As Tribune Co. shareholders prepare to gather in Chicago Tuesday to vote on the $8.2 billion plan that would take the company private, speculators question whether the deal will even go through.

Since April, when Tribune accepted real-estate tycoon Sam Zell's offer to go private, the company's debt has continued to mount, making the $34 per share deal tough to go through, according to industry analysts.

The Tribune, one of the largest U.S. newspaper companies, includes flagship papers such as The Los Angeles Times, The Chicago Tribune and Newsday. It also owns 24 television stations, Superstation WGN on national cable, the Chicago Cubs baseball team, 13 daily newspapers, three Spanish-language newspapers, a radio station and seven national classified Web sites, including Careerbuilder.com and Apartments.com.

Zell's deal of $34 per share was for stock that was selling for about $30 at the time. Tribune bought back half its outstanding shares in May, planning to buy the rest in the fourth quarter. However, since then trading prices have continued to decrease, and dropped to below $25 last week, its lowest in nine years. A discount of about 25 percent has led to a lot of uncertainty.

“A lot of people are betting it won't get done, at least not at that price,” Dave Novosel, a senior analyst at market research firm Gimme Credit, is quoted as saying in an International Herald Tribune article.

Yet despite the market's doubts, many still think it is not only very likely the deal will close, but that it also makes economic sense.

Deutsche Bank analyst Paul Ginocchio said his bank has a “buy” rating on Tribune stock, according to an International Herald Tribune article.

“The biggest risk to the deal is Zell getting cold feet and trying to reprice the deal, but we think that's very unlikely,” he is quoted by the International Herald Tribune as saying.