“Hey there, where to?”

“30 St. between 1 and 2 Ave.’s”

“Sure thing. How’d your day go?”

“Long.”

“Usually is for most people when they get out at this hour.”

So I made my way crosstown through the occupational centers of the Mad Men and the money shufflers, before whizzing down 2 Ave, engaging in a conversation with my lively passenger. Eventually, the topic of the inauguration after the New Year came up as I made the turn, proceeded to park, and stopped the meter:

“Are you ready for the new Mayor to take office next week?”

“Not really. I”m going to miss Mike.”

“Me too. There were a few things I don’t like about him but I think he’s not being judged fairly and only time will prove that he did a good job running this place for the last 12 years.”

“What don’t you like about him?”

“Well, here he is – running one of the largest and arguably the most important city in the world. He has power, lots of it too and what does of focus on? Trans Fats. Soda. Cigarettes. Bike Lanes. Now me, I don’t smoke, always buckle up and I don’t eat a lot of foods that are bad for me. You’ll never catch me doing that but if someone were to, I don’t think that it’s the job of the government to look over my shoulder and tell me what I can and can’t do. It’s the nanny state at its worst and a waste of time that could be spent on much more important things, like economic competitiveness, quality of life issues, and of course, housing.”

“I see your point but let me put it this way. Bloomberg realizes that all of those issues are negative drains on this city in terms of lives and capital. Take care of them now and they’re not issues down the road. Spiraling healthcare costs are something that could be averted ahead of time, saving billions from future budgets and allowing people to live longer as well. He’s doing his best to take care of those who have proven that they could be more capable of taking care of themselves.”

“Fair point.”

Three weeks ago, a ceremony as frosty as the weather that descended over Gotham this January took place in Lower Manhattan. Bill de Blasio was sworn in as 109th Mayor of the City of New York. What people remembered more was not the peaceful transfer of power from one administration to another, but the overall tone of the day. Ex-President Bill Clinton was there to swear in the former Public Advocate into his new position and singer Harry Belafonte gave a speech comparing New York is to a plantation. Making the spectacle that much more uncomfortable was that the outgoing Mayor was present throughout the whole ordeal, as other officials and dignitaries joined in in the proverbial trashing of his administration and its policies.

For someone that rose up at Solomon Brothers to the point of running its trading floor, to the founding of the media and financial information company that still bears his name to this day, to the running of North America’s most influential City on a self-financed campaign, the proverbial ending of his political career could not have been any more demeaning. Had anyone not noticed the relatively clean streets, low crime rate, return of cranes to the skyline, and the record 50 million tourists that came to New York last year, they would have possibly believed that the first decade of this Century had been a mistake, once the rubble at Ground Zero was cleared away in March of ’02.

So was New York really better off than it was 12 years ago?

There was no doubt that the resolve of New York had never been tested as much as it was on 9/11. A nation that was pulling out of the recession of the dot-com era was threatened with another economic downturn as the World Trade Center was leveled in a matter of hours, in what turned out to be the first shots of the War on Terror. The Mayoral Primary that was scheduled to be held that day was pushed back by a few weeks as emergency crews rushed down to Lower Manhattan and the rest of the nation came to a standstill. What looked like something catastrophic turned out to be awkward pause in the city’s recovery from the bankruptcy and municipal malfeasance that nearly drove New York into oblivion in the 70’s. Narrowly beating out former Public Advocate Mark Green that November, Mike Bloomberg was the choice of New Yorkers to continue the recovery both from the days of malaise and the mess that covered 16 acres in Lower Manhattan.

Bloomberg was unlike anyone that ever ran for the position of the second-most powerful person in the United States (apologies to the Vice President). Rich, centrist, and self-financed, Bloomberg stated that if elected, would serve the city for the salary of $1 per year. Given that New York hadn’t elected a true Republican to the office of Mayor in generations, he only switched affiliations to get on the ballot and to stand out from his Democratic challengers. New Yorkers did not know what they were getting with him since he didn’t have a track record and when he left office 12 years later, many were still unsure as to what his legacy would be for the overall metropolis at large.

Critics would say that he ignored the outer Boroughs at the expense of Manhattan and it’s monied elites while spending too much time worrying about trivialities like landing the 2012 Olympic games or redesigning streets for bikes and hastily-designed pedestrian plazas that were demarcated by spaced-out planters and concrete blocks and balls. Proponents pointed to the economic health of the City, low crime rate, and a majority of New Yorkers stating that they approved of his policies on the day when he left office. As is the case with anyone in a position of power, time will ultimately prove whether these claims have any real validity, but the early cues point to tenure that left New York in better shape than it was before he entered office.

