Record and Background

Age: 47

Previous Organizations:
Boston Red Sox, 2003-04: Scout
Colorado Rockies, 2005: Head of scouting department
Arizona Diamondbacks, Oct. 2005 – Oct. 2011: Director of scouting and player personnel (with stint as interim GM from June to September 2010)
Los Angeles Angels of Anaheim, Oct. 2011 – Jun. 2015: General manager

Current Status: Free agent
Cumulative Record: 306–262 (excludes interim tenure with Arizona)
Playing Career: Pitched nearly 500 innings as a reliever for the Indians, Mets, and Rockies in the 1990s. Was an above-average pitcher, though never a dominant one. Closed for parts of three seasons.

Personnel and Philosophy

Any notable changes from previous regimes?
In Arizona, it seemed as though the Diamondbacks' impatient management group installed Dipoto specifically to do the dirty work his ousted boss, Josh Byrnes, had refused to do. Tasked with cutting payroll and laying positive groundwork with which his permanent successor might work, Dipoto did a brilliant job in three notable July trades. His substantial professional playing career and player-development background gave him a different air than Byrnes had carried in his day-to-day work, and his presence and decisions set the stage for the team's transition to a very different paradigm going forward.

When he took over for Tony Reagins in Anaheim, however, Dipoto struck a somewhat different chord. The creeping narrative in the lead-up to Reagins' dismissal had been his staff's lack of analytical acumen, highlighted especially by the trade early in 2011 that had sent Mike Napoli away and brought back the onerous contract attached to Vernon Wells. Perhaps sensing what needed to be projected, Dipoto (no enemy to numbers all along) played chameleon and set a sabermetric tone in his new front office (which he also stocked full of his own people). He was even known to conduct his own internal studies, of varying degrees of sophistication.

What characterizes his relationship with ownership? What type of people does he hire? Is he more collaborative or authoritative?
Here again the term "chameleon" might apply. Dipoto followed Byrnes to Arizona after working with him in Boston and knowing him during his playing days (and Byrnes' time in the front office) in Colorado. They were close, yet Dipoto took the post from which Byrnes was unceremoniously swept. That's not an indictment of Dipoto's character; it's just interesting. So is the fact that Dipoto stepped right back into a different role with the Diamondbacks after his stint as interim GM and remained there for a year.

Yet the reason he's currently looking for a job is that he ultimately clashed with Angels owner Arte Moreno. Maybe it's better to say that he clashed with manager Mike Scioscia, and that he simply left over what he felt was inadequate support from Moreno. In light of the general esteem in which insiders and those who have worked for Dipoto apparently hold him, the best interpretation might be that he offers full and far-reaching loyalty to his higher-ups, but demands the same in turn.

With a bunch of seats to fill in the Angels' front office upon taking over, Dipoto set about staffing up with former players like himself. Hal Morris, Scott Servais, and Gary DiSarcina were among his first and most trusted hires, though he also retained and promoted the Angels' incumbent statistical chief. By all accounts, Dipoto likes to gather and share information in as collaborative a setting as possible, which became part of the problem between he and Scioscia.

What kinds of managers does he hire? How closely does he work with them?
Dipoto has never hired a manager. It seems safe to assume that he was part of the decision to insert Kirk Gibson as interim manager when he took over as interim GM in Arizona as well as the decision to retain Gibson on a permanent basis, but he has not undertaken his own managerial search and made a fully independent hire.

As for the closeness between Dipoto and, most importantly, Scioscia, that seems to have been at the crux of the conflict between them. Dipoto wanted a cooperative relationship that would allow him and his baseball operations staff to communicate directly with players and provide Scioscia with more information about pending decisions, but Scioscia bristled at that, and implicitly sided with players who rebuffed those efforts directly.

Player Development

How does he approach the amateur draft? Does he prefer major league–ready players or projects? Tools or performance? High school or college? Pitchers or hitters?
Though Dipoto was a player-development guy, not principally a scouting guy, and though he ran only four drafts as Angels GM, he and his staff established an extremely clear set of preferences in that arena. They love college players, especially college arms, and they much prefer players close to the majors, with high floors, over those who offer more risk and greater potential reward. It's possible these preferences were the expression of a strategy formulated to respond to the fact that they often did not have a first-round pick, thanks to aggressive free-agent spending, but they even went with college players when they did have top-level picks.

