to “The Curious Guy,” where I e-mail questions to somebody successful
— whether it’s a baseball pitcher, an author, a creator of a TV show,
another writer or whomever — and we trade e-mails for the rest of the
week. Previous editions featured Red Sox pitcher Curt Schilling, Mavs
owner Mark Cuban, author Chuck Klosterman, “OC” creator Josh Schwartz
and NBA commissioner David Stern (transcript of an in-person interview).

week’s exchange is with Malcolm Gladwell, the best-selling author of
“Blink” and “Tipping Point” as well as the longtime cleanup hitter for
the New Yorker. You would never think that the most successful
nonfiction writer alive would double as a huge sports fan … but he
does. So I couldn’t resist the chance to exchange e-mails with him
intermittently over the past six weeks. Because of the length of the
transcript, we’re breaking it up into two parts. Here’s section No. 1:

When I started reading you back in the mid-’90s, I remember being
discouraged because you made writing seem so easy — technically, you
were almost flawless, and since I knew I couldn’t write that well, you
were one of those visible writers who made me feel like I was going to
be bartending my whole life. You never waste a word. You come up with
cool arguments and angles for your pieces, then you systematically
prove/dismantle those same arguments and angles, and you do it in an
entertaining, thoughtful, logical way. You never allow your biases to
get in the way. You’re better at writing than me in every way.
Basically, I hate you.

Find out why the Sports Guy is insanely jealous of Malcolm’s writing.



“The Tipping Point”

So I always thought to myself, “Well, maybe he kicks
my ass as a writer, but I guarantee he’s a huge dork who knows nothing
about sports and couldn’t talk to a girl to save his life.” Then we
went out for drinks in New York City in December, argued about
basketball and football for three hours, and then some smoking-hot
bartender started hitting on you at the end of the night. She was
giving off that same vibe that the 25 girls give the “Bachelor” during
the first episode when he has, like, only four or five minutes to meet
everyone, so everyone has to hit on him at warp speed. Now I have
decided that you need to die. It’s like that “Saturday Night Live” skit
when the teleprompter for the morning show stops working, chaos ensues,
then Will Ferrell and David Alan Grier fight to the death because
Grier’s weatherman character felt threatened. Well, I feel threatened
by you. And if you weren’t Canadian, I would probably have you killed.
But I have a soft spot for all Canadians and Australians — I have
never met anyone from either country who wasn’t entertaining in some

Leading me to my first two questions: First, why
wouldn’t this be your third book? There is clearly something happening
in Canada and Australia that makes their citizens more friendly and
entertaining than anyone from any other country. You need to figure out
the reason, and only because that book sounds like the logical
successor to “Tipping Point” and “Blink.” And second, how did you learn

A. write so well
B. care about sports other than hockey
C. appreciate pop culture

…while you were
freezing your butt off in Canada as a kid? Why weren’t you cranking
cheesy Bryan Adams songs, choking up over the Gretzky-Jones wedding and
watching “Youngblood” twice a week like everyone else your age?

Let’s get one thing straight. At the time the bartender came up to us,
it was not at all clear that I was the object of her attention, and the
fact that my first words to her (“See that guy over there. He’s a
famous sportswriter”) only muddied the waters further. For all I knew,
she was a Red Sox fan wanting to trade Oil Can Boyd stories with you.
(By the way, amidst all the talk about the misguided Reggie Bush
lateral after the Rose Bowl, why nothing on the equally problematic
romantic lateral? It just never works, even though — in the thick of
things — you’re always convinced it will.) Secondly, even if she was
hitting on me, let’s also be clear that this never happens. You were
the Martian who came down to earth, saw Kelly Holcomb throw for 300
yards against the Bengals, and went back to your planet convinced you’d
seen the future of this strange earthling game “football.”

