To date, there are twenty-seven members in the so-called Fifth Generation of the Ochs-Sulzberger family, at least three of whom are already active in the company: James Dryfoos works as a systems analyst; Michael Greenspon works in strategic planning; Rachel Golden works on digital media. (Sulzberger’s son, Arthur Gregg Sulzberger, is also in journalism, reporting for The Oregonian.) In addition, Carolyn Greenspon serves as the only trustee from the Fifth Generation. The family works to cement its bond to the Times, including holding one-day orientation sessions with family members at age eighteen or twenty-one or when they marry into the family; convening an annual family business meeting with executives from the paper and additional meetings on media-industry developments; and holding annual family reunions, where reportedly they sing songs like Sister Sledge’s “We Are Family.” Though the trust is designed to guard against infighting by giving the family the right to buy out dissenters, and though Arthur Sulzberger has publicly assured that “the center will hold” in the next generation, there is no absolute defense against a disgruntled family, particularly if the engine that drives its wealth begins to sputter. At one time or another, the Chandlers, the Bancrofts, the Ridders, and the Binghams all seemed like dedicated newspaper families committed to defending their heritage. All happy newspaper families are alike; each unhappy newspaper family grows unhappy in its own way. In an e-mail, Sulzberger stated that passing the unique culture of the Times Company on to the next generation is his “final and greatest business challenge.”

Whether he will be able to meet that challenge may depend on Sulzberger’s leadership during the next few years. To date in his tenure as publisher and chairman, he has at times displayed the immaturity that made some think him unsuitable to run the company and at other junctures been prescient in his vision of both the paper and the industry.

In assessing his job performance, it is useful to separate Sulzberger’s two roles at the Times Company. As publisher of the Times, the two most prominent blowups during Sulzberger’s tenure involved Jayson Blair, the young reporter found to have fabricated stories in 2003, and Judy Miller, a veteran reporter who was judged to be too cozy with government sources in the run-up to the Iraq war, and who later ran afoul of special prosecutor Patrick Fitzgerald in the Valerie Plame leak investigation. The details of both cases have been well hashed out (including in these pages), but as they pertain to Sulzberger’s leadership style, both are instructive. The defining moment for Sulzberger in the Blair case came when he convened a townhall-style meeting for the staff and walked onto the stage with a stuffed toy moose, a symbol, he thought, that one should not ignore uncomfortable facts. But the impression it left was that he was tone deaf to the gravity of the situation and out of touch with the newsroom, particularly with the deep staff dissatisfaction with Sulzberger’s handpicked executive editor, Howell Raines. Though Sulzberger initially supported Raines, as the scandal dragged on, he did a swift about-face, dumping Raines as well as managing editor Gerald Boyd.

Douglas McCollam is a contributing editor to CJR.