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Playing True-and-False with the future of Bobby Webster in Toronto

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It’s not a surprising turn of events to see teams, or in this case, the Chicago Bulls, take an interest in Toronto’s GM Bobby Webster. But is there any truth to the idea that he’d leave the Raptors?

Philadelphia 76ers v Toronto Raptors Photo by Cole Burston/Getty Images

The future of a great many things is uncertain right now, so it feels almost rude of the Chicago Bulls, that once proud, now hapless franchise, to float out the news item that they were pursuing the services of the Raptors’ young general manager, Bobby Webster. I mean, the absolute nerve of these guys.

Here’s the specific report from ESPN’s Adrian Wojnarowski, one of a few tweets on the subject:

(You can read the full story here.)

This news is, as the timestamp on that tweet can attest, from last Friday. You rightly might wonder why we’re only getting to it on the following Tuesday, especially since, uh, there’s not much else to write about at the moment. So did we miss this news? False. Did we decide it was beneath us to comment on it? True. Are we now writing about it because there truly is nothing else to discuss with regards to the Raptors?

Well, before confirming the truth or falsity of such a question, let me introduce you to...

The Bobby Webster True-False Challenge

As the above subtitle implies, we’re going to run through a series of skill-testing statements on the matter of Webster, the Raptors, and, sure, the Bulls and their interests. I’d like to believe the concept here is self-explanatory, so let’s just get to it with a softball fact to start.

Bobby Webster is the General Manager of the Toronto Raptors.

True. (Thanks to Masai Ujiri promoting himself to team president after losing his lieutenant Jeff Weltman in 2017 to the Magic, the role of GM was made vacant. Webster was swiftly promoted, making him, then at just 32 years old, the youngest GM in the league.)

Bobby Webster is the all-time youngest GM in the NBA.

False. (That would be Rob Hennigan, hired by the Magic in 2012 at the young age of just 30. He would go on to oversee five of the more useless years in Magic franchise history, arriving at his end after trading Serge Ibaka — who he’d acquired less than a year before — to Toronto. Hennigan’s Magic never made the playoffs during his tenure.)

Bobby Webster is a high quality executive whom many teams would love to hire.

True. (Webster checks a lot of boxes for the modern day NBA owner. He’s young, smart, discrete — a not-underrated skill — and has made his name by involved in: the drafting of Pascal Siakam, the signing of Fred VanVleet, acquiring Kawhi Leonard, and, of course, the shaping of the current Raptors, the reigning 2019 NBA champions.)

The Chicago Bulls are run by John Paxson (VP of Basketball Operations) and Gar Forman (General Manager).

True. (At this moment, as has been the case, the executive duo known as GarPax are still in charge in Chicago. Paxson has been with Bulls management since 2003, with Heard joining him in 2009.)

The Bulls have been a well-run organization under Paxson and Heard.

False. (In one sense, 11 post-season appearances across 17 years for Paxson should equate to astute management ability, but a deeper dive into the reasons for Chicago’s success suggests otherwise. The current Bulls, with their argumentative coach Jim Boylen, and their rag-tag bunch of unhappy players, are going backwards. Not lucking into a number one pick — as they did with Derrick Rose in 2008 — or stumbling into an all-NBA talent — like Jimmy Butler in 2011 — has meant the Bulls have had to fend for themselves purely through shrewd management. Since those high times, they’ve made the playoffs once in five years, and been below .500 for most of this stretch. In short, it has not gone well.)

It makes sense for the Bulls to find a new GM and team vice president.

True. (If you ask Bulls fans, who have built an entire identity around a desire to see GarPax fired, it made sense years ago for this to happen. Some would go as far to note that this organization has now somehow burned through all of the goodwill it accumulated in the 90s thanks to Michael Jordan which is grounds for a business malpractice lawsuit.)

The Bulls can pursue whomever they’d like to fill their management positions.

True. (It’s a free country, ain’t it?)

The Bulls need to be granted permission to speak with candidates currently under contract with other teams.

True. (There are limits to that freedom, though. Also, it’s just good manners.)

Bobby Webster’s dad is a native of Chicago.

True. (Wait, where are you going with this?)

Bobby Webster has been largely overlooked during his time in Toronto.

False. (Obviously Webster’s name is far less known than the Raptors’ chief architect, Masai Ujiri, but this is in part by design by the man himself. As various Toronto beat writers have noted, Webster is not much one for interviews, and despite being seen around the team — usually with a friendly wave ready as he steps through the locker room — his work has mostly been done in the shadows. As noted in the lone long feature on Webster, at one point in his life, he was interested in working for the CIA.)

Both Masai Ujiri and Bobby Webster have contracts that expire after the 2020-21 season.

True. (Though now with the 2019-20 season on hold, it becomes unclear how exactly those contract terms will play out and what situation the Raptors will be in when that expiration date arrives. Will Toronto get to finish its inspiring championship defense? Will the squad have to just restart cold in for 2020-21? Do the pair of Ujiri and Webster want to find a new challenge or is keeping this successful show rolling in Toronto enough? Yes, there is a lot of uncertainty here, despite the ironclad nature of those aforementioned contracts.)

The Raptors will lose both Ujiri and Webster over the next 12 to 18 months.

False. (It’s easy to see how this will play out. If Ujiri commits to Toronto long term, maybe Webster seeks a bigger opportunity elsewhere, which is his right. If Ujiri makes it clear he’d like to move on to some new challenge — running a small but powerful nation, for example — the Raptors can offer Webster everything he desires to stay with the Raptors as team president. It remains hard to see how Toronto could lose both of their key executives in short order.)

The Bulls have made it clear they want to hire a new GM and Vice President now.

True. (Again, as originally reported, it does sound like the Bulls are finally ready to move on from Paxson and Heard — well, sort of. As most of the news makes clear, both Paxson and Heard are likely to stay on with the Bulls in some capacity. What that capacity will ultimately be is anyone’s guess at this time. It bears mentioning however, because whoever the new GM and/or VP is, they’ll have to know that Paxson and Heard will still be around in Chicago. Anyway, the timeline here for a replacement does not appear to align with Webster’s availability.)

The Raptors will grant permission to the Bulls to interview Webster.

False. (It feels exceedingly unlikely at this time. Here’s Sportsnet’s Michael Grange, as plugged in a reporter as you’re likely to find in Toronto, saying much the same thing. We’re so confident in this conclusion, we don’t even need to pose any Raptors minority owner Larry Tanenbaum true/false statements to make our point.)

Bobby Webster will leave Toronto to run the Bulls.

False. (See above.)