04/26/2013 04:57 pm ET | Updated Jun 26, 2013

Lessons Learned From New York Mayor Michael Bloomberg's Time in Office

New York City Mayor Michael Bloomberg often likes to quote former mayor John Lindsay, who called being mayor of New York "the second toughest job in America." Coming to the end of his third term in office, Bloomberg might now call being mayor the toughest job he's ever had, and possibly the most frustrating. He came into office determined to reform the education system and whip into shape the behemoth of mismanagement that is the city's budget -- and leaves the job with little to show for his efforts. Once gone, the city will lumber on without him just as before, with its bloated bureaucracy, its soaring cost-of-living, its faltering education system, its fractious special interest groups, and its endless array of political infighting.

Most ironic, the people whose lives he tried so hard to improve ultimately might be the very people he alienated the most -- the working class. While he enjoyed approval ratings as high as 68 percent in his earlier years, he now takes that long, final walk to the exit with just a 50 percent approval rating, perhaps reflecting the conflicted nature of his relationship with the people of New York.

A Class by Himself

If there was ever a public official who deserved to be called a "poor little rich boy," it would have to be Michael Bloomberg. One of the 20 richest people in the world, according to Forbes, the last thing he needed when he launched his quest to aright the tilting Titanic that is New York City's financial and educational systems was the aggravation that comes with the thankless job of being mayor. Throughout his many years in office, he tried to love the job, but it turned out to be the type of job that would never love him.

As founder of Bloomberg L.P., one of the world's most successful media companies, he was widely admired and respected as a bold and visionary businessman. As mayor, his actions have been labeled as petty and short-sighted. Lately, ramping up his focus on health and lifestyle issues, he has also come under fire for transforming the city into a "nanny state." He often seems determined to shove through unpopular policies that lead to heavy public and political backlash.

In business, he was lauded for his pragmatic and "hands-off" approach to management that gave wide autonomy to his people in making decisions. As mayor, he appears determined to run the whole show. He becomes irritable around people with dissenting views and chastises those who question the wisdom of his policies or persist with a line of inquiry that he has already dismissed as irrelevant or ludicrous.

Taxing Their Patience

Meanwhile, throughout his tenure, Bloomberg often appeared to raise revenues for the city in the most expedient way possible -- by cutting social services, increasing city fees, and further taxing the working class. He laid down the blueprint for this practice in his first year in office, following the national recession and economic devastation of 9/11, when he faced a budget gap of more than $5 billion. He implemented what Tom Lowry of Businessweek called, "a new model for public service that places pragmatism before politics." He saw "New York City as a corporation, its citizens as customers, (and) its sanitation workers, police officers, clerks, and deputy commissioners as talent."

Lowry noted that Bloomberg faced three unpleasant options: "cut services, raises taxes, or both." He did both and more, enacting the highest property tax rate increase in the city's history and hammering the middle class with user fees for public service in almost every aspect of daily life. It was a bold move that got the job done and earned him the title of "CEO Mayor" for doing the practical thing that any sensible boss would have done in business, but it drew fire from many critics for its heavy reliance on penalizing the poor. Unlike the world of business, city "customers" -- its residents -- cannot simply take their businesses elsewhere.

In the years that followed, Bloomberg's habit of balancing the budget on the backs of the poor and middle-class began to wear thin. With his final proposal for Fiscal Year 2013 featuring strikingly similar initiatives to those he enacted in his first term, the city's long-suffering working class no longer believes in the necessity of his tough love approach. It suspects he could accomplish the same goal of balancing the budget through more innovative initiatives, including streamlining city bureaucracies, which he never seemed to have done.

Back to Schoolin'

A surprisingly insightful and educated man, Bloomberg has always believed in the power of education to change lives -- following his own intellectual awakening at John Hopkins University, his alma mater. At the same time that he sought to reign in the city's runaway budget, he took on the mind-numbing bureaucracy, corruption and incompetence that city leaders and educators considered to be the New York Board of Education.

"We talk about all the civil rights... about voting... about the ability to be in charge of your own destiny..." he said in his first State of the City address, "but if you don't have the skills to get a good job, so what? If you can't read, write, do math, work collaboratively, raise a question, understand an answer--"

Within months of taking office, he won control of the Board of Education and fired all of its top leaders. He looked for someone completely outside the system -- who would therefore be untainted by unhealthy allegiances -- and appointed former head of Bertelsmann and U.S. Department of Justice antitrust attorney Joel Klein as schools chancellor, a post traditionally held by educators.

Eleven years and three schools chancellors later, whether Bloomberg achieved his goal of improving the school system remains a point of debate. In his State of the City address recently, he talked about raising "high school graduation rates by 40 percent while they've gone up only 9 percent in the rest of the state" during his tenure. Student test scores also appear to have risen during his terms in office; yet critics contend that the numbers are misleading, as they are not based on the same criteria. Recent studies also suggest that city high school graduates are still unprepared for college and many must take remedial courses in their first year to achieve basic competency. Also, the number of complaints alleging that tests have been tampered with and grades changed by educators to achieve better numbers has more than tripled since he took control of the school system.

Can't Buy Me Love

Recently, in his final State of the City address, in reeling off his extensive list of accomplishments, Bloomberg sounded like a desperate man facing a grim and hostile judge, pleading his case before the hammer of a harsh sentence comes down upon him. Yet, the overriding irony to all this is that Bloomberg might not leave a clear imprint as a great mayor upon the city, but he will leave a lasting legacy as one of the country's leading philanthropists. Despite his bumpy career as mayor, in his private life, he continues to champion educational initiatives and research, and to give a substantial amount of his money to causes that help the poor gain access to a better education.

He has already donated more than $2.4 billion to various causes and organizations -- nearly 10 percent of his current estimated wealth. He was among the top five in The Chronicle of Philanthropy's list of American philanthropists in 2011. To date, the $1.1 billion he has donated to Johns Hopkins also makes him the largest living donor to higher education in U.S. history.

In an interview last year with Scott Pelley on the CBS Evening News, Bloomberg vowed that he would give away his entire fortune before he dies.

"I've been very lucky in terms of making a lot of money and I'm going to give it all away," he said to Pelley. "I've always said, my great ambition in life is to bounce the check to the undertaker."

Based on his current track record, he probably will. Critics, however, will mull over his comment about bouncing the check "to the undertaker" and exclaim, "There he goes again: as his final act on earth, he's still talking of screwing the little guy!"