Passan: The 10 MLB execs with the most at stake at the trade deadline

Over the next three weeks, ahead of Major League Baseball’s July 30 trade deadline, a complicated web will fully form. The deadline is about more than contenders landing players who best fit them. It’s a juggling act between now and the future that overlaps with payroll considerations while being colored by decisions from executives whose own jobs could be on the line. The deadline grays hair at a rate just behind the presidency.

The executives with the most riding on this deadline aren’t necessarily the ones who will be the most active. Los Angeles Dodgers president of baseball operations Andrew Friedman will amend his roster, but he’s on the verge of his 10^th playoff appearance in 10 seasons with the Dodgers, so the pressure, even with a $300 million-plus payroll, isn’t quite as acute. The Texas Rangers are perhaps baseball’s most disappointing team this season, but Chris Young is less than a year removed from winning a World Series, easing the need to make a rash, win-now move.

Some of their peers do not share that luxury. These are the kings of urgency, whether it’s rooted in their franchise’s long-term doldrums or compelled by rough recent stretches. The latter case certainly applies best to the first entrant in the group of those with the most at stake as July 30 approaches.

Brian Cashman, general manager, New York Yankees

Three weeks ago, the Yankees were a juggernaut, and it looked like Cashman had done one of the best roster construction jobs in his 27 seasons running baseball operations for New York. Now the Yankees are desperate for upgrades — in the infield and bullpen particularly, though it’s impossible to discount their rotation cratering, too.

In 2022, New York started 52-20 and added significantly — if ineffectively — at the deadline. The Yankees were 50-22 in 2018 and got a pair of starting pitchers and a late-inning reliever. Their 50-22 start this season has been dented by a 5-15 stretch since. At the very least, the Yankees should get a bat-first infielder — the Los Angeles Angels’ Luis Rengifo fits, though the hand injury that sent him to the injured list is alarming and untimely — and a late-inning reliever, a la Miami’s Tanner Scott or Angels closer Carlos Estevez, who has issued one unintentional walk in 27 innings this season.

Cashman also, at the very least, ought to monitor the starting pitching market. Over the past month, Yankees starters have the worst ERA of any staff in baseball. Before he kept Boston at bay Sunday night, Luis Gil had been a mess since his brilliant first two months. Marcus Stroman’s annual midseason swoon is happening. Carlos Rodon has allowed seven home runs in his past 26 innings. Gerrit Cole’s stuff is down a tick (though his increased cutter usage has paid dividends and is worth watching). Clarke Schmidt still hasn’t thrown off the mound since being shut down with a strained lat.

The Yankees haven’t won a World Series since 2009. They have Juan Soto guaranteed in pinstripes for only another three months. They can’t expect Aaron Judge to carry them. Anthony Volpe is a very good player, and Ben Rice looks real, and maybe Giancarlo Stanton and Anthony Rizzo and Scott Effross and Nick Burdi return from the injured list and suddenly the juggernaut reforms. But the Yankees — and Cashman by extension — cannot rely on hope. This team needs more. And the exigency can’t be overstated.

Ross Atkins, general manager, Toronto Blue Jays

At this point, it’s becoming obvious the Blue Jays are going to be trading away talent before the deadline. They have the fourth-worst record in the American League and a run differential to match. Calling them anything less than a tremendous disappointment would be sugarcoating the situation.

Exactly how they disassemble this current incarnation is Atkins’ challenge. Because this team — which had such high expectations, adding pricey free agents (George Springer, Kevin Gausman, Chris Bassitt) and top trade acquisitions (Jose Berrios, Daulton Varsho) to surround a homegrown core (Vladimir Guerrero Jr., Bo Bichette, Jordan Romano) — can go in two directions.

Option No. 1: Move only the free agents-to-be and retool for next season. It’s certainly a rational route. The returns on DH Justin Turner, left-hander Yusei Kikuchi, catcher Danny Jansen and center fielder Kevin Kiermaier wouldn’t particularly enrich a bereft Blue Jays farm system, but they’d help. And with next year’s estimated payroll at around $185 million, they’d have enough room to add that a contender could blossom from the current roster and several savvy moves.

