You know, I was at a game just last week. It
was one of those electric nights, fourth quarter,
tie game, absolute bedlam in the arena. The best
kind of chaos. Oh, the best. That's why we go,
right? The point guard is dribbling out the clock.
The coach is just, I mean, screaming his lungs
out on the sideline. Fans are spilling beer on
each other. It was just pure chaos. I love that.
Exactly. But then right before the final shot,
the camera pans up. And it goes past the sweating
players, past the manic coach, you know, past
the nosebleed seats. And it locks onto a luxury
suite way, way up in the rafter. Fishbowl. The
fishbowl, exactly. And there's a guy standing
there. He's usually wearing a suit that, like,
costs more than my car, arms crossed, face completely
stoic. He looks like he's watching a funeral
while everyone else is at this massive party.
And it hit me. We spend thousands of hours analyzing
the guys on the floor, but we almost never talk
about that guy. The architect. The architect.
The person who decided which players are on that
floor, who hired the coach that's screaming at
them, and who is probably doing mental math on
next year's luxury tax apron while the rest of
us are just praying for a bucket. It is arguably
the most stressful job in professional sports.
I mean, you are the invisible hand. When things
go well, players get the shoe deals. When things
go bad, you're the one packing up your office.
And that is exactly where we are going today.
We are walking off the court, taking the elevator
to the executive level and kicking down the door
of the front office. We are doing a deep dive
into the NBA Executive of the Year Award. This
is one of my favorite topics because it's right
at the intersection of art and science. You have
the money ball aspect, the data, the cap management,
asset accumulation, all that stuff. The spreadsheets.
The spreadsheets. Yeah. But then you have the
human element, ego management, negotiation, just
pure. gut instincts. It's fascinating territory.
And we aren't just guessing here. We have a serious
stack of source material to get through. We're
looking at the official historical records, the
complete winner lists, and the organizational
data spanning over 50 years of NBA history. A
huge sample size. A huge sample size. And our
mission today, to figure out who actually wins
the decade, not just the game. I love that distinction.
Because there's an old adage in front office
circles that really, really rings true. Players
win games. Coaches win series. Okay. But executives,
executives win decades. They build the ecosystems
that allow all that winning to happen in the
first place. Executives win decades. I'm going
to write that down. That's our mantra for today.
It has to be. I mean, think about the great dynasties,
the Celtics of the 60s, the Bulls of the 90s,
the Spurs, the Warriors. None of those happened
by accident. Right. They were engineered. Decisions
were made years in advance that allowed those
moments on the court to even exist. And today
we're going to find out who the best engineers
were. OK, so before we start naming names and
we have some massive ones from the godfather
of Phoenix to the legend himself, Larry Bird,
we need to set the ground rules. Let's unpack
the mechanics of this. What exactly is this award?
Is it just like the MVP for old guys in suits?
Not quite, though. The demographic is certainly
older than the roster. The award is officially
the NBA Executive of the Year, and it's given
annually to the league's top decision maker.
Okay, so the GM, basically. It can be the general
manager. Sometimes it's the president of basketball
operations. The title on the business card can
vary. But it goes to the person who is undeniably
calling the shots on personnel. And how far back
does our data go? What's our starting point?
We are starting in the 1972 -73 season. That
is our year zero. Wow. OK, so that's crucial
context. 1973. The NBA is a very, very different
place compared to today. Oh, completely. We're
talking about a league that hasn't even fully
merged with the ABA yet. There is no three point
line. The salary cap didn't exist in the structured
way we know it. Free agency was what, just a
rumor? Practically medieval. So the job of an
executive back in 73 was fundamentally different.
It was about scouting and, you know, handshake
deals today. It's about capology, analytics,
and managing a global brand. So one was a talent
scout who smokes cigars in a back room and the
other is a mathematician with an algorithm. That's
a perfect way to put it. But the goal, you know,
the core goal remains the same. The accumulation
of talent to win a championship. Now, I found
something in the notes about the voting process
that actually kind of shocked me. I just assumed
like the MVP or the all NBA teams that this was
voted on by the media. You know, the beat writers
and the national pundits who drive the narrative.
