FanSided GM Simulation: Red Sox slash payroll with Nathan Eovaldi trade

NEW YORK, NEW YORK - OCTOBER 08: Nathan Eovaldi #17 of the Boston Red Sox throws a pitch against the New York Yankees during the first inning in Game Three of the American League Division Series at Yankee Stadium on October 08, 2018 in the Bronx borough of New York City. (Photo by Mike Stobe/Getty Images)
NEW YORK, NEW YORK - OCTOBER 08: Nathan Eovaldi #17 of the Boston Red Sox throws a pitch against the New York Yankees during the first inning in Game Three of the American League Division Series at Yankee Stadium on October 08, 2018 in the Bronx borough of New York City. (Photo by Mike Stobe/Getty Images) /

Every FanSided MLB site participated in an offseason simulation where we traded away Nathan Eovaldi to slash payroll for the Red Sox.

Chaim Bloom is entering his first offseason at the helm of the Boston Red Sox but before he gets to work on implementing his blueprint on the organization, we thought we’d take a crack at it. Our Site Experts participated in the FanSided GM Simulation, an annual event where representatives from each MLB site in our network serve as the general manager of their respective teams.

One of the stipulations of this event is that our decisions must be realistic. Sure, it’s fun to fantasize about signing the top talent on the market with our imaginary money but that’s hardly the point of this exercise.

Every team was asked to set a budget before our free agency period opened. Knowing the Red Sox have set a goal of dipping under the luxury tax line in 2020, our first priority was finding a way to shed payroll. We accomplished this mission by negotiating a trade with Southside Showdown, FanSided’s site for the Chicago White Sox.

Our big payroll slashing move for the purposes of this simulation was trading right-handed pitcher Nathan Eovaldi to the White Sox in exchange for infield prospect Nick Madrigal.

Boston’s trio of high-priced starting pitchers were all discussed in various potential trades but Eovaldi proved to be the easiest to move. We received several offers for Chris Sale and David Price from teams aiming to take advantage of our payroll problems to acquire a front-line starter for an underwhelming return but we weren’t interested in a pure salary dump.

We are pleased with the player we received in exchange for Eovaldi. Madrigal is the No. 40 prospect in’s rankings.

He’s a natural shortstop who moves well enough to handle the position but has mostly covered second base since shifting over to the position in college. He’s probably a better fit at second base due to his average arm strength but that suits the Red Sox just fine since Xander Bogaerts is locked in at shortstop for the foreseeable future and they need a long-term solution at second.

Some scouts considered Madrigal the best pure hitter in the 2018 draft. He sprays line drives to all fields and rarely strikes out. He may not bring much power to the plate but he’ll be a great contact hitter who can rack up doubles and has the speed to swipe a base when he settles for singles.

Madrigal reached Triple-A last season where he hit .331 with a .822 OPS in 29 games. He could make his big league debut in 2020 and challenge for the starting role at second base if he were traded to the Red Sox.

The Red Sox currently have a hole in their infield that can be filled by plugging Madrigal at second base to allow Michael Chavis to take over as the primary first baseman. In the unlikely event that Dustin Pedroia contributes on the field in 2020, Madrigal would still provide value as a utility infielder.

Boston’s payroll sits at just under $227 million. Eovaldi is owed $51 million over the next three years and counts for about $17 million toward the luxury tax in 2020. Trading Eovaldi and non-tendering Sandy Leon, who is projected to make $2.8 million in arbitration, would put the Red Sox under the $208 million tax threshold.

This deal doesn’t leave much wiggle room to fill two spots in the starting rotation and upgrade the bullpen, preventing us from jumping in on the free agency bidding for our simulation. Another trade to free up more room in the budget would be necessary and there were a few other scenarios we discussed with our fellow site experts.

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Trading Jackie Bradley Jr. for a starting pitcher who makes less than the $11 million the center fielder is projected to earn in arbitration would kill two birds with one stone. Receiving prospects in return would shed enough payroll to afford a stater in free agency. We talked to a few teams about Bradley but weren’t able to strike a deal.

We were on the verge of a blockbuster trade that would have expanded upon our Eovaldi deal with the White Sox to include J.D. Martinez. Chicago would have sent us Andrew Vaughn, the third overall pick in the 2019 draft and No. 21 ranked prospect on, in addition to Madrigal and a couple of other promising prospects.

Losing the bat of Martinez in the heart of the order would certainly hurt but removing his $23.75 million salary from the payroll would give us plenty of financial flexibility to upgrade the pitching staff. We would have been thrilled to acquire a pair of top-40 prospects in exchange for a player the Red Sox secretly hoped would solve their payroll problems for them by opting out of his contract and leaving them for nothing.

Trade talks fell apart once the White Sox signed Yasmani Grandal and reached an extension with Jose Abreu. We decided that these real-life transactions should have ramifications on our simulation and it wasn’t feasible for Chicago to take on Martinez’s salary once those other moves were made. We had an agreement with Southside Showdown on the players involved but never made the deal official in this simulation.

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The Eovaldi trade ended up being the only move we made on behalf of the Red Sox but this event was only meant to simulate next month’s winter meetings. It’s not intended to finalize what the roster will be heading into 2020. There’s still work to be done but this would be a promising start to the Red Sox offseason.