A conversation on the Wizards’ off-season Part 1: Tommy Sheppard’s promotion, culture, and more

With the big off-season free agent moves and trades in the books (assuming Bradley Beal is staying...), Kevin Broom and Yanir Rubinstein decided to share part of a conversation they had about the Wizards’ moves this past month and what the future holds for the franchise.

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Yanir Rubinstein: Kevin, totally off topic, to warm up: have you gotten a chance to watch some sports this summer? What was the most memorable sports moment for you this summer?

Kevin Broom: This reminds me of the time Ben Becker and I spent a bunch of time in a season preview podcast talking about the team’s backup point guard...in the following off-season. I mean, the Wizards just stripped Tommy Sheppard of the interim label and will make him the full-time general manager and you’re asking me about non-basketball moments?

But, I’ll play along: Kawhi Leonard’s four bounces on the rim buzzer beater to win game seven against Philadelphia. Close second was the U.S. women’s team wining the World Cup against the Netherlands.

What stands out for you?

YR: With Copa America, the U.S. women’s national soccer team’s fourth Women’s World Cup championship against the Dutch, the Raptors’ championship, it’s really tough... I actually attended three of the six NBA Finals games and I agree with Hubie Brown: for me, the most epic moments in that series were some of Fred VanVleet’s ridiculous shots...

Ultimately though, I think the Roger Federer show in Wimbledon wins. If I have to choose a moment it’s the (sad) moment when it was clear that the fifth set is going to a tie-break for the first time in Grand Slam history. He lost both tie-breaks earlier in the match but won the other sets easily and it was clear Novak has the upper hand in those situations. Then Federer lost the tie-break, the set 12-13 and along with it the title without losing any set by two games. Tragic.

KB: Wait, VanVleet as FINALS MVP?! Let’s just say I disagree with you and Hubie, but Hubie was part of my favorite NBA-related story (he yelled at me in a locker room because he didn’t like a question I asked) so I’ll let it go.

YR: OK, so where were we? Ah, Wizards, right..! I guess we should talk about Tommy Sheppard. Thoughts?

KB: I’ve known Tommy for 13-14 years now, and he’s one of the good guys. He’s smart, creative and he knows EVERYONE. I’ve thought for years that he’d make a good GM somewhere, and I’m happy he’s getting the chance. I’m also glad he’s talking culture change.

All that said, I’m not convinced he’s the right person to run the Wizards at this juncture. I think they need a major culture transformation, and it would be challenging for anyone to lead that transformation when he’s been part of it for 16 years. If anyone is up to that task, it might be Sheppard. But I am dubious.

YR: The possibility of a culture-change-from-within does sound a bit of science fiction. By the way, I totally get the same vibes from talking to other people around the league: Tommy is a very likable guy.

He rubs people the right way. He is respectful, encouraging, open-minded, well-traveled and does his homework. But isn’t it just a bit outlandish to talk about a culture change towards accountability from the top down and then leave the ownership, general manager and head-coach intact modulo a slight reshuffle?

KB: It’s hard to say, but they did bring in some new voices in leadership positions within the organization and they promoted Brett Greenberg, who’s excellent on analytics. And this was all constructed with the help of Mike Forde, who’s had success with other organizations, including the Spurs. The process seems strange, but at least they have good people in key positions.

YR: I agree with you: some of these front office hires/promotions (that were just announced a couple days after the Sheppard promotion) are encouraging.

The Wizards front office has made so many terrible moves (for at list up to 2016 see here; oh there is also this). I get it that many front offices make awful moves but I have also seen some in-depth draft analytics ranking the Wizards as one of the bottom three draft picking organizations in the 21st century NBA.

From my understanding many of these decisions are done jointly within such organizations, which would mean Grunfeld, Sheppard, their various scouts and assistants sit down together.

