The funny/ironic thing is that attending the Stewart Ceremony is almost the perfect indicator of the future awaiting Sox fans if someone who couldn't handle a GM-like role properly with the DBacks was for whatever reason given control of those decisions in Chicago almost a half decade later.
Ranking the five worst moves of the Dave Stewart era with the Diamondbacks - CBSSports.com
The five biggest gaffes of the Tony La Russa era with the Arizona Diamondbacks - AZ Snake Pit
Yasmani Tomas and Yoan Lopez have to go here somewhere as well...
1. Making Tony La Russa Chief Baseball Officer (May 17, 2014)
It seemed a wise and popular option at the time, James Parziale of Fox Sports saying, "It's hard to view La Russa's presence in Arizona as anything but a huge win for the organization." But it was a radical departure from normal front-office structure, effectively creating an entirely new level for La Russa: it’s this at which (Derek/Derrick) Hall’s "too many cooks" (GEE, THAT DOESN'T SOUND REMOTELY FAMILIAR, NOW DOES IT???) comment seems aimed. It was also a position with which La Russa was inexperienced, having no front-office experience. While there’s no denying his managerial skills, after 33 years in the dugout and more MLB games than any other living person, what transpired shows they don’t necessarily translate to the front-office, any more than great players automatically become great managers.
#2. Hiring Dave Stewart (Sep 25, 2014)
Before this season, Stewart was asked about the PECOTA projections. "Think we only win 78 games? That’s a joke." Turned out the joke was on him, as the team fell nine games short of that mark. I never thought D-backs fans would look back on the Kevin Towers era with nostalgia. But for all his flaws (not least of which was a large mouth), Towers at least knew the role and how to handle the processes. In early 2015, Stewart reportedly "tried to make a trade with another team that would have violated MLB rules, and the GM of the other team had to explain to him that such a move was not allowed." Stewart’s lack of experience was painful, and often exploited.
#1 The Shelby Miller trade (Dec 9, 2015)
Really, Dave? A trade about which, for example, Yahoo’s Jeff Passan said at the same time, it "has a chance to go down as one of the worst trades of the last 25 years"? That’s doubling-down and going all in. Got to admire the guts there. The intelligence? Less so. Because if true, it demonstrates an abject failure to learn from mistakes (ideally, other people’s, but more importantly your own). Mind you, it could have been worse, considering there was discussion with the Marlins about Jose Fernandez; Miami wanted A.J. Pollock and Patrick Corbin. If subsequent events had all still occurred, that would have been quite the steal for the D-backs in 2016... Not so much, going forward.
It’s interesting to imagine an alternative timeline, where La Russa was not hired. It’s likely this would have led to someone other than Stewart taking over as GM, and in turn that makes #3-5 probably evaporate. Perhaps, say, the team goes with Mike Hazen as GM, two years earlier. Simply by not doing anything, never mind making any positive moves, the team would likely be little or no worse off in the standings, and would certainly have a much better future.
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