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Uncertainties surround LA Unified Superintendent John Deasy. He doesn’t see eye-to-eye with board members on a host of issues. Questions are swirling about whether he’ll quit or be fired.

That was last year.

But here he is again, weeks away from his next performance review, and not much has changed.

This time, Deasy finds himself at the center of a two major controversies. Questions about his involvement in securing a deal for iPad maker, Apple and software developer, Pearson, have lead to a renewed investigation by the district’s Inspector General, and the bungled launch of a district wide data system, have put Deasy’s “autocratic” management style in stark relief, according to his critics.

The troubled superintendent also has a potential teachers strike on his hands if the district and their union, UTLA, can’t reach an agreement on a new contract.

Whether Deasy can weather the latest storms — or whether he even wants to — remains unclear, but if his days are numbered, and the board votes him out after next month’s evaluation, he would hardly be the first superintendent to leave LA Unified after a tumultuous tenure.

Here’s a look at his three most recent predecessors:

ROY ROMER (2000 – 2006)

A former three-term governor of Colorado, Romer has been the longest serving LA Unified superintendent in the last 27 years. He retired at the age of 78.

Over his time in charge, Romer grappled with severe over-crowding in classrooms, abysmal test scores and one of the highest drop-out rates in the country. No new schools had been built in more than 20 years but after a long slog, he succeeded in getting a  $19.5 billion construction bond passed. It remains the the largest municipal public works project in the nation’s history.

In addition to foes on the board, Romer also battled Mayor Antonio Villaraigosa, who was trying to take mayoral control of the district. That effort failed but it left the relationship permanently strained.

DAVID BREWER (2006 – 2009)

Brewer took charge of the district after an exhaustive nationwide search following Romer’s retirement. But unlike the septuagenarian, Brewer was pushed out after just two and half years.

From the start, the former Navy admiral was criticized for lacking the education background and management skills required to run the second largest school district in the country. He also had an annual salary of $300,000 and, according to the LA Times, a $45,000 a year expense account. When he decided to bring on Ray Cortines as Deputy Superintendent, Brewer was attacked for outsourcing the most basic responsibilities.

His time at LA Unified was rocky from the start and he described his first months on the job as a “cascade of crises” in an interview with the LA Daily News. Early in his tenure, the district became embroiled in a payroll software fiasco that left some teachers unpaid and others overpaid. This was also the beginning of the great recession, which left Brewer the task of beginning the process of gutting a number of school programs.

After a failed attempt to fire him, the board paid him $517,500 to leave. He accepted, saying it was in the interest of the district’s children — his departure, not the settlement.

RAY CORTINES (2009 – 2011)

Cortines, a former Superintendent in San Francisco, San Jose and Pasadena, and a former New York City Schools Chancellor, rose to superintendent following Brewer’s swift and expensive departure.

As the financial crisis deepened over the next three years, Cortines was forced to cut a staggering $1.5 billion from the budget, leading to layoffs of 2,700 teachers and 4,900 other employees.

Cortines was Mayor Villaraigosa’s choice for the post and under his direction, the district developed the “public school choice” model, which allowed a proliferation of charter schools to set up shop in the district. That put him at odds with several board members who opposed charter school growth.

However, it wasn’t until after Cortines retired from the top spot that his reputation was marred by scandal. Shortly after stepping down, a former LA Unified senior manager sued him, charging sexual harassment.

Previous Posts: As work on MiSiS continues, LAUSD is creating MiSiS 2.0; LAUSD says concerns cited in iPad report were expected; What’s next *if* Deasy is out? Speculation abounds