In an effort to raise cash for a government bailout repayment, American Insurance Group (A.I.G.) has sold its longtime stake in the private equity firm, The Blackstone Group (NYSE:BX) . The sale came in at $500 million.

A.I.G. purchased a seven percent share in Blackstone back in July 1998 for approximately $150 million and invested about $1.2 billion into the firm’s investment funds. This came before the firm went public in 2007.

The two companies have a relationship that extends past their investment history. According to The New York Times, A.I.G.’s long-term CEO Maurice R. Greenberg sat on Blackstone’s advisory board and the company had invested in Blackstone funds.

In their reciprocal relationship, Blackstone has served as an adviser to A.I.G. during these tough economic times. John Studzinski, head of Blackstone’s advisory team, helped A.I.G. weather the storm by advising the company as it stumbled toward bankruptcy.

AIG dodged this 2008 bullet as the Federal Reserve Bank threw them a lifeline.

Since that time, Blackstone has counseled A.I.G. for seven asset sales that has assisted them in repayment of the bailout, according to The New York Times.

Friday’s sale wasn’t the first one for A.I.G. The company has slowly been chipping away its Blackstone stake including a sale in 2010 for 10 million shares. With this most recent transaction, it represented the end of A.I.G.’s stake in the company and possibly an end to an allegedly growing hostility between the two companies.

The transaction took place before the market open on Friday. The purchaser of the AIG’s stake is currently unknown and both companies did not comment on the trade.

Shares of both companies dropped on the news.