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How San Diego Padres' A.J. Preller, other MLB GMs decide when to go for it

Orlando Ramirez/USA TODAY Sports

The Aug. 31 MLB trade deadline was exhilarating if you were a San Diego Padres fan, and some version of frustrating or anticlimactic if you were an Atlanta Braves fan. While the short-term takes about deadline winners and losers have come and gone, it might be more instructive to take a step back and consider from a 30,000-foot view of what each team's general manager is trying to accomplish.

That might seem a little high-minded -- the vast majority of GMs are just trying to win, right? -- and you're correct to think that, but there are some important stylistic and strategic variations under that "win some games" umbrella. We'll chart out the different approaches, slot each team based on where it fits and draw some conclusions about the pros and cons of each strategy.

Mindset and risk tolerance

The first concept I'll use to categorize GMs is the spectrum of decision-making from progressive to traditional. Broadly, progressive means that data (advanced modeling, TrackMan/Statcast numbers and the like) drives the majority of decisions, while traditional means that scouting, player makeup and other methods that have been used for decades drive most decisions.

This is the evolution of the tired "scouts vs. stats" argument. No club is 100% on one extreme and no club thinks the side it leans away from is useless, so that isn't a debate anymore. Classifying teams can be tricky since it's somewhat common for departments within clubs to be on different parts of the spectrum -- a progressive club can lean hard on analytics in the big leagues and lean to traditional methods when scouting 15-year-olds in Latin America, as the depth and quality of the analytics differ wildly in each context -- but in this era, GMs have more control and influence across departments than ever before, so the tendencies don't vary much within individual organizations. More than a few GMs made every pick for their clubs in this year's draft, and that was unheard of a decade ago.

Eric Longenhagen and I created a grid with this traditional/progressive spectrum on the X axis in our book "Future Value" and, at first, we thought it would be hard to pin down. After consulting with people in the game, nobody quibbled more than a notch or two (on a eight-point scale) despite the subjective nature of the grades. The people who work in front offices know what information is driving decisions and which staffers have the most pull with management, so it's not hard to then figure out which clubs are using what sort of information in making those decisions, while it's almost impossible to prove it objectively by just looking at the transactions log.

I use that on the X axis for this exercise as well, while the Y axis represents risk tolerance. The risk-tolerance values also are subjective and apply across a number of departments. This becomes useful when a club is rebuilding, doesn't have veterans to trade and isn't active in free agency. In that case, the types of players a club targets in its small amount of trades or free-agent signings can inform a risk-tolerance grade, while the way it uses its capital in the draft and international markets largely defines its risk tolerance.

Here's the grid as I've put it together in consultation with sources around the league (click here to enlarge):

You can probably see the big trend I'm going to focus on: Outside of a handful of exceptions, the trend line is clearly down and to the right, meaning that clubs largely have less tolerance for risk the more they lean on analytics in their decision-making. Another way to read this is as a BuzzFeed quiz "What GM Style Are You?" because if you'd be on the opposite end of this graph from your favorite team's GM, you're likely frustrated with him constantly.

I don't think this relationship is a universal truth across other sports or other industries. Baseball is uniquely set up to encourage a lower-risk approach, with clubs having six-plus years of cost control over young players and no one player being able to define a team's success or franchise's value, not to mention the inherent luck in the short-run playoffs. It's defensible to look at success for a baseball GM in terms of his team's odds of winning a championship over a long-term window, rather than the odds of winning in any particular year.

The upper left: old-school go-getter

In the upper-left quadrant, we have almost all of the traditional clubs in baseball, which is anywhere from 10 to 15 teams depending on where you draw the line. The broad idea here is that the information driving decisions is largely found in scouting reports and these clubs are overwhelmingly willing to make bold moves based on what these reports say. By their nature, these reports can vary a lot by scout, whereas statistical models are very similar from club to club. Higher risk tolerance, or higher confidence, is typified by handing out a big contract in free agency, regularly shopping at the top of the July 2 market, making trades where you receive one or two players instead of four or five, targeting over-slot players later in the draft and mostly paying full freight for the best available player at high picks in the draft.

