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Wednesday, 30 July 2014 13:14

If the Red Sox Trade Jon Lester, is Oakland a Viable Option?

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With the MLB non-waiver trade deadline looming at 4pm EST on July 31st, a deal for Red Sox ace Jon Lester seems imminent. 

 Jon Lester was originally drafted by the Boston Red Sox back in 2002 out of Tacoma, Washington. He moved up the ranks in the minors rather quickly before making his debut on June 10, 2006. That was also the season that he was diagnosed with non-Hodgkin Lymphoma. He battled the treatable form of cancer and made his return in the summer of 2007 just in time for a pennant race that ended in his first World Series ring. 

  Fast forward six years and some 100 victories later, and a no-hitter on his resume as well, Lester was dominant again in securing his second World Series ring. If it not were for David Ortiz batting an otherworldly .688, Lester was the clear MVP winning both games that he started against the St. Louis Cardinals. He gave up just three runs in those two starts giving up just one earned run in 15.1 innings pitched.

 Going into this season, Lester has won at least 15 games in five out of the last six seasons and also pitched at least 200 innings in all of those seasons except 2011 when he went for 191.2 innings pitched. With 10 wins this season and 143 innings pitched already, he is on pace to continue that trend. He has been the definition of a workhorse. Unfortunately, he is coming to the end of a six-year, $42.75 million deal that he signed back in 2009.

  That brings us to today. The trade deadline is coming and rumors are flying all over the place. The Red Sox have had their opportunities to extend Lester's contract. It was reported that the team extended an offer of four years and $70 million before the season that for all intents and purposes was a slap in the face to Lester. He has been a good soldier all along, saying all the right things in the media and claiming that he would accept a "hometown discount". He has expressed his interest in staying in Boston long term and also claiming that he hates change. His family is well engrained in Boston now and they love the area. At every step of the way he has continued to be the consumate teammate, trying his hardest to minimize the distractions and deflect any contract talk. He made the announcement several weeks ago that any contract talk would be tabled until after the season and the team has obliged, making their own statement on the matter as well. 

  With all of this love and admiration for the city he plays in and the team he plays for, why are we 24 hours away from Jon Lester pitching in another uniform? Where is the breakdown in communication? Lester's agents have not made a counter-offer to date. It must have somehow gotten to the point where the Red Sox organization feels it has no shot at re-signing Lester now. They would rather get top prospects for him now, then see him lost to another team for nothing. They also seem to really be sticking to this philosophy of not extending a 30-year old pitcher beyond four years. 

  Teams from Baltimore to Seattle are reportedly engaging in talks with the Red Sox for Lester's services. These contending teams know full well that this is a rental agreement. It's a short term lease with a potential for a huge gain: a World Series title. Though Lester has said that he would not be opposed to re-signing with the Red Sox after the season even if he is traded by tomorrow. Let's assume for the sake of argument that there are a couple of these teams that he might be traded to that could actually become a long-term option for Lester as well. 

   Lester is comfortable in Boston, and happy here. He has friends here. He has a great relationship with manager John Farrell whom was previously his pitching coach. That said, are there other teams that have some of those intangibles that would ease Lester's comfort level. One team comes to mind...the Oakland A's.

   First things first, Lester is from Tacoma, Washington so on paper Seattle would seem to be the next best option outside of Boston. But Oakland is the next closest MLB destination as it sits just slightly northeast of San Francisco. It is 800 miles away from his hometown and less than a two hour flight. Seems reasonable. 

  Lester has had a few different pitching coaches in his time with the Red Sox, including Farrell and the current pitching coach of the Red Sox, Juan Nieves. We'll leave out the debacle of 2012 when Bobby Valentine was managing and had Bob McClure and Randy Niemann as his pitching coaches and Lester went 9-14 on the season.  There was only one other pitching coach that Lester had, and that was Curt Young. Young was only the pitching coach of the Red Sox for one season, and was not brought back when Terry Francona was ceremoniously dismissed. It just so happens that Young returned to become the pitching coach of the Oakland A's after having spent seven seasons with the team previous to the brief stint in Boston. At least Lester is familiar with him and did go 15-9 with a 3.47 ERA under his tutelage in 2011. 

