Ranking The Former Red Sox Still Playing In The 2016 Playoffs

In an 11 year stretch from 2003-2013 the Boston Red Sox were the envy of the baseball world. During parts of this time frame they would employ several hall of famers, big game playoff pitchers, one of the best managers in baseball, and maybe the best General Manager of all time. It should come as no surprise that the last place finishes of 2014 and 2015 occurred without most the names on this list. The franchise redeemed themselves this past season by winning the AL East. However, the core of the team was built by the former GM. Let's take a look at who else Boston has let slip through their fingers over the past decade, and which losses have hurt the most:

*Honorable mention to Mike Napoli, Dave Roberts, Coco Crisp, Jed Hoyer

6. Adrian Gonzalez, Dodgers

Gonzalez is probably the easiest of the bunch for Boston fans to grasp with. All we heard when he first came over was  how perfect his swing was for Fenway and how he would use the short right field to hit 50 homers. He didn't meet those ridiculous expectations but that's not to say A-Gon was a disappointment in Boston, at least production wise. In his only full season with the Sox, 2011, he hit .338 with 27 homers and a MLB leading 213 hits. He was an all star, won a gold glove, a silver slugger, and finished seventh in the MVP voting. But 2011 was the season the Sox went 7-20 in September to choke away a playoff spot. 

Additionally Gonzalez complained about the Boston media and didn't seem to care whether the team won or loss, which is a big no no in this market. Finally, he was lumped in a trade with Carl Crawford, Josh Beckett, and Nick Punto to shed salary and give the Red Sox a reset. It worked out perfectly as the team won the World Series the very next year, which has led Sox fans to think we were better off without Gonzalez. While he was never a winner in Boston it's still somewhat bittersweet to see him still contributing as a 34-year-old in LA, especially when you consider what we had to give up to get him...

5. Anthony Rizzo, Cubs

We had him. We had him and gave him away. It's not even as if the Sox didn't realize what they had in Rizzo. They did. Jed Hoyer has proven that by trading for him when he was GM of the Padres and then again when he reunited with Theo in Chicago. Rizzo was the centerpiece of the Gonzalez deal. The thought process at the time was he was a great prospect but Gonzalez is a sure thing and we are signing him to a long term deal. Two years later trading Gonzalez away created the blueprint for the 2013 championship team. So in a weird way trading Rizzo gave the Sox a World Series. But man it's tough to not day dream about adding Rizzo to the current roster with Betts, Bradley, and Bogaerts.

Squarely in his prime at 27 years old Rizzo has become one of the best players in baseball. In 2016 he ranked fifth among NL position players with 5.7 WAR according to baseball-reference. Over the past three season he has hit at least 30 homers and ranked inside the top 10 in OBP in the National League. He has been an all star each of those seasons, finished 4th in the MVP voting last year, and should finish top three in 2016. Furthermore, unlike Gonzalez, Rizzo is a gamer who gets along with the fans and his teammates and loves playing for an iconic franchise. Sox fans didn't really get to know him but can only wonder what could have been.

4. Terry Francona, Indians

Wherever Tito goes he wins. Since becoming manager of the Red Sox in 2004 he has not had a losing season either in Boston or Cleveland. His wins by year since '04 go 98, 95, 86, 96, 95, 95, 89, 90, 92, 85, 81, and 94. Sure you could make the argument that he had great talent in Boston. But so did Bobby Valentine. So has John Farrell. And what about Cleveland? Not many were predicting them to win the World Series back in spring training. Francona has to be considered a major reason for their success.

Francona took over the Indians in 2013 and improved them by 24 games in his first year. Nobody has ever not loved playing for Tito. He incredibly handled the egos of Manny Ramirez, Curt Schilling, Pedro Martinez, and many more during his Sox years. He is an old school players manager that isn't afraid to try new school ideas. His usage of Andrew Miller this postseason is changing the game and could bring Cleveland their first World Series title since 1948.

3. Andrew Miller, Indians

It's tough to rank Miller this high on the list because when the Red Sox dealt him away at the trade deadline of 2014 it was perceived as a genius move. Miller was having a second straight dominant season, but he did not have the track record to warrant the idea of having to re-sign him. The prospect they traded him for, Eduardo Rodriguez, looked great in his rookie season last year by going 10-6 with a 3.85 ERA, furthering the belief that dealing Miller was the right move. 

But since the trade Miller has only gotten better. Already an elite strikeout artist with the Red Sox, Miller has greatly improved his command in New York and Cleveland. With the Sox in 2014 Miller had a 5.31 strikeout to walk ratio. In two months with Cleveland this year that number rose to 23. Lastly, Miller is changing how relievers are used before our very eyes. Not only is he able to come into the game in the fifth inning, he is willing to. So far in the playoffs he has thrown 11.2 shutout inning with 21 strikeouts. He was named ALCS MVP. 

2. Jon Lester, Cubs

Jon Lester could start his next playoff game, give up 40 runs without recording an out, and still have a better playoff ERA than David Price. The Sox offered Lester four years and $70 million. They offered Price seven years and $217 million. Now the circumstances were different. This past off-season we desperately needed an ace and did the right thing by getting Price no matter the cost. He was a big part of winning the AL East. But it may not have had to come to that had the front office not low balled Lester in the spring of 2014. 

The most infuriating part for Sox fans watching Lester in Chicago is that he wanted to stay here. If we had given him the money he deserved he never would've left. He's a smart guy though and saw what Epstein was building with the Cubs. He's a big game playoff pitcher and wanted to be a part of what's happening right now. The Cubs got him for six years and $155 million, which is a contract the Sox would happily give him now. Unless Price figures out his playoff woes we could be hearing about losing Lester for a long time in Boston. In 119 postseason innings he has a 2.50 ERA.

1. Theo Epstein, Cubs

Epstein is already one of the best front office executives of all time. He was a local kid who ended the most daunting sports curse of all time. He followed it up with another championship three years later. He drafted Mookie Betts and Jackie Bradley. He signed Bogaerts. When the Red Sox stupidly let him go after 2011 he rebuilt the Cubs and has turned them into baseball's version of the Patriots and Warriors - a team built so insanely well to win both this year and for the next five seasons to come. 

Losing Epstein should hurt Boston fans so much more than losing Francona does. It was time for Tito to go. The players had tuned out. That happens with managers. Eventually you have to move on. He should've been treated better throughout his entire tenure here but at the end of the day it had to be done. It's much tougher for a GM to get burnt out. Now Epstein has said he think it was the right time to leave, but it's hard to believe he would have if the Sox had given him the keys to the franchise the way the Cubs did. 

Epstein and Larry Lucchino were basically in a power struggle that Lucchino won. That's fine except Lucchino is now gone. So Boston pretty much chose a few years of Larry over an eternity of Theo. He has already done his job with the Cubs and turned them into a perennial contender. If he ends their World Series drought, to go along with breaking the curse of the Bambino, he's the best baseball executive of all time and it's not close.