Using the San Diego Padres under A.J. Preller as an example, there are some clear positives and negatives to this approach. This confident approach leads to bold player acquisitions in all markets, which, when combined with an above-average ability to pick players, results in one of the best farm systems and young cores in baseball. When it's time to flip the switch and become a contender, there will be all kinds of activity to bust open that window of contention. This also can lead to telegraphed, slow-motion car-crash decisions such as the $144 million Eric Hosmer contract and the Wil Myers extension, along with the ill-advised go-for-it moves that came before Preller tore it down to create what the Padres are now.

There was a period between the teardown and the present phase of building a contender when Preller didn't make many trades (he was 28th out of 30 GMs in trades per year from 2017 to 2019) because the roster was mostly marginal veterans and youngsters who needed time to improve. Looking at the precedent-setting amount the Padres spent in the international market and the swaggering way San Diego moved money around every year in the draft revealed that the inherent tendencies hadn't changed, the action was just happening under the radar in less publicized areas.

The bottom left: tentative gut feels

With the inherent tendency to be bold when a club is traditional, the bottom-left quadrant is the least populated corner and no team is very deep into this area. The Texas Rangers are the best example, as the Chicago Cubs and St. Louis Cardinals have big league payrolls that are maxed out and generally pick later in the draft, so their lack of bold moves is in part forced and might change soon.

Texas was aggressive and traditional to strong success in the amateur markets when Preller was Jon Daniels' scouting czar, but the hit rate went down after Preller left. The Rangers have gone with lower-upside college hitters in the past few drafts as part of a more conservative approach. Combine that with a lack of major prospect breakthroughs, a rash of surgeries for pitching prospects and Joey Gallo being the only emerging young core player in the organization in years, and the talent base is down dramatically. On top of this, the big league team hasn't had much direction, handing out sizable contracts to veterans and refusing to sell high on Mike Minor and Lance Lynn thanks to what sources have told me are very unreasonable asking prices.

There is a lack of clear direction in any department in the Rangers organization, a lack of aggression due to the lack of direction, and no clear competitive advantages to leverage. All of which sums up why Texas is in such bad shape right now. On top of all that, the new stadium hasn't drawn a fan yet and the payroll is above league average without the associated revenues for it to go any higher. It's hard to succeed in this quadrant in general, and Texas specifically calls for a full teardown (and has for a couple of years now). It's unclear if that admission will come with a regime change as well.

The top right: advantage gamblers

In the top right quadrant, we find some of the best-run organizations in baseball, with the Tampa Bay Rays the most notable example. The Rays are pound-for-pound the best-run organization in the sport, and that's not just anonymous praise from people around the game; owners from other teams keep hiring Tampa Bay's execs to try to replicate what they're doing. Andrew Friedman with the Los Angeles Dodgers, Chaim Bloom with the Boston Red Sox and James Click with the Houston Astros are all doing a version of what has made the Rays so successful. GM Erik Neander seems to have trouble sitting still, constantly swapping out players, but this appears to be because of two key components: The Rays have a bottom-five payroll and they think they have an edge in evaluation.

Tampa Bay is among the top five analytics teams in the sport, but the Rays also sometimes make decisions based on traditional methods because they have a top-tier scouting staff and an executive group that melds the two together well. They don't feel compelled to trade solid players when they hit arbitration, but if they think they can buy low on two players close to the big leagues who two years from now will be just as good as the arbitration-eligible guy, and can bridge that gap with a player from their Triple-A squad, why not swap everyone out and save some money that can be used for something else? Do that successfully a dozen times a year for a few years and you'll have the best talent base in the league.

The bottom right: the hedge funders

That brings us to the bottom-right quadrant, the area where a number of teams seem to be trying to copy all of what Jeff Luhnow did in Houston. There's some scholarship (though I haven't seen anything definitive relating it specifically to baseball) that no sports team has a sustained edge in its ability to draft, in terms of picking players better than its rivals for years at a time. Teams in this quadrant acknowledge this in the way they draft, acting as if no one has a real edge in picking players and leaning heavily on models to strip out all bias (often at the expense of scouts) and play into the odds.