That is a very, very common misconception. And
to be fair for a lot. long time, it was a bit
muddy. So prior to 2009, the award was actually
presented by the Sporting News, which is a publication.
Oh, OK. It was recognized by the NBA, but it
was technically given out by a media entity.
But then in 2009, the NBA officially took the
awarding duties in -house. All right. So the
league takes control. Who gets the ballot now?
Is it a committee? This is what makes this award
perhaps the most cutthroat honor in the entire
league. The voting is conducted by the executives
of the league's 30 teams. Wait, wait. So it's
a peer vote? It is strictly a peer vote. Stop
and think about the psychology of that for a
second. This isn't a sports writer who loves
a good underdog story voting for you. This is
the guy you were screaming out on the phone two
months ago during the trade deadline. Exactly.
It's the guy you tried to fleece in a deal. It's
the guy whose free agent target you stole at
the 11th hour. It's the guy who is actively plotting
to get you fired so he can take your job or,
you know, poach your star player. And that is
the person who has to sit down with a ballot
and check the box next to your name. That's the
guy. So does that make the award more valid or
does it make it more political? I would argue
it makes it significantly more valid. Think about
it. A writer looks at a team that wins 50 games
and says, Wow, great season. A rival GM looks
at that same team and knows, wait a minute, he
managed to get off that terrible contract, he
used the mid -level exception perfectly to get
that bench score, and he found a starter in the
second round of the draft. They see the degree
of difficulty. They respect the degree of difficulty.
They know how hard it is to do what you just
did. Real recognize real. Exactly. But you're
right to mention politics. Of course there are
rivalries. There are cliques. Maybe you don't
vote for the guy who embarrassed you in the press.
But generally speaking, over a 50 -year sample
size, the cream rises to the top. If you win
this award, it means your enemies had to admit
you were better than them that year. That is
a heavy crown to wear. My enemies chose me. Okay,
so we know the stakes. Let's get into the history
books. When we look at the gold standard of MBA
executives, Who is the guy on the mountaintop?
There is one name that just dominates the data.
If we are talking about the godfather of the
front office, it is undoubtedly Jerry Colangelo.
The face of Phoenix basketball. For, like, ever.
He is the undisputed king of this award. He is
the only person in NBA history to win it four
times. Four times. I feel like in the modern
NBA, most GMs don't even last four years in the
job. The turnover rate is just incredibly high.
I mean, if you miss the playoffs two years in
a row, you're usually updating your LinkedIn
profile. Right, you're gone. For Colangelo to
win four times, it implies a level of longevity
that is almost impossible to replicate in the
modern game. And looking at the data here, these
weren't four wins in a five -year span where
he just had one great roster and kind of rode
the wave. No, and that's the genius of his resume.
Let's look at the timeline because the dates
really tell the story of his adaptability. His
first win is in 1976. Okay, set the scene for
76. That's the Sensational Suns, right? A team
that finished 42 -40, barely made the playoffs,
and then went on this miracle run to the NBA
Finals against the Celtics. That's the famous
Gar Hurd shot era. The shot heard around the
world. Exactly. So he built a Cinderella story
in the chaos of the post -merger 70s. And then
he wins again in 1981, then again in 1989, and
his final win is in 1993. Pause on that. 1976
to 1993. That is a 17 -year gap between the first
and last trophy. Think about how much the sport
itself changed in that window. In 1976, there's
no three -point line. The league has a different
kind of public image. The finals were on tape
delay. The finals were on tape delay. And by
1993, you have the global explosion of the Dream
Team, the marketing machine of the Jordan era,
and the salary cap is fully instituted. It's
a different universe. And Colangelo mastered
all of it. He didn't just survive the changes,
he exploited them. Take the 1989 win. He orchestrated
this massive turnaround by trading away a proven
all -star, Larry Nance, to Cleveland. A move
which usually gets you fired if it doesn't work
out. Oh, immediately. But in return, he got Kevin
Johnson, who became the point guard of the future,
and Mark West, and a bunch of other pieces. People
thought he was crazy, trading Nance. But he saw
where the game was going. Faster, more guard
-oriented. He was ahead of the curve. And then
1993. That's the big one. That's the Charles
Barkley trade. The blockbuster. He looks at a
roster that is good but not great. They had won
53 games the year before, and he decides. It's
not enough. He pushes all his chips into the
middle of the table to get Charles Barkley from
Philadelphia. Which is terrifying for a GM. Barkley
was controversial. He had baggage. If that trade
busts, Colangelo's entire legacy is tarnished.
