Dave Stewart’s transition from agent to Diamondbacks general manager was both brief and frenetic. Not afraid to make moves that bucked industry trends, Stewart’s regime aggressively moved young talent for veterans, seemingly placed a lower value on draft picks than other clubs and made what proved to be a pair of high-profile missteps on the international market as they set out on a clear win-now path.
In 2016, the Diamondbacks marketed an “evolutionary” year for the franchise following an offseason that was headlined by their stunning signing of Zack Greinke to a six-year, $206.5MM deal. That 2016 campaign did prove to be a major turning point for the organization, although surely not in the manner the front office had hoped; Arizona finished out the year with a 69-93 record that led to a swift front office overhaul and the dismissal of manager Chip Hale.
Here’s a look back at the two years of hectic wheeling and dealing under the watch of Stewart, Tony La Russa and De Jon Watson…
2014-15 Offseason
- Acquired RHP Jeremy Hellickson from the Rays in exchange for OF Justin Williams and SS Andrew Velazquez
- Acquired LHP Robbie Ray and 2B/SS Domingo Leyba from the Tigers in a three-team trade that sent SS Didi Gregorius from D-backs to Yankees and RHP Shane Greene from Yankees to Tigers
- Acquired RHPs Zack Godley and Jeferson Mejia from the Cubs in exchange for C Miguel Montero
- Acquired RHPs Rubby De La Rosa and Allen Webster and INF Raymel Flores from the Red Sox in exchange for LHP Wade Miley
- Acquired RHP Myles Smith from the Red Sox in exchange for RHP Zeke Spruill
- Acquired OFs Josh Elander and Victor Reyes and cash from the Braves in exchange for RHP Trevor Cahill and a Competitive Balance Round B pick (announced as two separate deals on April 2 and April 6, as competitive balance picks couldn’t technically be swapped until after Opening Day)
2015 Season
- Acquired C Welington Castillo, RHP Dominic Leone, OF Gabby Guerrero and INF Jack Reinheimer from the Mariners in exchange for 1B/OF Mark Trumbo and LHP Vidal Nuno
- Acquired SS Phil Gosselin from the Braves in exchange for RHP Touki Toussaint and RHP Bronson Arroyo (the Braves effectively purchased Toussaint by taking on the remainder of the injured Arroyo’s contract)
- Acquired SS Dawel Lugo from the Blue Jays in exchange for INF Cliff Pennington
- Acquired LHP Junior Garcia from the Astros in exchange for LHP Oliver Perez
- Acquired RHPs Matt Koch and Miller Diaz from the Mets in exchange for RHP Addison Reed
2015-16 Offseason
- Acquired C/OF Chris Herrmann from the Twins in exchange for OF Daniel Palka
- Acquired RHP Sam McWilliams from the Phillies in exchange for RHP Jeremy Hellickson
- Acquired RHP Shelby Miller and LHP Gabe Speier from the Braves in exchange for SS Dansby Swanson, OF Ender Inciarte and RHP Aaron Blair
- Acquired SS Jean Segura and RHP Tyler Wagner from the Brewers in exchange for RHP Chase Anderson, 2B Aaron Hill, 2B Isan Diaz and $5.5MM
2016 Season
- Acquired INF Luis Alejandro Basabe and RHP Jose Almonte from the Red Sox in exchange for Brad Ziegler
- Acquired RHP Vicente Campos from the Yankees in exchange for RHP Tyler Clippard
- Acquired OF Jason Heinrich from the Orioles in exchange for OF Michael Bourn
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How would you grade Stewart’s swaps as general manager in Arizona? (Link to poll for Trade Rumors mobile app users.)
Grade Dave Stewart's trades as D-backs GM:
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D 34% (2,291)
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C 30% (2,026)
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F 23% (1,549)
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B 12% (818)
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A 2% (143)
Total votes: 6,827
Curious to look back on additional GMs and their trade histories?
