Consider this scenario: On July 1 a butterfly flaps its wings, which causes Red Sox president of baseball operations Dave Dombrowski to scratch his nose two weeks later, briefly postponing a scheduled phone call with Padres general manager A.J. Preller. In the meantime, Josh Byrnes, senior vice president of baseball operations for the Dodgers, calls Preller for a casual pre-deadline chat . . . so, how are the kids? Wait, do you have kids? Is Drew Pomeranz available? Dombrowski calls Preller, but it’s too late—by the time he gets through, LA’s cavalry of current and former GMs have all talked to Preller. Pomeranz is a Dodger, and the world is changed forever.

It’s a silly scenario, sure, but it’s fun to think about how much the trade deadline could have changed if just a single move had gone another way. The deadline—and the weeks preceding it—consists of many (many!) discrete trades, all interesting in various ways, even in isolation. But they’re all connected, too, and it’s always more entertaining to imagine what could have been rather than what is, at least after we’ve already analyzed what is to death. How would the baseball world have turned out different if Josh Byrnes beat Dave Dombrowski to A.J. Preller’s smart phone?

Los Angeles Dodgers

Actual Trade: Dodgers acquire LHP Rich Hill and RF-L Josh Reddick from Oakland Athletics in exchange for RHP Frankie Montas, RHP Grant Holmes, and RHP Jharel Cotton. [8/1]

Butterfly Effect Trade: Dodgers acquire LHP Drew Pomeranz from San Diego Padres in exchange for RHP Jose De Leon and RHP Frankie Montas. [7/16]

The Dodgers need starting pitching. In this universe, they don’t have Rich Hill, and Clayton Kershaw is still hurt (a butterfly’s wings can’t change everything.) Just prior to our proposed trade, LA’s rotation looked something like this:



Kenta Maeda


Scott Kazmir


Bud Norris


Brandon McCarthy


Julio Urias


That’s a workable staff, maybe, but the Dodgers aren’t in the business of workable staffs. Plus, Urias is not yet 20 years old, and his innings count this season, already at 85-plus, will be monitored closely from here out (he’s in the bullpen now). Further, none of the five pitchers listed above averages six innings per start this season, and three of them (Norris, Urias, and McCarthy) are averaging under five innings a turn. The Dodgers need starting pitching just to save their bullpen, especially when you consider that Kershaw, recently transferred to the 60-day DL, isn’t eligible to return to a big-league mound until August 27.

Enter Pomeranz, perhaps the most coveted starting pitcher to change teams in July. If you’re thinking that an intra-division trade between the Dodgers and Padres isn’t practical, remember that these two teams swapped Matt Kemp and Yasmani Grandal (and others) a couple Decembers back. Pomeranz fits in LA because he helps the rotation now—he’s working on a 2.89 DRA this year and, health risks aside, he’s the closest thing the Dodgers have to a true no. 2—and later, as he’s under control though 2018. So he slides into the rotation long term, next to some combination of Kershaw, Kazmir, Maeda, McCarthy, Urias, and currently injured Hyun-Jin Ryu. That might be a bit lefty-heavy, but—time-traveling here—the real-life Dodgers actually did acquire lefty Rich Hill, so they probably don’t view it as a major concern.

Boston Red Sox

Actual Trade: Red Sox acquire LHP Drew Pomeranz from San Diego Padres in exchange for RHP Anderson Espinoza. [7/16]

Butterfly Effect Trade: Red Sox acquire LHP Chris Sale from Chicago White Sox in exchange for RHP Anderson Espinoza, 3B-L Rafael Devers, C-S Blake Swihart, and RHP Michael Kopech. [7/29]

With Pomeranz off the table and Dombrowski unknowingly lamenting the existence of the Danaus chrysippus—and still itching to deal some prospects for a win-now player—the Red Sox are left with two clear options for a significant upgrade to their starting rotation (at least in our all-lefty world): Rich Hill or Chris Sale.

Hill makes sense. His return to stardom began last year in Boston, where he reeled off four improbable starts that he eventually parlayed into a one-year, $6 million offseason deal with Oakland. Of course, the Red Sox could have had him back then for $6 or $7 million and a guaranteed rotation slot, but instead they got too comfy with Clay Buchholz and Joe Kelly, letting Hill head west. A midseason reunion is logical, but now Billy Beane and David Forst are asking for Anderson Espinoza or Rafael Devers, and Dombrowski and Mike Hazen just aren’t feeling good about the whole thing.

Instead, with Espinoza still in the organization, the Red Sox work out a megadeal with the White Sox, hold onto their top two prospects in Yoan Moncada and Andrew Benintendi, and transform an iffy starting five into, at least, a dominant one-two punch. Consider the new Red Sox rotation:



David Price


Chris Sale


Steven Wright


Rick Porcello


Eduardo Rodriguez


Among AL playoff contenders, only the Indians—with Corey Kluber and Carlos Carrasco—can boast a top two as good as the Red Sox’s, and, per PECOTA, opting for Sale over Pomeranz nets Boston a one-win upgrade down this season’s stretch alone. Further, Sale (like Pomeranz) isn’t just a pennant race rental, as he's under control through 2019 with no-brainer options. With Price and Sale signed through the rest of the decade, the Red Sox—with a young offensive core including Xander Bogaerts, Mookie Betts, Jackie Bradley Jr., Benintendi, and Moncada—might be the prohibitive divisional favorite until the next, ahem, Presidential election.

