How Theo Epstein shaped the 2018 Trade Deadline

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ANAHEIM, CALIFORNIA - APRIL 04: Chicago Cubs President of Baseball Operations Theo Epstein looks on prior to the Opening Day game against the Los Angeles Angels at Angel Stadium of Anaheim on April 4, 2016 in Anaheim, California. (Photo by Sean M. Haffey/Getty Images)

It’s no secret to anyone that the Chicago Cubs have been quiet at the trade deadline. They didn’t go after Manny Machado, they didn’t appear to be a front-runner for Zach Britton, nor were they key players for J.A. Happ.

As of right now, their only move was for Rangers’ swingman Jesse Chavez, not a sexy move by any means. Their farm system, now with only one top-100 prospect in catcher Miguel Amaya, is devoid of much talent available to acquire some of the big names.

With all that being said, it’s not like the Cubs haven’t influenced the market. The Cubs and their boss Theo Epstein have influenced this year’s trade market more than anyone else, including those who have acquired the big name players.

Epstein’s influence on this trade market dates back two years, to July 25 of 2016. It was that day that the Cubs acquired Aroldis Chapman from the Yankees, a rental who the Cubs were rather obviously not keeping, for Gleyber Torres, Billy McKinney, and Adam Warren.

The trade market has not recovered from this trade yet. This was made evident by the Yu Darvish trade last year, which brought back a top-100 prospect in Willie Calhoun, and has reared its head again. This time, however, Dan Duquette is the main benefactor.

Duquette and the Orioles had the two biggest rentals on the market this year, shortstop Manny Machado and reliever Zach Britton.

By all accounts, Duquette got more for both these guys than what conventional wisdom says is value for a rental player. Yusniel Diaz, the main piece in the Machado trade, is already Baltimore’s top prospect, and a top-60 prospect in baseball. Dillon Tate, the former 4th overall pick, headlined the Zach Britton deal, a haul for a reliever who just a month ago came off of a long-term injury.

Neither of those trades happens without the Chapman deal. With that one move, Theo Epstein changed the entire dynamic of the rental trade market. It’s crazy to think about now, but that Chapman trade was the signal to the rest of baseball that the Yankees were starting to rebuild, as they’d trade Andrew Miller just a few days later.

Sure, Chapman being a crucial piece on a World Series roster made the trade worth it from the Cubs’ perspective. The Indians win the World Series in five games if the Cubs don’t make that move. However, looking at it purely from a value perspective, Theo Epstein gave up what was, at the time, an unprecedented package to get Chapman.

Back to Baltimore, however, they do not get anything close to what they did for either of their two guys without the Chapman trade. Baltimore had to create their own leverage with the Machado situation, they couldn’t suddenly hold onto him and declare they were going to go for it in free agency the following year. The Yankees could have. Dan Duquette’s ability to get one of minor league baseball’s top power bats and three solid minor league arms for Machado and Britton is a direct result of Theo Epstein willing to overpay for Aroldis Chapman.

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I have been saying a lot of bad things about Dan Duquette leading into the Machado trade. I thought he was going to screw it up badly. He didn’t, and I give him a ton of credit for launching his rebuild with a bunch of really solid guys.

Epstein’s influence doesn’t stop with the precedent he set regarding rental players, though. Epstein’s other marquee trade, acquiring Jose Quintana, may have directly harmed the Mets in their search to launch their rebuild.

Epstein gave up Eloy Jimenez, at the time a top-10 prospect in baseball, and Dylan Cease, another top-100 guy, for Jose Quintana a little over a year ago. The jury is still out on Quintana in a Cub uniform, but it was clear at the time that Quintana’s pedigree (7th among pitchers in fWAR over the past season and a half at the time of the trade) and contract made him a lot more desirable than many thought.

The Mets have two main assets available to trade right now: Noah Syndergaard and Jacob DeGrom. Syndergaard has almost an identical situation to Quintana last year, by which I mean they both had 3.5 years of control left and were both relatively young (Syndergaard is 25, Quintana was 27). We know how good Syndergaard can be, but he hasn’t stayed healthy long enough to make him worth as much as Quintana.

DeGrom is a little bit older and has a year less of control, so he likely isn’t as valuable either. However, DeGrom is having a year that Jose Quintana could likely only dream of having, which may cancel out the year of control and age difference.

Either way, the Mets are going to want something similar to what the White Sox got for Quintana. Unluckily for them, there isn’t a team that is able to match that big price of the Quintana deal. The closest team with a need in the rotation to a match would be the Yankees, and now there is a precedent of marquee trades between inner-city rivals due to Theo Epstein, but even the Yanks don’t have a prospect like Eloy Jimenez to headline.

As much as we would like to think they do, MLB front offices do not operate in a vacuum. A single move can have ramifications for years to come. One domino falling can cause a chain reaction felt years into the future, and it’s hard to have the foresight into these things.

The Cubs recent dealings are that first domino. Both the Quintana and Chapman trades have been huge beneficiaries to some teams, and huge detriments to others. I’m honestly not sure whether the market will recover next year or even the year after that. Theo Epstein and his staff, despite only making one minor trade, have put their stamp on this trade deadline heavier than most other teams that have made bigger moves.

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