Red Sox: Chris Sale trade is a template for future trades

A past and present look at the Boston Red Sox Chris Sale trade.

Science fiction and pop psychology are filled with stories about what you would do if you had the chance at a Mulligan in life. The same could apply to baseball at the signature trade of the Dave Dombrowski reign. On December 6, 2016, the Boston Red Sox sent four players – Yoan Moncada, Michael Kopech, Luis Alexander Basabe, and Victor Diaz to the Chicago White Sox for lefty Chris Sale. Such a deal also gives insight into the present with Boston. Let’s take a review of how the participants have performed.

This was a transaction that seemed to parallel to a certain degree the deal that brought Pedro Martinez to Boston – a young pitching star that is a rare find. Sale was simply one of the best in all of baseball and his first season demonstrated that. Sale’s second season was less productive with arm issues surfacing, but he played his part out of the bullpen, including a knee-bending last out in the World Series.

Sale soon made his money – big money – after years of being “underpaid” by baseball standards. A risky move of five-years at $145 million that would kick in for the 2020 season – a season in which Sale spends his time recovering from Tommy John Surgery. A $30 million vacation to mend. Sale will be 32-years-old next season and just how productive is a huge question mark for a team desperate for an ace.

Basabe is a switch-hitting outfielder who had wallowed in the lower depths of the farm systems of the White and Red Sox. Last season at Birmingham (AA), Basabe hit just .246 with little power. Basabe is not listed among the top 30 prospects of the White Sox nor is the now 26-year-old right-hander Diaz who last pitched in 2017 with a history of shoulder woes.

Then there is Moncada and Kopech. The switch-hitting Moncada was what can best be described as a Bonus Baby from Cuba that thanks to his projected upside the final cost to the Red Sox – including penalties – exceeded $63 million. Moncada became a fixture on the list of the top prospects of baseball and the same applied to hard-throwing Kopech.

For Moncada, a legit five-tool player, the breakout came in 2019 with a slash of 25/79/.315 and a reduction in strikeouts. The White Sox have signed Moncada to a five-year and $70 million extension. This season, despite an early bout with COVID-19, Moncada has continued to do well, but the average is down compared to 2019.  Still a solid contributor to a playoff-bound White Sox team.

A different story for Kopech this season. Kopech, also a regular on the list of best pitching prospects, broke in during the 2018 season with a flourish. The poor control had been reduced and Kopech’s high 90s fastball and devastating slider and occasional change looked like the White Sox had a gem and then Kopech blew his arm out. Kopech chooses to sit out in 2020 as a COVID exemption to further his rehabilitation.

If you knew then what you know now, would you do it? The weighing is a World Series title against the rupture of the farm system. After an 86-year drought, I would always take the title, but that was all erased in 2004.

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The tables are turned on the deal and Sale certainly was a solid contributor to a World Series title, but the stripping of the farm system had eventual consequences. It also creates a benchmark for what Boston should do when dealing with a talent for prospects. The deal is therefore important in the context of the present.

The Red Sox recent transactions brought no influx that is considered on a baseball par with Moncada and Kopech. The Mookie Betts deal had that potential but Betts’ value was limited by the free-agent calendar. Alex Verdugo appears to be a potential star player for Boston. The prospects have promise but none were number one in all of baseball. The other deals bought a journeyman pitcher in Nick Pivetta and a young arm in Connor Seabold that even the most optimistic evaluator places as a mid to bottom rotation starter.

To get the best in prospects you have to offer something of value in return and that value has to be needed. The Red Sox’s two most prized possessions are Xander Bogaerts and Rafael Devers. Trade them and you most certainly would expect a team’s top pitching prospect or one with a season or two experience in return – and more. And there is the problem of finding both a system with the necessary talent and a slot for either Bogaerts or Devers. Will the Red Sox shop Bogaerts and Devers this winter? If they do the price must be in the Sale category.

The path of trading Devers and Bogaerts would be a foolish one from my soapbox. Bogaerts is signed for several seasons (with possible opt-outs) and Devers is team controllable through 2024 and both are strategic to the core of this team. The Red Sox have some money and maybe Chaim Bloom is far more adept at free-agent decision making than some of the litany of past failures.