Once a club leans more to analysts than scouts in the draft room, it's easy to justify having fewer scouts and reducing travel across the board and relying more on data and hiring more analysts. When there are 10 other clubs using the same data and passing it through very similar models, it's hard to match up to make trades because teams will value players similarly and have the same long-term goal of being somewhere around contention every year. If you're minimizing risk, that means making trades for more players of lower quality rather than one or two players of higher quality, waiting as late as possible in free agency and signing guys to one- or two-year deals, and spreading bonuses in amateur markets across more players rather than concentrating them on a few prospects.

As mentioned at the top, using modeling and McKinsey-style risk analysis, this leads to making decisions in the context of five-year World Series title odds, rather than believing a GM should be trusted to make bold win-now moves at the expense of title chances on the back end of that five-year window. After all, if you think playoff outcomes are largely a crapshoot, why not make decisions to get the most bites at the apple than go all-in on the idea that this year is your year?

As with San Diego or Tampa Bay, any approach can work if it is executed well, you emphasize whatever your competitive advantage is, you adapt to the situation and you have a little luck. The Astros under Luhnow were a good example of this, but they got bolder as they got closer to a title, doing something that teams in the extreme of this bottom-right quadrant would never do: trading prospects and taking on lots of guaranteed money to acquire older pitchers in Gerrit Cole, Justin Verlander and Zack Greinke. Houston did this for three reasons: The Astros had money to spend (with a top-five payroll ceiling) and not that many holes, they rightfully thought they were the best team in baseball at pitcher development, and the core pieces of the team were going to be there for a while. They were increasing their odds of a short-term title but not materially taking from future years.

Once Houston made those moves and won a title, it had adjusted its risk tolerance, driven by its payroll giving the Astros the margin for error to be bold. Now they're less bold as they are at their payroll ceiling. The Rays don't have that margin for error in payroll, but they think they have a big edge in evaluation. Payroll seems to be keeping Tampa Bay from the top tier of risk tolerance because it hasn't made the sort of deal where it swaps three top prospects for a few years of an elite player. If the Rays had the payroll ceiling of the Padres, I think they would have done that by now, probably a few times.

Two other clubs that use their payroll limitations to avoid taking big risks are the Cleveland Indians and the Milwaukee Brewers. The Brewers are run by David Stearns, Luhnow's former No. 2 in Houston, and they took a real shot by trading a lot of prospect capital for Christian Yelich, then extending him. They can't afford to do that again, so their moves are now limited to tinkering with the role players on the big league team, and wading into the middle-to-lower tiers of the amateur markets.

Cleveland also has payroll limitations and has a clear edge over the market with its excellent pitching development. The Indians also have a strong young core of pitching, plus Jose Ramirez and Francisco Lindor. The boldest moves Cleveland has made in the past few years were (1) selling low on right-hander Mike Clevinger at the deadline after his COVID-19 protocol violations to acquire six players, none of whom projects to be better than league average, (2) trading Trevor Bauer with a year and change left of control for a rental of Yasiel Puig and three young players, none of whom projects to be better than league average, and (3) signing 34-year-old designated hitter Edwin Encarnacion to a three-year, $60 million deal. Encarnacion was traded to Seattle after Year 2 of that deal, in a convoluted swap where Cleveland acquired Carlos Santana, a similar player with even more guaranteed money left on his deal.

All that is to say Cleveland has had some holes to fill in its lineup, particularly in the outfield, and has chosen to address them by tiptoeing around the issue, not spending in free agency to solve them, not selling high on a pitcher and looking for its Yelich, but acquiring a bunch of fringe players, hoping one of them delivers a huge return on investment by turning into a core piece. That hasn't happened and now its franchise player, Lindor, is set to leave for a megadeal in free agency after next season.

Cleveland's approach in the amateur markets (covered in depth in "Future Value"), while more successful than league average on the whole, is also risk averse. The Indians rely heavily on a model in the draft, most notably that pushes up players with long track records, so no one executive is forced to go out on a limb in making a pick. Internationally, they focus on players outside of the top tier in terms of bonuses. Within these constraints, they get solid results, but it also further shines a light on how managing risk as low as possible is the overarching strategy.

