Shares of Tribune gained 1.9% to $38.41 on Wednesday, and were unchanged after-hours. Sinclair increased 3% to $40.40 on Wednesday and gained another 1.4% to $40.95 after the close.
"We don't see a better buyer for (Tribune) given (Sinclair)'s diversified portfolio and size," Marci Ryvicker of Wells Fargo Securities wrote in a Wednesday note.
Tribune has a "complicated mix of assets," she wrote. The Chicago broadcaster owners or operates 42 TV stations, the WGN America cable network and the Tribune Studios programming production unit, and has stakes in Career Builder and the Food Network. Tribune was even more complex before the company spun off its newspaper division into the unfortunately named Tronc (TRNC) in 2014.
Sinclair owns or provides programming services to 173 TV stations and has a portfolio of cable networks such as the Tennis Channel and American Sports Networks, which covers college and high school sports.
Tribune has been taking a close look at its assets since February 2016. The company divested $506 million worth of real estate and sold its Gracenote digital media business to Nielsen (NLSN) for $560 million.
In January the Chicago broadcaster announced a $499 million special cash dividend equal to $5.77 per share.