Spied: A Critical Evaluation of Spy Magazine’s Ten Most Embarrassing New Yorkers of 1986


Spy Magazine, Issue 1, October 1986

by Elias Tezapsidis

Wit or Snark?

From its very first issue in 1986, Spy Magazine was a radical project. It was not the product of celebrities and their PR teams, nor did it aim to please those in the public sphere. Voicing the frustrations of intelligent journalists in a sardonic way, it acquired a thinking following that hungered for the esoteric references that abounded in its pages.

The distinction between ‘witty’ and  ‘snarky’ is noted over the passage of time: ‘witty’ holds long-lasting entertainment value and continues to be relevant, while ‘snarky’ seems pejorative, as its satire becomes dated faster. ‘Witty’ is cerebral, whereas ‘snarky’ leans towards ad hominem.

Today’s media culture – largely affected by the Internet and the anonymity it generously offers its users – looms more ad hominem than ever. Yet the upfront, quirky, accusatory tone of Spy rarely appears in print, and when it does, the subject is most frequently a persona non grata for mainstream audiences, an individual nearing tabloid infamy[1].

To appreciate the diachronic journalistic and entertainment value of Spy, the reader needs to be immersed in the particular sentiment of the late 1980s, as Spy conveys a moment in print media that denotes the shift from wit to snark.

Spy’s pilot issue allocated a two-page spread[2] to present New York’s top ten most embarrassing residents. Who deserved to be on the list and who did not?

1. Rex Reed

Reed started off as a very promising writer in 1968, and was expected to be a journalist that entertained the masses without compromising quality. However, by 1986, compromises had already begun and quality dwindled as Reed moved to The New York Post and his criticisms became visceral and often ungrounded. The largest irony is that eventually, his praise also came disguised as a literary attack and became pernicious. Rex Reed loved New York, but it was an unrequited love.

Reed writes ‘On the Town with Rex Reed’[3] for The New York Observer. He has frequently reminisced about the important role film critics played in the 1970s – when he produced his most poignant work – before the internet existed and everyone could critique a film. Maybe he is not familiar with Roger Ebert?

An abundance of embarrassing moments have occurred for Reed, the most severe being his assertion that Marisa Tomei received her 1992 Academy Award as a result of Jack Polance’s poor eyesight and inability to read the actual winner. This action was certainly a gigantic insult to the Academy, a strategic faux-pas as audacious for a film-critic as it would be for an aspiring journalist writing a take-down on journalists who matter.

Reed then pulled a ‘Winona’, getting caught shoplifting at Tower Records. It did get more embarrassing for this Judy Garland fan: he stole records of Mel Torme, Peggy Lee and Carmen McRae. As if liking jazz isn’t embarrassing enough as it is.


Right. Reed’s writing remains insipid and full of unjustified hatred[4]. He continues to insult even when he praises, and his tone still appears fake.

Spy Magazine, Issue 1, October 1986

2. George Steinbrenner

Mentioning Steinbrenner’s name elicits sour facial expressions among many sports fans. Steinbrenner was the principal owner of the Yankees, and served an important role from 1973 onwards. He was an easy target: affluent, and a vocal proponent of capitalism for the affluent. Steinbrenner was someone who did it for the fiscal rewards, not his love for the Yankees, nor his love for the game.

Hair mattered to Steinbrenner, and this fixation caused him trouble during the ‘80s. He introduced and imposed his corporate aesthetic standards upon Yankees players, a source of a lot of turmoil. He hated facial hair and alternative haircuts too much.

A not-so-transparent strategy of contributing to the Nixon campaign was an additional stain on Steinbrenner’s record. His involvement in this political scandal preceded his sports career, but buttressed the fans’ suspicions of his relentless greed.

Steinbrenner had a public, media-documented feud with Dave Winfield, a result of their miscommunication in regards to Winfield’s salary allocation for a ten-year contract of $23 million that was intended to be $16 million. Steinbrenner’s biggest mistake during this feud was paying Howie Spira, a gambler who moved in the mafia circles, $40,000 to substantiate accusations against Winfield. This controversy acutely affected how Yankees fans viewed him, and also resulted in getting him banned from the management of the team in 1990.