This approach has spread all over the game with Mark Shapiro's success (and connection to search firm Korn Ferry) placing former Indians executives with a number of clubs and influencing owners to pick chief executives who follow these trends. It also happens that not making bold moves, managing risk close to zero and being a playoff contender every year, with a clear strategy that's based around cost efficiency, is a good way to get promoted and at the very least not get fired, which begins to get into the realm of a moral hazard.

This general approach in a major market allows clubs to have flexibility but always have a bullet left when they want it: The Yankees can play it pretty safe but still get Gerrit Cole; the Dodgers can do the same with Mookie Betts. The Braves aren't that high up the payroll rankings (they're around average, maybe a tick above), but in terms of risk, they've been operating more like Cleveland than Tampa Bay.

Braves GM Alex Anthopoulos walked into arguably the best group of young talent in the game, certainly one of the top few. Since then, he plucked the low-hanging fruit of extending Ronald Acuna Jr. and Ozzie Albies but hasn't taken any risks since taking the job, following most closely to Cleveland's model, despite a payroll advantage.

There were multiple opportunities to package some top-100 type prospects together to acquire J.T. Realmuto or other elite players, but Atlanta chose not to. There was a shot to pounce on the goodwill created by Josh Donaldson's rebirth on a one-year deal, but Atlanta was outbid for his services by Minnesota, which is in the bottom third in terms of payroll. Every notable free-agent signing was for a one-year deal, designed to limit risk and maximize flexibility, but there's no real way to benefit from being right beyond that first season, as Donaldson proved. Nothing risked, nothing gained.

No one of these choices was indefensible, but then we consider last month's trade deadline. The Braves' rotation had an ace in Max Fried and a recently promoted top prospect in Ian Anderson, who had a good debut right before the deadline. They needed at least two starters to fill their biggest holes, but they made no trades beyond adding left-hander Tommy Milone weeks before, who by the deadline had an ERA of 5.68 and since then has seen it balloon to 6.69. A week later, Fried went on the injured list and now Atlanta's ace was an unproven Anderson, with FanGraphs' Craig Edwards crunching the numbers to find it was the worst rotation in baseball at the time.

This is especially interesting because Anthopoulos' most notable quality when he ran the Blue Jays from 2009 to 2015 was taking risks. He completed blockbuster deals for Roy Halladay, Jose Reyes, R.A. Dickey, Josh Donaldson, Troy Tulowitzki and David Price. He also gave Jose Bautista a prescient five-year extension after a breakout 2010 season, while selecting for upside in the draft and landing Noah Syndergaard and Marcus Stroman. Anthopoulos also notably failed to sign an industry-leading number of top picks such as Brady Singer, Phil Bickford and Tyler Beede. Some of the trades went well, while others did not. Trading for the tail end of Dickey's career cost Toronto Syndergaard (and more), while Tulowitzki was released with $38 million of guaranteed money left on his deal after posting 4 WAR that cost more than $60 million.

Historical context

I'm sympathetic to the approach of maximizing the odds of success (playoff appearances or titles) in a five-year window. I use spreadsheets every day, I don't make a major purchase without consulting Consumer Reports or Wirecutter, and I'm all for stripping out the sorts of gut feels that we can prove get us in trouble. But the whole point of running a baseball team is to win a title at some point, so let's take a look at the winners of the most recent titles to see where they would fall on this graph.

In 2019, we had the Washington Nationals, and they've been in the upper-left quadrant, in a pretty extreme part of it, for years under Mike Rizzo. In 2018, we had the Boston Red Sox under Dave Dombrowski, who were the Platonic ideal of the old-school gunslinger mentality of bold moves; they might have even been more extreme than Rizzo. In 2015, we had the Kansas City Royals and Dayton Moore, who might be the most traditional GM in baseball, and he's taken fewer risks in the draft during his present rebuild by relying on college pitching, but he clearly was in the upper-left quadrant when he won, even more extreme than he is now. In 2014, we had the Brian Sabean-led San Francisco Giants, who were basically battling the Royals for the most traditional approach in baseball at the time, leaning on scouts, veteran free agents and homegrown stars signed to big extensions, all of it built around starting pitching.

