Jonathan Lippman and Shelly Silver grew up together on the Lower East Side in the 1950s, living next door in the insular Grand Street projects and sitting near each other’s family in the neighborhood’s Orthodox shul. After both graduated from law school in 1968 and drifted into low-level courthouse gigs in Manhattan in their early careers, one went on to become the longest-serving Democratic legislative leader in modern New York history, master of an unprecedented 107 to 43 majority in the State Assembly. The other remained largely unknown, except inside the state’s vast court system.
Last month, the two old friends reunited in the Red Room in the State Capitol to celebrate their emergence as the most powerful duo in state government.
Below the political radar, the black-hatted, still religious, and gravel-toned Silver, who is celebrating his 65th birthday and 15th year as speaker this month, has been quietly boosting the more secular Lippman for years. Last month, he finally pushed Lippman from the series of back-office management posts where he had labored for years to the job of top gavel in the State Judiciary.
Appointed Chief Judge of the Court of Appeals in mid-January by the accidental governor, David Paterson, whose troubled tenure continues to erode his own ranking among the state’s power elite, Lippman is awaiting virtually certain confirmation in the next few days from the new and narrow Senate Democratic majority. He will take over a court system that spends $2.3 billion a year, employs 21,000, and is likely to deal with issues like gay marriage, the housing foreclosure crisis, Wall Street criminality, and the still anti–city school aid formula during the six years he will reign until his mandatory retirement at 70.
A year younger than his boyhood friend, Lippman awaits State Senate confirmation before becoming the first chief judge since 1898 to lead the state’s highest court without ever serving as one of the court’s nine members [actually, there are seven seats — ed.]. When Silver gave a short speech at Paterson’s announcement of the appointment, Lippman quipped: “Two kids from the Lower East Side—not too shabby.”
In fact, the story of how Lippman reached this pinnacle has its shabby side. He exudes an above-politics reform aura, but he did not climb to the top of the state’s judiciary without making some stops in the dark along the way. His ally, Silver, helped clear that path to power, working a system whose anti-democratic ways have been rebuked by two federal courts.
Lippman has been a hardworking ambassador and manager of the courts for decades, visiting almost all of the system’s 343 locations and acquainting himself with virtually every one of its 1,300 judges. But he has also been its consummate political player, seemingly more interested in influence than law.
Jonathan Lippman will soon preside over the most complicated and significant cases in New York, even though he’s never practiced as a private attorney.
His legal career began in a judge’s chambers as a law secretary and, when he turns 70 in six years, it will end there. In fact, he has spent so much of his career as a bureaucrat that he’s written only 16 signed judicial opinions, 14 of them since Paterson’s predecessor, Eliot Spitzer, made him the presiding justice of Manhattan’s Appellate Division in 2007. With that scant a record as a jurist, it’s impossible to know what his judicial philosophy is, and even his 24-year tenure in three appointive administrative posts offers no consistent thread about his judicial values or independence.
On one hand, he described himself in a 2006 speech as “unencumbered by parochial or partisan or political agendas,” and is so widely considered a champion of court reform that New York’s Bar Association found him “exceptionally well qualified” for chief judge, ahead of the “well-qualified” ratings it gave long-standing Appeals judges. The Times endorsed him, and he was given the Rehnquist Award for Judicial Excellence in November by U.S. Supreme Court Chief Judge John Roberts.
On the other hand, he is such a skilled and connected insider that when he ran for the first and only time in 2005, he was the only candidate in the state running for Supreme Court who couldn’t be voted against. Lippman was on all five ballot lines: Democratic, Republican, Working Families, Conservative, and Independent. In fact, he had refused to allow his name to be put in the nomination unless every party backed him for the seat, which is the top trial court of the unified court system. (In New York, the “Supreme” Court is not actually supreme: The Court of Appeals is at the top of the judicial pile, above the Appellate Division and the Supreme Court, where major civil and criminal cases are heard.)
David Alpert, the onetime Democratic leader in Lippman’s home county of Westchester, says the first time he ever heard of the man was when he got a call from a Republican, State Senator Nick Spano. Spano told him that he and a Westchester Democratic assemblyman, Richard Brodsky, had passed an amendment creating a new Supreme Court seat in Westchester, and Spano wanted Lippman “to be cross-endorsed for it.” That meant Spano wanted the Democrats, Republicans, and other minor parties to all vote at their judicial nominating conventions to put Lippman’s name on their ballot lines for this new, vacant seat, in exchange for which the Republicans would demand that the Democrats endorse at least one of their candidates.
