What Should the Red Sox Do With Jon Lester?

As the July 31st trade deadline gets closer, many are holding their breath to see what the Red Sox do with their ace. Jon Lester is numberFire's seventh-best pitcher (2.20 nERD) this season, making noise to earn a massive contract. He hasn't signed an extension with the Red Sox, and has been involved in many trade rumors over the last two weeks with the Dodgers, Cardinals, and Pirates among teams looking to acquire his services.

So the topic was brought up between two of our writers: Should the Red Sox trade Jon Lester?

Chris Kay: Cash in on His Value

With Boston struggling mightily in 2014, the Red Sox roster has become more expendable, and stud pitcher Jon Lester seems to be the guy that everyone wants. It has been reported that at least six or seven teams have inquired about him in recent days.

This is great news for Red Sox fans, as the likelihood of the Red Sox making the playoffs is minuscule (0.7% according to numberFire projections). There's a reason why the Red Sox are last place in the AL East, and this is the time to improve for 2015 and beyond.

Now, trading one of the best pitchers in the American League for chump change would be ridiculous, but that won’t be the case. His dominance this season should return an elite prospect at the very least.

This 2014 dominance is really the biggest reason why Lester needs to get dealt. His ERA is on pace to be a career best, and his K/9 has also improved, going from 7.47 in 2013 to 9.38 in 2014. His BB/9 has dropped from 2.83 to 2.01. His HR/FB has improved from 8.3% to 6.5%. One number that hasn’t improved though is his fastball velocity, as we’ve seen it go drop 0.7 MPH from 92.7 to 92.0.

All of those are career bests though, and at the age of 30 in a contract year, should scare the Red Sox. During spring training, Lester turned down an offer that was in the range of four years and $70 to $80 million. What will he want after potentially posting his first ERA under three?

We have seen how pitchers have done after signing big contracts in their late 20s and early 30s. Justin Verlander signed a massive seven-year, $180 million contract just after his 30th birthday last year, and he's struggled big time since. Not only has he posted some of his worst numbers since 2008, but his velocity has dropped almost two mph since inking that deal.

While Verlander is easy to pick on, there have been other cases of major deals gone bad. CC Sabathia signed a huge seven-year contract for $161 million when he was 28. Sabathia did pitch great for the first four years of that contract, but not so much in years five and six of the contract. Not surprisingly, his velocity has fallen from 94.2 MPH (the first year of the contract) all the way to 88.8 MPH in 2014.

Matt Cain signed a five-year $112.5 million deal in April of 2012 when he was 27 years old. He rewarded the Giants with a 16-win season and a 2.79 ERA. His 28- and 29-year-old seasons, however, have been 4-plus ERA campaigns. And we can't forget Mike Hampton's deal when he was 28, or Barry Zito's $126 million deal also at the age of 28.

It’s time for the Red Sox to reap the only benefit to being this far from playoff contention and trade Jon Lester. They just can’t afford to sign him to a long-term deal or get nothing in return if or when he walks in the off-season.

Daniel Lindsey: Don't Ruin Your Farm System

For every trade of a big-name pitcher that netted a prospect that made it big, there's a trade for a prospect that failed. Trading Jon Lester is not a sure-fire thing.

Pawtucket has arms in waiting with Brandon Workman, Rubby De La Rosa, Allen Webster, Anthony Ranaudo and Matt Barnes. Three of the five listed have already made spot starts over the past season or two, and Ranaudo (2.41 ERA and 99 strikeouts in 119.1 innings) plus Barnes (65 strikeouts in 86 innings) could really be the best of the bunch. And I haven’t even started on possibly the best pitcher in the system, Henry Owens.

As noted, Jon Lester has posted a 2.20 nERD so far this season, good enough for seventh among all pitchers. His continuing production would provide protection for the pitching prospects due up in the next few seasons.

Among the current prospects at AAA, Webster may be the best bet to develop into a starter. Workman and De La Rosa may be relegated to the bullpen, especially if there are spots open next season. With John Lackey being a free agent (or likely trade candidate as well), that leaves Lester as the ace and Webster as a back-of-the-rotation starter.

After those two, the Red Sox should see what they have in Clay Buchholz now that Felix Doubront is with the Cubs. Buchholz could likely stay in the rotation unless a veteran arm is signed. The Sox could then fill the remaining two rotation spots with Ranaudo and Barnes if Buchholz isn't up to the task. Keeping Lester would allow him to teach the young guys and let Owens continue to develop in Pawtucket through 2015. Trading Lester could leave future rotations in shambles.

Not only does keeping Lester protect the pitching assets, it would have a ripple effect throughout the team’s position prospects. Xander Bogaerts and Jackie Bradley Jr. are the foundation of the team, and Brock Holt’s .306/.355/.428 slash this year has been a great spark plug alongside David Ortiz and Dustin Pedroia.

With two players showing signs of deterioration and four others set to be free agents after this year, the Sox would face some roster holes. We can add Christian Vazquez and Daniel Nava, but does that mean a handful of top-of-the-line prospects are needed from a trade?

I say no since Garrin Cecchini (career minor league numbers of .296/.449/.427) and Mookie Betts are primed for staying at the big league level in 2015. More prospects or someone like Matt Kemp (who missed 145 games in 2012 and 2013) is a big risk. There are plenty of options left for the Red Sox to fill out the rest of their roster in 2015 and beyond.

Holt has filled in admirably this year, playing every position on the diamond minus pitcher and catcher. His versatility allows the Red Sox to use Nava and Shane Victorino as necessary. When not playing the outfield, Holt would form some sort of combination on the left side of the infield with Bogaerts, Cecchini and Will Middlebrooks.

If Middlebrooks starts, the Sox have Ceechini to use off the bench and can supplement that depth with Alex Hassan or Travis Shaw which likely forms some sort of platoon at first base. Once you add Vazquez and another catcher (probably Blake Swihart), the Sox will have filled out a nice roster of position players.

No matter how you dice it, trading Lester will hurt the prospect system the Red Sox have been implementing the last few years. The Sox should keep him this year, sign him to a fat three-year contract in the winter, and enjoy another stretch of long postseason runs.