Late Scholastic Chief’s Sons Challenge Rival for Control

But Ms. Lucchese is facing resistance from Mr. Robinson’s family and the prospect of a messy court battle. His two sons are exploring avenues to challenge her ascension, according to people familiar with the family’s thinking—and friction between the two sides is escalating.

Mr. Robinson’s older son, John Benham “Ben” Robinson, declined to sign a document waiving his right to contest his father’s will, according to legal filings. He later received a court summons from Ms. Lucchese’s team in October seeking a response, according to legal filings.

On Nov. 12, Ben Robinson and his younger brother, Maurice “Reece” Robinson, responded to the summons, asking New York Surrogate’s Court—the venue for handling probate and estate matters—for documents regarding the will, written in 2018, and the right to examine related witnesses, according to a legal filing.

One issue of keen interest to the family is a pledge they believe the elder Mr. Robinson made years ago to give voting shares to his sons in return for borrowing money from their mother, his ex-wife Helen Benham, the people familiar with the family’s thinking said. The family also believes Mr. Robinson was at work on a new will when he died, they said.

Ms. Benham, who worked at Scholastic for more than three decades, is supporting her sons’ legal efforts. In an interview, she said Ms. Lucchese’s control of Scholastic is still in question. “She’s sitting on top of a mountain of gold,” Ms. Benham said, referring to control of the company, “but the question is whether she’s got the gold.”

Ben and Reece Robinson in interviews said they agreed with their mother’s view and were exploring their options.

If the Robinson brothers were successful in a legal fight or in reaching a favorable settlement, some or all of Ms. Lucchese’s voting power could shift to the family, giving them influence over everything from the leadership of the company to whether it should engage in any major transactions.

Thomas Rice, a partner at the law firm Baker & McKenzie LLP who represents Scholastic, said: “Creating legal delays and distractions isn’t in the best interest of Scholastic or its shareholders. We have no basis to believe a will contest will be successful.” Mr. Rice said that Mr. Robinson’s directive was to “ensure the continued professional management of Scholastic in accordance with its independent legacy and educational mission.”

Scholastic spokeswoman Anne Sparkman said of Ms. Lucchese: “Iole is committed to doing what’s best for all stakeholders, including the Robinson family. She’s trying to work constructively with Mr. Robinson’s sons.” The company declined to make Ms. Lucchese available for an interview.

The Scholastic saga is a testament to how turbulent succession can be without clear plans, especially in family-controlled companies. Mr. Robinson didn’t make his intentions known even to immediate family members, The Wall Street Journal reported in August. They were taken aback by his wishes and were left sorting through grief, anger and fear for their financial security.

The legal battle has dredged up old memories for a family that is still struggling to come to terms with Mr. Robinson’s relationship with Ms. Lucchese.

For Ms. Lucchese, the rift with the Robinsons comes as the 55-year-old is just settling into her perch atop Scholastic, whose directors named her board chair on July 18. Alongside the new chief executive,

Peter Warwick,

she is trying to guide the century-old publishing company—known for its school book fairs and major franchises such as “Harry Potter,” “Captain Underpants” and “Clifford The Big Red Dog”—through a recovery after its business took a hit in the pandemic.

Mr. Warwick in an email said he was working closely with Ms. Lucchese to “continue to grow and strengthen Scholastic for all of our stakeholders.”

Ms. Lucchese climbed the ranks of Scholastic over three decades, with the late Mr. Robinson at turns playing the roles of mentor, sparring partner and romantic interest, according to former employees. Mr. Robinson and Ms. Lucchese appeared to break up for good in 2019, people familiar with their relationship said.

Mr. Robinson died suddenly in June at age 84 while walking in Martha’s Vineyard. His sons and ex-wife were shocked and hurt, Ms. Benham said, when they discovered he left almost everything to Ms. Lucchese.

Mr. Robinson’s will and revocable trust named Ms. Lucchese the sole beneficiary of 53.8% of the company’s Class A shares, which hold the majority of voting power, a securities filing shows. Ms. Lucchese would become the owner of the underlying shares if the will is fully executed in Surrogate’s Court.

Mr. Robinson also gave Ms. Lucchese sole discretion over whether to distribute any of his personal possessions to his two sons, according to the will, reviewed by the Journal, “with the request, but not the direction” that she hand out items “as she believes to be in accordance with my wishes.”

