The Democratic Party in Essex was so powerful under Harry Lerner, sooner or later someone was going to come along and throw a punch to try to knock him off his throne.

That person proved to be the unlikely Peter Shapiro, the youngest ever person elected to the New Jersey General Assembly, who worked on the West Essex coalition that changed the county government charter to a county executive form. Up to that point, the nine county freeholders functioned as miniature county executives, each on charge of a separate fiefdom of government.

Lerner designated who served where.

That all changed in 1978, when Shapiro led a slate of reformers against the power structure and created the county executive position. Former Governor Tom Kean, Sr. of Livingston once described the office as the second most powerful position in the state. In that first election for the position, legendary Sheriff John Cryan (father of Union County Sheriff Joe Cryan) took a stab at the county executive’s seat, but so did then-Freeholder Donald Payne, Sr., who broke from the Democratic Party establishment to run his own candidacy.

Cryan and Payne sawed into each other, opening the way for Shapiro, who beat Lerner and ushered in a new board under his own auspices.

So began the era in Essex of the county executives, Shapiro cast early in the part of Augustus Caesar, followed over the course of the next 40 years by four more larger than life leaders, each of whom exhibited different traits as they tried to define the powerful role in their own right. One would take a preposterous shot at governor, two of them would end up in jail, and one of would – by the assessment of many of his peers – finally get the job right but find himself handcuffed to a heartbreaking alliance that hindered what should have been that statewide rise out of Essex County that the first among them so fervently craved.

Peter Shapiro

The Steve Fulop of the 1980s, Democrat Shapiro helped craft the 1978 charter to create the county executive form of government in Essex. Smart and ambitious, the youngest assemblyman in the history of the legislature came in on a wave of reform and never had his political legs under him. The old guard (then under the leader of Lerner successor Ray Durkin, who would go on to become state party chairman) re-positioned in 1981 with freeholder wins that weakened him. Unable to consolidate power at home, Shapiro took an ill-advised shot at governor in 1985 at the age of 33. Incumbent Republican Governor Tom Kean beat him 71-24% – the widest margin in New Jersey gubernatorial election history. Humiliated statewide, Shapiro limped back to Essex. A lot of insiders had thought his run for governor had come with the proviso that he wouldn’t run for reelection countywide, so he shocked Essex when he declared his intention to run for a fourth term. In a failed attempt to remold the Democratic Party, Shapiro put Steve Edelstein against Durkin and Durkin won. With the establishment still in payback mode, the Democratic incumbent lost to Republican Nicholas Amato by 14,000 votes in the 1986 general election. The man once regarded as a can’t miss future president was out of politics – apparently for good.

Nicholas Amato

A former Democrat, Amato ran as a Republican against Shapiro in 1986 and won. A lot of the old guard Dems backed the three-term county surrogate with relationships and name ID – against the infuriatingly Icaresque Shapiro. The Democrat turned GOP standard-bearer’s nail-down of the Republican nomination is one of the fascinating Essex political stories. As Amato pursued reelection to the surrogate’s office, Shapiro dumped him from the party line. Angry, Amato changed parties. Future Judge Jose Linares was the GOP candidate for surrogate, but told Amato he’d step down if the GOP decided to back the seasoned Amato to run for reelection as a Republican. Then Carl Orrechio decided that he didn’t want to run for county executive after all and a meeting of Republican pooh-bahs convened in Trenton. Those bosses tapped Amato to run against Shapiro. A Democrat just months earlier, Amato won to become the first Republican Essex County executive, and put together an interesting one-term record. He expanded the county food program, and created the incinerator when the state informed Essex that it could no longer dump garbage in the Meadowlands. He also sued then Chief Justice Robert Wilentz in a case involving the shooting of the Hollywood movie Bonfire of the Vanities. The film’s producers wanted to use the Essex County Courthouse and would pay Essex $250,000 in exchange. But Wilentz was concerned about the depiction of African Americans in the Tom Wolfe novel on which the movie was based. Even though the role of the judge was switched in the movie from a Jew to a Black, Wilentz stood firm. Intent on getting those funds for Essex and buoyed by the changes in the movie from the book, Amato pursued legal action, arguing that the judge was pursuing censorship and starving Essex in the process. The county exec won the initial judgement but then lost on appeal in the Third Circuit Court. He decided not to run for reelection in 1990. One source told InsiderNJ that Shapiro and Amato were both one offs, in the sense that the never politically secure Shapiro opened the possibility of an unlikely person beating him, which is exactly what happened. Having come into office without a strong mandate and always walking a fine line between two parties that didn’t fully trust him, Amato never could get the grip on government he needed to feel confident as the county’s chief executive but  ultimately left a legacy as a bonafide hard ass. A proud Republican to this day, he works as counsel for Genova Burns.

