Blockbuster summer? Why buying and selling at MLB’s trade deadline is more complicated than ever

The trade deadline is a last-chance saloon for clubs to make outside additions, and this year’s market could feature the kind of prize that would energize a fanbase dreaming of winning the World Series: Detroit Tigers ace Tarik Skubal.

But when it comes to the kind of big swing required to acquire a back-to-back Cy Young winner, most major-league executives have effectively become teetotalers. Billy Beane, the ex-player turned maverick executive who once reimagined the Athletics in ways that would challenge the sport’s Goliaths, recently used an equally boring description for himself and his peers as he discussed the changing nature of the trade deadline:
Actuaries.

“This is not a criticism. But by its nature, analytics generally are very conservative,” Beane said. “We sort of saw ourselves as actuaries, right? Actuaries from insurance companies.

“In a very crude way, that’s what we were doing. Now, they’re doing it in an even more sophisticated way. And what do actuaries do? They mitigate risk.”

The Aug. 3 deadline will still bring action. Though they’re not exactly taking on a gunslinger mentality, these traders are constantly reassessing their positions and exploring alternatives, working within a framework that should lead to a flurry of deals. But that more cautious approach comes with another consequence. The odds for the kind of jaw-dropping, what-just-happened deal that makes you squint at your phone to make sure you read that breaking-news alert right — in short, a blockbuster for a game-changer like Skubal — are dramatically reduced.

A confluence of factors could inhibit Skubal’s market, if the Tigers decide to trade him. A lockout hangs over the sport. Expanded playoffs muddy the postseason picture. And as the trade deadline approaches, every front office is engaged in a form of groupthink in which blockbusters are much more the exception than the norm.

“Over time, the way teams have valued players and prospects and years of control have started to converge,” Cleveland Guardians president of baseball operations Chris Antonetti said. “Not to say that it’s homogenous and everyone looks at it the same way. But they’ve converged and it creates fewer opportunities.”

For those reasons, club officials — including several who were granted anonymity to discuss the trade market in exchange for their candor — tempered expectations for this season’s deadline. Thanks to a particularly blurry playoff picture, many of the buyers and sellers remain undefined. All but seven of the 30 clubs reached the All-Star break in a leading playoff position or within four games of a playoff spot.

The limited group of obvious sellers includes the Colorado Rockies (under new management with Paul DePodesta, a key figure under Beane in Oakland’s “Moneyball” era); the Los Angeles Angels (now run by interim general manager John Mozeliak after the June dismissal of Perry Minasian); and the San Francisco Giants (where Buster Posey’s impeccable resume as a player has not overcome his inexperience as an executive).

Yet, the deadline again will be one of the biggest days on baseball’s calendar, a bazaar with such overwhelming fan and media interest that the wall-to-wall coverage begins months in advance. After the deadline, only minor leaguers not on 40-man rosters can be traded, a change the league instituted in 2019.

“I’m going to be interested to see how this deadline plays out,” New York Yankees general manager Brian Cashman said. “There are so many teams in it, even sub-.500 teams. Everybody’s in it, which creates, in theory, a paralysis. No one wants to trade from their big club. They’re all trying to add. But the sellers are few, in theory. And trying to make major-league for major-league deals is really difficult.

“But it feels like the last number of deadlines there have been a s—load of transactions. It feels like transactions have gone through the roof.”

Cashman is correct: Last year’s deadline day produced 36 trades, a record number. Between July 24 and July 31, clubs executed 63 deals involving 179 players.

Most of those deals, however, were marginal in nature.

Think about the risk in acquiring Skubal, which would be considerable. The left-handed ace will be a free agent at the end of the season, just before he turns 30. Six starts into his return from an innovative elbow surgery, he has yet to go beyond six innings. And, as a potential free agent, he will amount to a rental that costs his new team nearly $10 million in remaining salary, plus a strong package of young talent.

With certain exceptions, most notably the San Diego Padres’ A.J. Preller, baseball’s modern-day decision-makers likely would shy away from risks. Indeed, most executives recoil from the question one of Beane’s disciples, Theo Epstein, asked when he acquired Aroldis Chapman for the Chicago Cubs in 2016.

It is the same question an executive would need to ask before making a run at Skubal.

“If not now, when?”

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Beane distilled the game in a way that made sense to Major League Baseball’s owners as well as Hollywood producers. Eventually, all 30 clubs would play some version of “Moneyball.”

