The Gary Trent Jr. Investigation Could DESTROY the Franchise

Sports Illustrated
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Nov 14, 2026
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I got to be honest, and I'm almost embarrassed
that this story kind of fell off my radar
over the last couple of months
because we are still kind of picking up the pieces from
the historic punishment that the NBA handed down
to the L.A. Clippers for cap circumvention.
But they are not the only cap circumvention investigation
that the NBA is conducting.
The situation involving Gary Trent Jr. is still very much
a front burner issue for the NBA.
Remember, Gary Trent Jr. had a couple of kind of middling seasons
with Milwaukee, one bad one a year ago, and the Bucks turned around
and gave him a four-year, $64 million contract, which was crazy,
because they did it late, I think, in the cycle,
and to my knowledge, there was really no market for Gary Trent.
And the supposition that people are going with is that, hey,
Gary Trent took short-term contracts from the Bucks,
cheaper, signed there, play with Giannis, play with Dame,
and this is him being rewarded on the back end.
A very Joe Smithian type of situation
potentially developing in Milwaukee.
It was, I got to want to credit,
Brian Windhorst kind of brought it back to the surface
saying that he expects the penalty to be severe
for the Milwaukee Bucks.
You worked in front offices, you know how this goes.
I
You know, the NBA kind of,
Put the, laid the blueprint here for what
don't
the penalties can be for cap circumvention.
How likely do you think it is that the Bucks get hit
with something similar for what happened
with Gary Trent?
So I'm going to reference the executives I speak to on this one,
know.
because they're the
ones with the most knowledge right now.
And they're expecting, I mean, to them,
this is one of the most obvious cap circumvention
examples of practically all time.
There was no potential way for the...
I'm speaking from the executives I've spoken to.
There's no way that you could possibly explain
or justify that contract.
It just...
And you can go through every reason.
The apron system that they're in,
who else was getting deals,
and then just the player themselves.
And then on top of that,
they're not even playing him this year.
He's not playing.
To me, that starts wondering in my head,
is that like...
If they were going to force him to play,
I wonder if at some point Taylor Jenkins is like,
I don't want to be part of this type thing.
I don't want to be complicit in playing him now
or being part of this just
because I'm playing the guys that should be playing.
No, it's bad. It's really bad.
So my question to you would be, if we're talking similar,
At what point do you say the player themselves
and the impact of this player and the deceit that
went into it matters?
Because like the aspiration situation was so deceitful.
And we're talking about Kawhi Leonard
and the things that they had to do to make it work.
And just the levels.
This was elaborate.
That was elaborate.
It was elaborate.
This is more conventional cap circumstance.
And it was almost like,
they almost kind of made a mockery
of the, like, once it kind of got public,
like the Clippers were fighting so hard back about it,
whatever.
This one is just so surface level.
It's about Gary Trent.
I doubt it's, maybe this is me just assuming,
if a punishment were to come,
I doubt it's gonna be the same level of the Clippers
because I think the Clippers needed to be
like a real example of like, come on.
At the same token,
if they do punish the Milwaukee Bucks,
it's gonna be one of the more like,
there's the evidence is so strong
that there's just no way around it
because people were still kind of wondering
about the Kawhi situation.
There's some question marks,
who was involved, who knew, blah, blah, blah.
This one.
Eh, you know, it's kind of straight up.
So they only have so many assets.
Milwaukee has given away their assets.
They're kind of similar to Clippers in that vein.
So it's the 20, 30, 31, 32.
That's the area you're looking again.
It's just, it's kind of hard to really think about
how bad it could get in Milwaukee
for the state that they're in,
plus taking away assets, it's terrifying.
See, and I don't have any particular insight
into what the NBA is going to do.
But I've also talked to people that have said to me,
and I'm guessing you probably heard
the same, it's like, hey.
If it's good for the goose, good for the gander.
Like if it's, if you did
this to the Minnesota Timberwolves two decades ago, and you did
this to the LA Clippers two months ago,
how are you going to let the Bucks off the hook
if you've got them dead to rights?
And it sure seems like, unless there's some
explanation I don't know about, that they've
got them dead to rights here.
I mean, Gary Trent is not worth $16 million per year.
He was not when the deal was signed back in July.
Chris, just once, like, if he had gone to a one-year $16 million deal,
people would have thought cap circumvention.
That's how bad it is.
They gave four years.
If it was a one-year $16 million, people would have been like,
all right, something's up.
We need to investigate.
So please go on.
Yeah.
No, I just, I feel like people believe,
or at least that they think it should, this is how it should play out,
that if you're going to do, you can't, like,
you can't separate, like, level of player,
But you can't separate.
Layers of deceit, elaborate deceitfulness.
If it's cap circumvention, and this is more like Joe Smith,
as we talked about, Joe Smith signed short-term contracts in Minnesota,
winds up signing, I forget how it all kind of played out,
was going to sign a long-term deal there to make more money
to circumvent the cap.
This is kind of like that.
There's no aspiration here.
There's no sponsorship deals he didn't do,
but it's traditional cap circumvention.
There are people I've talked to that are saying like,
If you did it for these guys, you got to do the same thing for them.