“I didn’t even know [Lippman] lived in Westchester,” says Alpert, who was accustomed to promoting attorneys and county judges who had done their time for the party to Supreme Court slots. “I had breakfast with him, and the first thing he told me was that he and Shelly were raised together. He said he wanted to be cross-endorsed and that he wanted to go on to be an appellate judge.” Alpert was just one of a legion of county leaders Lippman had to deal with over the years as he sought a Supreme Court seat—five counties with five parties occupy the 9th Judicial District—but Alpert says “we tried twice” (in 2000 and 2002, he believes) to deliver a multi-party cross-endorsement deal and couldn’t.
Joseph Ruggiero, the Democratic leader from Dutchess County in 2002, said that on the day of the judicial convention when Democrats picked their Supreme Court nominees, Silver placed a conference call to a group of party leaders gathered at the Westchester headquarters and asked them to support Lippman. “We all said yes,” recalled Ruggiero. How could they say no? With a Republican governor and Senate majority leader at the time, Silver was New York’s top Democrat, and Denny Farrell, Silver’s right hand in the assembly, was the state party chair.
When the current Westchester Democratic leader, Reggie LaFayette, finally did deliver a deal for Lippman in 2005, he explained Lippman’s unusual candidacy—clearly more top-down than the typical grassroots designation—to his executive committee this way: “I told them I don’t create judge seats. It was created higher up than me, by the two houses of the legislature. And someone yelled out, ‘You mean Assemblyman Silver,’ and I said, ‘Well, he had to vote for it.’ ” But the bigger problem for LaFayette was cajoling his fellow leaders into giving up a seat in a cross-endorsement deal and backing a Republican. Cross-endorsements are easy when the two parties are competitive and no one knows who will win, but Democrats had won five of six judgeships in 2004, without any deals, and felt no need to give the GOP anything.
The executive committee understood LaFayette’s argument and signed on, but a few weeks later, the price of the Lippman package deal got much steeper. The leaders could live with cross-endorsing the initial Republican candidate, a respected county judge named Stewart Rosenwasser. But just days before the September judicial conventions, the Republicans replaced Rosenwasser with a candidate that horrified many Democrats: Joseph Alessandro, also a county judge.
Alessandro had been found “not qualified” by the Bar Association and was dogged by tawdry tax and lawsuit charges. The New York State Commission on Judicial Conduct is still investigating those charges, and Alessandro, who did become a Supreme Court judge, is now facing possible severe sanctions. Yet it was Lippman’s demands that would put Alessandro on the bench.
Lippman wanted to be endorsed by all five parties, and that insistence created an opening for the county’s most voracious party boss, Dr. Giulio Cavallo, who controlled the Independence Party. He wanted Alessandro, not Rosenwasser, to become Lippman’s opposite number in the multi-party swap and get the cross-endorsements. LaFayette and the Republican leader, RoseMarie Panio, eventually decided to back Alessandro, but fights against the deal broke out on the floors of both of these ordinarily scripted and staid conventions. Challengers ran against Alessandro and, had he lost at either convention, Lippman’s precious deal—and ultimately his route to the Court of Appeals—would have died.
The inclusion of Alessandro so offended Working Families party chair Pat Welsh that he endorsed Lippman but refused to back Alessandro, telling the Voice that the deal was “unconscionable.” (Lippman ran on five ballot lines; Alessandro, apparently unconcerned about the Working Families Party, four.) A disgusted Rosenwasser wound up quitting the bench altogether.
At Lippman’s January 2006 induction ceremony for Supreme Court in White Plains, Silver regaled the audience of bigwigs—at a special celebration separated from the swearing-in of the other new judges—with “our gang” stories from their first meeting at the age of six. Saying, “We have shared a common path,” Silver joined in celebrating “with my colleagues in the legislature,” many of whom were there, “who I say had a good hand in making today happen.” While Lippman is now said to be downplaying Silver’s role in his rise, he called him “family” in his speech and praised him for “marshaling the troops, and, boy, can he marshal the troops.”
Lippman called himself “basically an apolitical person,” and then thanked 16 party leaders, referring to each of the five from Westchester, including Cavallo, as “my leader,” singling out Spano, who, he said, “vouched for me on the Republican side.” Judge Gail Prudenti, the presiding justice in the Appellate Division covering Westchester, spoke on behalf of what she called “the many, many, many campaign advisers to the seemingly never-ending ‘Lippman for Justice’ campaigns.”