Option No. 2: Blow it up. Trade Guerrero. Trade Bichette. Trade Bassitt. Trade Gausman. Take advantage of a market with little talent, pit all the contenders against one another and jump-start the next crack at their first World Series appearance in more than three decades. Recognize that for all the promise of this roster, it hasn’t worked. Since Guerrero and Bichette debuted in 2019, the Blue Jays are 0-6 in the postseason, swept in three wild-card series. They are in an AL East that includes the best team in the American League (Baltimore), the Yankees, a Tampa Bay team that’s primed for an infusion of talent before 2025 and a Boston team already playing well, with significant talent in the minors and room to spend. Even if everything breaks right, the Blue Jays are losing simply because of geography.

As logical as the second option sounds, it also strikes at the heart of the difficulty for Atkins: A full tear-down doesn’t align with the Blue Jays’ recent $400 million upgrade to Rogers Centre, nor does it speak well of his ability as GM to field a championship-caliber team. On paper, these Blue Jays were great. In practice, it’s been something entirely different. If the aspiration is just making the postseason, running it back might work. If it’s a championship the Blue Jays desire, starting from scratch with a new young core might be the most prudent route.

Chris Getz, general manager, Chicago White Sox

Speaking of starting from scratch: The White Sox, a mess at the big league level, are open for business. In Garrett Crochet, they have the best available starter. In Luis Robert Jr., they’ve got the best available position player. In Erick Fedde, they’ve got the most cost-effective under-team-control starter. This deadline should be a wild success for a Chicago team that has been severely malnourished when it comes to wins.

In his first year as GM, Getz has shown a dealer’s mentality. He moved starter Dylan Cease to San Diego in spring training and also traded relievers Gregory Santos and Aaron Bummer. His willingness to deal Crochet in the middle of his breakout season suggests he recognizes not just how perfectly this deadline is lining up for Chicago but also how imperative capitalizing on it is to shorten the franchise’s turnaround time.

Remaining stagnant as a doormat, particularly when the collective bargaining agreement penalizes large-market teams that tank, won’t benefit the White Sox. So Getz must pounce on every advantage he’s given. Under-control, playoff-caliber starters are at their most valuable in July. (Even Crochet, who, as he blows past his career high in innings, warrants a plenty-robust market with two more years before free agency after this season.) Robert might fetch a bigger return this winter, but with his injury history, the White Sox maximizing his value now could be the more sensible move.

Most of the bottom teams don’t have a ton at stake. Oakland’s ownership would be just fine with the A’s never winning. Colorado’s mistakes have rendered the Rockies irrelevant. The Angels are the White Sox Lite in terms of being far away but with less high-end talent. Ditto Miami. If the White Sox are going to turn around this ugliness in the next five years, July 2024 will have been a seminal point in their glory story.

Jerry Dipoto, president of baseball operations, Seattle Mariners

There’s no sense in belaboring the fact that the Mariners were gifted an opportunity to run away with the AL West and frittered it away. On June 10, the Mariners led the Houston Astros by 10 games. In barely two weeks’ time, that advantage shrunk to two games.

What’s the blame? The same thing that has held back the Mariners ever since they assembled an Infinity Gauntlet worth of starting pitchers: the offense. Nobody expected Julio Rodriguez to be slashing .247/.295/.335, but those surrounding him aren’t helping matters either. Seattle ranks 27^th in runs in MLB, ahead of only Oakland, Miami and the White Sox, a trinity of tankers.

Everything else is set up for a deep playoff run. The Mariners have the pitching. They’re solid defensively. They’ve got one of the game’s best farm systems. All they need are bats. And all of this is against the backdrop that Seattle, a franchise in its 48th year of existence, has never so much as made a World Series, let alone won one.