am I a sports fan? I’m not sure. I grew up in small-town rural southern
Ontario. Neither of my parents or my brothers are sports fans, and we
never had a television growing up. (In fact, my parents still don’t
have one, which means that when I go home I’m reduced to trying to
catch the AM broadcasts of NFL games from the other side of Lake Erie).
I don’t think I saw a televised professional sports contest until I was
a senior in high school. Everything I know came from Sports
Illustrated, which I read at the town library. For some reason, I was a
huge fan of the Spurs. I had a George Gervin poster above my bed, and I
can talk quite knowledgeably to this day about James Silas, Larry
Kenon, Billy Paultz and all the others — even though I never saw any
of those guys play and I’m not even sure (with the exception of Gervin)
what any of them looked like. (Surely, with the nickname “Special K”
Larry Kenon was black.) Do you know how hard it is to understand what
finger rolls are — or even dunks — if all you’ve ever done is read
about them in magazines? Once, when I was in high school, Bobby Smith
— the great natural “athlete” of my hometown — tried a dunk during a
game and a great collective cry of amazement came up over the crowd, as
if Bobby had just whipped out a scalpel and was attempting an on-court
appendectomy. (I should point out that Bobby came up a little short,
and the ball caromed on the rim about 40 feet. The locals are still
talking about it). Rural Ontario is not, exactly, a hotbed of athletic
ability. I think I read somewhere that Jason Williams (the point guard)
and Randy Moss went to the same high school. How is that even possible?
If Brian Scalabrine went to my high school, it would now be called the
Brian Scalabrine Memorial High School.

As for your (very
kind) question about my writing, I’m not sure I can answer that either,
except to say that I really love writing, in a totally uncomplicated
way. When I was in high school, I ran track and in the beginning I
thought of training as a kind of necessary evil on the way to racing.
But then, the more I ran, the more I realized that what I loved was
running, and it didn’t much matter to me whether it came in the
training form or the racing form. I feel the same way about writing.
I’m happy writing anywhere and under any circumstances and in fact I’m
now to the point where I’m suspicious of people who don’t love what
they do in the same way. I was watching golf, before Christmas, and the
announcer said of Phil Mickelson that the tournament was the first time
he’d picked up a golf club in five weeks. Assuming that’s true, isn’t
that profoundly weird? How can you be one of the top two or three
golfers of your generation and go five weeks without doing the thing
you love? Did Mickelson also not have sex with his wife for five weeks?
Did he give up chocolate for five weeks? Is this some weird golfer’s
version of Lent that I’m unaware of? They say that Wayne Gretzky, as a
2-year-old, would cry when the Saturday night hockey game on TV was
over, because it seemed to him at that age unbearably sad that
something he loved so much had to come to end, and I’ve always thought
that was the simplest explanation for why Gretzky was Gretzky. And
surely it’s the explanation as well for why Mickelson will never be
Tiger Woods.

Speaking of Gretzky, my six degrees of
separation with him is that I was a contemporary of his little sister
Kim, in the age-class Ontario track-and-field circuits of the late
’70s. And no, she never hit on me.

Simmons: Wait,
I’m still reeling from the fact that you became an NBA fan just from
reading back issues of “Sports Illustrated” in a Canadian library. I
became a sports fan because my father was carrying me into the Boston
Garden to see the eventual ’74 and ’76 world champions … meanwhile,
you were stuck in the middle of nowhere reading about these games after
the fact. And yet, we like sports just as much. I find this amazing.
Have you ever written about this? You were like the sports fan’s
equivalent of John Travolta in the “Boy in the Plastic Bubble.” What
happened when you finally got TV? Did you not leave your house for,
like, three weeks? You need to start filming something for those ESPN
“SportsCentury” shows where they talk about stuff that happened 25-30
years ago — to cover every segment, you could just say, “I remember
reading about that in Sports Illustrated in my local Ontario library
and being totally amazed.” And then they could plug that little sound
bite into, like, 58 shows about anyone from 1975-81.

