10 decisions that helped lead the Red Sox to another World Series win

Dave Dombrowski finished what Ben Cherington started.

Los Angeles, CA - 10/28/2018 - Mookie Betts celebrates with Steve Pearce after hitting a home run in the sixth inning.The Los Angeles Dodgers host the Boston Red Sox in Game 5 of the World Series at Dodger Stadium. (Jim Davis/Globe staff)
Mookie Betts celebrates with Steve Pearce after hitting a home run in the sixth inning of Game 5 of the World Series. –Jim Davis/Globe staff


From the best record in spring training, to a 17-2 start, to a 108-win regular season, to a dominant march through the iron of the major leagues the Red Sox romped through the 2018 season on the way to claims that they’re the best team in franchise history — if not one of the best teams baseball has ever seen.

But the process of building these champs didn’t begin in February when the team reached Fort Myers. It’s a process that started more than four years ago, when the team had barely moved beyond the wake of their 2013 championship, and when Ben Cherington began the process of building toward the next great Red Sox team. 


He didn’t get to see it through, but what Cherington started, Dave Dombrowski came in to finish. That considered, here’s a look at 10 personnel decisions that ultimately helped to render the Sox’ latest world title (listed in chronological order): 

Moving Mookie

On May 18, 2014, after he’d started more than 200 minor-league games at second base, the Red Sox acknowledged that the vast offensive assets featured by one of their top prospects had put him on the fast track to the big leagues, and they needed to make preparations for his arrival. So they sent Mookie Betts to center field — changing the course of his career, and franchise history.

Betts, then 21, took quickly to his new position, and within two years he was in the midst of his first Gold Glove campaign. He added a second a year later, and metrics make the case that he has been the best right fielder in baseball over each of the past two seasons. His defense has become such a weapon that even when his bat has slumped he’s still had the ability to help win a game with his glove and arm, as he did at Houston during the ALCS.

That same week in 2014, the Sox re-signed Stephen Drew to play shortstop, and in the process initiated some struggles from Xander Bogaerts that coincided with his shift over to third base. So there was no guarantee that changing positions would work with Betts. Nor were there any assurances that it wouldn’t affect his offensive game. But it worked — giving Betts the chance to get to the majors later that year, enjoy some success, and blossom into an MVP-caliber player that by 25 was able to help carry a team to a title.

Porcello for Cespedes and the summer of 2014


Less than a year removed from a championship, things had fallen apart for the Sox by the summer of 2014. Coming out of the All-Star break there was some hedging about the state (and fate) of the club, but by the trade deadline Cherington was more decisive — and the reset had begun.

In June the team had drafted Michael Kopech and Jalen Beeks (each of whom later became a significant asset), then in July the Sox started to restart the system by unloading from the Major League team. And the 2018 roster says the Sox did relatively well in those dealings. 

Jake Peavy brought back Heath Hembree, who for a period of this season was a go-to reliever with men on base. John Lackey brought back Joe Kelly, whose dominant World Series thrust him onto the fringes of the MVP discussion. Andrew Miller brought back Eduardo Rodriguez, a rotation staple and a big reason why the Sox beat the Dodgers twice after losing in 18 innings. 

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And Jon Lester brought back Yoenis Cespedes, who Cherington then turned into Rick Porcello. That Cespedes-for-Porcello flip has long since been justified by Cespedes’s persistent injuries and Porcello’s Cy Young season, but beyond the quality starts and effective relief appearances the righty turned in this postseason, it’s clear he has become a valued leader for this club, and a steadying force both on the mound and in the dugout. 

Drafting Benintendi

Two years earlier, the Sox had used the No. 7 overall pick on Trey Ball, a big lefty pitcher who posted a 7.58 ERA in 34 appearances as a reliever for the Portland Sea Dogs this past season. And of those taken after Andrew Benintendi in the 2015 draft, only nine have reached the major leagues. Dodgers stud Walker Buehler and Cubs second baseman Ian Happ are the only ones among that mix who have been worth at least one win more than an average replacement-level player in the majors.


So the Sox did well to identify and select Benintendi where they did, further capitalizing on their failures of the 2014 season by taking advantage of their corresponding draft position. Having a five-tool threat like Benintendi, at his salary, is part of the reason Boston has been able to move other prospects and pour their monetary resources into pricier veterans. 

Adding Kimbrel and Price

Dombrowski moved quickly to address Boston’s needs in advance of the 2016 season, and so it was within a three-week span of November and December that the Sox added an ace to the front of their rotation and a closer to the back end of their bullpen. 

Both of those roles settled in other areas of the roster, and while each of them has experienced some inconsistency intermixed with dominance during his Red Sox career, the bottom line is that Boston finished last in each of the two seasons before Kimbrel and Price arrived — and with those three the club has won three straight division titles. 

Those results are hard to argue, especially when even signing Price for $217 million hasn’t prevented the Sox from pursuing other high-end pitchers and well-paid players, and when the bounty swapped for Kimbrel hasn’t exactly turned the fates of the Padres franchise. Manuel Margot, Javy Guerra, and Carlos Asuaje all played in San Diego this year — but combined for 0.8 WAR between the three of them. That certainly seems worth the 108 saves and 6.7 WAR Kimbrel has delivered the Sox over his three seasons.

Trading for Sale

The Chris Sale trade is the one that got Sox fans worried about Dombrowski destroying the farm system, largely because the principal prospects involved were familiar names. Kopech’s fastball had already started to tantalize the fan base. Yoan Moncada was considered the best prospect not only in Boston’s system, but in all of baseball.

