As the New York Times Company braces for a shareholder revolt at its annual meeting scheduled for April 24, Chairman Arthur Sulzberger may have found a potential lifeline: billionaire Howard Milstein.

Milstein, the C.E.O. of Emigrant Bancorp--the privately held New York bank with a history stretching back to 1850 and assets of $15 billion--bought 6 million shares of the New York Times Company in December, according to S.E.C. filings. He is now the sixth largest institutional shareholder with a 4.3 percent stake in the Times Company worth $150 million.

A person with knowledge of Milstein's investment said Milstein is an ally of Sulzberger. Before making the investment, Milstein called Sulzberger and said he was making a friendly investment in the Times, this person said. Another source said that while Milstein's investment is friendly, he is putting money into the Times Company as a long-term value play.

Milstein is the latest shareholder to emerge as a player in the proxy fight championed by Hassan Elmasry of Morgan Stanley Investment Management that is seeking to unseat Arthur Sulzberger's control of the paper.

The appearance of Milstein comes as the New York Times Company reported first quarter earnings results today, and a 9.9 percent decline in operating profit.

Milstein declined to comment. John R. Hart, vice chairman and treasurer of Emigrant Bancorp, declined to comment on the investment.

Times Company spokesperson Catherine Mathis, said: "We're delighted Mr. Milstein sees potential in the shares of the New York Times Company."

Still, Milstein's presence as the Times Company's sixth largest institutional shareholder is the latest twist in a deepening feud between Sulzberger and hostile shareholders, including Elmasry of Morgan Stanley, and Private Capital Management's Bruce Sherman.

In April, Institutional Shareholder Services and Glass Lewis both issued reports recommending that New York Times Company stockholders withhold their votes for the board of director nominees at this month's annual meeting. (Proxy Governance, another shareholder advisory firm, issued a report saying Times shareholders should approve the slate of board directors.)

Recently, Sherman placed a call to Milstein seeking comment on his intentions but the call went unreturned.

With Milstein's support of the Sulzberger family, one theory is that with access to Emigrant Bancorp's financing, the Sulzbergers, perhaps teaming up with private equity investor Steven Rattner, could take the Times private.

If so, this wouldn't be the first flamboyant investment for Milstein. The 56-year-old billionaire is the heir to one of New York's largest family real-estate fortunes that was ripped apart by an internecine struggle.

A media play for the New York Times would parallel other high-profile ventures Milstein has made over the years. In the 1990s, he owned the New York Islanders hockey team (he sold the franchise for $190 million in 2000), and in 1998, he made an unsuccessful $800 million bid for the Washington Redskins football team, then a record price offered for an NFL team.

by Gabriel Sherman