But he saw the fit. Yeah. That team wins 62 games.
Barkley wins MVP. Colangelo wins executive of
the year. And they go to the finals against Jordan's
Bulls. So Colangelo essentially built three or
four completely distinct iterations of the Phoenix
Suns and made them all contenders. Which is exactly
why the Phoenix Suns. as a franchise, are the
leaders in this clubhouse. When we look at the
total awards by team, Phoenix is sitting at hashtag
one with six total wins, four from Jerry, and
two others we'll get to later. It is absolutely
wild that they have six Executive of the Year
awards but zero championships to show for it.
That is the cruel irony of the architect, isn't
it? You can build a perfect house, but you can't
control the weather. Colangelo ran into the 76
Celtics and Jordan in 93. He did his job perfectly.
The ball just didn't bounce their way in the
end. It really highlights that difference between
process and result. The peers voted for him because
the process was flawless, even if the final result
wasn't a ring. Exactly. Now, Colangelo represents
the pure executive, the guy in the suit who started
in the front office. But there is another archetype
in our data that I find fascinating. Okay. The
player who walks directly off the court and immediately
into the boardroom. The legends. And nobody,
I mean nobody, embodies his transition better
than the man from French Lick. Cliff Bird. We
have to just stop and appreciate the sheer absurdity
of Larry Bird's resume. It reads like fan fiction.
It doesn't seem real. In 2012, Larry Bird won
the Executive of the Year award with the Indiana
Pacers. In doing so, he became the only human
being in history to complete the Holy Trinity
of the NBA. Okay, break that down for us. What's
the Trinity? He wins NBA Most Valuable Player
as a Player. We all know that. He won three straight.
Check. He wins NBA Coach of the Year as a head
coach, which he did with the Pacers in 1998,
leading them to the Eastern Conference Finals.
Also check. And then he wins Executive of the
Year. MVP, Coach of the Year, Exec of the Year.
He completed basketball. He really did. He got
100 % on the final exam. And we have to appreciate
how hard that is because the skill sets for those
three jobs usually conflict with each other.
How so? I mean, you'd think a great player would
know what a great player looks like, right? You'd
think so. But history shows us what we call the
great player curse. Great players often struggle
to coach because they lack patience. They can't
understand why a role player can't just shoot
like I did or see the floor the way I did. Right.
Magic Johnson's coaching career was short. It
was very short. And Michael Jordan famously has
had a very, very rocky road in the front office.
They trust their gut too much or they just get
frustrated with mediocrity. Then look at the
other transition. From coach to exec, great coaches
often struggle as executives because they are,
by necessity, myopic. Myopic how? A coach cares
about winning the game tonight because if he
loses 10 in a row, he's fired. An executive needs
to care about the salary cap three years from
now. Oh, that's a great point. The coach wants
to trade the first -round pick for a 35 -year
-old veteran who can help grab rebounds now.
