Illustrator Drew Friedman writes about working for Jared Kushner

"Hi Drew, I'd really like to talk to you, but there are many far more important people here for me to talk to right now."
— Jared Kushner, publisher of the New York Observer

In 1987, Arthur Carter began publishing The New York Observer, the salmon-colored broadsheet covering NY politics, show business, gossip and media. The Observer's first editor was SPY magazine co-founder E. Graydon Carter. Journalist Peter W. Kaplan became the Observer's new editor in 1994 and one of his first objectives was to line up four artists to create the newspaper's weekly covers each month. Peter first called me with an assignment to draw senator Al D'Amato and we instantly hit it off, realizing we shared a mutual love of old comedy films, Frank Sinatra and MAD magazine. Peter soon lined up the great caricaturists Philip Burke, Victor Juhasz and Robert Grossman as his other cover artists. He referred to the four of us as his "Murderer's Row", referencing the unbeatable 1927 New York Yankees starting lineup. Working directly with Peter, The four of us would create weekly covers for the NY Observer, (the NYO), for the next 15 years, with Barry Blitt drawing the small black-and-white cover caricatures.

In 2006, 25 year old real estate developer Jared Kushner bought the Observer and Peter Kaplan continued on as editor. When I first talked with Peter about the new publisher, he seemed excited about the future prospects of the NYO with this young, wealthy new publisher, equating him to Orson Welles as Charles Foster Kane, purchasing a money-losing newspaper and injecting new life into it.

It didn't take long before I started picking up on slight pauses and hesitations during our conversations about things, and Peter's pauses and hesitations spoke volumes. I sensed that things were perhaps not going according exactly to plan. I never pressed Peter for any details, we mostly talked about the Marx brothers, Jerry Lewis, Jack Benny, Popeye and Joan Blondell, but the writing seemed to be on the wall. Peter seemed increasingly frazzled during each phone conversation.

The first assignment Peter gave me under the new Jared Kushner regime was to draw Sacha Baron Cohen for a cover story, also in the guise of his two characters, Ali G. and Borat, (The Borat film was about to be released). When the issue hit the stands the following Wednesday, an very excited Peter called me to say that Jared, a huge fan of Ali G., loved the cover and wanted to purchase the original art for his younger brother Joshua as a gift. Peter also told me, (in his more subdued voice), that this was "finally really good news". Peter acted as Jared's liaison and we agreed on my fee, and at the end of the conversation he said, "Drew, thank you… thank you", as if I had done him a tremendous favor.

In 2007, the NYO switched from the large broadsheet format to a smaller, trimer, tabloid size, yet still retained its salmon hue. The first issue of the new Observer featured my illustration of a Hillary Clinton floaty-head on its cover, silhouetted from a larger drawing I'd created for an earlier issue. As a publicity stunt, the morning the issue hit the stands, the young publisher and the seasoned editor both hawked copies, ("extry, extry…"), of the new tabloid outside Grand Central station as Observer photographers snapped away.

Later in 2007, the NYO celebrated its 20th anniversary with a huge party at the Four Seasons Restaurant in Manhattan, which publisher Jared Kushner hosted. My wife, Kathy and I were invited, and we arrived to witness throngs of VIP's, media moguls, and young, tuxedoed real estate developers lined up to get in. The only one of my fellow cover artists attending was my friend Victor Juhasz and his wife Terri. A perpetually beaming Jared and his future wife Ivanka Trump held court and welcomed their friends and admirers. Peter made a short, optimistic welcoming speech and introduced Jared who discussed the future of the NYO, as well as his fondness for the Four Seasons.

After Jared's speech, I told Kathy and the Juhasz's that I was going to go introduce myself to Jared, knowing that he enjoyed, and had purchased my artwork. Jared was standing at the bar holding a glass of champagne. I approached him and said, "Hi Jared, I'm Drew Friedman". He grasped my hand, surveyed the crowds, and responded "Hi Drew, I'd really like to talk with you, but there are many far more important people here for me to talk to right now". I quietly nodded and retreated back to my wife and friends. Kathy asked me how it went and I repeated what he had just said. She was shocked: "You're joking?" "No, that's exactly what he said to me… and you know what, I admire him for it, his blatant honesty… and… I'm sure he's right, there are far more important people here for him to talk to then me".

By 2008 it was clear, at least to me, that the completely frazzled Peter Kaplan was at the end of his rope and after 14 years would soon be retiring from his beloved NYO. One of his cover assignments for me that year was to create a cover drawing for an article about Donald Trump's large, extended family, including Trump's ex-wives, his current wife Melania, their new baby son Baron, his, (then porky), son Donald, Jr, and Trump's daughter and Jared's future wife Ivanka, (to this day I'm not clear why I wasn't asked to include daughter Tiffany and son Eric. Such is their continuing lot in life). I asked Peter if I should perhaps hold back a bit as far as the caricatures went, considering that Ivanka was Jared's impending wife and Trump his father-in-law to be. Peter responded "NO!" I was later told that Jared was pleased with the drawing.

