News & Politics

Wayne Barrett: How Shelly Silver Made His Pal Chief Judge


This week’s Village Voice doesn’t hit streets until tomorrow morning, but for our Runnin’ Scared readers, we’re offering tomorrow’s cover story a day early. This one should rock Albany: our Wayne Barrett details state assembly speaker Sheldon Silver’s step-by-step scheme to boost his old LES pal Jonathan Lippman to the state’s highest judicial post, an appointment which is scheduled to be confirmed later this week. Read it and rage. –Ed.

Justice is Blindsided

Shelly Silver games Governor Paterson to get his childhood pal the state’s top courts job

By Wayne Barrett

Jonathan Lippman and Sheldon 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. Now, he’s finally pushed Lippman from the series of back-office management posts where he’s 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 seven members . 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

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

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’

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

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

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 for 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 an 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 judicial
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 five 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.

New York’s 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

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.

Research assistance by Dene-Hern Chen, Jana Kasperkevic, Sudip P. Mukherjee, and Jesus Ron



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