Exactly. And the executive wants to hoard that
pick for the future. They are naturally opposing
forces. The coach wants to survive the day. The
executive wants to survive the decade. And Bird
somehow mastered both mindsets. Bird is the anomaly
who understood the rhythm of the player, the
tactics of the coach, and the long -term strategy
of the executive. Is there anyone else who even
comes close to that triple crown? No one has
all three. But there is a very small, very exclusive
group we call the Coach Executive Club. These
are the guys who have won both Coach of the Year
and Executive of the Year. Okay, so who has a
membership card to that club? Red Auerbach, the
patriarch of the Celtics. He won Coach of the
Year in 65 and then Executive of the Year in
1980. The guy who invented the Victory Cigar.
Of course he's in. Then you have Frank Layden
with the Utah Jazz, who won the Exec Award in
84. And Pat Riley. The Godfather Part II. Riley
is interesting. He won Coach of the Year multiple
times with the Lakers, Knicks, and Heat. He won
the Executive Award in 2011 with the Miami Heat,
though it was technically a shared award that
year with Gar Foreman. So Auerbach, Bird, Riley.
Think about those names. These are the sharpest,
toughest, most demanding minds in the history
of the sport. Yeah, they aren't exactly the player's
friend type of leader. They're culture setters.
Exactly. But it's a very short list. It proves
that while you can do both, it's exceptionally
rare to be elite at both. Most coaches who try
to run the front office, well, they end up getting
fired from both jobs. Speaking of elite, I want
to talk about the logo, because you can't have
a conversation about NBA architects without discussing
Jerry West. You really can't. If Colangelo is
the longevity king, Jerry West is the adaptability
king. He won the award twice, and the locations
of those two wins tell the entire story. They
really do. His first win comes in 1995 with the
Los Angeles Lakers. Okay, let's play devil's
advocate here for a second. It's the Lakers.
You have the weather, the Hollywood stars, the
history. Is it really that hard to recruit people
to L .A.? That's always the knock on the Lakers'
job. The logo sells itself. The weather recruits
for you. But West did something remarkable in
95. This was the post -Magic Johnson era. The
team had totally collapsed. They were supposed
to be dead in the water for a decade. Right.
Showtime was over. And Wes rebuilt them on the
fly with guys he drafted, like Nick Van Exel
and Eddie Jones and Vlade Divac. He showed he
could draft and develop, not just write big checks
for superstars. But the real mic drop moment
for his legacy was his second win. Oh, yeah.
2004. The Memphis Grizzlies. You cannot get further
from Hollywood, both literally and figuratively,
than Memphis, Tennessee. It's a small market,
a franchise that, let's be honest, had been a
laughingstock since they moved from Vancouver.
No history of winning. No appeal as a free agent
destination. None. If you can win there, you
can win anywhere. And he did. He went there and
built a 50 -win team with Pau Gasol and Hubie
Brown coaching. That is the ultimate validation.
It proved that Jerry West wasn't just successful
because he had the Lakers checkbook or the forum's
allure. He was successful because he had the
best eye for talent in the league. He found value
where others saw nothing. It's the ultimate I
can build a winner in a cave with a box of scraps
moment. That's exactly what it is. Now, we've
been throwing around all these awards, 1995,
2004, 1976. But there's a burning question that
I have. We talked about process versus result
with Colangelo. Does the executive of the year
actually win the championship in the same season?
You would assume the correlation is one to one,
right? The best executive builds the best team.
The best team wins the ring. It makes perfect
sense to me. The data says absolutely not. Really?
That's surprising. It is actually surprisingly
rare for the executive of the year to be the
one hoisting the Larry O 'Brien trophy in June.
Okay, why is that? What's the logic there? It
goes right back to the voting psychology we discussed
at the top. Remember who is voting. The other
29 GMs. His peers. His peers. If you have a super
team, say the 90s Bulls or the KD Warriors, the
other GMs look at that and they say, well, yeah,
you won. You have Michael Jordan. That's easy
mode. So they don't give you credit for maintaining
the Ferrari. They give you credit for fixing
the broken down Honda Civic. That is a perfect,
perfect analogy. The award almost always goes
to the turnaround story. The team that was projected
to win 25 games and won 45. The voters are impressed
by the delta, the change. You took a complete
mess and made it a playoff team. That's impressive.