Conciliatory start

The sons initially wanted to take a conciliatory approach with Ms. Lucchese, believing it was the best route to ensure they would get a financial payout from the estate and access to their father’s belongings, the people familiar with the family’s thinking said. In July, Reece Robinson signed a document waiving his right to challenge the will, a legal filing shows.

Conflict between the two sides started to take hold at a July meeting at Scholastic’s headquarters in New York. David Ferris, who has been a financial adviser to Ms. Benham for years, said he attended the meeting and brought up a $2 million interest-free loan Ms. Benham gave to

Richard Robinson

over a decade ago at the peak of the financial crisis.

In a written response to the Journal’s questions, Mr. Ferris said he told Ms. Lucchese in the meeting that the late Mr. Robinson had promised voting shares to his sons in return for the loan. Mr. Robinson was in a precarious financial position at the time because of a margin call, Mr. Ferris recalled saying in the meeting. A margin call is when an institution that has lent someone money for investments requires that more cash be put in the account to offset losses.

“Dick called in a panic and had no other options,” Mr. Ferris said in his written response. Ms. Benham helped him, he said, even though they weren’t on good terms, to ensure “the Scholastic legacy would be inherited by Ben and Reece.” Ms. Benham said she didn’t have signed paperwork regarding Mr. Robinson’s promise to give the shares to his sons. “He made a commitment,” she said.

Ms. Benham and her sons have been unhappy Ms. Lucchese hasn’t shared more information on how she is handling Mr. Robinson’s personal estate, the people familiar with the family’s thinking said. The sons want more information because they fear that, after assets are sold to pay off a hefty estate-tax bill, there may not be much, if anything, left over for them, the people said.

Andrew Hedden,

Scholastic’s general counsel, said in an email that in his role as co-executor of the estate, “My focus there has to be on carrying out my attendant responsibilities, regardless of what others may publicly speculate.”

Mr. Ferris said that he estimates the value of Mr. Robinson’s estate at almost $100 million but that Ben and Reece Robinson could get less than $1 million each, because of taxes on the estate and voting shares, executor fees paid to Ms. Lucchese and Mr. Hedden, and other costs.

“Mr. Robinson amply provided for his family throughout his lifetime,” said a company spokeswoman. “We have no evidence that any commitment concerning the distribution of shares was ever made.” She also disputed that Mr. Ferris is positioned to provide a “credible estimate” of Mr. Robinson’s estate.

Reece Robinson, a 25-year-old documentary-film maker, in an interview said he had sent Ms. Lucchese an email in October asking about “non valuable mementoes” of his father’s that he said she hasn’t committed to giving over.

The Scholastic spokeswoman, Ms. Sparkman, said it was unclear which email Mr. Robinson was referencing and that the tone of correspondence has been cordial.

Ben Robinson, 34, is a writer, operates a sawmill and workshop in Martha’s Vineyard, and lives off the land. Like his brother, he was counting on an inheritance to provide some financial cushion. It was his father’s intention to change his will, he said in an interview.

“I know from conversations with him that he was working on a new draft but he was consumed with bringing Scholastic through Covid,” he said, adding that this was supported by documents the family retrieved from the late Mr. Robinson’s briefcase.

Richard Robinson’s siblings have given no indication they want to challenge Ms. Lucchese’s rise, people close to the family said.

Succession surprise

Succession planning had been a sensitive topic inside Scholastic for years. Former board members said that they pushed Mr. Robinson repeatedly to disclose his plans or groom successors but that he brushed them off.

Ramon Cortines, a former Los Angeles school superintendent who served on the company’s board and stayed on as an adviser until a few years ago, recalled telling Mr. Robinson, “You have a majority of the board that is upset with you.” Mr. Robinson responded that his legal adviser, Mr. Hedden, would know what to do if he died, Mr. Cortines said.

Mr. Hedden said in an email he hadn’t known to whom Mr. Robinson would leave his voting shares, “viewing that as a personal matter.”

Privately, Mr. Robinson had set out some plans. He had penned a will in 2014 in which his sister, Mary Sue Robinson Morrill, was slated to be the co-executor of his estate, according to family members and a person close to Mr. Robinson. That would be superseded by the will he wrote in 2018, which left his holdings to Ms. Lucchese and named her co-executor of his private estate.

Ms. Morrill in an email confirmed that Mr. Robinson had asked her to serve as an executor of his estate “at some time in the past” but said she never saw the estate-planning document.