You might have noticed I skipped 2016 and 2017. They're a little different, but they still fit in this trend. In 2016, Theo Epstein led the Chicago Cubs to breaking their 108-year World Series drought. Epstein was seen as a progressive early in his Red Sox tenure but has been a moderate for a while now. He was a very aggressive, risk-seeking moderate leading up to the title, signing Jon Lester to a six-year, $155 million deal, Jason Heyward to an eight-year, $184 million deal, trading Gleyber Torres for a rental of Aroldis Chapman. Then, after the championship, he traded Eloy Jimenez and Dylan Cease for Jose Quintana and signed Yu Darvish to a six-year, $126 million deal to try to keep that window of contention open for his core. So while Epstein isn't a staunch traditionalist across the board like those other examples, he also wasn't progressive, and he was very aggressive, even if you ignore the big payroll that fueled the free-agent signings.

Last we have the 2017 champion Astros. Obviously they were the standard-bearer for a lot of things, but most of all for a progressive approach to the game. As mentioned earlier, like the Cubs, they got very aggressive before their run, both in taking on money but also in trading a lot of prospect capital to upgrade the club. Luhnow's Astros were never not progressive, but their aggression and risk-seeking, even if it was in their comfort zone of staying barely within their payroll and choosing from elite, non-optimized starting pitchers, was distinct.

Is there a superior strategy?

That brings us full circle on this journey of risk assessment. When Padres fans were excited at the deadline because of Preller's many moves, it was in part because his strengths (aggressive approach, stockpiling young talent) perfectly matched the moment. Yankees fans were enraged that Brian Cashman didn't upgrade the team, but that's not shocking in light of how the club has positioned itself: The Yankees want to be entering the playoffs each of the next five years in a good competitive position, and that's what they're going to do this year.

Braves fans were befuddled that Atlanta couldn't afford to deal for Clevinger, Kevin Gausman or, heck, even Robbie Ray. Taking on a reclamation project like Ray demands confidence in pitching development, which the Braves can't have at this point; it's unclear what their competitive edge is other than a decent-sized payroll and an inherited young core. Landing Gausman required a depth of solid prospects that aren't the top-tier untouchables or possible short-term MLB pitching help, and Atlanta didn't have that to the Giants' liking. Clevinger required trading multiple MLB-ready pieces who could all turn into solid players with six years of control and make you look bad down the road, and the Braves have never shown willingness to trade those sorts of players because of the hedging mindset. Of course, the value of Atlanta's young pitchers aside from Mike Soroka and Fried has gone down the past few years, so now they would yield almost nothing on the field and less than ever on the trade market.

No strategy is inherently correct or incorrect, but you could argue that one quadrant becomes a better option when the contenders you're competing with start clustering in another area on the graph. For Yankees or Braves fans who think their GM doesn't want to win, you're missing the forest for the trees. You might accuse someone on the opposite political extreme of hating America. You probably don't think they're a sleeper agent trying to ruin the country, they just like power or money or being reelected more than they love the country. From your perspective, that priority is too far down the list, to where it seems like it isn't on their list at all. The Braves and Yankees are interested in trying to win the World Series this year, they're just more interested in keeping their odds of winning over the next five years high than they are in winning this year in particular.

Looking at the evidence of what clubs have done to win the past six World Series, it doesn't seem the playoffs are some totally random, emotionless eight-sided (or this year, 16-sided) die where having the best team increases your odds by only a percent or two. It seems being aggressive and actually trying to win, even for a two- to three-year window instead of a five-year one, might actually improve your odds.

Where a team was on the traditional/progressive spectrum mattered greatly at the dawn of Moneyball, when there was a lot of low-hanging fruit. Now that every team is considering analytical data to some degree, one could argue that risk tolerance is the most important separator for a GM to achieve success in today's game. It's unclear if this is causal or correlative, but confidence in your ability to evaluate talent seems to map well with risk tolerance, with a nod to payroll size.

Preller overcame his many mistakes and is the toast of the industry with the most fun, young team in the game and the second-best farm system. Anthopoulos' seemingly prudent risk aversion has him in a position to possibly waste one of Acuna's prime years and one of the last two seasons when franchise icon Freddie Freeman is under contract at an affordable price. I'll be sure to keep you posted on who wins the Financial Flexibility World Series.