If owner John Stanton is not willing to raise the payroll to a level that allows them to add impact-type hitters in free agency (he hasn’t been), then trades are the way to do it — and Dipoto knows trades. He earned his reputation as the AL’s most aggressive executive by making well over 100 deals in his decade with Seattle. Whatever the Mariners do — and they will be busy — these might be the most important in his tenure.

Dave Dombrowski, president of baseball operations, Philadelphia Phillies

What exactly is at stake for the executive who oversees the best team in baseball? Just because something is the best doesn’t preclude it from getting better. And that’s where Dombrowski finds himself: potentially putting the finishing touches on a championship-caliber team with a third franchise.

There’s no legacy to burnish here (Dombrowski is a Hall of Famer already) or ego to stroke (the Phillies’ 58-32 record does that just fine). It’s more about ensuring a window doesn’t close without a team maximizing its opportunity. In this regard, the Phillies and Orioles are quite similar, though Dombrowski’s counterpart in Baltimore, Mike Elias, gets a little more leeway because the Orioles’ period of contention is longer than any team’s. The Phillies’ isn’t short, by any means, but every year Bryce Harper (31 years old), Trea Turner (31), J.T. Realmuto (33), Zack Wheeler (34) and Aaron Nola (31) age is a year closer to an inevitable downturn.

That’s when, as an executive in charge, you push. And when it comes to a willingness to look past what a computer system suggests is proper value and potentially overpay for talent, nobody matches Dombrowski. Robert fits the bill and fills a need. Others would be complementary pieces, though depth is never a bad thing for a team playing in October. Either way, the Phillies’ players have earned reinforcements. It’s on Dombrowski to provide them.

Peter Bendix, president of baseball operations, Miami Marlins

Another first-year GM, Bendix signaled what the standings already had suggested when on May 6 he dealt two-time batting champion Luis Arraez to San Diego: The Marlins are starting over, and just about anyone can be had for the right return.

It doesn’t help when an entire rotation of starting pitchers — Cy Young winner Sandy Alcantara, young star Eury Perez, left-hander Braxton Garrett, right-hander Edward Cabrera and Jesus Luzardo, who before his back locked up figured to be a prominent character at this deadline — is on the 60-day injured list. Even without them, the Marlins aren’t entirely bereft of players to move.

Center fielder Jazz Chisholm Jr. is a polarizing player among front offices, but star-level talent always finds a taker. Scott and Josh Bell, the Marlins’ lone impending free agents, are certain to go. They have power in the outfield with Bryan De La Cruz and Jesus Sanchez. And another arm, whether it’s Trevor Rogers or Ryan Weathers, could still move.

This isn’t going to be the bonanza deadline the Marlins once anticipated, but considering the positively barren nature of their farm system — especially on the hitting side — anything beats the present state of affairs.

J.J. Picollo, general manager, Kansas City Royals

No longer do the Royals hold one of the six AL playoff spots, and after at one point being 15 games over .500, they sport a 49-43 record and trail Boston by 1½ games for the final AL wild-card slot. The question for Picollo, then, is not whether the Royals are looking for upgrades — they are — but just how much talent they’re willing to cede in an effort to make this postseason.

Kansas City’s aggressiveness in the winter has paid off handsomely. Snapping up All-Star Seth Lugo on a three-year, $45 million deal was one of the coups of the offseason. Michael Wacha has been very good, too. The stability of Kansas City’s rotation has offset a bullpen with the 25th-ranked ERA and an offense held back by an outfield group whose collective OPS, over 1,017 plate appearances, is .624, better than only the White Sox’s.

Because the Royals operate on a relatively low budget, the balance between free agents and homegrown players dictates that they can’t afford to deplete prospect capital via trades, which limits their options. A mediocre farm system doesn’t help matters. Kansas City last made the postseason when it won the World Series in 2015, and Picollo reaching October in his second full season as GM would be a huge win.

The Royals aren’t going to be in the Crochet or Robert sweepstakes. They don’t need to be. There are enough relievers available for Kansas City to elevate its leverage options. And seeing as they’ve booked nearly 1,000 plate appearances of negative production from outfielders, just about anything is an upgrade from what they have.