Less than two years later, Sale has posted a 2.56 ERA for the Red Sox, and just got the final out of the World Series, while Kopech will miss all of 2019 with Tommy John surgery and Moncada struck out more than any other major-league hitter this season (once every three plate appearances). Both of them could yet be good players. Even great players. Sale’s left arm his leadership will still have been worth it, even if he leaves in free agency after 2019.

Moving on from Panda and Hanley

Of the Sox MLB-leading payroll this season, more than $40 million was effectively dead funds being paid to Hanley Ramirez and Pablo Sandoval. It says a lot about ownership that John Henry and Co. were willing to absorb those losses in the interest of moving on from a couple of players who were signed in the winter before the 2015 season with the expectation that they would be the veteran leaders of the Red Sox renaissance.

But on top of the eating the money, the club’s decisive actions to move on from those two players directly opened up opportunities for the team to get better on the field. If ownership had forced the team to make it work with Sandoval beyond 2017, the likelihood of having a spot for JD Martinez would’ve significantly dissipated. And if the Sox had decided to let Ramirez stick around for the rest of the 2018 season, there would’ve been no need to go out and acquire a right-handed first-base type. That would’ve likely left Steve Pearce in Toronto.

Hiring Alex Cora

Every time a Red Sox player repeated the phrase “from Day 1 of spring training” amid Sunday night’s euphoria at Dodger Stadium, it served as a testament to the wisdom of hiring Cora. But the decision wasn’t so universally approved when it was announced last October. 

Firing John Farrell, even after a pair of East championships, wasn’t the issue for some people. It was bringing a first-year manager into the Fenway pressure cooker, and doing so under expectations that even 93 wins and division titles wasn’t good enough. Cora didn’t even have minor-league managerial experience to refer back to if trouble surfaced. 

Further, if the Sox were willing to be patient there would be more veteran options available. Dombrowski has a tendency to trend toward the familiar, and Brad Ausmus’s name was surfaced. Joe Girardi was at that point said to be on his way out with the Yankees. Others would’ve been safer bets, too, at least on paper.

But the Sox settled on Cora, who embraced all that came with Boston, with the intense responsibilities of the manager’s room on Jersey Street, and with the lofty demands of a gradually disengaging fanbase. And it’s hard to imagine a better fit.

Holding onto JBJ

Jackie Bradley Jr.’s name has surfaced in trade rumors for years, but last year those rumors made as much sense as ever — especially given the names being attached to a potential swap. The Sox were in need of a big bat after failing to replace David Ortiz, and after struggling to hit home runs in 2017, so a potential deal with the Indians for slugger Edwin Encarnacion seemed like a win-win. There was another report suggesting the Dodgers wanted Bradley in exchange for Yasiel Puig.

Later reports suggested that it was the Red Sox who turned down those deals, and any others that would have included Bradley. They held on to their center fielder for the sake of his defense, and instead of spinning him to get their bat they waited out the market and signed Martinez around the start of spring training. All it cost them was money, and they still had the outfield defense they so valued in Fenway Park. 

Defensively, Bradley saved more runs than any outfielder in the majors. Offensively, he had a good second half. A collectively the Sox scored more runs than any other AL team — even without Puig (2.7) or Encarnacion (1.9), each of whom finished the season with roughly the same WAR value as Bradley. On top of that, JBJ delivered the three biggest hits in the ALCS, on the way to MVP honors. Then he blasted another homer in the World Series, further stamping his value to the Red Sox as a member of the Red Sox.

Signing J.D. Martinez

Fearful of bidding against themselves in a market where the value of a designated hitter-type was suppressed, and where there wasn’t an overwhelming demand for Martinez’s services, the Red Sox played the waiting game. They needed Martinez. Badly. If they’d lost him, it’s hard to envision how they would’ve filled the gaping hole in the middle of their lineup without further depleting their resources, or without moving Betts from the leadoff spot that proved to be so vital to their approach.

Boston played its cards almost perfectly — the only mistake potentially being their decision to give Martinez opt-out opportunities that could force them to pay him more money sooner than they would’ve needed to by guaranteeing all five of the years on the contract. Still, they managed to get Martinez for below-market value, with minimal relative risk, and came away with a Triple Crown candidate who precisely plugged the gap in the Sox order, and who was also eager to work with teammates to make them better in the name of winning. He fit in right away, he was as consistent as he was spectacular, and he was the perfect player for what the Sox sought.

Striking early for Eovaldi and Pearce

As the trade deadline approaches every July 31, the urgency to make a move increases. So can the price from a team looking to sell, especially as the alternatives dwindle.

But as this season’s deadline approached, Dombrowski had long since identified areas of need for his team. He also had a realistic view of his farm system, and what it could likely afford to send away. So rather than wait for July 31, he swung a deal for Pearce on June 28. Then swung another for Eovaldi on July 25. 

It cost him Beeks, who projects to stick around in the big leagues — but in return his decisive action didn’t force him to delve deeply into his system, and he wound up with two ultra-useful pieces who fit important roles and who’ll forever be remembered in Red Sox World Series lore. 

Dombrowski is known best for his big, bold, star-searching moves. But these were two trades that came in under the radar, before the rest of baseball was really ready to act, and both turned out to be strokes of genius that helped define an absolutely brilliant campaign.