As the first owner of a baseball team to commercialize cable TV rights, Steinbrenner possessed unquestionable business acumen. In 1997, he signed a $95 million deal with Adidas[5] and entered popular culture as the caricature of the daunting boss, an ubiquity that even led to Seinfeld fan fiction[6]. Steinbrenner might have even manipulated this image for his advantage at certain points. He passed away in 2010 at the age of 80.


Debatable. Sure, Steinbrenner was embarrassing, but he was also a persona. He was a businessman with questionable ethical beliefs, but a good one, nonetheless.

Mug shot of Leona Helmsley, 1988

3. Leona Helmsley

The primary accusation against Helmsley is the arbitrary velocity of her rise to the top, as she escalated from a receptionist at a real estate firm to being Leona Helmsley, the Queen, after her marriage to Harry Helmsley. Some say he was the only person Leona ever had an emotional response to; others say “they deserved each other.”

The title “Queen of Mean” that accompanied the Queen of the Palace Hotel doesn’t seem unjust. Helmsley committed mundane white collar crimes such as tax evasion and fiddling with bookkeeping to manipulate fiscal allocations, such as charging work being done to her home to her company’s finances.

Possibly ahead of her time, she liked to ‘be able to fire people’. So strong was her affinity for this that Helmsley former executives landed on the Joan Rivers show[7] discussing how frequently they got fired and her inexplicable, erratic behavior. The characterization seems to hold a gender connotation, and Helmsley’s story can easily be viewed as the misogynistic portrayal of the status-and-money-driven working woman. But it is not, and Helmsley herself seemed cognizant of her inhumane behavior and utter lack of empathy in a professional milieu, as she endorsed a campaign ad that portrayed her as a demanding queen that obeyed a rampant capitalist agenda where the smallest mistake was cause for firing an employee. When Rivers questions why they continued to work for her under such circumstances, an executive hilariously attributed it to Stockholm syndrome.

Were her lovers sadists? Helmsley had married thrice, once to Leo Panzirer, twice to Joseph Lubin, before her romance with Harry Helmsley bloomed. Initially Harry was married to someone else, but after they did some unethical real estate things together their connection took over. They built the Helmsley Palace and by 1989, the “Queen of Mean” owned 23 hotels that she controlled.


Right. Ultimately, Helmsley herself suffered the most because of her behavior. Alienated from high society, it appears that the mean greed that drove her was also her Achilles’ heel. She passed away in 2007 at the age of 87, leaving her Maltese dog, Trouble, a $12 million bond. Like pet, like owner: trouble, literally[8].

4. Geraldine Ferraro

Ferraro rose from obscurity to political stardom overnight when she became Walter Mondale’s choice for the U.S. Vice Presidential candidate position. Ferraro was the first female VP candidate and also the first Italian-American one. Despite her election to the House of Representatives in ‘78, ‘80 and ‘82, she was considered ‘inexperienced’ in 1984.

A lot of image-damage may have contributed to the Mondale campaign losing to Reagan and Bush. Ferraro’s private life made headlines. The favorable media coverage she was receiving decreased until her finances became public. The fact that she filed her taxes separately from her husband, John Zaccaro, birthed scrutiny: she wasn’t the simple Queens native the Democratic campaign was marketing. When she was asked to address Zaccaro’s tax malpractice[9], she responded with a tongue-in-cheek joke that cost her: “You people who are married to Italian men, you know what it’s like.” She was accused of ethnic stereotyping. Eventually Zaccaro released his taxes to the public and the impact further revealed that Ferraro was no Cinderella; she led a luxurious life.

Following the 1984 political defeat, Ferraro liquidated her political celebrity by publishing Ferraro: My Story[10] to chronicle her personal narrative, and by appearing in a Diet Pepsi ad.[11]In 1988 her son, John Zaccaro Jr., showed his preference for coke[12], further hindering his mother’s political presence. Ferraro died in 2011, at the age of 87.


Wrong. Ferraro’s harshest critics could imply that she was just the earlier version of Sarah Palin. In context, being selected as the first female VP candidate of a major party makes her a timeless inspiration. She was a vocally pro-choice Catholic woman.