Craig Breslow, chief baseball officer, Boston Red Sox

While the vast majority of the talent on the surprising Red Sox are holdovers from the Chaim Bloom regime, some of Breslow’s additions — pitching coach Andrew Bailey, outfielder Tyler O’Neill, relievers Justin Slaten and Greg Weissert — have helped their staggering turnaround. Boston entered the season with, at best, an outside shot at a postseason berth. As of today, it would be playing Seattle in the wild-card round.

So, yes, this is a team worth supplementing — and with first baseman Triston Casas nearing his return, the Red Sox have the ability to go from a maybe/maybe not playoff contender to a favorite. They could use a middle infielder. They could use another starting pitcher. Incremental gains could go a long way.

While it’s clear that the Red Sox should add, it’s easy to wonder if they can. Breslow’s limited spending this winter was more of a reflection on ownership than him. Over the first 21 seasons this century, the Red Sox entered Opening Day with a top 5 payroll 20 times. The past four years, they’ve been sixth, eighth, 12^th and 12^th. For reasons that have not been explained by an ownership group that for so long was regarded as one of the game’s best, the Red Sox have spent the post-COVID era acting like a midmarket team, not one of the game’s behemoths.

Boston’s first half should be evidence enough for John Henry that money should be no object at this deadline. The Red Sox have Roman Anthony, Marcelo Meyer, Kyle Teel and Kristian Campbell coming. There will be plenty of production at low salaries. There aren’t always opportunities to make the playoffs, and when a clear one exists, it’s incumbent on ownership to give a front office exactly what it needs, especially if money for a team worth $5 billion is the consideration.

Erik Neander, president of baseball operations, Tampa Bay Rays

The Rays have spent most of the season in the vicinity of .500. Their run differential is the sixth worst in MLB. They’ve already traded one of their starting pitchers. More moves are coming.

Unlike most other teams looking to deal away players, the Rays don’t need to. But they aren’t regarded as among the two or three smartest organizations in baseball because they’re bound by need. They recognize that in years when they’re unlikely to make the postseason, there is no shame in addressing the future.

And that future includes the return of Shane McClanahan, Jeffrey Springs and Drew Rasmussen from elbow surgery, the arrival of top prospects Junior Caminero and Carson Williams, and more spending, especially if a trade of Zach Eflin clears his $18 million salary for next season. There are few untouchables for Tampa Bay. Randy Arozarena could go. So could Isaac Paredes or Yandy Diaz or Brandon Lowe or anyone, really, who’s in arbitration or beyond — closer Pete Fairbanks and top reliever Jason Adam included.

Neander’s creativity will serve him well over the next month. The Rays’ combination of scouting and analytics is among the best balanced in the industry, and if the lack of talent elsewhere slows the market, Tampa Bay will be on speed dial for every contending team.

Chris Antonetti, president of baseball operations, Cleveland Guardians

Rarely does Cleveland go for it at the deadline, but then rarely are the Guardians in the position they presently find themselves. The closest facsimile to this season is 2016, when Cleveland needed relief help and went out and got the best reliever on the market in Andrew Miller. The result: a march to the World Series, where Cleveland lost a classic to the Chicago Cubs in seven games.

Antonetti has spent a quarter-century working in Cleveland’s front office, and he is perhaps the embodiment of a small-market baseball ops executive. The Guardians draft well, they develop well, their front office-manager relationship is excellent and they do it all on a shoestring budget.

If the Guardians want to argue that their 56-32 start isn’t enough to add the biggest names on the market, the team could still use depth on the offensive side, a relief arm in case of injuries to their big-league-best bullpen and especially a starter or two, with Shane Bieber out for the season and Triston McKenzie back in the minor leagues.

The Guardians signed veteran left-hander Matt Boyd last week, but he isn’t the answer by himself. It’s a move that costs only money, so it’s difficult to criticize, but it’s also a fraction of what Cleveland should do considering its level of play. In order to get to the World Series, the Guardians will need to act like making moves are a priority, not a privilege.