Also in 2008, To help celebrate the 20th anniversary of the NYO, an anthology, "The Kingdom of New York" was published by Harper Collins, edited by Peter Kaplan and designed by NYO Art director Nancy Butkus, and featuring a new cover by me, (using the same Trump ref I had used for my earlier "Meet the Trumps!" cover). Tom McGeveran was now interim editor of the NYO, and Peter planned to stay on at the Observer as advisor, until the book was completed, and a new permanent editor was chosen. A publication party was planned at the Soho designer handbag store Longchamp, where Jared planned to formally introduce his new editor Kyle Pope. Again, my wife Kathy and attended the party, this time attended by all four of the NYO cover artists under Peter Kaplan's regime.

Jared's fiancé Ivanka Trump, his brother Joshua and his father, real estate magnate Charles Kushner were also in attendance. The elder Mr. Kushner, on learning that Kathy was married to me, gushed to her that what he loved most about his son's publication were the covers.

Once again, I decided to greet Jared Kushner. He was preparing to make his speech to the assembled crowd when I approached him. Going over his notes, he looked up and recognized me: "Hi Drew". I answered "Hi Jared, would you do me a favor and please mention my name during your speech?" He looked bemused but said "sure".

Peter Kaplan addressed the assembled crowd, thanked Jared, discussed how proud he was of the new NYO book, and wished Kyle Pope luck as new editor, (also mentioning that it was perhaps the first time a "Pope" replaced a "Jew"). Jared stepped up next, thanked Peter for everything, introduced his new editor and discussed the new NYO anthology and said "the cover was drawn by Drew Friedman, who is here… " he paused and continued "… and who I mentioned because he asked me to," which got a big laugh.

I continued creating covers for the NYO after Peter retired, (he became editor of Conde Nast Traveler, an odd choice since Peter hated to travel), for Jared's rotating door of new editors, starting with Kyle Pope, then Aaron Gell, and then Elizabeth Spiers, founder of Gawker. For Elizabeth I created the above drawing of embattled congressman Anthony Weiner channeling Burt Reynolds. After this cover appeared, Weiner, (finally), retired from congress the following day.

Elizabeth Spiers left the NYO in 2013 and journalist and ex-punk musician Ken Kurson, a rabid comics fan and the brother of Robert Kurson, author of The Three Stooges Encyclopedia was hired as new editor. We hit it off.

Under the new editors, the NYO became even more streamlined, the articles grew shorter and the focus centered more on tech, power brokers, and especially Manhattan real estate. It was also transformed into an oversized magazine, finally retiring the salmon to sea. New artists were hired to create cover art, and the "Murderers Row" that Peter nurtured for 15 years ended, although Burke, Juhasz and I continued to do occasional covers. I asked Ken to only consider using me if the article seemed to be a good fit, like the above Joe Lhota and Kevin Spacey, or this interior drawing of Gilbert Gottfried:

In 2013, Peter Kaplan died of cancer at age 59. Over 700 shocked and saddened friends, family members and admirers attended his funeral. Jared Kushner wrote this tribute to him for the NYO.

My final "encounter" with Jared came indirectly. I was contacted by an employee from Jared's real estate company "Kushner Industries." He told me I was Jared's first choice to illustrate a huge fold-out brochure promoting luxury condos for sale in the Puck building on E. Houston St, (where SPY magazine once had offices). Jared had recently acquired the Puck building. The complex job would include rendering the history of the Puck building, detailed maps of all the available units, and dozens of drawings of notables who had either lived or worked there, a "Sistine Chapel extravaganza", to quote Victor Juhasz. The deadline was very tight and the whole job had very little appeal to me but I asked for what I felt was a fair fee, considering the amount of work and the short turnaround. The reply was basically a low-ball counter-offer, and I was also reminded that "Jared knows what his illustrators get paid". I thanked him for that information and politely declined the job. Victor Juhasz would tell me later that he was next contacted and also requested what he felt was a fair fee for the enormous amount of work, and he was also reminded that Jared knew what his illustrators got paid. Victor also declined.

My final cover for the NYO appeared in Dec, 2015, a portrait of the "world's greatest Cartoonist" Robert Crumb, (I concur), posed in his living room in France, for what turned out to be a highly controversial interview with him.

The NYO's new art director contacted me several times in 2016 to create covers, but I felt the ideas just weren't a good fit for me, especially an assignment to draw the Republican presidential candidate and Jared's father-in-law Donald J. Trump. The NYO had been one of the only publications to endorse Trump in the New York presidential primaries. I declined the job.

After Trump won the presidential election in November, Jared Kushner immediately ceased publication of the print edition of the Observer and he and his young family packed their bags and moved to Washington, DC. The rest you probably know. (The NYO still exists as a digital site).

My thanks To Victor Juhasz

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