Chicago entrepreneur Michael Ferro is investing $44.4 million in Los Angeles Times owner Tribune Publishing Co. The Los Angeles Times reported Thursday that the move makes him the company’s largest shareholder and gives the company cash that could bolster a planned bid for the Orange County Register.

Ferro, through his firm Merrick Media, bought 5.22 million newly issued shares of Tribune Publishing stock, giving him a 16.6% stake in the company, which also owns the San Diego Union-Tribune, the Chicago Tribune and several other daily newspapers.