By MICHAEL SCHENKLER

It’s very sad.
No, Sheldon Leffler is not a personal friend. But I knew him pretty well. We could have been friends, but his slightly oddball persona made him somewhat difficult to embrace. 
I’ve known Sheldon for decades. I’ve run into him and his wife Joy at restaurants, movie theaters and Queens political and charitable dinners. The Lefflers were nice enough to show up when I was the Salvation Army’s honoree at their annual awards dinner a couple of years back. 
I interviewed him in depth during his Beep run and we talked politics and policy on a number of occasions. 
Sheldon has always been interesting and pleasant. Friends we’re not but he certainly is an acquaintance I’ve known for sometime who I respected for his hard work, intelligence and integrity. 
Yes, in years past, if you asked me to describe how the Harvard-educated Leffler was perceived of in Queens political circles, I would have responded “bright, independent, honest and perhaps slightly out of step with the mainstream politician.” But “honesty” would have been there.
He was concerned about his community, he was concerned about our society, and he cared at least as much as the other elected officials — perhaps more.
He was bright, perhaps a bit too bright. He seemed to think he always had the answers and others rarely did.
Sheldon marched to the tune of a slightly different drummer and it seems it led him astray. His fierce independence seemed to have been rooted in the belief that he was the best thinker on the block.
And when he couldn’t sell his ideas to the group, he became obstinate and a bit difficult to get along with. His colleagues didn’t particularly like him. He was somewhat of a loner, a bit of an outcast.
He was never one of the boys. I wonder if he wanted to be. At times, watching Sheldon, you felt sorry for him. He worked hard but never really achieved the level of his intellectual potential or so he believed.
In politics, Sheldon was the proverbial fish out of water. But for most of three decades, he chose to swim in the pond. He couldn’t wheel and deal with his colleagues. He couldn’t capture the imagination of the voters or offer the press those 30-second sound bites. Sheldon was straight, boring, and bright.
I hate to say it again but Sheldon was also honest — straight, boring, bright and honest.

So where did he go wrong?
Sheldon played in a game in which he didn’t belong.
Sheldon tried to move up to the big leagues and was over his head.
Sheldon ran for Borough President.
He faced the high-power sophistication of Carol Gresser and a network of business, political and educational professionals. Carol Gresser could raise money; she maxed-out (raised the maximum matching and spending limit).
He also faced the eventual winner Helen Marshall. She came armed with the Queens Democratic political machine. It can be a formidable foe and in this case delivered most elected officials and enough regular and big business contributors to make Helen competitive with Gresser in fundraising.
And Sheldon’s quarter of a century of public service, Harvard network, and superior intellect left him in a pathetic third place (out of three) in the fundraising game.
It didn’t really matter; Sheldon wasn’t going to win no matter what. He just didn’t have “it.”
But sometimes the brightest people just don’t get it. I remember back in the early ‘80s when Gary Ackerman was first elected to Congress. I ran Gary’s campaign and recall chatting with Sheldon, one of several challengers. Sheldon was convinced he was going to win. He was probably the only person on earth who believed that.
Well, Sheldon also probably believed that if he could remain competitive financially, he could win for Borough President. He probably believed he deserved the office. He was bright, experienced and he cared. In his mind, he was the best of the field.
So when he saw the Borough Presidency drifting away, Sheldon broke the rules. He was complicit in the act when Southeast Queens landlord Rita Stark delivered her $10,000 contribution disguised as 40 separate contributions of $250 each. 
You see, the city matches up to $250 per city resident making a $250 contribution worth $1,000. Sheldon was able to claim an extra $29,250 in city matching funds — illegally.
Now, Rita Stark is no saint. Several who know her or of her have described her as a “slumlord.” One community planner told us that she was responsible for the biggest blight in Jamaica. He put her atop the list of targets that had to be hit in order to truly revitalize the downtown Jamaica area.
Rita Stark purchased 40 consecutively numbered money orders, filled in names of her tenants and donated them to Leffler, who in turn filed for 40 individual matches. We heard the two of them discuss the matter on tape. Stark came to one of their meetings wired by the Manhattan DA’s office. Stark goes free. Sheldon (likely) goes to jail.
It’s very sad.

THE SADDEST OF ALL
But the saddest part is what it says about our system — our system of politics and government which constantly places big money in the path of candidates and elected officials. 
To end this sad tale with the colloquial “money is the root of all evil,” seems trite. To point to contributors buying access or lobbyists buying influence all on the good side of the gray area seems simplistic. To suggest that with great regularity, officeholders flirt with acts of accepting meals, gifts, and contributions illegally or in exchange for access or influence is the cold hard truth of the story of American government — probably a problem a lot wider than just our country.
Yes, the election system is much too dependent on money. It exposes candidates who become officeholders to the fat cats who write the checks, bundle contributions and entertain with excess. And once elected, those fat cats keep on writing the checks, bundling the contributions and entertaining with excess.
And our honest elected public officials, recipients of the checks, the bundled contributions and the entertainment with excess, pass laws which affect the businesses of those fat cats. And those fat cats send their check writing, contribution bundling, entertaining with excess lobbyists to influence the public officials.
And gray areas and black and white all begin to blur.
And every several years someone is made an example of and goes to jail.
But it goes on everyday. It’s merely a question of staying in the gray area. And that line of demarcation between gray and illegal seems to move depending upon who you are, who the prosecutor is, and which way the wind is blowing.
It’s all very blurry.
There are no easy answers.
There are no quick fixes to our flawed system.
It’s just very sad. .