We’ve already polled on Diamondbacks GM Mike Hazen, recently fired Astros president Jeff Luhnow, Brewers president of baseball ops David Stearns, Angels GM Billy Eppler, Rockies GM Jeff Bridich, Tigers GM Al Avila, Braves GM Alex Anthopoulos, Blue Jays GM Ross Atkins, Mariners GM Jerry Dipoto, Phillies GM Matt Klentak, Padres GM A.J. Preller, Dodgers president of baseball operations Andrew Friedman, Rays GM Erik Neander, ex-Red Sox front office leader Dave Dombrowski, Mets GM Brodie Van Wagenen, Reds GM Dick Williams and Orioles GM Mike Elias.
Oh these comments should be lovely.
Lmao
uh oh
to be fair, Miller trade aside, i dont see any big issues here
They traded their 16th overall pick from 2014 one year later for only $10MM in salary relief. That’s brutal.
Touki was and is a pretty flawed prospect anyway. i think that was more a misplay in the draft if anything.
Agreed , Touki got electric stuff , just hasn’t harnessed the control yet
We could defend that statement, if Stewart’s own comments didn’t already show an error in critical thinking.
One of his many flaws in logic was that He thought since $10M was more than Touki’s bonus demand, it was a good deal.
Never mind that draft bonuses are artificially suppressed, and market demand isn’t.
He was horrible at running a front office. Maybe some of his deals didn’t blow up like they could have, but his logic and defense and thinking at the times of them are horrendous out of a front office executive moving assets for a billion dollar company. He was in way over his head.
I love how people talk about $10,000,000 as if it is just change found in the couch cushions. Even in the cartoon world of pro sports salaries, that was still a significant savings to their overall payroll.
Plus the forgotten guy in that deal, Phil Gosselin, was actually a decent bench player for Arizona for a year and a half. In fact as of right now, Gosselin supplied 1.1 WAR to Arizona. Touki -0.3 WAR to the Braves. So hen you factor in the cost savings, this deal might turn into a big win for Arizona.
That’s brutal.
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I liked the Braves’ side of the trade, but so far, AZ is winning that.trade.
You can just name the name, but it would hurt your argument. They traded Touki Toussaint for $10MM. The fact that Touki Toussaint is not good makes it a win, not brutal.
Not too good
oh lord…Hey Steve!..I would’ve ‘accidentally’ left the Shelby Miller trade out of the list and hoped no one noticed ha!…Here comes the arguing lol
It’s funny, he made a few decent-to-good trades, but the trades he lost were so terrible that it totally negates any positive trades he made. I gave him a D, but can’t fault anyone for giving him an F.
He made a couple of solid under the radar trades like picking up Dawel Lugo for Cliff Pennington. And then he picked up Ray and Leyba for Didi. But the Shelby Miller trade was brutal. Never really looked too good. Moving on from #1 overall picks early in their careers is usually not a good plan. Enciarte has always been a solid CF.
Has any other team actually moved on from a #1 overall pick that quickly? Maybe it happened… but definitely not in a very long time.
Closest thing I can think of was Moncada for Sale. Moncada was the consensus top prospect I think at the time… not a #1 pick. But the Red said had him for what? 2 years before they traded him? And they landed a perennial Cy Young candidate.
I mean the Miller/Swanson trade was stunning when it went down.
Exactly. I think DD saw a window to win arising with the Yankees nipping at their heels and cut Moncada loose to pry Sale to capitalize.
I think the Miller/Swanson trade was an attempt to do something in the same vain as the Chris Sale Red Sox trade. Problem is that Miller never had the extended track record that Chris Sale had at the time of their trades. Yes, Dbacks got fleeced but another thing to think about is that Swanson is not a star. He is an above average big leaguer but not a star.
When you’re saying “at least he’s not a star” as your best defense of a trade though…
It really feels like Stewart didn’t look at anything past Miller’s ERA. In the two seasons before the trade, Miller had a 6.9/3.4 K/W, and I seldom see much success with that ratio. In addition, Miller’s 2015 season was the result of a great start, poor finish. After 7/5, Miller had an ERA of 4.10 and a K/W of 83/39 in 96.2 IPs.
There is nothing wrong with that, unless you are tagging him as an ace.
give him a little credit – that’s a solid D
That’s what she said.
Well done sir.