So who are the rare exceptions? Who actually
pulled off the double dip? We have to look at
the bolded names in our records. These are the
guys who defied that turnaround bias. Red Auerbach
did it in 1980s. The Celtics won the title and
he won the award. That was the year he pulled
off the heist of the century to get Kevin McHale
and Robert Parrish. That's the one. He traded
the number one overall pick to Golden State for
Parrish and the number three pick, which he then
used on McHale. It is widely considered the single
greatest trade in NBA history. If you commit
grand larceny like that, your peers have to give
you the award. Okay, so you have to do something
legendary. Who else? Jerry Krause did it in 1996
with the Bulls. The 72 -10 season. You just can't
ignore 72 wins. Even if the other GMs were jealous
of Jordan, that level of dominance was undeniable.
And Kraus had also retooled the roster that year,
bringing in Dennis Rodman. Which was a massive
risk at the time. A huge risk that paid off.
And then more recently, Danny Ainge in 2008 with
the Boston Celtics. The big three era. He traded
for Kevin Garnett and Ray Allen in one single
summer. They went from the lottery to the championship
in one year. So that covers both bases. It's
a championship team and it's a massive turnaround
story. That's the sweet spot right there. That's
the formula. But then look at a guy like Bob
Myers with the Golden State Warriors. He won
in 2015 their first title. But in 2017, 2018,
when they were dominating the league with Kevin
Durant, the voters looked elsewhere. It's classic
voter fatigue. It's voter fatigue and it's super
team bias. Once you are on top, your peers stop
being impressed and start being resentful. They
start voting for the guy in Utah or Portland.
who is overachieving with less talent. It's so
funny. We talk about dynasties, but the award
itself doesn't really like dynasties. It doesn't.
But we have to acknowledge the dynasty builders,
even if the hardware doesn't always reflect their
sustained greatness. You mentioned Krauss winning
twice, 1988, 1996. Right. And Myers won twice,
2015, 2017. And you have to mention R .C. Buford
with the Spurs, who won it twice in 2014 and
2016. The Spurs are the absolute model of consistency.
They are. And Buford winning in 14 and 16 proves
that the Spurs weren't just about Tim Duncan
and Greg Popovich. They had a front office that
kept finding incredible talent late in the draft.
Cowie Leonard, Manor Ginobili, Tony Parker, to
keep that machine running. for 20 years. I want
to pivot here a bit because we've been talking
about very American stories, Colangelo, West,
Bird, Ainge. But the NBA has gone global on the
court. You have Jokic, Giannis, Luka, Wemby running
the league. For a long time, though, the front
office was an old boys club of American coaches
and scouts. It was an impenetrable fortress.
If you look at the nationality of every single
winner from 1973 all the way to 2012. It is 100
% American -born. 40 years. 40 years of American
exclusivity. Until 2013. The year the glass ceiling
finally shattered. I saw you, Jerry. The current
Raptors boss, but back then he was running the
Denver Nuggets. Correct. Born in England of Nigerian
descent. Didn't play in the NBA. He didn't coach
in the NCAA. His story is incredible. He started
as an unpaid scout, traveling around Europe and
Africa, sleeping on couches, hustling his way
into gyms just to watch players. He essentially
willed his way into the league through sheer
effort. And in 2013 with the Denver Nuggets,
he proved that an outsider perspective was actually
a massive advantage. That Nuggets team he built
was fast, deep, and unconventional. He saw value
in international players and different styles
of play where the traditional basketball lifers
didn't. So what was the long -term significance
of that win? It opened the floodgates. It completely
validated the idea that you can find executive
talent anywhere in the world. Now you look around
the league and front offices are incredibly diverse.