Mickelson and Sports Lent, I remember watching one of those
20/20-Dateline-type pieces about him once, and he was adamant about
remaining a family man, taking breaks from golf and never letting the
sport consume him … and I remember thinking to myself, “Right now
Tiger is watching this and thinking, ‘I got him. Cross Phil off the
list. This guy will never pass me.'” The great ones aren’t just great,
they enjoy what they’re doing — that’s why MJ’s first retirement
always seemed genuine to me. He had pretty much mastered his craft, and
the media was wearing him down, and then his father was murdered, and
for the first time in his life, basketball was looming as a chore for
him. And he was smart enough to get away and recharge his batteries. I
always respected him for that. Well, unless the real reason he
“retired” was because of his gambling problems and an ominous “You
screwed up, you’re gonna walk away for 18 months, and we’re gonna
pretend this entire discussion never happened” ultimatum from
commissioner Stern.

But I think there’s a certain amount
of professionalism that needs to be there, as well, because there will
always be days when you don’t feel like doing your job, and those are
always the true tests. Halberstam has a great quote about this: “Being
a professional is doing your job on the days you don’t feel like doing
it.” I love that quote and mutter it to myself every time I don’t feel
like writing because my allergies are bothering me, or my back hurts,
or my head hurts, or there’s some random dog barking, or any of the
other excuses I use when I’m procrastinating from pumping out
something. So how easy is the writing process for you? Are you one of
those guys who writes from different locations or does everything at
one desk? Do you keep hammering out drafts and tinkering with what you
wrote, or does it all come out in one felt swoop? Do you ever get
writer’s block? How long does it take you to finish one of your New
Yorker features after everything is researched?

just for the record, if you say something like, “I usually write a
first draft in about 5-6 hours, then go back over it the next morning,
fix the typos and send it right in,” I’m making a Gladwell voodoo doll
and jamming 50 safety pins into it.)

Gladwell: This
is actually a question I’m obsessed with: Why don’t people work hard
when it’s in their best interest to do so? Why does Eddy Curry come to
camp every year overweight?

The (short) answer is that
it’s really risky to work hard, because then if you fail you can no
longer say that you failed because you didn’t work hard. It’s a form of
self-protection. I swear that’s why Mickelson has that almost absurdly
calm demeanor. If he loses, he can always say: Well, I could have
practiced more, and maybe next year I will and I’ll win then. When
Tiger loses, what does he tell himself? He worked as hard as he
possibly could. He prepared like no one else in the game and he still
lost. That has to be devastating, and dealing with that kind of
conclusion takes a very special and rare kind of resilience. Most of
the psychological research on this is focused on why some kids don’t
study for tests — which is a much more serious version of the same
problem. If you get drunk the night before an exam instead of studying
and you fail, then the problem is that you got drunk. If you do study
and you fail, the problem is that you’re stupid — and stupid, for a
student, is a death sentence. The point is that it is far more
psychologically dangerous and difficult to prepare for a task than not
to prepare. People think that Tiger is tougher than Mickelson because
he works harder. Wrong: Tiger is tougher than Mickelson and because of
that he works harder.

To me, this is what Peyton
Manning’s problem is. He has the work habits and dedication and
obsessiveness of Jordan and Tiger Woods. But he can’t deal with the
accompanying preparation anxiety. The Manning face is the look of
someone who has just faced up to a sobering fact: I am in complete
control of this offense. I prepare for games like no other quarterback
in the NFL. I am in the best shape of my life. I have done everything I
can to succeed — and I’m losing. Ohmigod. I’m not that good. (Under
the same circumstances, Ben Roethlisberger is thinking: maybe next time
I stop after five beers). I don’t know if I’ve ever felt sorrier for
someone than I did for Manning at the end of that Pittsburgh playoff

