Wentworth was formed by James D. Delaney and Gary Veloric in 1991 as a merchant bank specializing in transactions in the healthcare industry.

[6][7] In 1992, the company began to purchase New Jersey auto insurance deferrals from claimants who could not afford to wait twelve to eighteen months for their settlements.

Wentworth's parent company, JGW Holdco LLC, entered Chapter 11 bankruptcy protection partly as a consequence of the 2007–2008 financial crisis.

The company cited "liquidity problems amid a tightening credit market" as the motive for filing.

[12] In June 2009, JGW Holdco LLC received $100 million in equity from primary stakeholder JLL Partners, which allowed the company and its subsidiaries to emerge from bankruptcy.

Wentworth expanded their financial offerings with the purchase of WestStar Mortgage for US$44 million in common shares and cash.

Wentworth was delisted from the NYSE for failing to satisfy the continued listing rule of having an average 30-day market capitalization of at least $15 million.

[18] Later that month, the company began trading on the OTC Markets Group under the symbol JGWE.

The company was expected to emerge from bankruptcy in or around January 2018 after coming to an agreement with lenders prior to filing.

[citation needed] More recent series feature Wagnerian opera singers performing the company's jingle.