The unexamined side of the Lippman saga is revealed in these salty Westchester tales, where the judge who pretends he is above self-serving politics played it as skillfully as his sidekick from the neighborhood who does it for a living. Lippman created the state’s Judicial Campaign Ethics Center to guide candidates for elected judgeships, but he told Alpert, and many others, that he wanted the seat handed to him without the inconvenience of an election because it would be unseemly for the chief administrative judge to solicit contributions.
Yet he had no problem brandishing the calling card of Silver’s friendship, or dialing up county leaders and other powerbrokers, some of whom, including Senate Assistant Majority Leader and onetime GOP boss Spano, were receiving lucrative patronage assignments from his courts. He even had no hesitation about going forward with the deal though he knew it would result in the elevation of an already tarnished judge, Alessandro, who may soon be repudiated by the Conduct Commission.
In fact, just as he began his efforts to secure a Supreme Court slot in 2000, he opened an elaborate office for himself in state space, across the street from the White Plains courthouse, and began spending a lot of time there, deeply involving himself in the judicial politics of that district. Shortly before that, he abruptly asked the district’s administrative judge, Angelo Ingrassia, a Republican from a small county in the district, to step down a year before his mandatory retirement age. He even gave Ingrassia a car and chauffeur for his final year to induce him to do it.
He then split Ingrassia’s job into two positions and gave both to Spano allies—one a Republican and the other an influential Democrat from Westchester, the populous center of the district. The new administrative judge, Frank Nicolai, denied in a Voice interview that he “campaigned for Lippman” in the long-running effort to secure a Supreme Court seat, as some sources contend. That would be a violation of judicial ethics, which only permit judges to campaign for themselves. “If someone asked,” Nicolai said, “I’d say he’d be an outstanding judge.” Asked if he might have initiated some of those conversations, Nicolai added: “I might have.”
Nicolai presided at Lippman’s 2006 swearing-in, where Lippman, Silver, and his other prestigious friends were so self-congratulatory it was almost as if he had actually won an election—when all he’d really done was collect chits and lean on the party bosses who’d installed him. With all the editorial hubbub about the judicial nominating process in New York, spurred by the federal court decisions that the process was an unconstitutional infringement of the franchise, Lippman the reformer had inadvertently established by his own experience how poisonously anti-democratic it was.
Yet, at his induction, he called his campaign “a unique experience,” and even praised the mix of elective and appointive positions in New York’s judicial system. Indeed, he has proven, from his Supreme Court fix to his culminating appointment as chief judge, that he is the master of both processes, each with their own brand of incestuous networking. If that is merit, then Lippman is what many of his supporters see him as, the embodiment of the merit system in our courts.
Lippman wanted a Supreme Court spot to make himself legally eligible for appointment to a second-tier appellate post, which he saw as a vital stepping-stone to the top-tier Court of Appeals. He had to do it then because his other sponsor, Chief Judge Judith Kaye, would have to step down when she turned 70 in 2008, and even a brief stint on the appellate bench would give him an opportunity to build a record as a scholarly jurist, though it would be quite a lean one in comparison with competitors who’d actually written opinions over lifetimes.
But his timely and controversial “election” was hardly the only awkwardly abetted step on his unprecedented career ascension. Prior to it, Lippman had only been a Court of Claims judge—an appointment bestowed by Governor George Pataki a few months into his first year in office (1995), when the Democrat Lippman managed to secure a spot despite the hunger of Republicans eager to grab judicial patronage slots after 12 years of Democratic rule.
At the time, Lippman was the top deputy in the Office of Court Administration, and all he had going for him were his Silver ties; an assiduously cultivated friendship with GOP Senate Judiciary Chair Jim Lack; and the backing of Judge Kaye, who argued that Lippman should hold a judicial title since she intended to install him, as she did a few months later, as the chief administrative judge.
Spano, who had just become the Republican county leader in Westchester in 1995, met Lippman in the few days between Pataki’s appointment and the Senate’s confirmation. Since Lippman was technically a candidate from Spano’s home turf, he had to sign off and did, endorsing Lippman on the Senate floor and launching what he concedes became a series of efforts on Lippman’s behalf that he would make over the coming years. Three of the pivotal party brass—Westchester Conservative Gail Burns, Rockland County Republican Vince Reda, and Cavallo—were on Spano-engineered Senate payrolls when Lippman collected his cross-endorsements in 2005, and the senator concedes that he spoke to them, as well as to Westchester Republican RoseMarie Panio, a close ally. “I’m sure I expressed support for Judge Lippman,” Spano tells the Voice. “Anytime his name was up, I was an enthusiastic supporter.”