So do I work hard on my writing? Well, yes. But
not that hard. I’m a five- or six-draft kind of person, not a 10- or
12-draft kind of person. Plus, I write for the New Yorker, so I have an
entire army of high-IQ fact checkers, and editors and copy editors
working with me. To stretch the quarterback analogy here, I’m Jake
Plummer: I work in an offensive system designed to make me look way
better than I actually am. Speaking of which, how fascinating was the
Plummer meltdown in the Pittsburgh game? People have been beating up on
Plummer, saying that his true colors emerged in that game. I prefer to
look at it the other way. Shanahan managed to put in place an offensive
system so brilliant and so precisely tailored to his quarterback that
he could make Plummer — Plummer! — look like a great quarterback for
17 consecutive games. That’s pretty remarkable. The Plummer story is
not about the frailty of individuals. It’s about the redemptive power
of environments. As I said, I think I’m Plummer.

Wait, I know Jake Plummer, I watched Jake Plummer, I wagered on Jake
Plummer … you, sir, are no Jake Plummer. Shanahan’s system was
predicated on the Broncos’ jumping out to leads, then protecting those
leads in the second half with their running game and Jake’s occasional
play-action passes (which were always wide open because their running
game was so good). The catch was that they could never fall behind in
any important game; there was no way Jake could be effective under
those circumstances, and only because Shanahan inadvertently undermined
his confidence (by creating the “Now don’t screw this up, Jake!”
offense), so Plummer’s meltdown against the Steelers became a
self-fulfilling prophecy of sorts. If the Patriots had gone to halftime
with a 6-0 lead, it would have happened a week earlier. But it was
going to happen. You can’t make it through a 20-week season without
your QB carrying the team at some point. It’s impossible.

sincerely doubt that the New Yorker carries you like the Broncos
carried Plummer all those weeks. Besides, you could never grow one of
those lead-singer-of-the-Black-Crowes-level beards like the one Jake
has been working on.

Gladwell: You’re probably
right. But imagine Plummer was drafted by Shanahan and came to maturity
in the NFL entirely within a conservative, run-first offense. Imagine,
as well, that the Broncos were every bit as successful in those years
as they were in the pre-Plummer era. What would we think of Plummer?
We’d say that he was an efficient, intelligent quarterback. We’d call
him an adept game-manager. We’d marvel at his discipline. John Madden
would go on and on about how the value of a quarterback who doesn’t
make mistakes has been vastly underestimated, and if Plummer
occasionally imploded while playing catch-up in a big game we’d say
that the one problem with a Shanahan offense is that it can’t score in
a hurry. We’d blame Shanahan, in other words, not Plummer. Plummer
would still be Plummer. But inside of a very structured system — one
that played to his strengths — he would seem to us like a totally
different quarterback. And after five or six years or so with Shanahan,
he really would be different: all vestiges of the old swashbuckling
Jake the Snake would largely be obliterated.

My point is
its almost impossible to know where the person ends and their
environment begins, and the longer someone is in a particular
environment the blurrier that line gets. More specifically, you can’t
make definitive judgments about the personal characteristics of people
who come from structured environments. What does it mean to say that a
Marine is brave? It might mean that a Marine is an inherently brave
person. It may also be that the culture of the Marine Corps is so
powerful, and the training so intensive, and the supporting pressure of
other Marines so empowering, that even a coward would behave bravely in
that context. That’s what I mean when I say I’m Plummer: I’m working in
a such a supportive and structured environment that I no longer know
where my own abilities end and where the beneficial effects of the
environment begin. Just think if you were a New Yorker writer, Bill.
Suddenly your editors would be asking you to make your stories longer.
You spend the summers at a writer’s colony in New England, working on a
historical novel based loosely on Freud’s famous falling-out with
Adler. And girls would hit on you in bars because they would think of
you as cute in that nerdy, bookish way. But you’d still be Simmons,
wouldn’t you?

Switching gears, I have one last point on
the fact I never really watched sports on TV until I was in college.
That’s not as crazy as it sounds. I would grade major professional
sports in terms of their TV/live watchability in the following order:

NFL: A-plus televised. B-minus live.
NBA: B-plus televised. A live.
NHL: C-minus televised. A-plus live.
PGA: A-televised. D live.

