Former Red Sox Playing in the World Series

The Red Sox are not playing in this year's World Series.  They made it to the postseason but were swept out of the first round by the Indians, who are in the World Series.  I am disappointed, but not unaccustomed to this, after all they have only been to the World Series four times in my entire lifetime.  But just because the Red Sox are not in, does not mean that there is no one to watch.  Each team has four players on their World Series roster that have been members of the Red Sox organization.  That is no surprise.  The Cubs' president is former Red Sox GM Theo Epstein, who was instrumental in building Red Sox teams that won two World Series, and the Indians' manager is Terry Francona, who was the Red Sox manager for those same World Series championship teams.

So these are the players, and others who have been with the Red Sox that are in the World Series this year:

CHICAGO CUBS

Theo Epstein

As mentioned, Epstein was the principal architect of the Red Sox teams that won the World Series in 2004 and 2007.  He brought a heavily-analytical approach to building the team that borrowed initially heavily from the methods used by Billy Beane of the Oakland A's.  Epstein was brought on as GM for the Red Sox in 2002 and stayed with the organization through the 2011 season when he went over to the Cubs. 

John Lackey

Lackey looked like a very expensive free agent bust for the Red Sox after struggling through two sub-par seasons in 2010 and 2011 then missing the entire 2012 season after undergoing Tommy John surgery.  But he came back in a big way to be a major part of the Red Sox team that won the World Series in 2013, including winning the final game of the World Series.  Lackey was traded to the Cardinals for Joe Kelly and Allen Craig at the 2014 trading deadline and then signed with the Cubs as a free agent.

Jon Lester

Lester was the best pitcher the Red Sox developed since Roger Clemens.  He was a second round draft pick in 2002 and made his Major League debut in 2006.  He won the final game of the World Series in 2007 after a successful fight with cancer and then threw a no-hitter in 2008.  Lester then developed into Boston's ace for several seasons, and led the rotation to another World Championship in 2013.  Lester was a three-time All Star with the Red Sox and finished in the top five in the Cy Young vote in 2010.  He developed a reputation for being a big-game pitcher with Boston.  Like Lackey, Lester was traded at the 2014 trading deadline, to Oakland for Yoenis Cespedes.  He signed with the Cubs as a free agent during the offseason.

Anthony Rizzo

Rizzo never played a Major League game with the Red Sox, but he was drafted by them in the sixth round of the 2007 draft out of high school.  Rizzo moved quickly through the minors with the Red Sox and was considered a big-time power threat.  He made it to Double A ball in 2010 but was traded in the offseason as part of the package sent to San Diego in exchange for Adrian Gonzalez.  Rizzo was the only player that has performed well from that trade, but San Diego sent him to the Cubs before he really arrived.

  

David Ross

Ross spent two stints with the Red Sox, originally coming over late in the 2008 season and playing just eight games with them.  He returned as a free agent on a two-year deal prior to the 2013 season.  Despite a 20 homer season in 2007 with the Reds, by this time, Ross was a backup catcher known more for his glove than his bat.  Ross had several key moments for the Red Sox during the 2013 season and some clutch hits in the World Series that year.  He ended up playing the majority of the World Series at catcher due to Jarrod Saltalamacchia's defensive deficiencies. 

CLEVELAND INDIANS

Coco Crisp

Crisp was acquired by the Red Sox in a trade with the Indians in 2006 after losing Johnny Damon as a free agent to the Yankees.  He suffered an injury early in the season and struggled after coming back.  He was decent in 2007 and 2008, but did not develop into the all-around talent Boston thought they were getting when he was acquired.  He was a terrific defensive outfielder with a lot of speed though.  After the 2008 season, he was traded to the Royals for reliever Ramon Ramirez.  Crisp then played for Oakland for several seasons before being traded to the Indians late in the 2016 season.

Terry Francona

Francona replaced Grady Little as the Red Sox manager for the 2004 season and immediately led the Red Sox to the World Championship.  Francona also led the Red Sox to a title in 2007 and to the postseason in 2005, 2008, and 2009.  He goes down as one of the most successful Red Sox managers in history.  He also tied for the second longest stint as Red Sox manager, although in number of games managed, he would be in sole possession of second place.  Unfortunately, he was fired amid some troubles after the 2011 season.  He found a job with the Indians fairly quickly.

Michael Martinez

Almost forgotten in a flurry of moves in 2016 in which the Red Sox picked up Aaron Hill, Brad Ziegler, and Drew Pomeranz, Michael Martinez was picked up from the Indians for cash.  He played just four games with one hit for Boston and had some questionable defensive plays.  He was placed on waivers in August and the Indians picked him back up.  He almost certainly will never appear on cardboard with the Red Sox.

Andrew Miller

Miller was a former first-round draft pick by the Tigers who was once the primary return in the trade for Miguel Cabrera.  He was traded to Boston for relief pitcher Dustin Richardson before the 2011 season.  Miller struggled as a starter for the Red Sox in 2011 but began to attain success as a relief pitcher in 2012.  He was having a terrific season in 2013 before suffering an injury and missing the postseason.  Too bad, based on how he has been pitching in this year's postseason.  Miller terrific out of the pen for Boston in 2014 before he was traded to Baltimore for Eduardo Rodriguez.  He signed with the Yankees as a free agent after the season and was traded to Cleveland at the trading deadline this season.  Miller unfortunately has no Major League cards with the Red Sox.

  

Mike Napoli

Napoli signed as a free agent with the Red Sox in 2013 after several seasons as a power-hitting catcher.  Napoli transitioned smoothly to first base while with the Red Sox and had two very good seasons at the plate.  He hit two home runs in the ALCS and drove in four runs in the World Series.  He hit 53 home runs in two-plus seasons with the Red Sox before being traded back to the Rangers during the 2015 season.  Napoli signed with the Indians prior to the 2016 season.