In a sport like baseball, where transactions are common, every move, whether a free-agent signing or a trade, comes with some level of inherent risk.
The risk of a free-agent signing is losing money on the deal, either because the player doesn’t perform to the level of the contract or because the back half of the deal goes bad as he declines.
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A trade adds different layers of risk: either losing blue-chip prospects in exchange for the player being acquired or losing an impact big leaguer to obtain unproven prospects who might never pan out. In every transaction, it’s the responsibility of front offices to mitigate that risk while making calculated decisions that make the gamble worth it in the pursuit of winning.
But risk mitigation in baseball can be a double-edged sword. Yes, the need for caution comes with the job title for any general manager or president of baseball operations, as balancing the present against the future is a critical part of the gig. However, the adage “fortune favors the bold” has also shown itself to be true in baseball, specifically when it comes to player acquisition.
As Brewers president of baseball operations Matt Arnold put it, “If you haven’t made a bad trade, you haven’t made enough trades.”
There was a time not too long ago when MLB teams seemed more willing to take big swings in the trade market, moving highly touted prospects in order to acquire established big-league talent. But those days seem to be gone, as front offices have taken a more risk-averse approach in recent years, trying to be more cautious when it comes to making trades.
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“There might be something to that,” St. Louis Cardinals president of baseball operations Chaim Bloom said. “[But] if you want to be really risk-averse, you wouldn’t do this job. You wouldn’t decide to make a career out of a zero-sum game where there’s one trophy of the year. So all of us take risks — it’s the nature of doing this.”
Even so, it seems that the modern front office is reluctant to trade prospect capital. The value of prospects has never been higher in baseball. That could be because talent is more developed and ready to provide impact at the big-league level sooner, or it could be due to the fact that prospects are more cost-effective than veterans. Either way, moving prospects seems to be a tall order these days.
“It’s a fair question,” Red Sox chief baseball officer Craig Breslow told Yahoo Sports. “I’m not sure it’s risk aversion, though. I think everybody in my seat is in fear of the nightmare scenario of trading a prospect that turns out to be a great player.”
Beyond that fear, though, there are also some industry-wide trends impacting the trade market.
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“I would argue instead, what is maybe making it more difficult to trade for players is most teams are looking at players through the same lens,” Breslow continued. “They’re collecting the same information. They’re using a lot of the same tools, and so very rarely do you see a player that you think is significantly better than another organization.”
To show just how much baseball’s trading landscape has changed, let’s go back 10 years to when three major trades captured the ideology of the times.
The first was the Arizona Diamondbacks’ trade of shortstop Dansby Swanson, the No. 1 pick in the 2015 draft, to the Atlanta Braves for a package that included Shelby Miller, then the biggest name in the deal, during the 2015 winter meetings. The next came seven months later at the 2016 trade deadline, when the Chicago Cubs were looking to go all-in to win the World Series and traded blue-chip prospect Gleyber Torres to the New York Yankees for two months of closer Aroldis Chapman. But maybe the biggest trade that year came during the 2016 winter meetings, when the Boston Red Sox acquired ace Chris Sale from the rebuilding Chicago White Sox for a huge return that included baseball’s No. 1 prospect, Yoán Moncada.
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In the years since, trades such as those — deals involving notable stars and the game’s highest-ranked prospects — have been few and far between. These days, the idea of moving the top prospect in the sport would raise a lot of eyebrows. In fact, zero top-100 prospects were dealt at the 2024 trade deadline, showing just how much the value of prospect capital has increased.
To hear team execs tell it, much of this shift has to do with how teams are scouting players today and the amount of information available to them.
“I do think that we’ve just become a little bit more sophisticated and evidence-based in a lot of ways, which you could say limits risk or just enhances confidence in the decisions that you’re making, in terms of properly evaluating players that are coming up through the system and potentially what else is out there in the industry,” Texas Rangers general manager Ross Fenstermaker said.
“So maybe you could argue that we’ve become too smart for our own good in some ways. But I do think we have some great minds in baseball, and teams have hired some incredibly thoughtful people that blend baseball minds with maybe a more academic approach, and it’s just maybe dialed up the confidence interval in terms of how we feel about certain players and certain acquisitions in terms of player evaluation.”
