Article: Looking Back Upon Old Trades: #3 Dave Dombrowski Gets His Ace in Chris Sale

[Nick John]

Continuing our small series on major trades by Red Sox general managers during the John Henry era, we move on to Dave Dombrowski and a move that started out so brilliantly that it made the long, sad end worth it.

Welcome back to another entry in our short look back upon major trades from recent Red Sox GMs. After reviewing Ben Cherington’s trade for Eduardo Rodríguez, we move on to one of the game's most famous traders. You might know him as Dealing Dave Dombrowski, who ran baseball operations for the Red Sox from August 18, 2015, until September 9, 2019. Throughout his highly decorated career, Dombrowski has earned a reputation as a win-now GM and an owner whisperer, convincing ownership to authorize major moves to improve the major-league squad, often at great cost in terms of both money and prospects. He built the World Series champion 1997 Marlins, the Tigers team that went to three American League Championship Series and one World Series between 2011 and 2013, the 2018 World Series champion Red Sox, and the current Phillies squad that has been to three NLDS, an NLCS, and a World Series over the past three seasons.

He lived up to his reputation when he took the reins in Boston, trading away much of the farm system to bring in All-Star caliber players. Although he made several major trades during his tenure, the move I want to look back on should come as no surprise: Chris Sale trade.

Following a loss to Cleveland in the 2016 ALDS, the Red Sox and Dombrowski looked at ways to improve the team and get past the first round of the playoffs. While the front of the rotation was led by David Price and Cy Young Award winner Rick Porcello, the back end struggled. Clay Buchholz ran a 5.01 ERA as a starter and was demoted to the bullpen, Eduardo Rodríguez took a step back after an impressive rookie season in 2015, and deadline acquisition Drew Pomeranz regressed after coming over from San Diego. Dombrowski went after the right pitcher.

Left-hander Chris Sale had spent the first seven seasons of his career with the White Sox. He had two dominant years as a reliever, then spent five as a starter, during which he earned five straight All-Star selections and never finished worse than sixth in the Cy Young voting. In both 2015 and 2016, he earned MVP votes. He had a career 3.00 ERA and a record of 74 wins and 50 losses in 1110 innings pitched. Over those last five years, his 25.4 fWAR trailed only future Hall of Famers Max Scherzer and Clayton Kershaw (and ranked just one spot above David Price). Still only 27 years old at the end of 2016, he was a no-brainer for a Red Sox team ready to go all in on a championship run.

On December 6, 2016, that deal was finalized. In return for Sale, the White Sox received highly-touted prospects Michael Kopech and Yoán Moncada, along with Victor Diaz and Luis Alexander Basabe. The Red Sox won the four-for-one trade easily, as Sale picked up right where he'd left off in Chicago. His streak of All-Star selections, top-six Cy Young finishes and MVP votes would continue for two more years.

In 2017, Sale finished as the runner-up for the AL Cy Young Award and helped the Red Sox win their second consecutive AL East title. Across 32 starts and an MLB-leading 214 1/3 innings, he went 17-8 with a 2.90 ERA and an MLB-best 2.45 FIP. But what may be most impressive was his career high of 308 strikeouts and a (then) career-high 12.9 strikeouts per nine innings. Both marks were the highest in baseball. Sale was everything the Sox could have hoped for, anchoring a rotation plagued by inconsistency and injury. Unfortunately, the Red Sox would fall to the eventual World Series champs, the Astros, in the ALDS.

Sale’s continued dealing during the 2018 season. He was once again was tasked with leading the rotation. Alongside David Price and midseason acquisition Nathan Eovaldi, he did just that, winning 12 games and only losing four. He did so in just 27 games, as shoulder inflammation forced him onto the IL in both August and September. Despite the injury, Sale still threw 158 innings and struck out 237 while making another All-Star game and finishing fourth in the Cy Young voting. Over three postseason starts and two relief appearances, he ran a 4.11 ERA, but that was likely due more to bad luck than anything else, as he struck out a jaw-dropping 14.1 batters per nine innings. He appeared to be healthy in the ALDS, pitching in two games against the Yankees, but following that, he was not his usually effective self. In the ALCS, he made a single appearance, allowing two earned in four innings, before starting game one of the World Series. When it mattered the most, the ball was in Sale's hand. With the Red Sox up, 5-1, in Game 5, Sale blew the Dodgers away in the bottom of the ninth, striking out Justin Turner, Enrique Hernandez, and Manny Machado swinging to clinch the championship.

Sale signed a five-year, $145-million extension with the Red Sox prior to the 2019 season, but it didn’t work out too well. In the five seasons that followed his injury in 2018, Sale’s body could not keep up. After throwing the sixth-most innings in baseball from 2012 to 2018, he underwent Tommy John surgery in 2020. From 2019 to 2013, he he pitched in just 56 games with a 4.16 ERA. Following the 2023 season, the Red Sox would be trade Sale to Atlanta for infielder Vaughn Grissom. He would immediately make the Red Sox regret the move, bouncing back to claim his first Cy Young Award and returning to the All-Star game for the first time since 2018.