In fact, Spano, who was widely viewed as the Senate Republican closest to Silver, confirmed his call to Alpert and acknowledged that he’d pushed midnight legislation through in 2005 and earlier, aided by Brodsky, that created new Supreme Court seats in the judicial district covering Westchester. The bill in 2005 was introduced by Pataki on June 24 and passed by both houses that day. While Spano said he didn’t think “it would be fair to say” the seats were “created for anyone,” he concedes that “Lippman’s name came up” when the bills were adopted. Lippman needed more than one bill because the cross-endorsement deals with the Republicans fell apart, for reasons having nothing to do with him (once the Republicans demanded four Republican cross-endorsements for Lippman). He even went so far as to be nominated by the Democrats in 2002, only to file a formal declination when the deal with the GOP broke down.
A few months after Spano helped engineer Lippman’s 2005 cross-endorsement, his brother, Mike Spano, an assemblyman mired in the hopelessly outmanned Republican minority, quit the Assembly and joined a premier Albany lobbying firm run by Silver’s former chief of staff, Pat Lynch, who is perceived to be the lobbyist closest to the speaker. When Nick Spano was defeated for the Senate in 2006, he formed his own lobbying company that Lynch invested in and allowed him to operate until this month out of her Albany suite. Mike Spano eventually went back to the Assembly, but he later became a Democrat at a press conference attended by Silver. Nick Spano, who reported half a million dollars in lobbying fees in 2007, denies vociferously that his aggressive support for Lippman has anything to do with his current business. But his ties to Lynch, and Lynch’s hiring of his brother (who was hardly an influential Albany player), are a measure of his alliance with Silver, who Nick Spano says he “might have talked to” about Lippman’s candidacy over the years “in social settings.”
All the while that Spano was aiding Lippman’s candidacy, he was reaping at least $79,739 in fees as a “court evaluator,” a person paid to measure the mental competency of someone named in a legal petition. Though Spano isn’t a lawyer, he has received 31 of these assignments and four other referee assignments. OCA regulations require the disclosure of these fees, but Spano’s fees in 15 cases aren’t listed on the office’s printout. While Lippman’s OCA had nothing to do with choosing evaluators (individual judges do that), it did collect applications for appointments; approved evaluators, like Spano, for the list; and set the qualifications for appointment, which appear to permit just about any professional to sign up.
Evaluators look into the eyes of the subjects of these court petitions, many of whom are elderly and in nursing homes, and decide whether they should retain control of property and other assets, the value of which they also consider. Spano sponsored the law that created this position, and he and other pols in Westchester, including then Senator Guy Velella, wasted no time collecting assignments. Velella, who has since been convicted on unrelated charges, was another social friend of Lippman’s, and dined with him and Senator Lack and their wives at Rao’s, the famously exclusive restaurant in East Harlem. Even one of the restaurant owners collected 19 appointments as court evaluator.
Lack, however, never dipped into the evaluator till, but he did collect 66 court appointments as a guardian or referee while chairing the Senate Judiciary, 26 of which were from Judge Prudenti, who spoke about her adviser role in Lippman’s never-ending campaign at the 2006 induction. A Court of Claims judge himself by then, Lack was also present at the swearing-in and was saluted by Lippman, though he’d left the Senate after chasing a woman to her home in a road-rage dispute and ducking under the garage door when she tried to hide from him. “Do I think it’s a terrible thing that people involved in public office receive this?” Lippman once told Newsday, referring to judiciary patronage. “No, I don’t.”
There’s no indication that Lippman did anything more than oversee this grab bag of goodies—with evaluators often earning $3,000 for a couple hours of work. But if Lippman was so concerned about the appearances of being political that he effectively exempted himself from the requirement that he actually compete in the electoral arena, he might have been a bit more careful about the appearances of his alliances with the beneficiaries of this dubious bonanza.
The day after Lippman became a Supreme Court Judge, in 2006, he asked Judges Kaye and Prudenti to name him to the Appellate Term, a job he would perform in addition to the administrative post he retained. This assignment—which allowed him to hear appeals of some lower court decisions—was his only way of acquiring appeal experience without being formally elevated by the governor to the full Appellate Division.