This guy has been trash as a GM.. Part of the problem was his conflict of interest as an agent., when he gave the keys to his agency to his wife and allowed her to run it (which is another story). He signed a number of his own guys who, quite honestly, didn’t deserve the value of the contracts they received. Scumbag move and a terrible move for the Dbacks. Very good player, very bad GM, average agent. I’m afraid his performance as a GM tainted his lifelong contributions to the game.
Random thoughts:
I note that Dave Stewart’s name does not pop up on any GM short lists in conjunction with openings;
I’m not 100% certain, but I fear LaRussa is a consultant with the Angels. Arte Moreno and Tony LaRussa, a match made in heaven… and Billy Eppler’s wildest nightmare;
Thank goodness for MIKE HAZEN.
His legacy will be the Miller-Swanson trade, much like Steve Phillips’ legacy is the Zambrano-Kazmir trade (which was actually made by his successor Jim Duquette).
Rumours was the Mets we’re looking at Jose Cruz Jr in 2002 and offered the Blue Jays David Wright. JP Ricciardi declines and never dealt Cruz. Mets dodged that bullet. Maybe Keith Law advised JP to avoid Wright. Wouldn’t be a shock.
I think Stewart gets a little too much flak for the Miller deal. Sure, Shelby Miller was a colossal flop in Arizona, but no one knew he was going to fall off the Earth like that. He was an excellent All Star caliber pitcher when he as acquired. And honestly, the Braves return has not been THAT spectacular. Swanson has been just OK, Inciarte is a good defender, and Blair flopped. Yes, the Braves still did better, but it’s not nearly as great as people make it out to be. I believe the two Cuban signings were much worse than the Miler trade overall, but other clubs (Dodgers, Braves, Red Sox) made similar mistakes with Cuban signees.
Dave Stewart was not a good GM, but he definitely was an interesting one.
He was wildly entertaining. I miss having characters like him running clubs. He was outspoken, valued players in a completely different way than more analytical clubs … it helped keep things fresh and unpredictable when there were a handful of GMs who still had different approaches.
I’d disagree on the Miller point, though. While no one knew Miller was going to completely turn into a pumpkin, his 2014 season appeared pretty unsustainable at the time. He basically had two crazy good months with a .150 BABIP and then went back to pitching like a mid-rotation starter.
Regardless of the results, Swanson had enormous trade value at the time of the deal. He was barely six months out from being the No. 1 pick and was a top 10 prospect in all of baseball. And Inciarte had put up 8 WAR over two seasons with four years of club control remaining. Blair had value as a pitching prospect as well.
At the time of the trade, those three assets should’ve commanded an astonishing haul if they were to be moved in conjunction. Getting three years of Miller back in return didn’t qualify. It wasn’t even clear that the D-backs were a better club by swapping out Inciarte alone for Miller.
Should be five years of Inciarte** whoops
Miller was only 2 years removed from being a top 10 prospect himself. If I am not mistaken, he was the #6 overall prospect in the game, just ahead of Jose Fernandez. So it is understandable to think that Miller had not yet peaked, even if some of his numbers did suggest a regression. Regardless, I don’t think many people considered him to be a mid-rotation starter as a peak value.
As far as trading a top prospect like Swanson, Arizona had already set a precedent with trading a high draft pick early with Trevor Bauer. Yes, it was a different GM, but it was the same ownership. I’m not saying it was a good idea, but trading him wasn’t against type for the franchise.
lol Bauer was traded for another highly regarded rookie in Didi Gregorius. He wasn’t traded months after signing either. He was in the major leagues when they dealt him. This deal was ridiculous. The Dbacks are fortunate it only bit them this much
In no way whatsoever was Didi Gregorius anywhere near the prospect level of Trevor Bauer. He was a decent middle infield prospect, but Bauer was TOR potential. In hindsight, it looks like a fair deal since both prospects successfully acclimated to MLB, but at the time it was a case of Arizona giving up a much better prospect simply because thy didn’t like his quirks.
This is patently false. Gregorius was a highly rated prospect and Bauer’s ranking was sinking because his performance was not coming close to measuring up to expectations. And, in fact, it took him until he reached his age 27 season before he did approach those expectations. Just in time to become expensive. And it wasn’t simply because they didn’t like his quirks. it’s because he had become a cancer in the clubhouse and the veteran leaders on the team couldn’t stand him. The trade looked perfectly fine both at the time and in hindsight.