  Lester has development many long time relationships with teammates in his tenure with the Red Sox. David Ortiz and Dustin Pedroia have been with him his entire career and three amigos have celebrated two titles together among many other successes in the last eight seasons. This version of the Red Sox is not 25 players, 25 cabs like many of the teams in the late 1970's and 1980's. They are friends off the field and from the looks of it, they genuinely like each other. 

 Oakland happens to be littered with players that are former Red Sox with whom Lester is very familiar. A's centerfielder Coco Crisp spent two full seasons with the Red Sox while Lester was there, in addition to the brief period Lester was on the big club's roster in 2006, and was a part of the World Series champion team from 2007. 

Rightfielder Josh Reddick was first called up to Boston in 2009 and was on the "Route 95 express" between Boston and Pawtucket, RI where the team's Triple-A affiliate plays for the next two seasons but did play in a total 130 games with Boston in that time when Lester may have been at his most dominant, other than maybe this season. Reddick was traded to Oakland in a package for Andrew Bailey, a deal now seen to be very one-sided in the A's favor. 

We're not done. Jed Lowrie, the A's shortstop came up with the Red Sox in 2008 for 81 games and spent the next three seasons on the same bus as Reddick. Lowrie did see much success in Boston when they were one game from another World Series berth in 2008 before losing in game seven of the ALCS to the Tampa Bay Rays. 

 First baseman Brandon Moss also came up with the Red Sox, spending parts of 2007 and 2008 with Boston before being traded to the Pittsburgh Pirates, another team currently hot on the trail of Lester for their pennant push. 

 Last but certainly not least, the Shredder himself, Nick Punto who plays a utility role this year for the A's, spent 65 games with the Red Sox before becoming an afterthought in a blockbuster deal between Boston and the Los Angeles Dodgers that saw Josh Beckett, Adrian Gonzalez, Carl Crawford and $256 million go west while changing the direction of the organization forever. 

 That makes five players and a pitching coach with whom Lester is familiar. That should help his comfort level and help him adjust to this change, which he hates so much by being sent to a contending team in the heat of a pennant race (though it seems Oakland is a shoe-in for the AL West title) with whom he is familiar with many key pieces in the organization. 

 Now the question of the return. The Red Sox have stated that they want a package of two to three prospects, one of which needs to be a top prospect. One of Oakland's top 5 prospects from 2013, Matthew Olson is a power hitting first baseman whom hit 23 home runs and drove in 93 runs in the Midwest League last year. There are two outfield prospects, an area where the Red Sox organization could certainly use some depth, that could be on the Sox radar as well. Billy McKinney is a left-handed outfielder with above average power who batted .320 in 46 games in the Arizona League and B.J. Boyd could be the leadoff hitter of the future who has above average speed and plays center field. Boyd also batted .285 for Vermont of the NY-Penn League last year. The A's do have pitching prospects among their top crop as well if that is the direction they would like to go, although the three mentioned here seem to address more glaring needs at the farm level. 

 In 24 hours time (or less by the sounds of it), it is very possible that Jon Lester may not be wearing #31 in the Red Sox uniform any longer. The fans of the Red Sox will need time to recover from this move. If a deal is done, it may even put 2015 in jeopardy. Ben Cherington has a plan however, and he is sticking to it. Will Oakland offer the best package? Perhaps not, but it seems that it would be the best fit for Lester and the Red Sox owe him that much to put him in the best situation. 



Sean Bakke

Sean Bakke is co-owner of North Station Media. Bakke is an experienced blogger and podcaster. Bakke is the Content Director at the CLNS Radio online magazine. and responsible for managing all written content as well as any related media content on CLNSRadio.com. He oversees the management of all CLNS Radio beat writing teams and their managers with regards to editorial content and promotion in order to ensure the quality and integrity of its published work. His role includes the recruitment of talented contributors who are dedicated to the same values and the continuous improvement of all CLNS Radio products.


  Sean will mentor you in how to incorporate writing into your podcast promotions. Bakke is also the Director of Sales at CLNS Radio. He will mentor you on how to monetize your production in a realistic and viable program that will not make you false promises, or give you false hope for getting rich quick in the podcast world. Bakke will plot you a realistic course thru monetizing your show with tempered, yet realistic expectations for how to monetize. Sean also happens to be the co-host of his own podcast on CLNS Radio, The Evening Score Sports Podcast.

You can download the podcast on iTunes at www.clnsradio.com/ESPiTunes OR on Stitcher below.