What was once Indianapolis-based MH Private Equity's most valuable portfolio company has filed for bankruptcy.

Entertainment Publications LLC, which produces fundraiser coupon books, filed for Chapter 7 liquidation Tuesday in Delaware.

The Troy, Mich.-based company was founded in 1962 and acquired in 2008 by MH Private Equity, which said at the time that the sale and accompanying tax benefit to seller IAC/InterActive Corp. was valued at about $135 million. Documents in a court case concerning MH Private Equity's management show that the fund paid $36 million in cash for Entertainment Publications.

Hardware king John Menard, who put up $500 million to create MH Private Equity with Steve Hilbert, alleges that the portfolio has lost 70 percent of its value, and he recently ousted Hilbert as CEO over the decline.

Entertainment Publications faced a liquidity crisis more than a year ago, but Menard declined to bail the company out unless he gained the right to fire Hilbert without cause, documents in a Wisconsin court case show. Hilbert had requested a $20 million line of credit, which Menard would grant only with a revision of the MH Private Equity Fund operating agreement, according to a Feb. 28, 2012 letter to Hilbert from the Menard Inc. legal department.

Hilbert resisted the change. "We also understand that an amendment to the agreements is unacceptable to you," corporate legal manager James Anderson wrote. "Therefore, we plan to discontinue our work on the funding at this time."

The same letter said that a sale of Entertainment Publications could have brought $100 million.

The bankruptcy petition described assets as worth less than $50 million with debt totaling more than $50 million.

The company, which sold coupon books in more than 150 cities, had as many as 250 employees in recent years, but almost all of them have been laid off.

The firm was founded as Sports Unlimited in 1962 and changed its name to Entertainment Publications two years later. The business has had several different owners since its founding.