That best-selling book was published in 2003, and the movie in which Brad Pitt portrayed Beane was released in 2011. But the “Moneyball” concepts stay relevant because the entire industry is trying to exploit market inefficiencies and unearth hidden value.

Every front office is staring at the same sets of data, checking internal projection systems and weighing the costs of buying and selling.

“It’s more like managing a portfolio,” an American League executive said. “Shorting certain stocks and investing in longer-range options. But I dislike that because we are talking about human beings.”

The expanded playoff format, which began in 2022, presents different paths through October, forcing clubs to assess the importance of a first-round bye and question the wisdom of going all-in for a three-game series that feels random.

An expiring collective bargaining agreement makes it harder to appraise players under club control through 2027, given the threat of a lockout that puts next season in jeopardy.

“For this generation of executives,” a National League manager said, “the deadline is the one thing that pushes them to transact.”

As the sport evolved, Beane’s frequent dealings with Cashman reached the point where their organizations viewed enough things through a similar lens. After the Boston Red Sox unsuccessfully tried to hire Beane after the 2002 season, they elevated Epstein, a young unknown who would adopt many of those same principles at Fenway Park.

Even while going for a World Series three-peat, Los Angeles Dodgers president of baseball operations Andrew Friedman remains cognizant of future considerations, attempting to load up in the offseason to avoid exorbitant prices at the deadline.

“In the early days, I felt our market was an advantage,” said Beane, who remains a senior advisor to the Athletics as the franchise plans its relocation to Las Vegas. “We valued young players. Why? Because they were cheap and they were cost-effective. The Yankees were a bigger-market team and would sort of value proven players. It was an easier negotiation.

“The game started changing when teams like the Yankees and Red Sox a long time ago, and certainly the Dodgers now, started valuing players at the same level. That transaction was harder.

“Now, whether you’re with the smallest team or the largest team, every one of these guys understands present value, future value and surplus value of every single player in their organization, starting in the Dominican.”

And some of those executives, as they run their models, see little value in all of the midsummer wheeling and dealing, contending that most trades rarely translate to a meaningful shift in a team’s playoff and World Series odds.

“The deadline is way less impactful than people want to make it out to be,” an NL executive said. “Every year, there’s a team that sells and gets better. Every year, there’s a team that buys and falls out of the race in mid-August.”

“The buzzword is ‘opportunistically buy,’” another NL executive said. “I always think of that as, ‘I want to find something in the last six hours of the deadline that helps the team without giving up a lot of prospect capital.’”

Playing it safe might be the right choice for the actuaries the game’s current executives are trying to emulate. But it’s not always the right choice in the business of baseball, where the passions of players and fans come into play.

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At the 2016 deadline, Epstein sent blue-chip prospect Gleyber Torres, a future All-Star, outfielder Billy McKinney and two others in a larger package to the Yankees for Chapman, a rental closer the Cubs felt like they absolutely had to have to win a championship.

“From the outside looking in, or if you take just a purely analytical look at baseball, you don’t understand the impact that it has in the clubhouse,” Epstein explained to Anthony Rizzo and David Ross on “The Lovable Reunion” podcast. “These guys have done all their offseason work, grinded all of spring training, put the nuts on the line the whole season. And then they look at the front office like, ‘You guys have one f—ing job! Get us what we need.’

“I’ve been through years where you just can’t get it. Because you’re asking to be paid like five times the prices. You just can’t do it, and you feel like you just let everybody down. So take it very personally as an organization: We need to deliver.

“We’re not going to always mortgage the future, but we have to do our job and give these guys what they need, because it gives you that boost of energy. And then you feel connected, like, ‘Hey, they have our back. All the sacrifice was worth it.’ It has an amplifying effect.

“That was a deal that — I would have mocked it if someone else did it.”

Chapman, though, helped the Cubs win their first World Series since 1908 — and he isn’t the only player this century who was acquired in a midseason trade and dramatically altered his franchise’s fortunes.

Even when the risks are daunting and demand outstrips supply, the exceptions at the trade deadline still break through the computer screens and seep into your imagination.

CC Sabathia’s spectacular run with the Milwaukee Brewers after a 2008 deal (11-2, 1.65 ERA in 17 starts) would lead to a seven-year, $161 million commitment from the Yankees as a free agent and enhance his Hall of Fame credentials.

J.D. Martinez launched 29 home runs in 62 games after getting traded from the Detroit Tigers to the Arizona Diamondbacks shortly after the 2017 All-Star break, giving his new team an instant jolt.