Album cover of Inside Story, Grace Jones, 1986

5. Grace Jones

“I’m bold! I’m a revolutionary!” Jones knew ahead of anyone else that she was destined for success. Such statements bring to mind the bravado of more recent starts like Maya. Jones was accused of being too confident, too convinced in her greatness in a way that implied an idea of greatness. The omnipresence of her ‘indistinct sexuality’ in provocative photography yielded an argument for her sceptics to question her genuine artistic value.

Maybe 1986 was a reasonable year to be frustrated with Grace Jones: she made Vamp[13] — maybe an entertaining movie because of its bizarreness, but certainly no masterpiece — and commercialized her recognizability (as in this quirky Citroen ad). Jones introduced an androgynous look, signed with Island Records, made records, appeared in campy movies and was a downtown fixture and in Studio 54. She was also a muse, an artist who inspired artists and entered the scene with the air of a provocateur. She collaborated extensively with Andy Warhol, became a disco sensation and a gay icon. In a time before TMZ, Jones was a media sensation. Rumors of her diet consisting of oysters and cocaine attained legendary status[14].

Jones was a pioneer in the New Wave music scene and a revolutionary, indeed. She challenged notions of sexuality, femininity and blackness. Her loudness is particularly impressive if one considers her hyper-conservative background: her family was very religious and her father a bishop.


Wrong. Jones did ‘crazy’ before it was a de rigueur marketing technique. An intentionally intimidating artist, she has inspired contemporary culture in ways many who are not familiar with who she is do not see.

6. Andy Stein

Stein was portrayed as the Lana Del Rey of politics in the 1980s: an individual without the background or ability to be in the position he finds himself in, who also changed his name. He graduated from Southampton College — some guffawed at the sound of his alma mater — and proceeded to politics right away, gaining election to the New York State Assembly. His father, Jerry Finkelstein, was the publisher of The New York Law Journal. Stein’s primary fault was obviously using the prowess his father’s position provided, never working in a different industry prior to entering New York politics.

Stein was elected as President of New York’s City Council in 1985 and 1989, and became influential due to his role in the Board of Estimate, which the Supreme Court eventually ceased due to its unconstitutional structure which gave more prowess to the Mayor, the City Comptroller and the City Council President.

Stein most recently received deleterious attention because he lied when testifying to the IRS in regards to a $30 million Ponzi scheme.[15]


Right. He dated Ann Coulter.[16]

Andy Stein at the 2009 Tribeca Film Festival. Photograph by Andrew Shankbone

7. Midge Decter

Decter is listed here due to what Spy considers her fickle politics and opinions. Hypocrisy is embarrassing, and Decter, a catalyst in the resurgence of the neoconservative movement, was accused of practicing socialism in the guise of neo-conservatism. Beyond this hypocrisy, she was also considered embarrassing for appearing in the vacuous and exclusive circle of New York intellectuals.

Decter writes well: she argues academically, uses theses, agrees or disagrees. Thus, her writing is polemical and prone to enemy-making. “Precisely because the issue is one of life and death, the liberal dream of Eden becomes all the more- dangerous,” she concluded in a 1963 Harper’s profile[17] of the organization Women Strike for Peace, not sugar-coating her bountiful disdain for liberals and their naiveté throughout the article. Her scorn towards liberals remained intact in 1968’s ‘Anti-Americanism in America,'[18] Anti-Americanism in America maybe, but her frustration with the political condition of the ‘60s became larger to include her frustration with her contemporaries in the culturati sphere.

Beyond writing, Decter founded the Committee for the Free World in 1981, with funding stemming from conservative foundations, including major right-wing foundations: Scaife, John M. Olin and Smith Richardson. The Committee for the Free World states its devotion to representing the non-communist world, and Decter would certainly be able to write a sharp profile on the organization were there no conflict of interest.


Right. She married Norman Podhoretz.

8. Barbara Howar

Howar rapidly lost her credibility as a writer. Following her chick-lit novels Laughing All the Way and Making Ends Meet she had received too much exposure. It warranted: “The brilliant, bestselling author of Laughing All the Way now unleashes her sizzling talent in this fascinating and witty novel about a beautiful woman trying to survive in a sex-obsessed world.” She openly expressed her frustration with the status-quo of writing in an Anthony Burgess interview[19] and sacrificed quality for commercial success and the fiscal rewards with which it brought. The fact that Howar was a proto Lohan – a serial fake-tanner – made matters worse.