Of course, we can’t say Sheppard is to blame for the Mahinmi contract. Or for the Nicholson one. Or for overpaying Brooks in money and years, or for all those ridiculous player options (Howard, Meeks, etc.) or for Issuf Sanon (more on that later). Or for that 1st rounder to Brooklyn for three months of Bogdanovic. Or for trading Oubre, Morris and Porter for a protected 2023 2nd rounder and a trade exception.

But shouldn’t he be blamed for part of all of the above? And if so, if we are talking about a culture change, accountability top-down, how come he is not just staying but actually being promoted?

KB: Grunfeld managed by letting people give him advice before he made the final decision. I know of at least two instances where Sheppard (and others) talked him out of bad moves. But, one of the problems in the Grunfeld front office was too many people being too quick to agree. Hopefully that ends under Sheppard, but this goes back to the difficulty of leading a culture change when you’ve been part of that culture for so long. Old habits die hard.

YR: Now that he’s the guy, what do you think the team’s strategy will be and do you think it’s the right way to go?

KB: Sheppard did a solid job with what I called “marginal moves” earlier in the off-season. His biggest whiff was not listening to the Clippers when they were trying to add an All-Star to pair with Kawhi Leonard. But, I just can’t see anyone doing a deal like that with “interim” in the job title. That “whiff” goes on Leonsis.

The moves suggested to me the plan is to be bad this season and then return to playoffs contention in 2020-21. That was confirmed when Leonsis said the turnaround would be quick. I think they’re deluding themselves and merely postponing the ground-up rebuild they need to at least 2021.

They seem to believe that Wall and Beal make them contenders. That’s wishful thinking — Beal is very good, but not the sort of elite player around which a contender is built. The same was true of Wall when he was healthy, and by the time he’s back on the court he’ll have missed huge chunks of three consecutive seasons. My analysis of players like that isn’t encouraging.

YR: We started talking about culture. Jerry Brewer of The Washington Post wrote last season that:

“There’s a belief that Wall has been coddled for too long and that neither the coaching staff nor the front office can properly manage him ... Until Brooks coaches him harder — until the front office creates an atmosphere of accountability in which it is easier to coach Wall harder — the Wizards won’t excel.”

As noted, Sheppard has talked about changing the culture. In his first move, he effectively terminated Devin Robinson after the latter apparently had a nightclub incident. Could this have been a message to Wall (did someone say Rosebar?)?

KB: Brewer’s point about Wall is correct, but the issue goes back to the very beginning of Wall’s time with the team. Remember, when he arrived in D.C. for his introductory press conference, the team literally rolled out the red carpet and anointed him the franchise savior.

While I understand the desire to have a PR and marketing splash, that was too much to put on a 19-year old kid with significant holes in his game. That star treatment persisted and made the job of coaching him more difficult than it needed to be.

What I know of Sheppard makes me doubt he’d cut one guy to send a message to another. He’s more direct and he’s a good communicator. I think if he wanted to send Wall a message, he’d just sit down and talk to him.

That said, I think everyone in the organization would be better by establishing a culture of accountability at all levels. Accountability encourages coaches and players to take responsibility for being the best they can be within the role they’re best suited to fill.

In my professional life, I’ve been through two organizational culture changes. It takes patience and conscious, intentional words and actions over a significant time period to generate the buy-in necessary to trigger the kind of transformation I think the Wizards need. It’s a tough job, especially with the team’s long history of futility.

Back to Wall for a second, I do think it’s important to say clearly that Wall isn’t an egomaniac who’s wrecking team cohesion. He’s human and has strengths and weaknesses like anyone else. Like anyone else, those weaknesses sometimes create challenges.

And, some of those challenges go straight back to management because the Wizards invested a ton of hope and salary into Wall as a player, but not as much in the personal and professional development that was necessary for him to maximize the job of being a franchise leader.

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In part two of the conversation tomorrow, Kevin and Yanir talked more in-depth on the Wizards’ off-season moves and more.