Risks of Trump’s ‘Winning’ Obsession

Donald Trump’s more pragmatic approach to foreign policy may be an improvement over the recent ideological obsessions but his own obsession with “winning” could cause trouble, says ex-CIA analyst Paul R. Pillar.

By Paul R. Pillar

A slogan from the sports world—”winning isn’t everything; it’s the only thing” — which usually is associated with Vince Lombardi, although he probably got it from another football coach, has always had a vacuous quality. It sounds like an attempt to make a contrast where there isn’t really a contrast. What meaningful difference is there between “everything” and “only thing”?

Donald Trump speaking with supporters at a campaign rally at the Prescott Valley Event Center in Prescott Valley, Arizona. October 4, 2016. (Flickr Gage Skidmore)

But if there is any semantic substance to the phrase, maybe it has to do with winning as a pure, abstract value in its own right, separate from anything about the specific endeavor that was the vehicle for one contestant winning and another one losing. Winning per se is seen as the only thing that matters because everything else about the game that was played and won doesn’t matter. And in the sports world, this begins to make sense; the activity is just a game, and it really doesn’t matter in the larger course of human events.

Apply this frame of mind to more consequential endeavors, however, and the implications are more disturbing. In this regard, consider the incoming U.S. president and what we know, and don’t know, about his outlook on foreign policy. Despite the earnest and usually sincere efforts by many commentators to discern pattern, direction, and purpose amid Donald Trump’s tweets and other utterances, the dominant picture is still one of inconsistencies, contradictions, slogans, and lack of a record. We are, late in the transition period, still mostly flying blind regarding the actual future foreign policy of this new presidency. We have little idea of what Trump really cares about in the substance of U.S. foreign policy, as distinct from rhetoric that has worked in a campaign and that helps in his effort to portray himself as a populist.

We do know, however, that Trump cares a lot about winning — or more precisely, about being seen as a winner. He constantly returns to the framework of “winners” and “losers” as his way of identifying what is good and bad and what matters to him. His repeated stress on associating himself with the biggest or best or most successful whatever is part of making sure that he is always seen as a winner. And on November 8th he registered the biggest win that any individual could. The slogan about winning being the only thing does appear to apply to Donald Trump and to what drives him.

The Drawback of ‘Winning’

There are many drawbacks in applying to foreign policy an outlook that is more appropriate to sports, but one set of drawbacks is suggested in a perceptive piece by Mark Katz about prospects for U.S.-Russian relations in the Trump administration. Katz observes that the principal demands that Vladimir Putin is likely to make as conditions for an improved relationship are ones that Trump would have good reason to agree to.

Russian President Vladimir Putin. (Russian government photo)

Accept the Russian annexation of Crimea? It’s a fait accompli that is not going to be reversed anyway. Lift Ukraine-related sanctions on Russia? The sanctions are bad for business. Promise that none of the former Soviet republics apart from the Baltic states will join NATO or the European Union? The Europeans don’t want them as members. Accept continuation of a Russian-allied Assad regime in Damascus? The jihadist alternatives are even worse.

Although Katz doesn’t say so, these are valid reasons and low-cost ways for not just Trump but any U.S. president to accept much of what Putin wants in the interest of a better relationship that would have benefits for the United States. The problem, as Katz points out, is that Trump cannot be perceived as caving in to Putin. He has to be seen instead as having wrung concessions from Putin, and preferably as having gotten the better of him. Katz emphasizes that Trump especially must be seen doing so in the eyes of a domestic audience that includes hawkish, anti-Russian Congressional Republicans. Trump has the added baggage of the alleged Russian hacking and interference in the U.S. election; any favorable move he makes toward Putin risks being interpreted as payback for election favors.

On top of this is Trump’s personal fixation about winning. He will feel a need to get Putin to back down on some of his demands not only to satisfy John McCain and Lindsey Graham but to satisfy himself that he can tout himself as having “won” a negotiation. The result may be that potential trades and understandings that could serve both U.S. and Russian interests will be forgone.

The general point that Trump is ill-disposed to understand and accept is that what best serves U.S. interests is not always easily recognized or defined as a “win”. The most effective diplomacy yields agreements that both sides can honestly describe as successes. The sort of foreign government behavior most likely to serve U.S. interests over the long term is what the foreign government perceives to serve its own long-term interests, rather than being a concession that was wrung out of it and that it will seek the first opportunity to reverse.

