Born in 1942 to a middle-class Jewish household, he earned an Ivy League degree in 1966, and rose to prominence in the mid-80s, transforming an industry from his New York City throne. When he steps down in 2014, he will have served as long as any man who had held his post before him. If you think I’m talking about Mayor Michael Bloomberg, you’re right. If you think I’m talking about NBA Commissioner David Stern, you’re also right. But Stern, who announced Thursday that he would soon end his 30-year stewardship of the NBA, has more in common with Bloomberg than biography.

Stern, who began his tenure in the NBA’s mid-80s heydey, would like to be remembered as the guy who expanded professional basketball from a mid-market attraction to international prominence, all while rooting out serious drug problems and ushering in the women’s game. Though he did all that and more, his legacy may end up looking rather different. First, as Tommy Craggs noted in 2009, Stern’s predecessor Larry O’Brien, and the Magic-Bird phenomenon of the early ‘80s, arguably played an equally significant role in the NBA’s global rise. Second, especially in the past few years, Stern’s behavior has been heavy-handed and scheming, and that may ultimately define him.

There has been some good meddling. In 1986, Stern banned New Jersey Net Micheal Ray Richardson for life for repeated drug use, ushering in an era of tough crackdowns that more or less rid the league of its bad coke habit. But there has been far more bad meddling. Last year, acting “in the best interests” of the league, in his capacity as temporary owner of the orphaned New Orleans Hornets, Stern vetoed a trade that would have sent superstar Chris Paul to the Los Angeles Lakers. Put aside the fact that the trade was widely considered to be fair, Stern’s was an unprecedented encroachment. Before that, in 2005, he banned inactive players from wearing what Allen Iverson called “hip-hop” clothes on the bench. Rumors continue to fly about a rigged 1985 draft and 2002 Finals.

The common denominator is Stern’s paternalism, pulled off with a pronounced disdain for transparency and democratic decision making. As Marc Tracy put it yesterday at the New Republic, Stern’s tenure embodies “the dilemma of the liberal in power.”

The liberal side of him has always wanted to let the league’s disproportionately undereducated and black employees thrive; the management side of him has been overcautious and controlling. The results have been economic success, but they’ve also left it unclear as to just what Stern’s ultimate values really are.

A similar point can be made about Bloomberg, who may be remembered less for the generally positive imprint he left on New York City, but the iron-fisted way in which he did it. The recent soda ban, for instance, smacked of the same paternalism as Stern’s moratorium on baggy jeans. His swift, quasi-brutal clearing of Zuccotti Park last November betrayed his annoyance at the rabble, in the same way that Stern hasn’t quite shed the Proskauer Rose labor lawyer in him that has locked out his players four times. But more than anything, it’s Bloomberg’s casual disdain for political process that mirrors Stern’s M.O. He thwarted his term-limited tenure, ostensibly so he could steady New York through the financial crisis. He ordered his police force to keep watch on many seemingly innocuous Muslims all over the country, in order to prevent another terrorist attack. Likewise, his more laudable efforts to turn around New York schools have been somewhat overshadowed by his ill-fated 2010 decision to install a business-savvy superintendent that was ignorant about education. Same goes for his refusal to adopt a political party; claiming sanctimonious Independence instead.

Bloomberg’s soda ban was a good first step in addressing obesity. And if Stern did rig the NBA draft to bring Patrick Ewing to the New York Knicks, well, that probably boosted the game’s popularity. Ironically, however, both Stern and Bloomberg may have damaged their own legacies simply through their own neurotic insistence on shaping them every step of the way.

Simon van Zuylen-Wood

Simon van Zuylen-Wood is a writer for Philadelphia Magazine.