If it does go that route,
like you asked like kind of how low it could get.
It's like Chernobyl.
Like, Milwaukee becomes basketball Chernobyl.
Like, who are they building around?
Like, who are the young pieces on that team, Grant,
that you're excited about?
Like, they got some of the guys from...
I like Braden Burries.
I actually am a big fan of Braden Burries.
So, am I allowed to say that?
Now you're glass half full right there.
Okay, that's great.
I like Braden Burries.
But you got Tyler Hero, who is on an expiring contract.
Miles Turner, who nobody seems to want.
Um...
Yakushone, who's just a good potential prospect.
We'll
You know, Brian Rollins, you got Ware,
and A.J. Green I like as a rotational piece.
But yeah, I hear what you're saying, for sure.
be
But it's Chernobyl.
It is basketball Chernobyl.
Like, you lose a bunch of draft picks.
right
You have, presumably, your GM, you know,
suffers some kind of punishment as a result for it.
I don't know what, I mean, again,
this is one of those things where I don't know
what the blast radius would be.
back.
Like, you know, before, like,
we were so locked in on the Clippers grant.
Like, we were like, all right, is it going to be?
Is it going to be Lawrence Frank?
Is it going to be Trent Redden?
Is Lee Jenkins going to get dragged into this?
We were scrutinizing the minutia of the Clippers on a weekly basis.
This one, it's kind of like slid under the radar
to the point where I don't know,
is there a Gillian Zucker in all this?
Is there a president of business affairs,
or is it just going to be the basketball ops kind of people
that wind up taking a fall there?
This is...
This is interesting.
And if it does go against the Bucks
in the same way it went against the Clippers and
Timberwolves, it might set
the Bucks back longer than it's setting back the Clippers.
Because at least the Clippers are kind of in LA,
you know, and you've got opportunities
there.
They've got a couple of young pieces there
that you kind of like as part of that team.
The Bucks, a decade.
This could set them back a long, long time, man.
Like this, this to me feels like it could get worse than it does in LA.
Yeah, it's bad.
And the reason I haven't mentioned John Horst or those guys
is because I don't want to put out there,
like, John, those guys, they're good people.
They've done smart things over the years.
And it's like, I don't want to say that, like,
any of these people are the reason, like, why this happened.
It could, as you said, we don't know.
It could have been ownership that just said, like,
this has to happen.
And people are like, so we don't know.
But that is a tough, that is a tough, like, you know.
People know like, all right,
I'm going to give Gary Trent Jr.
Four years of 60.
Yeah.
Yeah.
So, so these are really smart guys.
Like to your point, like they built a contender.
They kept Giannis happy in a small market year after year after year.
Like these are excellent basketball people.
Like they are, they're proven they want a championship.
They've got a ring to prove.
It's not like, like, you know,
everybody loved the Clippers for a long time,
but the Clippers didn't have the hardware
to back up that those feelings.
The Bucks got the hardware, the Bucks got a title.
And I like those guys.
I don't know.
I've got to know them over the years in the front.
They're good dudes.
So again, I don't know where this goes,
but if we're ignoring the people behind this or any of that,
if you just look at the surface level
and you can talk to literally any executive in the league about this,
that was one of the more ridiculous,
blatant, weird contracts they've seen.
And I don't...
Will it end up being cap circumvention?
Maybe there's something else going on
that I don't know about
that maybe it doesn't consider cap circumvention.
But right now, on the surface,
that is one of the more obvious
cap circumvention situations we've seen.
I would think, too, that if it's not a real penalty
or it's a small penalty,
like, the people within the Clippers
would lose their minds.
Like, they would lose their minds.
They'd say, you just set us back.
Maybe a generation.
You sent our owner packing for a year.
You sat down our president of business operations,
our general manager.
Um, and it.
And if you don't hand out a penalty commensurate with that,
I can see people within the Clippers getting upset about that.
Very upset about that.
Yeah, and one last piece is,
for...
I feel for Milwaukee in this way,
is that they had Giannis for all his years
trying to make him happy.
Whatever happens, they have to move him, right?
And then they get stuck in a situation
where Giannis only wants to go to one team,
and this happens, and they try to appease him,
but at the same time, he has this contract situation
where he gets to kind of dictate where he goes a little bit
because he'll only resign at certain places.
So they only got...
Listen, they got a good package back,
but they could have gotten better
if it was an open market, open season to moving him.
So you already have that.
And that kind of set them back a little bit
because they could have done better probably
with the Yan situation
if they had done it at a different time.
And then this happens.
And it's just such a bummer
because like you have this moment in time
where you're like, let's reset this franchise and go again.
Thank
And has a chance to just be the repercussions
can be awful.
Yeah. Yeah. And then I, like that, like, yeah, again,
give credit to Bryant for kind of bringing this up again.
I think there'll be a lot more interest now
in people finding out where the
NBA is at. Like, as far as I know,
there's no white collar law firm investigating.
It's just the NBA kind of doing their thing on this one.
you.
And I'm sure Adam's always going
to get some questions about that in the
weeks and months they're ahead.
