Bobby Webster
89
MENTIONS
32
EPISODES
15
PODCASTS
Search complete. 89 mentions across 32 episodes found for "Bobby Webster".
Sep 12, 2026
GeminiSOUNDBITE_SPEAKER
Barnes can't achieve GROT status in a vacuum.
Will LouHOST
The Bobby Webster factor?
GeminiSOUNDBITE_SPEAKER
The path requires general manager Bobby Webster and the front office-
Will LouHOST
No. What?
GeminiSOUNDBITE_SPEAKER
... to successfully execute long-term roster management that perfectly complements-
Will LouHOST
Fair.
Will LouHOST
That's true.
Will LouHOST
You know, that's actually a good point there c- that Jem raised, 'cause I'm not gonna lie, I'd never thought about [laughs] the Bobby Webster factor in the GROT.
Sid SeixeiroHOST
So in terms of why the Raptors trade isn't done yet, it's complicated.
Sid SeixeiroHOST
But the Raptors knew that back on June 30th and didn't care, and thought they were too cool for school, and said, "We're gonna do this anyway." Bobby Webster said, "We're gonna do this anyway." Okay.
Sid SeixeiroHOST
Have you been listening to the pugilatory thing? There's a lot of stuff.
Sid SeixeiroHOST
Like, yeah, we're gonna do this anyway 'cause I got friends in the league office.
48 MINS LATER
Sid SeixeiroHOST
How upset are they? If you can get rid of Jakob Poeltl in that deal-
Jeff AzzopardiHOST
Mm-hmm
Sid SeixeiroHOST
... which is Bobby Webster's biggest mistake before this one.
Sid SeixeiroHOST
Are, are Raptor fans that upset? Sabonis, I got news for everyone, pretty good player.
Randy UrbanHOST
And if it does, maybe that's the holdup that the Raptors are having.
Randy UrbanHOST
Maybe Bobby Webster and co. are looking at that and thinking, okay, well, we need to figure out what the consequences of this is going to be before we agree to this trade fully.
Randy UrbanHOST
So I don't know.
Randy UrbanHOST
Kind of scary.
Alex WongHOST
Like-
Will LouHOST
Yeah, he had his tongue out like Bobby Webster.
Alex WongHOST
Yeah, like, it just, it just didn't sit right.
Alex WongHOST
Um, I guess an addendum to this, uh, what if-
30 MINS LATER
Alex WongHOST
Or Olynyk is crazy
Will LouHOST
crazy...
Will LouHOST
Masai's first hire was Bobby Webster.
Will LouHOST
Yo, look at young Bobby
Randy UrbanHOST
But the sense is that he is coming to Toronto, okay? This is just, this is certain.
Randy UrbanHOST
The sense is that he's coming to Toronto, all right? I know Bobby Webster definitely wants to get this deal done, as do the Clippers, right? The Clippers are in desperate need of these picks back, okay? I do want to address this sort of Vitriol, I guess – well, it's not vitriol.
Randy UrbanHOST
It's an opinion and it's a valid opinion, this toxic kawaii opinion that some people have pointed out there.
Randy UrbanHOST
And there's a lot of validity to some of this stuff, saying that this is a pretty big scandal and why would you want a guy that left – And then, you know, there weren't obviously people aren't happy with, you know, what happened in L.A. And so they're, you know, they're they're titling that toxic kawaii.
Randy UrbanHOST
And so you want to keep these relationships because you just never know who's going to be available.
Randy UrbanHOST
And so I just don't see Bobby Webster available.
Randy UrbanHOST
Trying to pull a fast one on the Clippers and just take advantage of an already pretty sad situation for the league.
Randy UrbanHOST
So anyway, enough about that part.
Matt GeistHOST
It would go into somewhat of a retool period, but leading up to them trading away OGN and OB and Pascal Siakam in the 2024 season, they made some horrible trades.
Matt GeistHOST
And I mean, horrible trades with a very well-respected front office in Messiah Jiri and Bobby Webster.
Matt GeistHOST
So this is coming in at number 12.
Matt GeistHOST
It's basically the Raptors trading away first round picks.
Sam QuinnHOST
Immediately, this was kind of a confusing one for me.
Sam QuinnHOST
They fired Masai Ujiri last year, the day after the NBA draft, and they promoted internally with Bobby Webster, who had been his deputy forever.
Sam QuinnHOST
So it's a little tough to untangle some of the things that Masai Ujiri had done before he got fired with what Bobby Webster is actually responsible for.
Sam QuinnHOST
the biggest organizational win for Toronto in recent front office history was drafting Colin Murray-Boyles at number nine.
Sam QuinnHOST
I went back and I looked at some of the mock drafts.
Sam QuinnHOST
He should have gone higher.
Sam QuinnHOST
I think he has a chance to be an all-star.
Sam QuinnHOST
do we credit that with Masai Ujiri, who was technically running the Raptors during that draft, or do we credit Bobby Webster? I have leaned towards Webster.
Sho AlliHOST
I mean, a- aside from the Leafs, and God, God knows we don't need to litigate what the Leafs have done in, in our lifetimes.
Sho AlliHOST
But, uh, I mean, the Raptors are the only other team that have been able to do that, and the Raptors won an NBA title, so obviously guys like Masai Ujiri and now Bobby Webster are gonna get as long leashes as possible.
Sho AlliHOST
So it is true that I think in this city it's not always the case, and here you have Ross Atkins in, what, 10 plus years essentially on the job.
Sho AlliHOST
I, you know, I, on the Te'o trade it's interesting, 'cause I, at the time I felt that it was the right move, that his, his, his time as a Blue Jay had not necessarily come and gone, but that it was the right move I- in terms of the deal for Swanson.
Dave FeschukHOST
You, you gotta hope.
Dave FeschukHOST
I mean, you, you, as long as, as long as somebody is not suspended in a management position in LA that can actually consummate this trade with Bobby Webster and the Raptors, everything should be fine.
Dave FeschukHOST
But it's probably chaos at Clipper Central right now-
Michael DiStefanoHOST
Oh, yeah
22 more episodes mention Bobby Webster.
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