More Sports Guy
Curious Guy: David Stern
Curious Guy: Curt Schilling

Curious Guy: Mark Cuban
Curious Guy: Chuck Klosterman

Curious Guy: Josh Schwartz

what do you miss by not having a TV? Really just a great NFL
experience, and some golf. You will notice that I’ve left out baseball
and that’s because I don’t believe that actually watching baseball
under any circumstances enhances your appreciation of the game. As a
kid, I read Bill James and Thomas Boswell and Roger Angell and followed
the game through newspaper box scores, and I was a far more dedicated
fan back than I am today. Baseball is a great idea, and a great story.
But is watching it a great experience? Frankly I prefer the way the
game was played in my imagination. This, incidentally, is why I’m such
a fan of yours. I think that reading you on the Red Sox is more fun
than actually watching the Red Sox. And before anyone objects, I would
point out that there are lots of other human experiences that fall into
this category. When you hear a ghost story as a child, or watch a war
movie, or read a particularly powerful novel, you don’t want to be in
the story. You don’t even want to be in the stands when the war is
going on or the ghost is scaring the bejesus out of people. What you
want is to be told the story. Right?

Simmons: I can
totally see your point on that. My favorite Red Sox regular season was
1986, and only because I was stuck living in Connecticut before the
days of DirecTV and the Internet. We did have Channel 38 on our cable
system back then, but they didn’t show that many of the Red Sox games,
so either I had to climb on my roof to catch a static-filled radio
broadcast or wait for “SportsCenter” and Warner Wolf highlights on
Channel 2. (That was a big year for me and Warner because he also
announced the Drago-Creed fight in “Rocky 4.”) Still, I appreciated the
season more than if I had lived in Massachusetts and watched the games
— every telecast was a treat, every radio broadcast was an effort,
every highlight felt like a special gift, every box score was studied
and analyzed, every phone call from my dad felt like a live report.
It’s crazy, I remember more about that ’86 season than any other
season. And I missed most of it.

But I’m going to
disagree with you on one thing: There isn’t anything more exciting than
watching a big baseball game in person. Football has all the TV
timeouts, basketball has too many stops down the stretch, and hockey
can’t be exciting beyond a certain level because there just aren’t
enough people that care. (At this point, it’s Arena Football on
skates.) But when the stakes rise in baseball, and you’re sitting there
in the park waiting to see what unfolds, there’s nothing else like it.

example, the more time passes, the more I’m starting to realize that
being there for Games 4 and 5 of the 2004 ALCS at Fenway can’t be
topped, that I peaked as a sports fan on those two nights. The
Pats-Rams Super Bowl was unbelievable, obviously — you can’t top the
experience of watching your football team win its first championship as
a 14-point underdog — and I was fortunate enough to attend most of the
relevant games of the Larry Bird Era. But nothing compared to enduring
26 innings over 30 hours to stay alive against the Yankees in freezing
weather that October. The other games were incredible events; that Game
4/5 combination was a life experience. Grueling. Nerve-racking.
Emotional. Physically draining. Unbelievably rewarding. They wouldn’t
have won without us. We just wouldn’t let them lose. And if you watch
those games again, the number of twists and turns over those two nights
was almost incomprehensible. I still can’t believe what happened, I
can’t believe how each of those games unfolded, I can’t believe I was
lucky enough to be there with my father … and only 36,000 other
people know what I mean. That was one of the great memories of my life.
I can honestly say that. And anyone who was there for Games 4 and 5 of
the 2001 World Series, Game 6 of the ’86 World Series, Gibson’s homer
in 1988, or any other baseball game in that class knows what I mean.

for your Curry/Mickelson point about athletes failing to motivate
themselves out of fear more than weakness, I would argue that Eddy
Curry comes to camp overweight because he can’t stop eating. But I
agreed with everything else. Which leads me to a question that’s
definitely in your wheelhouse: Can you explain the Contract Year
phenomenon for me? What is it about the mentality of professional
athletes where they sign huge contracts, then they either mail in the
rest of their careers, or it takes them the requisite, “All right, I
just made a crapload of money, maybe I don’t have to try as hard” year
before they bounce back in the second year? It’s gotten to the point
where I specifically avoid picking players for my fantasy teams who
just signed huge contracts — it’s one of my steadfast drafting rules,
right up there with “never take a player who just spent more than 90
days in prison” and “never take anyone older than me.” But this only
seems to happen in sports.

