The five biggest gaffes of the Tony La Russa era with the Arizona Diamondbacks

In some ways, this counts as stating the obvious. Going into the 2015 season, the D-backs were in a bad spot, but had a chance to make a quick turnaround. They were coming off a 64-98 season, but had a farm system ranked 6th-best in the majors by Baseball America, with half a dozen names listed in the top 100 prospects, and were about to add to it, with the #1 overall pick in the June draft. They had just signed a new TV deal with Fox Sports Arizona, with a total value of $1.5 billion, including an equity stake in the network, which was expected to finance a payroll that would be capable of competing with the Giants and Dodgers.

Two years later, the team is barely any better, the farm system has been stripped to the point some now rate it dead-last, without a single D-back in MLB.com’s top 100 prospects. This season, $43.5 million, over 40% of current payroll - which really has not increased, despite the TV deal - is committed to Zack Greinke and Yasmany Tomas, who combined for less than two bWAR last year. The team has been unable to take part in the international market, due to blowing past their limit by signing Yoan Lopez, who looks a bust. And that #1 overall pick was dealt away in a deal for a pitcher who spent so long down in the minors, 2016 basically didn’t count on his contract.

I think it’s safe to say: yes, mistakes were made. The wholesale firings within the front-office at the end of last season are testament to that. But I think this is perhaps the first time we’ve heard team president Derrick Hall come out and directly say so. It’s perhaps interesting to speculate precisely what the team might have "done differently" though. Cranking back the time machine, we might even need to go back a bit further to find the fork in the road. Here are my picks, in chronological order, of the five things the team probably should not have done.

#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 Hall’s "too many cooks" 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.

#3. Signing Yasmany Tomas (Nov 26, 2014)

This could end up higher or lower, depending on what happens going forward. But so far, Tomas has just not delivered like an experienced major-league player - despite being paid like one. So far, he has received $13 million, and been 1.5 fWAR and 1.8 bWAR below replacement level. This and the next one both feel like Stewart succumbed to an "everybody’s doing it" mentality about signing Cuban ball player, in the wake of Jose Abreu winning Rookie of the Year in 2014. But as we’ve seen, for every Abreu, there’s a Rusney Castillo - and, thus far, Tomas hasn’t even produced at Castillo’s level. There’s still some reason for hope (more on which tomorrow), but 2017 feels like the last-chance saloon for Tomas.

#4. Signing Yoan Lopez (Jan 13, 2015)

The D-backs signed Lopez for an $8.25m bonus, the largest ever to an international amateur player. It blew way past the MLB limit, blocking them from significant action for two years. And in the 2015-16 cycle, we would have had the biggest available pool, due to our MLB-worst record in 2014. They also got hit with virtually the same amount in overage tax: scuttlebutt has it, this was an unpleasant surprise, perhaps factoring into the "sale" of Touki Toussaint, to get Bronson Arroyo’s contract off the books. And Lopez has been a disaster, with less than 120 innings of work, an ERA over five, multiple absences and a Snapchat video saying, "No mas D-Backs; ahora Miami Marlins."

#5. 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.