Does he tend to rush players to the majors or let them marinate?
With a few notable exceptions (such as 2012 ninth-round pick Michael Roth, who pitched for the parent club in April 2013), Dipoto and his staff have allowed players to take a longer developmental arc without penalizing them in any apparent way in their assessments. The strong performances of older-than-usual rookies were a hallmark of recent Angels teams, especially last year's division champion (Matt Shoemaker being the obvious example).

Roster Construction

Is he especially fond of certain types of players? Does he like proven players or youngsters? Offensive players or glove men? Power pitchers or finesse guys?
In 2014, Dipoto took pride in putting together an Angels bullpen that couldn't be pigeonholed, especially by opposing hitters. They gave teams many different looks and used many different primary skill sets. Dipoto also seems to target left-handed pitching prospects who have shown promise, but aren't yet established big-leaguers. In what is really a very short career to date, he's traded for Tyler Skaggs (twice), Patrick Corbin, David Holmberg, and Andrew Heaney, all while their rookie status was intact. It's not totally clear that Dipoto considers lefties (or specifically lefty starters, or specifically lefty starter prospects) some kind of market inefficiency, but there's something there. He's also acquired Jason Vargas, Hector Santiago, and Joe Saunders in trades, and signed C.J. Wilson as a free agent.

That's a bit strange, of course, because (conventional wisdom aside) being a left-hander is a disadvantage for a starting pitcher. Dipoto values the trait highly, though. On the other hand, being a solid veteran pitcher with little upside but a high reliability score (a good thing, by most accounts) is no way to impress Dipoto. He's happy to take chances on prospects and projects (like the ones listed, plus low-level signings like Joe Blanton and 27-year-old rookie Shoemaker), but he's quick to move on from pitchers whom he believes have begun permanent decline, even if that doesn't turn out to be true (as in the twin cases of Dan Haren and Ervin Santana, in late 2012).

On the positional side, Dipoto has notoriously chosen bat over glove a few times. He traded for Matt Joyce and David Freese. He sent Peter Bourjos packing in order to acquire Freese, which is about as clear a statement of prioritizing offense over defense as a single transaction can make. One of his first maneuvers upon taking the reins in Anaheim was a pair of deals that effectively replaced Jeff Mathis with Chris Iannetta behind the plate. He has also traded away the likes of Kendrys Morales and Mark Trumbo, who were so bereft of non-hitting value that they no longer fit his rosters, but in general, he's an offense-first team builder.

Does he allocate resources primarily on impact players or role players? How does he flesh out his bullpen and bench? Does he often work the waiver wire, sign minor-league free agents, or make Rule 5 Draft picks?
Here, again, it's important to establish that we don't know to what extent Dipoto has ever had full autonomy in choosing his direction or his targets. He's been a pretty heavy hitter, adding the likes of Albert Pujols, Josh Hamilton, and C.J. Wilson to his roster over his first two winters on the job in Anaheim. That's led to some top-heavy rosters. Of course, the general consensus is that those deals came at the urging—if not the outright order—of Arte Moreno. It's not clear whether Dipoto would have built a team in precisely the same way, if given the keys and left alone; in fact, some of his other moves suggest otherwise. He's willing to try scrap-heap finds sometimes, as when he gave significant playing time to Raul Ibanez, or this year's experiment with Johnny Giavotella at second base. He seems to enjoy taking risks, at least at the margins, rather than shelling out his last dollar to grab a player with name value just to plug a hole.

When will he release players? On whom has he given up? To whom has he given a shot? Does he cut bait early or late?
Hamilton is the most important and obvious case study in this area, but that's a frustratingly unclear situation. It's perfectly possible (even probable, given what we know of him so far) that Dipoto wanted nothing to do with Hamilton, and was forced to deal with him at Moreno's insistence. It's equally possible (though less probable, reading his quotes at the time) that Moreno also forced Dipoto to foist Hamilton off on whoever would take him, regardless of the cost or return.

