Dave Dombrowski has now officially been the architect of three different pennant-winning franchises, dating back to his tenure with the Florida Marlins that began 25 years ago and later during his lengthy stretch with Detroit Tigers.

And say what you will about Dombrowski’s ability to assemble a relief corps capable of handling October pressure, but this Boston Red Sox club – which has won three straight division titles since he joined the front office – is a true juggernaut.

So, prior to Game 1 of the World Series, let’s take a look at how Dealin’ Dave and his predecessors built this Red Sox team (in chronological order of when each player was acquired):

Method Players
Homegrown 9
Free Agent 4
Trade 12
Waivers 0


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Christian Vazquez (June 5, 2008): Vazquez’s pitch-framing ability helped him progress through the Red Sox system after he slipped to the ninth round (292nd overall) in the 2008 draft.

Xander Bogaerts (Aug. 23, 2009): Originally signed out of Aruba for a $410,000 bonus, Bogaerts is somewhat surprisingly one of the longest-tenured Red Sox players on this World Series roster.

Brandon Workman (June 8, 2010): After being selected in the third round of the 2007 draft by the Philadelphia Phillies, Workman opted to attend college and was later chosen one round earlier by the Red Sox in 2010, with a pick Boston acquired as compensation for the New York Mets signing Jason Bay.

Matt Barnes (June 6, 2011): The Red Sox called Barnes’ name in the first round of the 2011 draft, 19th overall.

Blake Swihart (June 6, 2011): Swihart was taken 26th overall in 2011 as a high-school catcher out of New Mexico.

Jackie Bradley Jr. (June 6, 2011): Bradley was taken 40th overall with the compensation pick received for Adrian Beltre, who departed that offseason via free agency.

Mookie Betts (June 7, 2011): Betts was taken after Barnes, Swihart, and Bradley in the same draft, as the current AL MVP favorite slipped to the fifth round before being selected as a second baseman out of high school with the 172nd pick.

Rafael Devers (Aug. 9, 2013): Devers signed out of the Dominican Republic in 2013 as one of the most highly touted international prospects available, earning a $1.5-million bonus.

Andrew Benintendi (June 8, 2015): In a draft loaded with polished college bats, Benintendi was taken seventh overall, behind Dansby Swanson (No. 1) and Alex Bregman (No. 2).

Free Agents

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David Price (Dec. 4, 2015): While Dombrowski is known for brokering deals, the Red Sox are certainly no strangers to spending, and the executive used his sizable budget to reunite with Price. While with Detroit, Dombrowski acquired the ace pitcher from Tampa Bay via trade, but this time it cost $217 million in free agency.

Mitch Moreland (Nov. 3, 2016): Having reached free agency for the first time in his career following the 2016 season, the lefty-hitting Moreland signed a one-year, $5.5-million deal with Boston. Then, after a 22-homer, 34-double campaign, he inked a new two-year contract to remain with the Red Sox.

J.D. Martinez (Feb. 26, 2018): After a long offseason dance during which it seemed nearly preordained that Martinez would eventually end up with the Red Sox, the slugger and Boston finally agreed on a five-year, $110-million deal that includes a trio of opt-outs. Year 1 has certainly paid early dividends.

Ryan Brasier (March 4, 2018): Brasier signed with Boston this past spring on a minor-league deal after spending last season in Japan. He ended up making 34 regular-season appearances for the big club in 2018.


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Steven Wright (July 31, 2012): The Red Sox acquired Wright from the Indians in a minor-league trade for Lars Anderson.

Brock Holt (Dec. 26, 2012): Following his rookie season with the Pittsburgh Pirates, Holt was jettisoned along with reliever Joel Hanrahan to the Red Sox in exchange for a package headlined by Mark Melancon.

Heath Hembree (July 24, 2014): With the San Francisco Giants making a push for their third World Series championship in five years, the Red Sox sent over Jake Peavy, who had more than $25 million remaining on his contract, in exchange for Hembree and Edwin Escobar.

Joe Kelly (July 31, 2014): Despite having “Great Stuff,” Kelly never figured it out for the St. Louis Cardinals, who traded him along with Allen Craig to Boston for John Lackey and minor leaguer Corey Littrell.

Eduardo Rodriguez (July 31, 2014): Originally signed out of Venezuela by the Baltimore Orioles, Rodriguez was the sole piece the Red Sox acquired in exchange for elite reliever Andrew Miller.

Craig Kimbrel (Nov. 13, 2015): In a trade that was widely considered an overpay at the time, the Red Sox sent four prospects – including two top-100 guys headlined by outfielder Manuel Margot – to the San Diego Padres. To date, San Diego’s prospect haul hasn’t lived up to expectations.

Rick Porcello (Dec. 11, 2015): Somewhat awkwardly, Dombrowski traded away Porcello to the Red Sox before leaving Detroit’s front office. The Tigers acquired Yoenis Cespedes and Alex Wilson for the right-handed starter.

Chris Sale (Dec. 6, 2016): In a blockbuster deal, the Red Sox broke their prospect bank to acquire Sale, trading away consensus No. 1 prospect Yoan Moncada, highly touted arm Michael Kopech, and two other minor leaguers. Moncada’s yet to pan out for Chicago, while Kopech is recovering from Tommy John surgery. Meanwhile, Sale has generated Cy Young consideration during both seasons in Boston.

Eduardo Nunez (July 26, 2017): Nunez comes with a bit of an asterisk because he re-signed with the Red Sox as a free agent this past winter. However, he originally landed in Boston in a trade from the Giants for a pair of minor leaguers.

Steve Pearce (June 28, 2018): In a deal that completed Pearce’s career trip around the AL East, the Blue Jays sent the platoon specialist to their division rival for minor-league utility infielder Santiago Espinal.

Nathan Eovaldi (July 25, 2018): There’s a case to be made that Eovaldi was actually the best pitcher available on the trade market this summer, and the Red Sox sent left-hander Jalen Beeks to the Rays in order to acquire him.

Ian Kinsler (July 30, 2018): Acquired out of necessity as a rental, Kinsler was traded from the Angels to the Red Sox for relievers Ty Buttrey and Williams Jerez and has started at second base for most of the postseason.