Chapman pitched in 10 of Chicago’s 11 victories during the 2016 playoffs, pushing himself to exhaustion, yet still remains an elite closer a decade later for the Red Sox, one of many teams now on the fence, with Epstein in the background as a minority owner and advisor to Fenway Sports Group.

Preller, the Padres’ hyperactive lead executive, acquired outfielder Juan Soto with two additional years of control at the 2022 trade deadline, thinking the outfielder would be the same kind of transformative figure as Chapman. The Padres reached the National League Championship Series that season and seemed on a path to winning their first World Series title. But after the 2023 season, Preller was under pressure to reduce payroll and needed to pivot quickly.

So, after initially parting with CJ Abrams, James Wood and MacKenzie Gore to obtain Soto from the Washington Nationals, Preller traded Soto to the Yankees in December 2023 to reshape the roster for a 2024 playoff run. He then pulled off another big move at last year’s deadline, making a prospect-heavy trade with the Athletics for Mason Miller, the All-Star closer who is under club control through 2029.

No doubt Preller would love to acquire Skubal, if the Padres — who entered the break at .500, 3½ games back in the NL wild-card race — warrant such a push. But given the labor uncertainty and an even bigger premium placed on high-end prospects, an NL executive expressed skepticism about the Tigers moving their ace.

“He might get traded, but the early asks are going to be outrageous,” the club official said. “And no one’s going to pay that. What the Cubs did to get Chapman, they were trying to break a 108-year curse. They were definitely overly aggressive. That kind of deal is not really happening anymore, especially going into a new CBA.”

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Detroit’s president of baseball operations, Scott Harris, once worked for Epstein in Chicago. The Tigers’ plight illustrates the AL’s weakened state. Even with a 44-52 record, the Tigers are only 3½ games out of a wild-card spot and 6½ games back in a division that still feels wide open.

The case could be made that the Tigers should try to wring one more playoff run out of Skubal, the looming free agent in line for a monster contract on the open market. The Tigers then would lose him only for a draft pick, the value of which they surely could beat in a trade.

At the moment, every possibility remains in play.

“There are a lot of confused teams right now,” an NL executive said. “You can talk to them one day and their mentality is to be more aggressive, then a week later they change their tune and are sitting back on their heels.”

That indecision will continue into the final days, if not hours, before the Aug. 3 deadline at 6 p.m. ET.

“A huge part of this, to me, is often emotional,” an AL executive said. “In our sport, unlike in the NBA, it’s really hard to know what you’ll get for a couple of months. The rosters are 26 deep. It’s really hard for one player to make a dramatic impact. But man, when it happens, it’s freaking awesome.”

The Brewers used the momentum from a playoff appearance with Sabathia to help create a consistently competitive organization that constantly outperforms expectations. They might squeeze more out of Skubal than any other club and mount the most serious challenge to the Dodgers in October. But the same discipline and focus that got the Brewers to this point will likely keep them out of the Skubal sweepstakes.

Milwaukee’s former head of baseball operations, David Stearns, is now running the New York Mets, trying to salvage a disastrous season with a productive trade deadline. The arbitrage is not unlike the financial trading that made Mets owner Steve Cohen a billionaire.

Stearns, though, is an example of how a go-for-it push can go awry, leading to the exact scenario many of today’s risk-averse executives fear. Often described as “unemotional” when making decisions, Stearns dealt approximately one dozen prospects last summer — and his team still missed the playoffs, triggering a dramatic overhaul during the offseason.

Now Stearns must try to unravel his team again, only this time as a lockout looms, adding a unique element to this year’s deadline.

If the lockout results in a partial cancellation of games next season, spring training will be abbreviated once a new labor deal is reached and a frenetic period of transactions will be unleashed. Clubs, then, might try to be proactive, gauging interest in players who are eligible to become free agents after the 2027 season.

“When I would go into the deal, I just assumed what I was giving up was going to be good,” Beane said. “I would joke with guys, like, ‘Listen, if I keep winning, I’ll keep getting contract extensions, regardless of how many Rookies of the Year or MVPs I’ve traded away.’ I traded a lot of good players away. Ones that I probably shouldn’t have.”

The business is humbling and unpredictable, played by people, not computers. Like all of his contemporaries, Beane has also been on the other side of those deals, acquiring three or four young players with fantastic projections.

“But it doesn’t always turn out that way,” Beane said. “And even if it does, if you’re the guy that acquires the player and you achieve what you want to do and you win, who cares?”

Additional reporting by Will Sammon.