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Trading Jon Lester Could Ignite a Red Sox Dynasty

Jon Lester before Tuesday night's game at Fenway Park. (Photo by Jim Rogash/Getty Images)

I love Jon Lester. As a native New Englander with a passion for baseball, I have always admired the intensity Lester brings to the mound every fifth day. He has been a reliable starting pitcher since his first full season, making at least 31 starts every year since 2008, and his 21 starts this season rank second amongst left-handed pitchers in the American League. Lester contributed to two World Series championship teams, played under multiple managers, and experienced the frustrations of a last place team while with the Red Sox. Despite his passion, perseverance, and experience, Lester should be traded before the 4pm deadline on Thursday.

The philosophy of the Boston Red Sox changed after the disastrous Carl Crawford signing. The front office is aware that signing players to large contracts after they’ve reached the wrong side of 30 can be a costly mistake. If it weren’t for the 2012 Nick Punto trade, Boston would be in significantly worse shape than they are today. With Lester, they have a second chance to recognize a bad contract before it’s signed.

Since Lester will walk at the end of the year in free agency, the Red Sox might as well trade him for a large package of prospects, rather than settle on the lone draft pick compensation involved in losing the pitcher. Reports across social media indicate that the market for Lester is heating up as the deadline approaches, especially with the Tampa Bay Rays pulling David Price from the market.

If the Red Sox were able to pull off a trade for Joc Pederson, a 22-year old outfielder hitting .318 with 22 home runs at Triple-A for the Los Angeles Dodgers, they could add the talented prospect to a increasingly potent young core. This core group of players includes those we’ve already seen at the major league level, like Xander Bogaerts, as well as the names thrown around in Pawtucket like Matt Barnes, Henry Owens, and Anthony Ranaudo. Despite the excitement over Pederson, it may be more likely that the team acquire Josh Bell from the Pittsburgh Pirates an outfielder with a high ceiling.

The Red Sox have been focusing on winning one World Series for years. In 2004, 2007, and 2013, they were successful, but none of those teams were built to last. With a young core of talent, Boston has the opportunity to develop a baseball dynasty, which could parallel that of the New York Yankees of the late 1990s, who won four World Series titles in five seasons. The Red Sox have a similar opportunity, which could come to fruition as soon as the 2016 season.

This year is already a lost one for the Red Sox, and realistically, Boston will struggle to compete for the playoffs again in 2015 without a true ace like Lester at the front of their rotation. However, 2015 can be a productive bridge year towards an everlasting future by showcasing the young talent the organization has to offer.

I believe the 2016 Red Sox roster could be one of the most talented in all of baseball, and with Lester out of the way, the Red Sox could use their financial flexibility to keep the team intact for many years. Here’s how I envision this team of the future:

2016 Offense

Nearly every position in the field has been covered for years to come. Christian Vazquez has the defensive talent to be one of the best catchers in baseball regardless of his offensive production, which has been above average early in his career. Dustin Pedroia is already locked up, and the hope is that his numbers will return to form next season and beyond. The left side of the infield is effectively set with Xander Bogaerts at shortstop and the likelihood that Garin Cecchini will win the third base job next year. If not, Bogaerts can play third and the Sox have shortstops like Deven Marrero in their system. There are several candidates for the outfield, with Jackie Bradley Jr. owning center field. I am optimistic that the team can acquire Joc Pederson from Los Angeles to play right field, but we’ll assume they do settle for Josh Bell from Pittsburgh, with Mookie Betts possibly sliding into left.

The key questions exist at both first base and designated hitter. It is hard to imagine David Ortiz still putting up great numbers when he’s 40 at the start of the 2016 season, and Mike Napoli’s contract also expires at the end of 2015. There won’t be much available at first base in free agency over the next couple of seasons, so Napoli may be the best option for the Red Sox as a 34-year old in 2016.

Despite the consistency David Ortiz has provided at the position, I’ve always valued flexibility with the use of the designated hitter. Since Mookie Betts is slightly out of position in left field, the Sox could target a veteran left fielder in free agency to platoon as a left fielder and designated hitter. This could allow for veterans like Napoli and Pedroia to receive half days off as the designated hitter without losing the biggest parts of the lineup. The two biggest names on the free agent market before 2016 include Justin Upton and Yoenis Cespedes. We’ll pencil in Upton.

I’ve included which way the player bats and their age at the start of the 2016 season.

C Christian Vazquez (R, 25)
1B Mike Napoli (R, 34)
2B Dustin Pedroia (R, 32)
3B Garin Cecchini (L, 24)
SS Xander Bogaerts (R, 23)
LF Mookie Betts (R, 23)
CF Jackie Bradley Jr. (L, 26)
RF Josh Bell (S, 23)
DH Justin Upton (R, 28)

2016 Pitching

Similarly, the Sox can afford to let Lester walk because of the talented collection of young starting pitchers they’ve assembled in the minor leagues over the years. Beyond the trade deadline and throughout 2015, I believe the Red Sox can allow these pitchers to showcase their talents.

I’ve included where the pitcher is in the Red Sox system and their age at the start of the 2016 season.

RHP Clay Buchholz (MLB, 31)
RHP Rubby De La Rosa (MLB, 27)
RHP Brandon Workman (MLB, 27)
RHP Anthony Ranaudo (Triple-A, 26)
RHP Allen Webster (MLB, 26)
RHP Matt Barnes (Triple-A, 25)
LHP Henry Owens (Double-A, 23)
LHP Edwin Escobar (Triple-A, 23)
LHP Brian Johnson (Double-A, 25)

By the end of the 2015 season, it can become clear as to which of these pitchers can be key contributors going forward. Some of these may be keepers for the future, while others could be used as trade bait, especially when you consider the fact that not all nine of these men can fit into one rotation!

Let’s assume the Miami Marlins are unable to piece together a successful baseball roster by the start of 2016, and return to their fire sale form by looking to trade ace Jose Fernandez. The Red Sox could use the appeal of an arsenal of young affordable pitchers to make a deal with the Marlins, or any other team looking to make a deal. Let’s dream that it’s Fernandez though, and acquiring him costs the Red Sox Matt Barnes, Henry Owens, and newly acquired Edwin Escobar. Suddenly the 2016 rotation includes a young established ace to pitch alongside Clay Buchholz and Rubby De La Rosa, with the other pitchers as candidates to earn a spot depending on how the next year and a half play out.

It will be sad to see Lester leave Boston. He’s been here longer than any other player in the Red Sox system since being drafted back in 2002. However, his departure can be used by the Red Sox for the greater good, which means building the type of baseball empire the city of Boston has yet to experience. Only time will tell how the Red Sox will utilize these young players, but the clock is ticking on their time with Jon Lester.

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