Honorable mention

David Stearns, president of baseball operations, New York Mets: Had the Mets not gone on a heater to climb back above .500, Stearns unquestionably would’ve been on the list above. His stakes, in that scenario, would revolve around a particularly hairy question: Will he trade three-time All-Star first baseman and impending free agent Pete Alonso? As things stand, the Mets shipping out talent runs the risk of alienating a fan base already disillusioned by the Steve Cohen era getting off to a slow start. Stearns is an inveterate balancer of present and future — he’s the one who traded away closer Josh Hader when the Brewers were in first place — so the notion of him recognizing the Mets’ flaws and shipping players out isn’t beyond the realm of possibility. But the likeliest outcome is more sparklers than fireworks.

A.J. Preller, president of baseball operations, San Diego Padres: Preller might need the Padres to make the playoffs to save his job, and while they’re in that position at the moment, he will not rest. The Padres need starting pitching more than any contender. Crochet is a perfect fit, but the White Sox want position players and San Diego is not giving up catching prospect Ethan Salas or shortstop prospect Leodalis De Vries, which could prompt the Padres to pivot. Preller will find something, even with a limited budget because San Diego ownership wants to stay under the $237 million luxury tax threshold. He always does. So while there is plenty at stake for Preller, that’s kind of how it is every deadline.

Matt Arnold, president of baseball operations, Milwaukee Brewers: Arnold made the first significant trade of summer deadline season by acquiring right-hander Aaron Civale from Tampa Bay, and it aligned with Milwaukee’s general philosophy of adding at the margins without having to surrender much in the way of prospect capital. The Brewers don’t need to go buck wild. They’re the best team in a bad NL Central. If anything, they could take advantage of the paucity of outfielders on the market and deal away a big leaguer while continuing to pursue for the starting pitching depth they need for this season and beyond.

Alex Anthopoulos, president of baseball operations, Atlanta Braves: The last time Ronald Acuna Jr. tore his ACL, the Braves were 46-47 and looked primed to punt on the 2021 season. Anthopoulos refused, added four outfielders at next to no cost and won the World Series. Hunting for value might wind up the preferred course of action here, too, but that doesn’t lessen the understanding that the Braves are smack in the middle of their winning window and sometimes a season simply isn’t what it could — or even should — be. If the Braves weren’t set up so well — and they still are, to be clear — Anthopoulos would deserve a place on the main list. Between the lack of high-impact players and Atlanta’s place in its contention cycle, Anthopoulos’ go-big-or-go-home instinct might not suit this particular version of the Braves, who at 49-39 still remain in position to host a wild-card series.

Jed Hoyer, president of baseball operations, Chicago Cubs: The denizens of Wrigley Field are restless. Early this season, the Cubs were the betting favorite to win the NL Central, and now they’re in last place, done in by a mediocre offense and a bullpen that can’t help but issue too many walks. Situations such as this should be easy: Get rid of the guys who don’t factor into post-2024 plans. Problem is, no one wants Kyle Hendricks, Hector Neris or David Bote. And everyone else is either signed long-term or pre-free agency. The Cubs are in no-man’s land, and in a game where the best routes are winning or losing, it’s a perilous place to be.

Farhan Zaidi, president of baseball operations, San Francisco Giants: Speaking of the middle, the Giants have lived there all season — for three years running, actually. They’re near the second luxury tax threshold and shed some of Austin Slater’s $4 million salary by trading him to Cincinnati on Sunday night. To get below the first threshold, they would need to deal away tens of millions more in annual salaries. Zaidi is under contract through 2026, but the clear expectation for San Francisco was to win this season. The Giants just returned Kyle Harrison and should get Blake Snell and Robbie Ray back in their rotation soon — and in an NL wild-card scene where 86 wins should be enough for a playoff spot, there’s reason for optimism. How to balance that hope with the abject averageness this team has displayed in recent seasons.