Complications for Trump

The issues of election interference and Trump’s professed admiration for Putin make relations with Russia an especially delicate case, but the impulse to win is likely to complicate other negotiations and relationships as well. This may be the case with China, as suggested by Trump already trying to put the one-China policy in play.

Iranian President Hassan Rouhani at a press conference in Iran. (Official Iranian photo)

Most of this mistake probably can be attributed to naïveté, and specifically to a failure to understand how the Taiwan issue figures in Chinese thinking, regardless of how justified or unjustified that thinking is to us. But it may also be an early indication, along with Trump’s mercantilist approach to trade and outdated perceptions of such things as currency manipulation and job losses, of approaching the entire U.S.-Chinese relationship in win-loss terms.

Another case is Iran, where there already is a recent important deal in the form of the agreement that limit’s Iran’s nuclear program. Here Trump’s self-promoted image as the man who can reach better deals than anyone else fits with the existing Republican Party mantra that we should have gotten a “better deal” with Iran.

All of this ignores the long and laborious negotiating history of this agreement, what the Iranians have given up, and the nonproliferation objectives achieved. A quixotic attempt to reach some alternative that could better be described as a “win” — even though it would not move Iran any farther away from a nuclear weapon than it already is, nor advance any other U.S. interests — risks destroying the very important benefits of the existing agreement.

Notwithstanding Trump’s trumpeting of his skills as a deal-maker, and notwithstanding all that has been said and written about the “transactional” approach this businessman is likely to take toward foreign policy, a man with his mindset is not about to operate in his new job the way he did in his old one. As head of a privately-owned business, profits and losses could be kept private — and with his refusal to make his tax returns public, they are largely staying that way. The public side of the business could be limited to his promotion of himself and his brand, with bragging about having the most luxurious buildings or the best golf courses.

Now the game has changed for him. The public perception of gains and losses is different. If Trump really were to approach foreign relations in a pragmatic, businesslike way, that in general would be good for U.S. interests. But probably his need to be seen to “win” will get in the way. When winning is the only thing for the chief executive, that is not so good for the country.

Paul R. Pillar, in his 28 years at the Central Intelligence Agency, rose to be one of the agency’s top analysts. He is author most recently of Why America Misunderstands the World. (This article first appeared as a blog post at The National Interest’s Web site. Reprinted with author’s permission.) 

27 comments for “Risks of Trump’s ‘Winning’ Obsession

  1. tom
    January 7, 2017 at 19:29

    this has really passed the lol stage now.
    trump has no idea what he is doing…he has no plan…he has no grand scheme.
    he is totally ignorant of the issues you describe and has no interest in gaining knowledge about them or anything else.
    he REALLY DOES believe he is smarter than the generals and if you don’t understand that…you are going to keep writing nonsense like this.

  2. Rob Roy
    January 6, 2017 at 18:38

    Both Pillar’s article and commentary are interesting. I get a bit tired of people guessing Putin and nearly always being wrong. No one can “wring concessions” from him. He is smarter than all the Congress put together. Look at real “statesmanship” recently from Obama (kick out Russian ambassadors) and Putin (not play the retaliation game, a favorite game of the US). Who was the statesman in that little drama? What demands from Putin have we heard about? I can’t think of any. He will handle Trump just fine. As for pleasing John McCain and Lindsay Graham, it can be only a good thing if those two are not pleased about anything, ever. Besides, Trump doesn’t seem to care whom he pleases, but he did choose the worst possible group of people to assist him, (my vote is still out on Tillerman; it’s great if someone can stave off the so-desired war for regime change in Russia, the most destructive idea I can think of) but no worse than Obama’s choices presented as knowledgeable people, except they screwed the American people behind closed doors. Trump’s choices are awful and out in the open, which makes for aiming shots with a clearer line of vision.

  3. Jerry
    January 6, 2017 at 15:33

    These things that Putin wants are what Trump wants. Trump ran against and defeated all the neocons (Rep. and Dem.) who wanted confrontation, arms races, even war. Trump wants peace and to do business. By going along with Putin, he continues to push his thumb in the eyes of his opponents and to pursue his own agenda. In this way he wins and looks tough. He does what he wants to do.