That doesn't absolve Dipoto of the poor decisions that were made, first to acquire Hamilton, and then to trade him for peanuts. A good GM wins arguments, sometimes even arguments with his owner. Dipoto either lost the one about Hamilton, or he never had it. Either way, that's a black mark on the record of all involved.

As I mentioned above, Dipoto has a tendency to cut bait on veterans in whom he no longer sees untapped potential, especially on the pitching side. He has a long fuse when it comes to cutting players with track records when they experience extended failure, but he doesn't create relationships with such players voluntarily. Bourjos and Hank Conger can attest to the fact that he won't wait forever for a player to develop, though it may also be that he recognized the futility of keeping each player if Scioscia had no interest in allowing them a prolonged chance to impress someone.

Is he active or passive? An optimist or a problem-solver? Does he want to win now or wait out the success cycle?
Again, parsing his ideal balance of long- and short-term planning is impossible, given his experience to date. He's been aggressive at every opportunity, dealing from a relatively weak system to add Zack Greinke at the trade deadline in 2012, optioning struggling players and adding new parts to his bench that might entice Scioscia to sit those whom Dipoto can't actually remove from the situation. He had marching orders in Anaheim, but nonetheless, he looked the part of a win-now pusher.

Trade and Free Agents

Does he favor players acquired via trade, development, or free agency? Is he an active trader? Does he tend to move talent or horde it? With whom does he trade and when? Is he willing to make trades with teams during the season? How does he approach the trading deadline?
For a guy without a lot of time logged behind the GM's desk, Dipoto can put his name next to some significant and fascinating trades. He's a willing and eager wheeler and dealer, not only at the big-time levels (the Greinke and Haren deals), but on the fringes (e.g. his addition of Gordon Beckham last summer or the swapping of Ernesto Frieri and Jason Grilli). He was able to trade a year of Howie Kendrick for six years of Heaney, and he did so within hours of the Dodgers landing Heaney, even though he had no ready replacement for Kendrick. He uses trades to take chances on players whose upside intrigues him, as when he traded Jordan Walden for oft-injured former phenom Tommy Hanson. He even did a rather nifty three-way deal, the one with the White Sox and Diamondbacks in which he got Santiago and Skaggs for Trumbo. Few executives are more willing to jump on a deal they and their staff believe is an upgrade, even if they need to turn around and do another deal (or two) to keep their bases covered.


Does he prefer long- or short-term deals? Does he backload his contracts often? Does he like to lock players up early in their careers, or is he more likely to practice brinksmanship? Does he like to avoid arbitration?
We all know about the Pujols, Wilson, and Hamilton deals. Beyond those, though, Dipoto was a fairly conservative investor with the Angels. He seems to prefer having a good deal of year-to-year flexibility, at least around a locked-up core, so that he can reinvent the team if a given model doesn't work.

Anything unusual about his negotiating style? Is he vocal? Does he prefer to work behind the scenes or through the media?
For a former player, Dipoto is pretty frank about the things that sometimes hold up deals with current ones, and about his own players' flaws. He's not infamous for it or anything, though, and doesn't seem to have earned any particular reputation for style at the bargaining table.


What is his strongest point as GM?
By many accounts, Dipoto is utterly beloved by those he hires and maintains as an advisory group. That's very valuable. He's also good, it seems, at making objective evaluations, if not always statistical ones. Trusting those around him and using the information they provide to make the most optimal, rational choice he can is Dipoto's forte. It's a combination that is sometimes hard to find in baseball men, and eminently hard to find in former players.

If he weren't in baseball, what would he be doing?
¯_(ツ)_/¯. This is a former player who does studies on baseball for fun. There are only a handful of more vociferous baseball rats in GM chairs right now.

Thank you for reading

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I love these GM in a Box write ups. Great stuff.
Owner in a Box writeups would also be good - even if there is no chance that it affects anything
I suppose he is a free agent in the sense of not being a sitting GM, but isn't he part of Boston's front office at the moment?
between him and Scioscia