from an 18-month period when Kasselakis was developing his shipowning ambitions with Silver Leaf's Kathleen Lauster, who was ultimately paid $2,000 for her work.

The filings record that Lauster introduced Kasselakis to dozens of potential investors, beginning in 2016, and that a letter of engagement promised the advisors an incentive fee based on investments that resulted.

Kasselakis told TradeWinds that Tiptree Marine regards the bank's claim as a "nuisance lawsuit" and points to a series of courtroom and arbitration victories.

"Tiptree and its affiliated defendants have and will continue to vigorously defend themselves and believe no payment is due to Silver Leaf under the engagement letter, and that the claims are without merit," he said in a written statement.

'No liability'

The investment bank has claimed that, based on the sums Tiptree Inc eventually invested in Kasselakis' projects, it should have been paid more than $5m.

But in an April 2018 email, Tiptree Inc general counsel Neil Rifkind disclaimed any liability on Tiptree's part for Lauster's work.

Documents reviewed by TradeWinds indicate that bulker owner AM Nomikos — not a party to the lawsuit — was closely tied to the project before Kasselakis sought investment bank help.

AM Nomikos has not responded to enquiries. Lauster confirmed that the legal action is ongoing but declined to comment.

This story has been amended since publication to reflect that Silver Leaf has reduced its claim from $22m to $4m and withdrawn fraud allegations.