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Analytics has become a buzz word in baseball in recent years, but it’s not unfair to say that most big-league front offices have used the increase in data to help them make what they believe are more informed decisions based on player projections. And while that increase in information can boost teams’ confidence, it can also give them reason to pause before moving a young player.
When it comes to making trades, Padres GM AJ Preller (center) tends to zig while the rest of the sports zags.
(Amy Monks/Yahoo Sports)
Of course, there are some exceptions to baseball’s current rule when it comes to trades. Back when he was running the Tigers and Red Sox, current Phillies president of baseball operations Dave Dombrowski was the poster boy for wheelin’ and dealin’ in baseball, never seeing a prospect he wasn’t willing to trade.
Today, no executive in baseball has been more willing to buck the trend than Padres president of baseball operations AJ Preller. Preller seems to be the last of a dying breed, as he has been willing to do something other executives wouldn’t in recent years: leverage an elite farm system to acquire elite major-league talent.
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The Padres’ exec has pulled off some of MLB’s most recent blockbusters, including trading then-prospects CJ Abrams, James Wood, MacKenzie Gore and Jarlin Susana to the Washington Nationals for superstar Juan Soto in 2022. His most recent trade sent shockwaves through the sport in July, when he sent MLB’s No. 1 prospect, Leo DeVries, to the A’s for the most dominant reliever in the sport, Mason Miller. Acquiring a player of Miller’s caliber, with four more years of club control, would be expensive no matter the context, and the No.1 prospect in baseball is about as expensive as it gets.
So what has made Preller and the Padres zig while the rest of the league zags?
“I don’t look at it like, we’re trying to be a certain way or not,” Preller told Yahoo Sports. “I think just for us, we look at our situation and what we think is best to be competitive. Yeah, I think sometimes, [teams] are operating in this market over here — sometimes a lot of teams are, so sometimes there’s value in doing it in a different way.
“But I think for us, it’s just more about your individual situation, trying to evaluate that. That’s what we’ve done the last few years. We’ve had good teams coming in, and we got good prospects that we feel like are of value to other teams. … Ultimately, it’s to do what we think is best to help us win, and then do it in a way that you can repeat year after year.”
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Now, some would argue that Preller’s bold strategy hasn’t worked, given that despite his efforts, the Padres have failed to reach the World Series during his tenure. Others would say it has, considering that the Padres have reached the postseason in four of the past six years and Preller’s moves have kept the San Diego fan base engaged, knowing their team continues to go for it.
That attitude of “going for it” clearly matters to a fan base, even one that hasn’t seen a World Series title in the franchise’s history. The fans in San Diego have consistently come out to support the Padres, eclipsing three million in attendance the past three seasons.
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Knowing that, if the majority of the industry has gotten more cautious when it comes to player acquisition via trade, where does this leave baseball?
A model-based approach might seem logically sound when it comes to future projections for players and teams, but the game has a way of throwing a monkey wrench in even the smartest plans. Some players get hurt, and others underperform; that’s one of baseball’s absolutes. When operating with so much caution, teams are likely leaving themselves little margin for error and putting more pressure on their player development processes. Not to mention, the risk-avoidance approach feels like the opposite of “going for it,” and fans are aware of that. Too much caution, and a team is in danger of giving its fan base a reason to check out.
Ultimately, if winning a championship is the goal, some amount of risk is necessary to accomplish that. Some big swings have to be taken en route to a title. No matter how much young talent a team stockpiles, not every prospect is going to reach the big leagues, and certainly not with his original club. Besides, there’s no trophy for having the best farm system. Winning the World Series is the prize.
Preller is aware of this — and seems to think the pendulum might be starting to swing back the other way.
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“I do think teams are obviously looking at their competitive window,” Preller said. “They get a lot of information from a lot of different sources in their organization. I think the value of young players, they’re looking at that, and then how important that is as the premium prices keep going up. So I think it’s a combination of all of that.
“But I think both things are cyclical, and I think if you look at the trade deadline [in 2025], you’ll see more teams that are trying to be aggressive.”