Arguably, the two biggest gaffes during his tenure turned out to be blessings in disguise. One was the failed attempt to land the 2012 Olympics in the Big Apple, under the pretense that it would show the World how New York had bounced back from the attacks of 9/11. Then-Senator Hillary Clinton got on board and was shown on TV as being quite disappointed the day the IOC chose London as the host site. Many New Yorkers were quite vocal in their opposition to the staging of the games in the Big Apple, for several reasons. First was traffic, as the West Side of Manhattan would have been the site of the Olympic Stadium. It lacked any nearby Subway access and those would have gone to the events via ferry would have had to trek around the still-awkward Javits Center, which was never fully integrated into the surrounds upon its completion in 1985. Most locals didn’t want the Jets to call the stadium him once the games were over, as would have been the case had New York landed the games. Housing would also have been a tough sell, as the proposed Olympic village in Queens would had to have been built from scratch, on the East River waterfront. Schools, parks, expanded mass transit, and affordable housing was what the West Side and the surrounds needed, not another monstrosity that would have sat unused much of the time.

The other big mistake that Bloomberg made was thinking that he could change the City Charter and easily be re-elected for a third term. For the record, it was indeed changed but not after a prolonged and nasty exchange, instigated by many New Yorkers who viewed it as a sign of hubris and arrogance by Hizzoner. Many of those displeased by the proposed alteration of the rules had a chance to voice their disapproval in a public hearing but in the end, it was Bloomberg who looked better for it. Both the City Council Speaker who silently went along with the other party’s figurehead and the opponent who ran against him in the Mayoral Election in ’09 ultimately ended up being harmed by the third thought that he eventually sought out and won.

Of course, they wouldn’t realize it until they ran for that same position four years later and lost to the person that was sworn in three weeks ago.

Bloomberg might not have known what to do when it came to issues but he put the right people into place that helped him craft the legacy that will define his years in office. Without a doubt,  the most important was Dan Doctoroff, who will be remembered for generations as the person who took the failed bid for the Olympics and reworked into the Hudson Yards proposal that’s finally starting to come into fruition. The parks, schools, open space, housing, new Class A office space, and Mass Transit extension that New Yorkers were clamoring for could all be found on the West Side, over a platform that would place the railyards there out of sight. It was being done on a smaller scale in Brooklyn at the Atlantic Yards side and since so many were enamored with the Barclay’s Center, they could only look uptown in greater anticipation at what would ultimately rise in the former wasteland between the Chelsea and Clinton neighborhoods.

It wasn’t all rosy for Bloomberg during his time in office, though. It took forever to get anything rising out of the ground at the World Trade Center site, although that was also the fault of the Port Authority, Governor of New York, the Lower Manhattan Development Corporation, the insurance companies that were sued, and a host of other agencies and corporations that had a stake in what would emerge from the ashes of 9/11. Housing and office space continued to skyrocket in cost around the city as the number of affordable units that were built were nowhere near enough to keep up with rising demand, and whole sections of Brooklyn and Western Queens became unaffordable to all but the uber-wealthy. Streets in the Outer Boroughs took forever to get plowed in major storms and even someone as powerful as him was unable to have a transit strike averted in the waning days of ’05, as Ed Koch and John Lindsay also found out during their helms of the World’s Greatest City.

Bloomberg also found out that being one of the 100 richest people in the United States doesn’t allow you to stand stoic as the tide of history threatens to wash over everything in front of it. As this cabdriver learned the hard way, Occupy Wall Street and Hurricane Sandy were two events that no one was unable to stop in their tracks. Both left New York radically different in their aftermath and had many questioning whether Gotham would be prepared for similar events that seemed inevitably on their way to striking. It was with that gusto, as well as the premise of change that elected a Senator from Illinois to become America’s Commander-in-Chief 5 years prior, that finally saw a Public Advocate become the person that New Yorkers trusted to lead them in the post-Bloomberg era.

Immediately into her new term, that leadership has already been called upon as a rash of pedestrian deaths via vehicles, a crippling snowstorm, and even the promotion of Hizzoner’s wife to a paid government position have drawn harsh lines in the proverbial sand. Is 30 M.P.H. too high a speed limit for traffic? Was the Upper East Side plowed properly for the evening rush hour? Did New Yorkers elect de Blasio’s family to serve the public-at-large? These answers remain to be seen, but before housing, inequality, taxation, universal Pre-K, and better representation of the Outer Boroughs could be addressed, this was what would have to be dealt with during the key “first 100 days”.

It’s way too early to tell whether New Yorkers pulled the lever voted for the right person last November but it’s pretty sure that they did the right thing during the previous three elections. For all the complaining that my fellow cabdrivers made about how overbearing the NYPD was on them (and I have to agree with my fellow drivers on this one), Bloomberg did his best to ensure that City would be left in better shape than how he found it. Leaving de Blasio with a balanced budget was the ultimate sign that whatever pitfalls faced in future could not be laid at his feet, even if the $35 billion budget that he submitted in ’02 was nominally half of that of the final one that he presided over years later.

Once the life expectancy of New Yorkers levels off or neighborhoods stagnate years after Hudson Yards is completed, the legacy that Bloomberg had a hand in creating will be fully visible for all to witness, and ultimately judge him by. His billions will continue to be donated to worthy causes and hopefully, his expertise in running a major city can be handed down to those entrusted to handle the challenge of the repopulating America’s urban centers in an increasingly technological and greening world. Those who wish to make cities relevant into the 22 Century and beyond would be wise to learn from the person who was able to successfully bridge the World’s premier metropolis from the 20 into the 21 Century, as it went through and emerged from its darkest hour.