Tom D’Alessio

Finally the establishment Democratic Party put up one off their own in the form of Sheriff D’Alessio. Never great at government, D’Alessio was a superb politician, who made every wake and funeral, and was a wonderful golfer. In over his head, by the reckoning of most, D’Alessio got slammed in the can in 1994 after extorting $58,000 from a solid-waste company to help it obtain a state environmental permit. The county business administrator briefly filled in prior to the election. He left the legacy, sadly, of being the first county executive to get jammed up on corruption charges.

Jim Treffinger

A Republican, Treffinger got into office after beating – with 51% of the vote – East Orange Mayor Cardell Cooper. Brilliant and ambitious – with all the obvious instrumentation to appear well on his way to greater things, Treffinger worked well with the Democratic freeholder board. On the Republican’s watch, county government built the ice rink and completed studies toward the county jail system, among other important initiatives. Running for reelection in 1998, Treffinger narrowly defeated former Newark Mayor Ken Gibson 50-47%. What appeared to be a very promising future with the potential for statewide office crashed when then-U.S. Attorney Chris Christie prosecuted Treffinger, who, in fact, backed out of a U.S. senate bid when the public became aware of the investigation. Having solicited an illegal $15,000 campaign contribution in exchange for a county contract, the county executive pleaded guilty to one count of obstruction of justice and one count of mail fraud. For Tom Barrett’s deep dive into Treffinger, please go here.

Joe DiVincenzo

In 2002, Freeholder Director Joseph “Joe D” DiVincenzo faced Freeholder Tom Giblin in a race that has stood the test of time as one of the best in state history. During that contest, DiVincenzo appealed to U.S. Attorney Chris Christie for a letter making it clear that rumors of the freeholder director being under federal investigation were not true. That letter proved to be the beginning of a longstanding and controversial relationship between the two men. DiVincenzo beat Giblin in the Democratic Primary, and marched through a forgettable general election. Haunted by two of his last four predecessors having landed in jail, the new county exec had an inspector general installed in his office as a watchdog against corruption. Early in his tenure, critics dismissed Joe D. as a hand-picked Steve Adubato cheerleader, but he defied expectations as a leader with a strong work ethic, irrepressible ability to build alliances across a broad range of would-be rivals, innate understanding of government, and dogged commitment to creative projects and public-private partnerships. Resoundingly reelected three times, DiVincenzo to many embodies the role of county executive as envisioned at the outset. They point to the county’s triple a bond rating and multiple projects, including the complete refurbishment and expansion off Turtle Back Zoo and investment in parks and recreation as evidence of the county executive’s leadership. To some of his closest allies, however, DiVincenzo’s close relationship with Christie – indeed going back to the origins of his tenure – ultimately proved politically tragic and that stumbling block to an expansion of power. If there was anyone truly designed to go higher than his countywide office based on his work product, it was billion dollar budget overlord DiVincenzo, they maintain. But Republican Christie demanded that the county executive endorse his reelection in 2013, which ever after made DiVincenzo persona non grata to the progressive wing of the Democratic Party and weakened his ability to gain meaningful traction statewide. One of Christie’s most loyal friends in government and politics, DiVincenzo and the governor finally parted ways last year when Christie – irritated by the county executive’s inability to lend meaningful backing on the newspaper legal ad bill – denied him $22 million.