Entertaining for you, embarrassing to Dbacks fans.
What about his pick up driving in LA back in day
I loved Stew as a pitcher, but he seemed to struggle as a GM. Too bad too because he seems like an awesome guy.
Please keep in mind that during that time the D-backs had 3 GM’s in 6 years… (2 years each) expecting each one of them to turn the team around in two years. Very difficult. It seemed as though all the crap rolled down hill. All the moves that Dave Stewart made had to be approved by Tony Larussa. However when they started to clean house Dave Stewart was fired and La Russa remained. They also felt the need to let go Watson. Let’s not forget that Watson put together that Dodgers team that continued to make it to the playoffs, so I wouldn’t say that he was incompetent either.
Dave had a 3 year contract with the D-backs, with the third year paying the most money. They let him go after the second year… Now hear is part that is not mentioned. The year after Dave Stewart was fired the D-backs went to the playoffs for the first time in a while and it was the very same team that Dave Stewart put together with approval from LaRussa and help from Watson. And Dave got no credit at all, not once was he mentioned and that was the team he put together and it would have been the 3 rd year of his contract…. Everyone talked about crappy moves and trades, but it all came together, and it came together in the time frame of his original contract of 3 years…. So everyone wants to give him an F or a D but refuse to admit the team that went to the playoffs was his… So he gets a B
They went to the playoffs in ‘17 because Hazen brought in JD Martinez who went on a tear and carried the team to the playoffs. Hazen also traded for Taijuan Walker who put up 3+ WAR. The only key contributor to that team brought in by Stewart was Robby Ray. Grienke did well, but that contract should have never even been offered. Sorry but Stewart/La Russa were a dumpster-fire and made AZ the laughing-stock of the league.
Drafting Swanson over Bregman was the worst move, but I think they had the Shelby Miller trade already in place cause Swanson was from there. Wish we had Bregman, tho he is kind of a weasel lately with his comments or lack of sincerity.
Trade History not draft history.
He was making a point with the front office. I am certain he knew this was a trade history article. Simmer down there Jax.
Drafting Swanson over Bregman was the worst move
Yeah. Of all the trades mentioned. Him drafting Swanson was the worst move.
Glad that point of drafting was brought up. Really affects his trade grade.
We really need to work on your reading comprehension man.
Pointing out things you failed to read yourself is a sign you might need to practice reading skills.
I guess the point is, yeah he was a bad GM, but trading wasn’t the biggest reason why when you look at it overall?
The point of showing you’re a knob was the fact you do not read or comprehend. But thank you for your input. Off the mark as always.
Swanson was drafted so they could trade him.
Swanson was not drafted just so they could trade him.
And by the way they passed on Bregman to go with Swanson! Yikes.
Swanson was the consensus top pick in a weak draft. You can’t really begrudge them taking him #1.
Swanson being “from there” had zero to do with the trade or them passing on Bregman to draft Swanson.
I honestly don’t see how Stewart is getting such terrible ratings in this poll, unless people aren’t separating his job as GM overall from what the question actually asked about, his trade history.
The Miller deal was awful, even at the time it was struck. He was fooled by half a good year. And… that’s about it. Getting Lugo was good, getting Ray was good. I even think the Godley-Montero swap was a good trade at the time, though Godley didn’t turn into much. Touki looked like a bad deal when it happened, but given that he hasn’t turned into anything it hardly hurt them. Everything else is pretty meh on both sides.
Dave Stewart as a GM? D. Dave Stewart’s trade history as GM? C at worst in my opinion.
Good points JB
Dave Stewart is a nice guy, was brutal as a GM, but at least got to experience what was said at the time to be a major professional ambition. Tony LaRussa was exposed, too, as way over his head in terms of player evaluation. But he was always confident to the point of arrogance (Google his confrontation with Pirates broadcaster Greg Brown). In their short history Dbacks have gone through a lot of GM’s and have had some awful ones and some outstanding ones (late Kevin Towers the former best). But the team is now fortunate to have Mike Hazen – top GM in MLB.
They were so bad that the only roster Hazen has won 90+ games with and gained a post season birth was their roster, not his.