Baltimore Orioles

Actual Trade: Orioles acquire LHP Wade Miley from Seattle Mariners in exchange for LHP Ariel Miranda. [8/1]

Butterfly Effect Trade: Orioles acquire LHP Rich Hill from Oakland Athletics in exchange for RHP Brad Brach and C-L Chance Sisco. [8/1]

As I mentioned in the actual transaction analysis on deadline day, the Orioles could use a good left-handed starter—for one because their rotation is full of righties and for two, and probably more importantly, because their rotation isn’t very good. Chris Tillman, career 4.46 DRA, looks like the on-paper ace, somehow, and even though Dylan Bundy (whom I originally neglected to mention) has emerged as a legit major-league arm, he hasn’t thrown 100-plus innings in a professional season since 2012.

With two of Hill’s most likely destinations choosing different options, the Orioles become a possible landing spot. Except, unlike LA and Boston, they can’t rely on a loaded farm system to pry the lefty away from Beane’s grasp. Instead, they get creative, wheeling Oakland their best position player prospect and relief ace Brad Brach, who basically works for the A’s as a ticket for a large package of prospects at a future deadline.

Toronto Blue Jays

Actual Trade: Blue Jays acquire LHP Francisco Liriano, C-L Reese McGuire, and OF-R Harold Ramirez from Pittsburgh Pirates in exchange for RHP Drew Hutchison. [8/1]

Butterfly Effect Trade: Blue Jays acquire LHP Wade Miley from Seattle Mariners in exchange for LHP Ryan Borucki. [8/1]

Wade Miley: everybody wants ‘em, everybody wants to get rid of him. With their two chief divisional rivals making plays for starting pitchers, the Blue Jays are pressed into making a trade, especially since they might eventually move Aaron Sanchez and his 3.37 DRA out of the rotation and into the bullpen. Francisco Liriano still works here—and he probably comes with more upside than Miley, despite the three-year age gap—but the Blue Jays move so quickly to respond to Boston and Baltimore that they instead settle for Miley without ever realizing Liriano’s available.

Pittsburgh Pirates

Actual Trade: Pirates acquire RHP Drew Hutchison from Toronto Blue Jays in in exchange for LHP Francisco Liriano, C-L Reese McGuire, and OF-R Harold Ramirez. [8/1]

Butterfly Effect Trade: Liriano stays put.

Let’s play the mystery player game:


Player A DRA

Player B DRA













Okay, so Player A is better, but he’s also world-famous Cole Hamels. Player B is—you guessed it—Francisco Liriano, whose been a poor man’s Hamels over the last few years, and at a fraction of the cost and notoriety. In real life, he was jettisoned off with prospects for Drew Hutchison, with just a year and not quite $14 million left on his contract after this season. Here, the Pirates realize there’s no pressing reason (besides money) to sell low on Liriano—even if his pitching style isn’t necessarily working as well as in the past—so they keep him and bank on a turnaround.

Minnesota Twins

Actual Trade: Twins acquire LHP Hector Santiago and RHP Alan Busenitz from Los Angeles Angels in exchange for RHP Ricky Nolasco, Alex Meyer, and cash. [8/1]

Butterfly Effect Trade: Twins acquire LHP Hector Santiago and RHP Alan Busenitz from Los Angeles Angels in exchange for RHP Ricky Nolasco, Alex Meyer, and cash. [8/1]

With Miley gone and Liriano stuck in Pittsburgh, every team still looking for a lefty starter scrambles for Hector Santiago, but only the Twins actually want him for anything more than a 25-year-old in Single-A. Some trades are immune to even our most elaborate alternate universes, and this is one of them.

Altogether, in our scenario, 20 players end up in different locales, affecting millions of fans, hundreds of family members and hotel valets, and countless other major-league roster moves, both at this trade deadline and in the future . . . all because Dave Dombrowski picked up his phone five seconds too late.

Thank you for reading

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Cool idea. You don't think the Twins would take a couple prospects to reunite with Liriano? Maybe Liriano/McGuire/Ramirez for Tyler Duffey?
Thanks, and you know, Liriano to the Twins would have made good sense, but I was too stuck on throwing that barb at them about trading for Santiago. Just a weird trade, I thought, even though I know Meyer has fallen a lot. He still seems plenty interesting as a late developing type if he can ever figure out the mechanics/control.
If this were the return for Sale, I would cry.
Way too low? Espinoza, by himself, did get Pomeranz, and I know there's a big, big gap between Pomeranz and Sale, but Devers is a top ~20 guy, Swihart is a buy-low catcher with offensive potential, and Kopech is a fast-rising 20-year-old with 100-plus heat.
You forgot about Pirates sending their top 5 prospects for any broken bats or sore-armed pitchers that will be free agents at the end of the year! Cheap is the word in Bucco land :-)