You have former agents, cap specialists, data
scientists, international scouts. Ujiri proved
you don't need to be part of the old coaching
tree or a former player to run a team. And speaking
of new perspectives, I want to fast forward to
the modern era, the 2020s, because looking at
this list of recent winners. Something feels
different. It's not just where they're from.
It's like how old they are. It's a definite changing
of the guard. Yeah. Let's just run down the list
since 2020. In 2020, you have Lawrence Frank
with the Clippers. 2021, James Jones bringing
it back to Phoenix. That's their sixth total
win. Of course, Phoenix. 2022, Zach Kleiman with
the Grizzlies. 2023, Monty McNair with the Sacramento
Kings. 2024, Brad Stevens with the Celtics. Another
coach -to -exec guy. Exactly. And the most recent
winner in our data? From 2025, Sam Presti finally
getting his due in Oklahoma City. What jumps
out at me is the age. Zach Kleiman was, what,
33 years old when he won? I believe so. That's
younger than LeBron James was at the time. That's
insane. It's like the tech CEO era of the NBA
GM. That is a great way to put it. We've really
moved away from the 70 -year -old patriarch who
relies on smell tests and gut feeling. Now it's
about analytics, asset management, and aggressive
maneuvering. These young executives treat the
league like a stock market. They're looking for
arbitrage opportunities. And notice something
else. No repeat winners in the 2020s yet. It's
a carousel, a different name every single year.
So what does that tell you about the state of
the league right now? It tells me the margins
are razor thin. In the 80s and 90s, if you had
a dominant system or a transcendent superstar,
you could exploit that for a decade. Now, everyone
has the same data. Everyone has the same tracking
software. If you find an inefficiency like the
corner three or undervalued second round picks.
The rest of the league copies you within six
months. So it's just harder to stay on top. Much,
much harder. The fact that we have a different
winner every year suggests that parity, for the
most part, is real. The dynasty is becoming an
endangered species because the rules, like the
salary cap and the draft lottery, are designed
to tear great teams apart. Which makes the job
of the architect even harder. You can't just
build it once and let it run. You have to constantly
be renovating. You have to renovate or you get
demolished. I want to go back to the franchise
leaderboard for a second. We mentioned Phoenix
is at the top with six wins. Who's chasing them?
This is where the data gets quirky and, honestly,
a bit surprising. Sitting there in second place,
tied with four wins, is the San Antonio Spurs.
Okay, that makes total sense. The model franchise
for 20 years. But tied with them at four wins,
the Sacramento Kings. Wait, what? The Kings.
I know. I know. It sounds like a typo to modern
ears. For the last 15, almost 20 years, the Kings
were the literal definition of dysfunction. Kangs
was the meme. It was. But the award has a long
memory. And the Kings have had these pockets
of absolute brilliance. Joe Axelson won way back
in 73 when they were the Kansas City Omaha Kings.
The nomadic Kings. And then Jeff Petrie. We have
to give Jeff Petrie his flowers. He won twice
in 1999 and 2001. That was a greatest show on
court era. Chris Weber, Vlade Divac, P .J. Stojkovic,
Jason Williams. Petrie built one of the most
aesthetically pleasing, beautiful basketball
teams in history. They passed the ball. They
were unselfish. They didn't win the ring, thanks
to the Lakers and some questionable officiating.
We will get into that. But they were brilliantly
constructed. And the Monty McNair winning in
23 brings him up to four total. It really shows
that even cursed franchises have these moments
of clarity. And it reinforces that turnaround
bias we talked about. The Kings were so bad for
so long that when they finally got good under
McNair, the voters rushed to reward him for it.
