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When the Dodgers and Red Sox completed their historic trade in 2012, the impact was far-reaching in terms of shaping identities for the respective franchises. Still riding the fumes from the team’s sale to a group led by Magic Johnson, the Dodgers made a bold, but yet simple statement with the acquisitions of hefty contracts in the likes of Adrian Gonzalez, Carl Crawford, and Josh Beckett. The statement was that they Adrian Gonzalez and Carl Crawfordwere ready to spend, spend, and spend some more – and they have.

In an era of Major League Baseball where lucrative  $20+ million-a-year contracts are dominating the headlines and payrolls, it is rare that a franchise ever gets a shot to make amends for these monstrosities that often stunt a team’s success for years to come (I.E. Ryan Howard’s $125 million extension signed in 2010). However, the Red Sox pulled off this seemingly impossible feat, shedding a lucrative $250+ million in salary through the 2012 deal with the Dodgers. Since then, the Red Sox have made it evident that they were going to scrap the careless spending that led them to handing Carl Crawford and Adrian Gonzalez a near combined $300 million when they signed in 2010 and 2011.

The stark change in thinking netted the Red Sox a historic worst-to-first finish last season. Meanwhile, the Dodgers have continued to add the zeros onto their paychecks, as they made Clayton Kershaw the richest pitcher in MLB history, signing him to a seven year – $215 million deal, earlier this year.

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On the heels of the 2013 season that was both cinematic and magical, 2014 has been nothing but dark and stormy for the Boston Red Sox. One of the few bright spots for the defending World Series champs has been Jon Lester. Over 21 starts this season, Lester has carved out a 10-7 record with a 2.52 ERA and 149 strikeouts across 143 frames. The ERA is on pace for a career best, while the strikeouts are on par with his Jon Lester Red Soxcareer bests from 2009 and 2010.

The 30-year-old has spent his entire nine-year career in Boston and has been a member of two championship teams. However, combine Lester’s impending expiring contract with the Sox being 12 games out of 1st place in the AL East and it has all the makings for a departure from Boston.

While Lester’s teammates would undoubtedly miss one of the most respected and talented players on the club, there are a few of his former teammates who would welcome Lester with open arms. Those being Josh Beckett, Adrian Gonzalez, and Carl Crawford – the focal points of the historic 2012 deal.

The Los Angeles Dodgers 2014 campaign has been nothing short of spectacular. Clayton Kershaw has turned in one of the most dominant seasons for a SP in MLB history, Yasiel Puig has broken onto the scene as a budding superstar, and Dee Gordon has finally leveraged his lightning speed to ignite the top of the L.A. lineup.

With the Cardinals, Pirates, and Athletics listed as potential suitors to strike a deal with the Red Sox for Lester, the Dodgers are the destination that makes the most sense. In complete win-now mode, the Dodgers have been throwing more money around than Pac Man Jones at a Las Vegas stripclub. 2012 trade history aside, the willingness to overpay (in both money and prospects) is the reason why the Red Sox should look no further than southern California as the location to ship Lester.

An integral element to the Lester trade-saga is the situation with Tampa Bay Rays ace, David Price. The Rays have climbed back into the hunt for the AL East by winning 11 of their last 12 games which naturally makes it a more complicated decision with Price. This makes Lester the bread-winner for the 2014 trade deadline, which comes to fruition at 4 pm EST tomorrow, July 31st.

The Red Sox have made it clear that they will not move Lester for anything less than two elite prospects, and I expect a few teams to pump the brakes. However, L.A. should remain committed in its pursuit of the Boston ace. Despite its deep rotation that includes Lester’s former top-of-the-rotation teammate in Boston, Josh Beckett, the Dodgers are no strangers to crowded talent. Two months before they acquired Crawford in 2012, the team gave OF Andre Ethier an absurd five year – $85 million extension, that has since seen him relegated to the bench with the inevitable emergence of Yasiel Puig over the past two seasons.

However, the situation with Lester is not comparable to the faulty course of action the team took in retaining the services of Andre Ethier. Success in the MLB playoffs are predicated on elite pitching depth: allowing the top two or three pitchers in your rotation to take the mound and silence the other team’s bats. While the Dodgers have two clear-cut candidates in the unworldly Kershaw and fellow NL All-Star Zack Greinke, Lester would provide the team with more dominant stuff than current #3 starter, Hyun-Jin Ryu. While Ryu has pitched at an extremely effective level this season (12-5, 3.44 era), it would give the Dodgers the luxury of having four highly reliable pitchers, while being able to lean on Dan Haren and Josh Beckett in a more situational/potential long-relief role out of the bullpen.

As the Red Sox look to net a couple blue-chip prospects in return for Lester, the Dodgers are an above-average fit. The main reason is the surplus of talent in L.A.’s outfield and the lack of talent in Boston’s. The end-result will depend on what the Red Sox value more: getting an established, but inconsistent (and injury-riddled) OF on the cheap or receiving a couple of high-level prospects. My inclination is that it could be a combination of both, but that propensity will depend on whether or not the Red Sox think a player like Matt Kemp could invigorate his career in Boston. The Dodgers are financially committed to Carl Crawford and it will be nearly impossible to get a team to absorb the remaining $70 million or so that he is owed through 2017.  It is a similar situation with Kemp, but it is possible the Red Sox would agree to eat some of his Matt Kempremaining $107 million on his deal.

If the Sox are to pursue the Dodgers farm-system, it all starts with the club’s top prospect, OF Joc Pederson. The 22-year-old has batted .318 with 22 HRs to go along with 25 SBs for Triple-A Albuquerque. Other top prospects include Corey Seager, a 20-year old SS, and Julio Urias, a 17-year old SP.

Despite waiting on the development of outfielders Mookie Betts and Jackie Bradley, the Red Sox have a clear need for an upgrade at OF, as Jonny Gomes, Shane Victorino and Daniel Nava will not be in the plans for the future. Boston could wind up hedging their bets by acquiring a MLB ready OF in Kemp and a top prospect in the minors in Pederson. With an already stacked SS position in the minors (Devin Marrero and Michael Chavis), it would not be pragmatic for the Red Sox to pursue Seager.

With Lester already 30 years-old and set to command $20+ million a season in his new contract, Boston could use their better judgement and acquire valuable, cheaper pieces, while getting something on the open-market for their ace. With the addition of Lester to the Dodgers rotation, they would instantly have the upper-hand in post-season pitching match-ups and would instantly become World Series favorites.

 

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After spending eight seasons with the Tigers, Manager Jim Leyland has stepped down as manager of the club. Leyland revitalized baseball in Detroit by becoming the first Detroit Tigers v New York Yankeesmanager in MLB history to reach the World Series in his first year with a team, a feat he accomplished in 2006 when the Tigers eventually lost to the Cardinals. On the heels of an impressive season last year that was highlighted by Miguel Cabrera’s triple-crown, the Tigers were swept by the Giants in the World Series. After suffering a heart-wrenching series defeat to the Red Sox in game six of this year’s American League Championship Series, Leyland has decided to move on.

Leyland and the Tigers will make this news official today during an 11:30 a.m. press conference. At sixty-eight years old, it is unknown whether Leyland will pursue other managerial positions in MLB, or call it a career.