With the Red Sox out of contention this season, Thursday’s trade deadline was one of the most action-packed days in team history. Eight players from the opening day roster left the club in the month before the deadline. Here’s my ranking of the top five moves Ben Cherington made to retool the roster for 2015.

Honorable Mention: AJ Pierzynski designated for assignment, Stephen Drew traded to New York Yankees for Kelly Johnson

We'll miss you Jon. Please re-sign after the season!  Photo by Kelly O'Connor of sittingstill.net

We’ll miss you Jon. Please re-sign after the season!
Photo by Kelly O’Connor of sittingstill.net

Or Ben Cherington rids the roster of the fans two least favorite players and two of his worst free agent signings. In his short time on the club, Pierzynski managed to lead the team in double plays, poison the “Bearded Brothers” team chemistry, and block catching prospect Christian Vazquez. The Red Sox spent 8.25 million for .2 WAR of production.

I actually advocated for the Sox to sign Drew in the offseason, but the panicky in-season signing only worsened the team’s play. Not only that, it sent Xander Bogaerts into a tailspin. Bad Drew! You broke Bogaerts! Stephen might be less popular with Red Sox fans than his brother JD, which seems almost impossible.

5. Felix Doubront traded to Chicago Cubs for a player to be named later

Everyone loves a “PTBNL” trade, and the Red Sox sent Doubront packing to old friend Theo Epstein with no word yet on the return. This trade screams missed opportunity to me, because the Sox moved Doubront when he had almost zero value. You have to wonder if there were better offseason offers after Doubront had a fairly successful 2013 season.

4. John Lackey and Corey Littrell traded to the St. Louis Cardinals for Allen Craig and Joe Kelly

In a vacuum, this trade doesn’t seem to make much sense for the Red Sox. Craig’s two best positions (DH and 1B) are already filled on the Sox, and the team’s righthanded pitching depth makes Kelly seem redundant. Lackey’s major league minimum salary for next season made him an extremely valuable asset for the Sox to keep.

Looking at some of the other trades from yesterday, I would have much preferred the package the Astros got from the Marlins to what the Red Sox got for Lackey. That deal may not have been on the table, but I was definitely hoping if Lackey went it would be for elite prospects. The one caveat here is that Cherington may not be done dealing. Craig and Kelly could be used in other deals to strengthen the club.

3. Jake Peavy traded to the San Fransisco Giants for Edwin Escobar and Heath Hembree

The Red Sox started their trading activity before Trade Deadline day. Since the Red Sox are loaded with starting pitching depth, the team should have little trouble replacing Peavy’s innings. In return, the club got a talented lefty starting pitching prospect in Escobar, and a hard throwing lefty reliever in Hembree.

Hembree features a mid 90’s fastball and hard slider, a profile similar to Andrew Miller. The Sox may have found Miller’s replacement, except they have Hembree under team control for several more years.

2. Andrew Miller traded to the Baltimore Orioles for Eduardo Rodriguez

Miller will be a free agent after the season, so the Sox got a top lefty pitching prospect for a two month rental. Rodriguez ranked #43 on Keith Law’s preseason top 100 prospects list, but has struggled a bit in 2014. This might be a good time to mention that the Red Sox now have 10 pitching prospects age 26 or younger either in the majors right now, or who should be ready by the end of 2015.

The Sox have hoarded prospect depth so far. At some point they will cash some of these prospects in as part of a major trade. Whether it’s Giancarlo Stanton, Troy Tulowitzki or an elite starting pitcher, the Sox have pieces to be super-aggressive in the trade market.

1.Jon Lester and Jonny Gomes traded to the Oakland Athletics for Yoenis Cespedes and a competitive balance pick

I’m going to get all crazy here and do a top five list within a top five list. My top five reasons why I love this trade:

5. The extra draft pick increases the Red Sox bonus pool money in the amateur draft
4. Sox fans gain a loose association with the fantastic Twitter account Cespedes Family BBQ (@CespedesBBQ)
3. The two best outfield arms in the American League are now on the same team
2. The Red Sox might still sign Jon Lester after the season (Please make this happen)
1. Yoenis Cespedes crushing home runs