    As for what his opponents say about his alleged subservience to Russia, he should continue to ignore these squeaking mice and even tell them to go to hell. After all, he won, and they lost. That’s what a strong winner does.

  4. angryspittle
    January 5, 2017 at 21:52

    He doesn’t really care if he wins or not just as long as he can convince everybody else that he has. As long as he looks like a winner that is all that counts. Even if he loses “bigly” he will claim he actually won. When he is sitting on a heating grate wrapped in a blanket and living in a box in front of one of his former properties in February after having been exposed as a fraud, being billions in debt to over 150 institutions he will be claiming what a winner he is.

  5. Gregory Herr
    January 5, 2017 at 21:41

    “…Trump cannot be perceived as caving in to Putin. He has to be seen instead as having wrung concessions from Putin, and preferably as having gotten the better of him. Katz emphasizes that Trump especially must be seen doing so in the eyes of a domestic audience that includes hawkish, anti-Russian Congressional Republicans. Trump has the added baggage of the alleged Russian hacking and interference in the U.S. election; any favorable move he makes toward Putin risks being interpreted as payback for election favors.”

    Who cares about stupid interpretations from people who are going to say the same thing regardless of what happens? And McCain and his sidekick can hold their breath till they turn blue. Mr. Pillar goes on to make an excellent point about the true nature of successful diplomacy, but “political” calculations like those described are tiresome. Do the right thing, be good at explanation, tell the truth, and let the chips fall. Screw the “perceptions” of those who are against what you are doing if you know what you are doing is right.

  6. January 5, 2017 at 18:18

    “Winning at all cost,” or “winning is the only thing that matters,” married with fragile egos and US defense establishment policy and practice of “Full Spectrum Dominance” through regime change or other means (nuclear war threats/blackmail) is a guaranteed recipe for nuclear holocaust. I think the whole planet is in a “dead man walking phase” anyway, which explains the infatuation with zombies. Yes, it would be great if Trump could push the nuclear clock back 5 minutes, but I’m doubtful. We live in a world disconnected from reality. Every year there are logical reasons to grow even more skeptical, matters not whether GOP or Dem governs. I’m not despondent btw, I’m a realist. IMO human species will be extinct in 20 years…if not the next 10. Harkens back to what one of my co-workers use to say to exacerbate me. “Its a good day to die.” After nuclear holocaust,wonder who will be the winners then?

  7. arnaud
    January 5, 2017 at 17:58

    In a similar historical de-construct it would be Gorbatchov “losing ” the Soviet Union, and ending the Cold War. Sometimes “winning” can only be achieved by losing. Winning the War against the Military Industrial Complex that is the backbone of ol USA will surely be a loss to some.

  8. backwardsevolution
    January 5, 2017 at 16:14

    What do you call a country who has couped, overthrown, crushed, minced, and pulverized countless countries and their leaders in the last few decades? A country that insists on being top of the heap, regardless of how many millions are killed? Isn’t this a country that “wants to win”?

    We’ve been living under the framework of “winners” and “losers” for decades (where the winners add a new wing on the Pentagon and the losers are either assassinated or have an unlucky accident), but somehow now we’re supposed to be all worried that Trump likes to win? Do you think that AIPAC wants to lose, or win? How about the warmongers, Wall Street lobbyists? Did Jeb Bush set out to win or lose? And when he did lose, wasn’t he the sorest of losers? In fact, even though Trump won, haven’t the Democrats (and some Republicans) been working very, very hard in order to oust Trump and declare themselves the “winners”? And they have played very dirty while doing it.

    This isn’t something new. It’s the way the U.S. works. The Hustler mentality.

    TPTB put forward Clinton as their “winner”. She couldn’t sell herself (because, well, she’s Hillary), so they paid a fortune to the media to package her up all pretty, but even they couldn’t put lipstick on a pig. Tantrums all round.

    And the intelligence community, by saying Russia “hacked” the election (with no evidence) is going all out to “win” right now, aren’t they? Trump is in-your-face loud, abrasive, yet the people behind the scenes, the silent ones, are the scariest of all. I’d much rather go up against someone who actually has the guts to show himself than those who will just wait and then assassinate you because they want to “win”.

    • Bart in Virginia
      January 5, 2017 at 16:31

      Right. Recall the anger that was directed against those who ‘lost China’ and Viet Nam.