So what’s the cause? And why
does this happen mostly in the NBA, and almost always with tall
centers? Do they fold from the weight of the contract and the
expectations that come with it? Do they lack a certain amount of
professional pride? Would most Americans do this if they were
guaranteed copious amounts of money regardless of the quality of their
work? I mean, imagine having a friend tell you, “Good news, I just
signed a big deal to stay with my law firm … I’m going to completely
mail in the next three years, this is gonna be great! Wow, did I dupe
them!” Would that ever happen? I’m convinced that it’s a phenomenon
unique to sports. Maybe you should follow Erick Dampier, Mark Blount,
Jerome James, Scot Pollard, Juwan Howard and Kwame Brown around for
three months for a book called, “The Dipping Point,” with special
forwards from Jim McIlvaine, Calvin Booth, Shawn Bradley and Michael

Gladwell: This is one of my favorite
topics. Let’s do Erick Dampier. In his contract year at Golden State,
he essentially doubles his rebounds and increases his scoring by 50
percent. Then, after he signs with Dallas, he goes back to the player
he was before. What can we conclude from this? The obvious answer is
that effort plays a much larger role in athletic performance than we
care to admit. When he tries, Dampier is one of the top centers in the
league. When he doesn’t try, he’s mediocre. So a big part of talent is
effort. The second obvious answer is that performance (at least in
centers) is incredibly variable. The same person can be a mediocre
center one year and a top 10 center the next just based on how
motivated he is. So is Dampier a top 10 player or a mediocre player?
There is no way to answer that. It depends. He’s not inherently good or
bad. He’s both. The third obvious answer is that coaching matters. If
you are a coach who can get Dampier to try, you can turn a mediocre
center into a top 10 center. And you, the coach, will be enormously
valuable. (This is why Phil Jackson is worth millions of dollars a
year.) If you are a coach who can’t get Dampier to try, then you’re not
that useful. (You may want to insert the name Doc Rivers at this point.)

the context of sports, none of us have any problem with any of these
conclusions. But now let’s think about it in the context of education.
An inner city high school student fails his classes and does abysmally
on his SATs. No college will take him, and he’s basically locked out of
the best part of the job market. Why? Because we think that grades and
SATs tell us something fundamental about that kid’s talent and ability
— or, in this case, lack of it.

But wait: what are the
lessons of the contract year? A big part of talent is effort. Maybe
this kid is plenty smart enough, and he’s just not trying. More to the
point, how can we say he isn’t smart. If talent doesn’t really mean
that much in the case of Dampier — if basketball ability is incredibly
variable — why don’t we think of ability in the case of this kid as
being incredibly variable? And finally, what does the kid need? In the
NBA, we’d say he needed Phil Jackson or Hubie Brown or maybe just a
short-term contract. We’d think that we could play a really important
role in getting Dampier to play harder. So why don’t we think that in
the case of the kid? I realize I’m being a bit of a sloppy liberal
here. But one of the fascinating things about sports, it seems to me,
is that when it comes the way we think about professional athletes,
we’re all liberals (without meaning to be, of course). We give people
lots of chances. (Think Jeff George). We go to extraordinary lengths to
help players reach their potential. We’re forgiving of mistakes. When
the big man needs help with his footwork, we ship him off to Pete
Newell for the summer. We hold players accountable for their actions.
But we also believe, as a matter of principle, that players need
supportive environments in order to flourish. It would be nice if we
were as generous and as patient with the rest of society’s