Absolutely. Who is in the next tier down? The
three -win club. In here, you have the heavyweights
you'd expect, Boston Celtics, Chicago Bulls,
Golden State Warriors, but also the Denver Nuggets,
the LA Clippers, and the Oklahoma City Thunder
Seattle Supersonics franchise. Ah, right. The
Sonics history counts for the Thunder. You have
to remember that. Correct. Franchise records
travel with the team. So Seattle won twice, Zolli
Volchok in 83, and the great Bob Whitsitt in
94. Trader Bob. A legend. He would trade his
own mother for a second -round puck if the math
worked out. He's the one who built the Sean Kemp
-Gary Payton Sonics. An iconic team. And then
Sam Presti brought the third one home for the
franchise in OKC in 2025. I love that lineage.
From Gary Payton to shy Gilgis Alexander, a legacy
of great guard play. And smart drafting. OK,
so let's talk about the guys who proved it wasn't
a fluke. We mentioned Colangelo winning four
times. Who are the double dippers, the guys who
won it twice? It's an elite list. We mentioned
Bob Myers and R .C. Buford, the modern dynasty
builders. But let's shine a light on a few others.
Wayne Embry. The Cavaliers legend. He won twice
with Cleveland in 92 and 98. Wayne Embry is such
a crucial historical figure. He was the first
African -American general manager in NBA history.
He didn't just open the door. He kicked it down
and won the award twice. That is huge. He built
those tough physical Cavs teams that battled
Michael Jordan every year. Exactly. Then you
have Bob Ferry. He won twice with the Washington
Bullets in 79 and 82. He built the team that
finally brought a title to D .C. with Wes Unseld
and Elvin Hayes. But there is one guy on this
list of two -time winners who did something that
I think is technically the hardest feat of all.
Stan Kasten. Stan Kasten, the only manager in
our detailed records to win the award back to
back. Back to back. 1986 and 1987 with the Atlanta
Hawks. Think about the voter fatigue we just
discussed. The GMs hate voting for the same guy
twice in a row. It feels boring. It feels like
you're just rubber stamping it. Exactly. For
Kasten to win in 86 and then for the voters to
look at the 87 Hawks and say. Damn it, he did
it again. We have to give it to him. That is
just incredible. That was the Dominique Wilkins
era, right? The human highlight film. Cast and
built a team that was consistently excellent
in a brutal Eastern conference that had the Celtics,
Pistons, and Sixers. To win executive of the
year twice in a row in that shark tank is remarkable.
Now, I want to get a little personal. We talk
about fathers and sons on the court all the time.
The Currys, the Thompsons, the Berries. But there
is a front office dynasty in our data, too. The
Colangelos. We know Jerry has his four wins,
but his son, Brian Colangelo, is on this list,
too. Twice. That is wild. Are they the only father
-son duo to win it? The only one. And the narrative
around Brian is so fascinating. He wins his first
one in 2005 with the Phoenix Suns. Which, let's
be honest, the critics at the time would say,
well, he just took over daddy's team. 100%. Born
on third base. Yeah. But to his credit, he didn't
just maintain the status quo. He was the one
who helped pivot that team into the seven seconds
or less era with Steve Nash and coach Mike D
'Antoni. A revolutionary style of basketball.
It was a radical shift. He took a huge risk on
a play style that a lot of old school basketball
people thought couldn't win. But he didn't stop
there. He didn't just stay in Phoenix. No. He
went to the Toronto Raptors, a completely different
challenge, different country, different market,
and he won again in 2007. That must have felt
so good. To win with a team his dad had nothing
to do with. It cemented his own legacy. He proved
he wasn't just Jerry's son. He was a top -tier
executive in his own right. He built a division
winner in Toronto. And we also see other executives
moving around and succeeding, which I think is
the ultimate test of pure skill. We mentioned
Bob Bass earlier. Yes, Bob Bass. He won with
the San Antonio Spurs in 1990, building the David
Robinson era. And then he went to the Charlotte
Hornets and won again in 1997. The Hornets, the
teal jerseys, Grandma Ma, Zoe, morning. That
90s Hornets team was iconic. And Bass showed
that the skill of roster construction. You can
do it in Texas. You can do it in North Carolina.
