By Julie Creswell

(FORTUNE Magazine) – IN RECENT YEARS ONE OF THE favorite games in media circles has been guessing how much longer the Bancroft family heirs, who hold 62% of the voting power in publishing giant Dow Jones, will stick around while their fortunes fall in tandem with the company's stock price. The answer? Maybe not much longer.

Roy Hammer, a longtime trustee to the Bancroft family, told FORTUNE that the heirs would prefer that Dow Jones, publisher of the Wall Street Journal, fix its problems and that they're not actively pursuing a deal. But, he added, "the possibility of a sale is never out of the question."

As it is, thanks to a sweetheart deal struck in late April that shocked corporate-governance watchdogs, the family can now cash out of more of its shares--albeit at depressed levels. The board and CEO Peter Kann supported a change to the company's bylaws that allows the Bancrofts to sell nearly half of their supervoting B-class shares without ceding control of the company. But with the stock price at $33, down 44% from five years ago, it's a hollow victory. "We'd rather sell at $60 a share," Hammer quips, adding, "If you know any buyers, send them my way." (Another source close to the board says some Bancroft heirs indicated last year that at $60 a share, they would indeed consider selling.) If the family did put Dow Jones on the block, it would have suitors lining up for the ultimate "trophy prize," says Mark Boyar of Boyar Asset Management, who owns 186,000 shares and favors a sale. Based on valuations of other recent newspaper deals, he thinks Dow Jones could fetch $70 a share--if not more.

Though the publisher's journalistic reputation remains stellar, Dow Jones has been hit harder than other newspaper companies because of its reliance on financial and tech advertising, admits Kann (who wouldn't comment on the Bancroft heirs' possible plans). And things don't seem to be improving: Earnings skidded 54% in the latest quarter.

"The advertising downturn has been a significant factor in the company's performance," says Hammer, who retired from the Dow Jones board this spring. "But I wouldn't say it's the only factor, because the performance of the company relative to its peers has been disappointing." Rivals have fared much better: The stock price of the Washington Post Co. is up 80% over the past five years, and at the New York Times Co. it's down, but by only 15%. Some family members hold Kann directly responsible for Dow Jones's lackluster performance, according to sources close to the family.

That said, the family appears willing to allow Kann another chance to turn things around, given that he's expected to retire in about two years, and that he's just placed two high-stakes bets. First, in January, Dow Jones completed its $410 million all-cash buyout of MarketWatch. Dow Jones hopes it can benefit from fast growth in online advertising, but critics say it paid too much. There's also the worry that this venture will fare as badly as the now infamous Telerate fiasco in the mid-1990s, which eventually cost Dow Jones about $1.5 billion. Kann maintains that Dow Jones did not overpay for MarketWatch and that the business is very different from Telerate. His second play is the rollout of a Saturday edition of the Wall Street Journal in September. He's hoping it will diversify revenues by attracting more consumer-based ads, but it risks simply cannibalizing sales from other days of the week. If that happens you can bet on one thing: an even more frustrated family. -- Julie Creswell