Ms. Lucchese said during the July meeting with Mr. Robinson’s sons that she was surprised Mr. Robinson left her his holdings—that she didn’t want the controlling shares, according to a person familiar with the meeting. Scholastic’s Ms. Sparkman said Ms. Lucchese was unaware of Mr. Robinson’s intentions.

Some close friends of the late Mr. Robinson said they were skeptical that Ms. Lucchese wasn’t informed about the will.

Ms. Lucchese voiced grief about Mr. Robinson’s death to a friend, saying: “I remain in denial and still expect him to wander down the hall to my office,” according to the friend.

Among issues Ms. Lucchese faced while taking control during the pandemic was how Scholastic should handle staff vaccinations. “I hear Dick in my head now as I ponder,” she told the friend. “He was so clear about our path, our mission, what our primary directive was,” and “he was at the same time, so clear in his directives around personal issues.”

The company said it disputed the account.

Ms. Lucchese, a daughter of Italian immigrants to Canada, joined Scholastic there in 1991 as an associate editor in book clubs. The romance with Mr. Robinson began relatively early in her career, former staffers said, and some Scholastic staffers knew about it by the late 1990s.

Family suspicions

Mr. Robinson’s family suspected he was having an affair with Ms. Lucchese, but he never acknowledged it, the people familiar with the family’s thinking said.

Ms. Benham said she knew about the relationship fairly early on. Ms. Benham and Mr. Robinson divorced in 2003. Ms. Benham received their Martha’s Vineyard property as part of her divorce settlement.

As Mr. Robinson’s sons grew older, their suspicions of his relationship with Ms. Lucchese deepened, and they wanted him to acknowledge it, the people familiar with the family’s thinking said. At one point, Ben Robinson found a pair of Prada boots in Mr. Robinson’s apartment when he was visiting and took them back with him to Martha’s Vineyard, the people said.

His hope was that it would force his father to request the boots back and come clean about the relationship. His father did ask for them, saying they belonged to his cleaner, the people said. Ben Robinson didn’t believe him.

Over the years, Richard Robinson would ask his assistants to help him buy name-brand gifts for Ms. Lucchese, including winter wear, a Prada purse and a $500,000 pink diamond ring she wore for a period, people familiar with the purchases said. He bought himself and her matching black Porsche Cayennes and took her on expensive vacations, including to Hawaii, one of the people said.

He opened a bank account with TD Bank in Canada and gave her access to money in it, the person said. He also bought her a New York City apartment, property records show. TD Bank declined to comment. Scholastic’s Ms. Sparkman declined to comment on any gifts Mr. Robinson may have given Ms. Lucchese.

Ms. Lucchese wasn’t the only co-worker Mr. Robinson had been romantically involved with. He met Katherine Woodroofe, who would become his first wife, when she was an editor at a Scholastic magazine named Scope, and they got married in 1968, according to a wedding announcement in the New York Times. He left Ms. Woodroofe—who had taken Mr. Robinson’s last name—for Ms. Benham, who worked in the art department at Scholastic earlier in her career.

Ms. Benham said Mr. Robinson had separated from his first wife and was living in his own apartment when they began to date. Ms. Benham rose through the ranks and became a Scholastic board member. Ms. Robinson died in 2002, according to an obituary.

Scholastic’s Ms. Sparkman said the company advises its employees on the risks and concerns regarding dating subordinates and co-workers but doesn’t prohibit such relationships.

Ms. Lucchese was elevated to chief strategy officer in 2014 and was appointed president of entertainment in 2018. She took a keen interest in a “Clifford” movie adaptation and later began a relationship with Blair Clark, the film’s visual-effects supervisor, people familiar with their relationship said. Ms. Lucchese and Mr. Clark are now engaged, Scholastic’s Ms. Sparkman confirmed. Mr. Clark couldn’t be reached for comment.

Mr. Robinson’s sons didn’t seek careers at Scholastic. Ms. Lucchese’s son from a previous marriage, Luca Kong, did—at his mother’s encouragement, former staffers said. He works in marketing for the book-publishing division in Canada. A Scholastic Canada webpage asks booksellers who want “to make arrangements to have Clifford or Geronimo Stilton [a mouse character] visit your store” to contact Mr. Kong. Mr. Kong didn’t respond to requests for comment.

—Joe Flint contributed to this article.

Write to Jeffrey A. Trachtenberg at [email protected] and Shalini Ramachandran at [email protected]