The only people giving him A’s are Giants and Dodgers fans
This guys logic when making trades was awful.
I mean, using the were logic by its strict definition there… cause it seems there wasn’t a lot of logic going into them
Quick question:
Are we grading Stewart in terms of trades for the Diamondbacks or for the benefit of the other teams?
I’m going with F- on the former, and A on the latter.
Lol
I gave his body of work an F, the best I could see would be a C, based more on his personality and reputation. Great guy, by all accounts, it’s just Stewart’s losses were so bad, I just couldn’t get past them.
You really take the genius of guys like Cashman for granted when you see so many swings and misses from other GMs in this series.
Lot of really bad deals on this list. Some not as bad as they seemed at the time… but even still I question them. Seems more left the team and became successful than came to the team and were successful
What’s all the fuss and low scores, Dave Stewart is the best GM the Braves ever had..
I don’t know why I’m saying this…
but can you evaluate the trade history of Neil Huntington??
Honestly not as bad as I remember. Not great, but not as bad as Bridich and he still has his job lol
I call Dave Stewart “the Destroyer” he practically destroyed an organization. Then they brought in a GM who actually knew what he was doing in Mike Hazen. It’s unbelievable how fast Hazen managed to fix things.
As a Giants fan, Hazen seems like a wizard. He inherited a huge mess, and the D-Backs were back to relevance only a few years later. Now I’m hoping Zaidi does the same for my team.
Yasmany Tomas was a low point among low points. It felt weird signing Grienke. While I liked pretending our team could play at the high stakes table, I felt really uncomfortable doing it, like we didn’t belong there.
I grade him an F because no one could do worse. His failure just shows how amazing Hazen has done to maintain winning and avoid a major rebuild in spite of so many bad contracts and historically bad decisions.
Dave Littfield disagrees
I think people poo-poo the Toussaint trade but need to remember that Touki was a much-hyped arm and the Dbacks just gave him away to get rid of Bronson Arroyo’s contract (who was hurt at the time). So Stewart gave away 6 years of controlling a top-level prospect to save $10m… that ALONE should get you laughed at and fired.
Dave Stewart was also the author of the best post-firing quote by a GM: “I’ve got better things to do”
Braveswould give touki back if the snakes will tale Melancon.
The worst part of the Miller trade was the rationale behind it.
They signed Tomas, but didn’t really have anyplace to play him. Goldschmidt obviously wasn’t going to move. Lamb got derailed by splits and injuries, but he was a #75-80 prospect coming in,
Once he made the mistake of signing Tomas, he was almost forced to make a second mistake. The second mistake should’ve been trading Lamb.
But instead, he broke up a fine young outfield in Pollack, Inciarte, and Peralta. They were the #1 OF in BB in 2015, and his instinct should’ve been to keep them intact for the next 5 years.
But replacing Inciarte with Tomas, in RF, was as bad a decision as he could make. I wasn’t the only one to notice, as other BB fans thought that adding Miller, and replacing Inciarte with Tomas, made AZ worse, not better.
So they traded their 1-1 and a decent prospect in Blair, and 5 years of Inciarte, they really had no expectation of improving the team.
That’s what makes it a classic BB blunder.
D is about right wow the public is smart! The Shelby Miller trade really sticks out. Swanson never should have even been discussed in that one. When that trade happened I remember by first thought, “stupid” but I value a good prospect more than dave stewart.
fun stuff – Stew was indeed entertaining – and, by all accounts, a truly good guy. but the grading here suffers from a fatal flaw known as “outcome bias” i.e. judging the decision-making process solely by a subjective and/or naive ‘win’ vs. ‘lose’ outcome. What we should be focused on is the extent to which, if any, the original objective of a trade or trades is achieved. Of course, in the case of Stew and TLR, it was not always clear just what the specific objectives were. in the case of dumping the Arroyo contract, sure, that was the objective, but there surely were others and a proper gradeis impossible to assign without taking those other objectives into consideration. My greatest concern with the Diamondbacks going back to the KT admin, was the organization’s systematic undervaluation of inexpensive, controllable talent and the embedded options therein. As a self-assigned middle-payroll organization, they dug themselves a serious whole from which to climb out of. TGFH (thank God for Hazen).