      And, in spite of St Reagan having allegedly beat the CCCP, we are still trying to knock them down a generation later.

    • January 5, 2017 at 18:02

      @backwardevolution. Well said. Though Trump will be unpredictable he is a hell of a lot more transparent than Obama or Bill Clinton. And given Wikileaks, we know Hillary was as two-faced as they come. Of course Trump needs to control his emotions or we’ll be nuclear toast in the first 100 days. In the interest of full disclosure I did not vote for either, but Trumps candor is naturally more refreshing and embracing. His refutation of political correctness was “yes” crude, uncouth at times, sexist, bigoted but nevertheless liberating. Wonkishness applied to Hillary is a euphemism for experienced liar. For my 2 cents, “don’t piss on my head and tell me it’s raining.” That’s what jaded progressives got from Obama for 8 years.

  9. Stiv
    January 5, 2017 at 16:13

    Folks… if Trump wants to be taken seriously on any proposal whatsoever, he needs to abate his troll-like behavior and start acting like a statesman. Chances of that seem to be slim. It’s all about him and for that reason all these “ponderings and scenarios” are drivel. I’m not about to be reactionary about every “policy proposal” ( hahaha! Will we ever see anything clear and concise with this guy? ) but it’s up to him to pave the path towards success. Until then, he gets no free pass here.

    • Joe Tedesky
      January 5, 2017 at 17:19

      Stiv although Trump’s 3am tweets are different and new to us, he is smart to bypass the media and drive his own narrative. I can see future presidents doing tweets, as this will be a sure fired way to control the message. Yes Trump is outrageous and unpredictable, and that scares everybody. I don’t have a clue at this point in time if Trump will be a good president or not, as only time will reveal this to us.

      Stiv I’m with you on making Trump earn our respect. In fact we should all hold his wealthy feet to the fire, and make him do what is needed done most, no matter what the issue. So Stiv for now it will be all about the drivel and summations to be made, since we will just need to wait and see what comes from a President Donald Trump. See you in the protest line, or at the celebration bar, but for now have a good one.

  10. backwardsevolution
    January 5, 2017 at 15:33

    A commenter said:

    “I remember when the City of New York had been “working on fixing” the crack in Wohlman Skating Rink in Central Park for about THREE YEARS (no skating, of course, for all that time, and no apparent progress in fixing the crack). It was in about 1985 that Trump basically stepped up and said “WTF, I WILL FIX IT” and set about to do so. It was operating within a couple of months. I was familiar with Trump at the time, but this act made him public spirited and heroic!”

    Was this a case of a big adolescent ape stepping up in order to win, or was it a case of someone who thought he could fix it, and did? Some might say he did this only for “bragging rights”, for good P.R., but do you think the skaters cared about his reasons? He fixed the damned problem! A problem that, after three years of being too complicated for the city to handle, was fixed by a simpleton (sarc) who just recently came out of the trees.

    People, give him a chance.

    • January 5, 2017 at 16:29

      It’s only right that he came forward after all the tax breaks he was given by the authorities in NYC, which had a lot to do with developing his wealth – Trump has a record of self-promotion as well as vindictiveness matched by few others. As a New York City citizen, I have followed Trump’s career (he’s almost as old as I am), and, in his public persona, he is exactly as I portrayed him – he was that way in the 1970’s and he’s the same way now. I served my country in Viet Nam while he evaded the draft (for purportedly having bone spurs in his feet! which seems odd given reports he was varsity level player in college baseball and football).

      • backwardsevolution
        January 5, 2017 at 16:53

        Gregory – oh, yeah, “it’s only right”! I’ll bet Trump was just having to beat off all of the other tax-breakers who wanted to get in there and fix the problem! At least he fixed the problem; give him credit for that. Tax reform is long overdue.

        As for Vietnam, how many rich kids ended up going there? It wasn’t just Trump. The American people who allow these wars to continue year after year are to blame. But as long as they have a polished, well-spoken puppet giving the orders, they seem to just go along.

        Along comes someone like Trump who wants to end these wars, and what is he labelled as – an uncouth, loud ape who wants to “win”. Go figure.

        Maybe we do get what we’re actually looking for.

        • January 6, 2017 at 11:50

          You’re in for a big surprise. And just why do you hide behind a cute moniker?