When a vacancy developed in the Manhattan Appellate Division and Spitzer selected Lippman as the county’s presiding judge, howls were heard because two of the most respected sitting judges on that Appellate Division were bypassed by the screening panel of lawyers that vets judicial candidates, narrowing the governor’s choice.
The same thing happened in December, when the screening panel for chief judge excluded two sitting Court of Appeals judges, as well as all women and Latino candidates—giving Paterson an invitation he couldn’t figure out how to refuse. The panel included four Kaye appointees and one from Silver. Panel member Leo Milonas was so close to Lippman he spoke at the induction. Lippman saluted Milonas then as “truly my friend for life,” calling their friendship, which began when Lippman worked for him at OCA, “an unforgettable relationship that, to my great benefit, continues today in every way.”
Reminded of that by the Voice, Milonas saw it as no reason to have recused himself from anointing Lippman, noting that he was “more qualified” to help pick a chief judge “because I know people.” The panel’s chair, John O’Mara, a Pataki appointee, sat with Lippman on the court’s Capital Construction Board for years.
An angry Paterson asked Attorney General Andrew Cuomo to investigate the panel’s exclusionary list of seven nominees, but he never released Cuomo’s report or recommendations. Instead, he began openly associating the chief judge selection with the other grand decision that faced him—the choice of a new senator to succeed Hillary Clinton—sending the signal that he had to pick a woman for the Senate since the panel’s list barred him from picking one for the court.
When Silver reversed course and supported Caroline Kennedy, insiders suspected it was all about his love for Lippman. At that point, the governor had also just about convinced everyone that he wanted Kennedy, and the assumption was that Silver got the message that if he wanted Lippman, he’d better sing “Auld Lang Syne” to his Kennedy animosity. Paterson was asked about this connection at the Lippman announcement and denied it, adding that he “actually did not know the extent” of Lippman’s “relationship” with Silver until he called the speaker to tell him about the appointment—which would make the governor the only high-ranking New York official unaware of it.
Ironically, of course, Paterson deserted Kennedy, and even claimed, improbably, that he never intended to pick her, though he revealed how important he thought Silver’s opinion was about his eventual choice, Kirsten Gillibrand (another woman, to balance Lippman), when he said at her announcement that he moved it up to Friday from Saturday so the Sabbath-observing Silver could attend. It would be par for the course in Paterson’s stumbling regime that he would agree to Silver’s choice for chief judge in return for Silver’s support of Kennedy, and then not get her, only to be stuck with Silver’s pal for judge.
Whatever the deal, Paterson appeared boxed in when he announced that he would choose from the screening panel’s list for chief judge. But there is one school of thought, citing interpretations from the OCA, that suggests that Paterson could simply have chosen to do nothing when the January 15 appointment deadline arrived. These analysts argue that Paterson could have named no one until later this year, when panel chair O’Mara steps down. That would have meant that Carmen Ciparick, a woman and a Hispanic, who has been on the Court of Appeals for 15 years, could have continued serving as the acting chief judge, a position the other seven [actually five — ed.] judges voted to give her when Kaye retired in January. The press office at the court says Ciparick is the chief judge “as long as the seat remains vacant.” If Paterson had simply done nothing, he could have eventually asked the new panel for a new list, and Ciparick, who applied and was rejected by O’Mara’s very politicized panel, might actually have gotten a chance to compete for the job.
The same is true should the Senate take no action now. In fact, several Democratic state senators have been making a fuss for weeks about the lack of Latino representation in positions of power—at any level of city or state government. It is an issue that threatened the Democratic takeover of the Senate majority at the same time that Paterson was deciding, unknown to anyone, to displace a sitting Latina chief judge he could have allowed to remain, and perhaps even wind up appointing. His simultaneous selection of the anti-immigrant Gillibrand for the Senate seat compounded Paterson’s trouble with Hispanics.
The first black governor preferred the comfort of Silver and Kaye and Lippman and the old-line judicial establishment. Lippman had even been careful enough to establish a personal rapport with the governor when Paterson was the Senate minority leader, meeting with him on OCA issues. Unelected himself and unsure of the extraordinary powers of his office, Paterson seems to shrink in Silver’s company, now blaming the millionaire’s tax on him as if the speaker sets the budget agenda.
The graying gang from Grand Street rolled the neophyte governor from Harlem, and will soon double their choke hold on state government, a triumph of loyalty and intrigue, which, in old New York, adds up to just another measure of merit.