As for the players the Red Sox gave up in the Chris Sale trade, things never really seemed to work out for the White Sox. Yoán Moncada and Michael Kopech headline the move. Both players showcased flashes of brilliance — Moncada put up excellent 2019 and 2021 seasons, and Kopech was solid in 2021 and 2022, but inconsistency and injuries kept them from reaching their potential

Moncada was a roughly league-average hitter in his first two full seasons with the White Sox, and 2019 looked like it should have been his breakthrough campaign. Moncada played in 132 games and put up 5.2 fWAR, slashing .315/.367/.548 to go with 25 home runs. He was also propped up by an absurdly high .406 BABIP, the highest among all qualified players. Unfortunately, that was as good as it would get for Moncada. In 2021, he ran a 120 wRC+ and hit 14 home runs, but that was the last time he would look like a star. Over the past three seasons, injuries have limited him to just 208 games. He only played 12 games in 2024. Now a free agent and the White Sox rebuilding once more, it’s unlikely he returns to Chicago.

Kopech is already gone, having been traded to the Dodgers at the 2024 trade deadline for Miguel Vargas, Alexander Albertus, and Jeral Perez. In 2018, Kopech made four starts for the White Sox before undergoing Tommy John surgery in September. He would go on to miss all of the 2019 season and sit out the 2020 season due to the COVID-19 pandemic, choosing to get his body right rather than playing in the shortened 60-game season without any buildup through rehab assignments. Kopech was then moved to the bullpen to help limit his innings. He performed well, running a 3.50 ERA over 44 appearances. Kopech returned to the rotation where in 2022, but despite his shiny 3.54 ERA, the numbers under the hood were concerning. His walk and strikeout numbers went in the wrong directions, resulting in a 4.50 ERA.

The bill came due in 2023, when he ran a 5.43 ERA. The White Sox moved Kopech back to the bullpen in 2024, and he pitched in 43 games before being traded to the Dodgers. Prior to the trade, he ran an ERA of 4.74 and a WHIP of 1.35, but with the Dodgers, his ERA dropped to 1.13 and his WHIP to 0.79. He got into 10 postseason games, running a 3.00 ERA.

As for the other two players in the trade, Victor Diaz only appeared in 14 games in the low levels of the White Sox organization, making it up to high-A Winston-Salem before being released in 2017. Luis Alexander Basabe never made it to the majors with the White Sox, making it as high as Double A in 2019 before having his contract purchased by the San Francisco Giants in 2020. The outfielder would play nine games in San Francisco before spending 2021 in the minor leagues once more. He signed a minor league deal with the White Sox for the 2022 season but was released in May and hasn’t played professional baseball since.

In the end, Dombrowski got his wish for an ace who could anchor the rotation through difficulties. While the extension didn't work out to anyone's satisfaction (save maybe the Braves), Sale did what he came to Boston to do: win a championship. It may be hard to separate the trade from the extension, but in those first three seasons, Sale continued to be one of the premier pitchers in all of baseball. Combine that with the fact that the prospects Boston coughed up for him never truly panned out, and the move is an easy victory for the Red Sox.

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[moonslav59]

The Sale trade shook the ground. To me, it was the biggest deal the Sox made since signing Manny. The 3 years of control was a huge part of my excitement on trade day. We got the best pitcher in MLB: "Chris Freakin' Sale!" (The Pedro trade was probably the most impactful in my lifetime.)

The Nate trade rivals the Schilling trade. Both led to rings and legendary playoff performances.

The Kimbrell trade seemed like an overpay, at the time, but shortly afterwards the price of closers skyrocketed.

The Pom trade seemed like an overpay, as well, but he did give us a very nice 2017 season. He was no help in 2018. The Thornburg trade looked good, at the time, but the injury ruined it.

The hindsight, all the prospects DD traded did not equal the returns we got. I counted over 20 players DD traded that were, at one time (not always at the time of the deal) were a top 20 prospects. It's easy to lazily blame him for the long lull we saw in farm help from his era into Bloom's, including the stretch from Devers to Houck/Duran, but as it turned out, he kept almost every prospect that amounted to anything, including Devers, Houck and Duran, and some of his far-away prospects have ended up doing better than the top prospects he did trade, namely Moncada (1) , Espinosa (3) Margot (4) Kopech (5) Beeks (6) and Guerra (6) 

He kept Devers, Houck, Duran, Casas, Bello, Crawford and others.

[smokedogg1982]

People blame Sugardaddy Dave Dombrowski for decimating the farm system and dealing the future for the now. The way I see it Dombrowski had a unique eye for talent and very rarely dealt a player who would amount to something. He traveled with the team and when they needed a player he went and got the best available player for the position.