It's not about the location. It's about having
the eye for talent. OK, let's bring it all home
by looking at the ultimate honor, the Hall of
Fame. We mentioned Colangelo and Embry are in
as contributors. Right. That's the specific category
for non -players and non -coaches. But it's really
interesting to see how many Hall of Fame players
also won this award. It's like the ultimate cherry
on top of a career. We talked about Byrne West,
but let's talk about Elgin Baylor. The Clippers
GM for what felt like decades. He won the award
in 2006. People forget this. Elgin Baylor is
in the Hall of Fame as one of the greatest plays
ever. The first true high flyer. But he ran the
Clippers for a long, long time under, let's say,
very difficult ownership. The Donald Sterling
era. Not exactly known for spending money to
win. The tightest purse strings in the league,
maybe in all of sports. And yet in 2006, Baylor
built a team with Elton Brand and Sam Cassell
that actually won a playoff series. Getting the
Clippers to the second round in that era, that
was a legitimate miracle. He deserved the award
just for dealing with all the headaches. Absolutely.
Then you have Joe Dumars. Hall of Fame player
for the Bad Boy Pistons. Two -time champ. And
then he becomes the architect of the 2004 Championship
Pistons. He won the executive award in 2003,
the year before they won it all. Dumars is fascinating
because he built a championship team without
a top 50 all -time player. There was no Shaq,
no Duncan, no Kobe on that roster. It was just
a perfectly fitted puzzle of very good players.
Which is arguably the hardest way to build a
team. He traded for Rip Hamilton. He signed Chauncey
Billups. He drafted Tayshaun Prince. He traded
for Rasheed Wallace at the deadline. Every single
move was a hit. He's the Catron Saint of the
whole is greater than the sum of its parts. And
one more contributor worth noting here, Rod Thorne.
Rod Thorne won in 2002 with the New Jersey Nets.
That was the Jason Kidd era when he traded for
Kidd and they immediately went to back -to -back
finals. Thorne is also elected to the Hall of
Fame. He's a massive figure in the league office
as well for years. He's the guy who drafted Michael
Jordan when he was with the Bulls. Wait, really?
Yeah, he was the GM before Kraus. That alone
should get you in the Hall of Fame, just being
able to say, I picked Jordan. It's a pretty good
line to have on the resume. So we have looked
at the history, the mechanics, the legends, the
families. When you step back and look at this
50 -plus year data set, from Colangelo all the
way to Sam Presti, what is the big so what for
you? Why does this award truly matter? It matters
because it reveals the cycles of the league.
When you see the Suns winning six times or the
Spurs winning four times, you see organizations
that established a culture of winning. It wasn't
just luck. But then when you look at the recent
winners, Kleiman, McNair, Stevens, Presti, Hosseini,
you see how quickly the league changes. It's
a copycat league. It is. A great player wins
a game. A great executive wins a decade. But
in the 2020s, With the voting done by peers,
the fact that we haven't had a repeat winner
in this decade yet suggests the league is tighter
and more competitive than ever. No single system
dominates anymore. You can't just run the triangle
offense for 20 years and expect to win. You have
to constantly adapt or you die. Exactly. The
competitive edge is just harder to find. The
information gap is closed. Every team knows who
the good players are in Europe. Every team has
the tracking data. So to win this award now,
you have to be bolder, smarter, and maybe a little
bit luckier than ever before. That is a provocative
thought to end on. We are in the era of hyper
competitiveness, not just on the court, but in
the boardroom, the war room. Absolutely. The
next godfather, like Colangelo, a guy who wins
four times, he might not exist because the game
moves too fast now. Well, next time you see a
trade notification pop up on your phone or you
see a team draft a guy from a league you've never
heard of, just remember, there's an architect
behind it, sweating out the details, trying to
win that vote from their peers. And trying to
build a legacy that lasts a little bit longer
than a shoe contract. Thanks for diving in with
us. It's been a pleasure exploring the front
office. Always a pleasure. We'll catch you on
the next Deep Dive. Take care.