          • backwardsevolution
            January 6, 2017 at 17:34

            Gregory – “You’re in for a big surprise.” You don’t know this.

  11. January 5, 2017 at 14:24

    In regard to Mr. Trump, I’d sum him up by quoting a favorite saying of a former manager of mine when I was much, much younger: “We have all come down from the trees – but some of us have come down more recently…” Mr. Trump is undeniably a septuagenarian adolescent – just recall his language, his gestures, his simplistic approach to complicated matters, and his almost invincible ignorance on so many serious issues. Heaven help us all!

  12. Bill Bodden
    January 5, 2017 at 14:02

    Katz observes that the principal demands that Vladimir Putin is likely to make as conditions for an improved relationship are ones that Trump would have good reason to agree to.

    That suggests a win-win outcome for Russia and the United States and something much better than a crushing win for the United States and ignominious defeat for Russia as Senators John McCain, Lindsey Graham, Tom Cotton and other war mongers and the neocons want.

    • Gregory Herr
      January 5, 2017 at 20:49

      And the reason Katz’s observation is true is because Putin isn’t about being unreasonable, especially insofar as making “demands”. Putin is smart, pragmatic, and grownup…Trump will deal with Putin in an atmosphere of determining mutual interests rather than the current atmosphere of contention and sophomoric finger pointing.

  13. Bill Bodden
    January 5, 2017 at 13:58

    A slogan from the sports world—”winning isn’t everything; it’s the only thing” — which usually is associated with Vince Lombardi,…

    Unfortunately, too many people interpreted this slogan as justification for cheating and other immoral and unethical behavior.

  14. mike k
    January 5, 2017 at 13:18

    Perhaps the most dangerous game Trump is playing is keeping people guessing what he will do next. In a poker game this can be useful, but only as a part of an overall coherent strategy. If it gets way out ahead of such a strategy, one can lose a lot of chips, or in Trump’s case, a valued ally, or a nuclear game of bluff. The question whether Donald really has a viable underlying strategy is keeping a lot of us awake too late into the night…… Will he end by betting the world’s future on a hunch bet?

  15. Brian
    January 5, 2017 at 12:09

    Jul 23, 2016 Trump Exposes Trump

    In his own words, Donald Trump reveals his hypocrisy about Iraq, immigration, health care, abortion, Libya, Hillary Clinton, Bill Clinton and more.


    Jul 7, 2016 The Close Relationship Between Donald Trump and the Clintons

    Donald Trump and Hillary Clinton act as if they are arch enemies. But is it all just politics?


  16. D5-5
    January 5, 2017 at 11:21

    “Accept continuation of a Russian-allied regime in Damascus? The jihadist alternatives are even worse.”

    Obviously the Obama supported jihadists are “worse.” But “worse” implies the alliance between Russia and Syria and the rest is also “bad.” Why?

    • Gregory Herr
      January 5, 2017 at 20:33

      I had the same thought while reading the article. Unless respecting the rights and well-being of the Syrian people is a bad thing (which it isn’t…so I dislike the innuendo).

  17. D5-5
    January 5, 2017 at 11:09

    It’s true that in the campaign Trump did say if he didn’t win his effort would have been meaningless. This is a puzzling statement, given his fame from his actions and rise in popularity to the tune of the sixty million plus who voted for him. What it indicates to me is we don’t really know what “winning” is for Trump, whereas this article assumes the answer is (for example) he must “wring concessions” from Putin due to the climate of Russian bashing. Once again we’re up against speculation, which seems to imply that there is only one way to interpret Trump’s obsession with “winning,” and due to this he will fail. This may be true, or it may not be true.

  18. Joe Tedesky
    January 5, 2017 at 11:01

    Trump could look like a winner just by turning back the minute hand on the Doomsday Clock, by maybe five minutes or more would win him the Nobel Peace Prize. Plus, if American business should get super large opening purchase orders in order to initiate any deal, I’m sure he would hold this kind of ‘deal’ up for the naysayers to be shut up with. The media already looks bad, and nobody in America believes them anyway. So, yes I can see Trump coming away from détente talks, as a super hero, and being an all around great president.

    There are of course other ponderings and scenarios I could imagine, but I could see Trump doing well with foreign policy. Now domestic social benefits, and police state programs, are of course another matter.

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