Howar’s media ubiquity was ephemeral, and her career appears to have transitioned to obscurity before the 1990s. A 1976 article[20] preceding the publication of her second novel – the one about the unlucky ‘beautiful woman trying to survive in a sex-obsessed world’ – perhaps serves as foresight: “Any woman who tells you that she can hold down a career — not a job, but a career — and raise children and keep up with a man and a home and social life and a sex life and not suffer for it is lying. It is not possible.”


Right for then; unknown for now. (Does ‘unknown’ make it right?)

9. Alfonse D’Amato

Alfonse D’Amato served as the New York Republican US Senator from 1981 to 1999. Joseph Margiotta, who was convicted of extortion in 1981 for his involvement in an insurance company money-laundering scheme, was his mentor. Being Margiotta’s[21] mentee might have cause skepticism for D’Amato’s integrity, but was probably the rapport that marked his successful political entry.

He lacked the finesse of a suave, sophisticated politician, and for this reason had to focus on being personable and accessible. His strategy of helping specific individuals in face of a problem let to his nickname[22]: ‘Senator Pothole‘. The nickname depicts D’Amato as a man of the people, and while this was definitely intentional, D’Amato also ascended to highly influential inside world of NY politics, due to his close friendship to Rudy Giuliani.

In 1991, the Senate Ethics Committee chastised D’Amato for allowing his brother Armand, a lobbyist, to utilize government stationary in an endeavour to manipulate mail recipients. Armand was a colleague of Paul Vario’s, raising further questions about how familiar his Senator brother was with the Lucchese mob.


Right. D’Amato comprises empirical evidence for the theory ‘it’s all about who you know’ in the realm of politics.

Donald Trump at CPAC in Washington D.C., February 10, 2011. Photograph by Gage Skidmore.

10. Donald Trump

In 1986, Trump agitated with his gauche uptown notion of class. He was self-important, self-absorbed and ignorant. His sheer idiocy could be succinctly summarized without anyone’s help: he has done an exquisite job[23] all by himself.

Trump was born privileged and worked for his father’s real estate firm while completing his degree at Wharton, an academic staple for the privileged business-oriented. He is undeniably a household name, owing some of his recognizability to the exaggerated caricature of the relentless business devil he portrays, or even, is. Identifying Trump’s embarrassing moments is like a quest for sand on the beach, and for this reason the focus is placed on the most recent past: 2010 to now.

Trump’s persistent challenging of Obama to provide his birth certificate, along with his conviction that it was not authentic entertained consumers of the media. His fervent passion to exacerbate conservatives’ doubts of Obama’s right to be in the White House became exhausting, but also demonstrated Trump’s stubborn ethos: if Trump says so, it must be so.

His sociopathetic view of the world made him consider running for President for the 2012 election, and was also a potential VP for everyone’s beloved Bachmann campaign. His old-school Christian beliefs – patriarchy always worked for him – might have diminished any progressive vision for the country.

‘Too simple’ would be a euphemistic synopsis of his suggestion of imposing a 25% import tariff when trading with China; the sort of undiplomatic idea that could belong to a college sophomore student of international economics. In the end, Trump decided to stay out of the political arena and endorse Mittens Romney.


Right for his haircut alone. Additionally, his family, his family [24].


Conclusive Verdict


Right → witty.


[1] Empirical evidence: “Here Is What Happens When You Cast Lindsay Lohan in Your Movie” was Stephen Rodrick’s NYT Magazine cover story on the conditions surrounding the filming of Lindsay Lohan’s most recent film ‘The Canyons.’



[4] Empirical evidence: He recently called Melissa McCarthy a ‘hippo’ and ‘tractor-sized.’  (hyperlink to:




[8] Pertinent movie made for television available on Netflix is highly recommended.








[16] “OVER ALREADY.” New York Post. N.p., n.d. Web. 09 Feb. 2013.;jsessionid=4332955D268D599F5663606222B542A1









About the Author:

Elias grew up in Thessaloniki, Greece, prior to attending Macalester College in Saint Paul, Minnesota. It was there that he discovered he was too neurotic and OCD for the Midwest and had a low-tolerance for the MN-nice. The move to NYC post-graduation seemed like the logical next step, and since then LES has been home.