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The Atrocity Of Trading Jon Lester

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2014 has been anything but pleasant for the Boston Red Sox, just six months removed from winning an unexpected World Series. Just one year after being buyers to help push into the postseason acquiring SP Jake Peavy in a three-team deal, the Boston Red Sox are in full implosion mode and are trading away anything that resembles the team from a year ago. If you’re well versed with the Sox minor league affiliate the Pawtucket Red Sox, you’re probably more well versed with the likes of those who take the field at Fenway these days. Today the fire sale continued with the trading of ace pitcher and a guy who rose through that very system, Jon Lester, and outfield utility man, and renowned clubhouse guy Jonny Gomes to the Oakland Athletics for outfielder Yoenis Cespedes. The sale is nowhere near being done either, so pull out the fire extinguishers, shield your eyes, and cover your ears, it could get ugly today.

Before we can really any further, we have to figure out how the hell they got here in the first place.

Jon Lester was entering the final year of his contract, and after being the staple figure in the Red Sox rotation en route to a World Series victory, his market value was skyrocketing. Not to mention the league as a whole has allowed the value of pitchers to skyrocket thanks to massive deals to the likes of Felix Herndandez, Clayton Kershaw, and Justin Verlander. The Red Sox and Lester naturally tried to work out a deal in the preseason with Lester noting that he’d like to remain in Boston and would take a home town discount to do so. For most fans who already loved the guy who came through their own system, had battled and won against non-Hodgkin lymphoma, and had been a perfect 3-0 in two different World Series, it was a get it done now thought. But after an extreme low ball offer to start the bidding -4-years $70 million- the talks made no progress in the preseason through Spring Training. I mean it is negotiating, you can’t go in and jump straight to the a max offer, especially when the man says he’ll take a discount, but perhaps that was a little too low, when did the Red Sox become so cheap? Lester then refused to discuss a new contract in hopes of focusing on the new season.

Well you know how the next narrative goes, the Red Sox struggle mightily out of the gate, even early on you could tell the expectations for this defending World Series champ might have to be set fairly low, but the team just continued to surprise with just how terrible they could be. Despite the team around him sucking erroneously, Lester took the mound every fifth day and proved why he was worth every penny he was seeking. Up until his trade, Lester is 10-7 with a 2.52 ERA. Despite the team looking out of it early, walking into the All-Star break with one of their worst records in franchise history, the two sides could not find the time to make legitimate offer for the southpaw.

Now on the day of the MLB Trade Deadline, with the team all but out of it, the Red Sox confirm the worst fear of many over the last few weeks, and have to wave goodbye to one of the better things this team had going for them this year. Barring any hidden agendas both sides might have, it also confirms that the Red Sox are going cheap officially (a move fans got a glimpse of in the handling of Jacoby Ellsbury), and it’s not necessarily a good thing. And also a spit in the face of the fans who pay the most on average for ticket prices, and over $9 a beer at Fenway Park. The Red Sox are in one of the biggest sports markets in the world, and they not only profit for a very healthy and large fan base, they own their stadium (something not all teams do) and also own a decently profitable regional sports network (NESN) to go with it. So what are they doing with all the money? Because for right now it’s not looking good in the eyes of the fans. Letting Lester go sets a new precedence in Boston.

Granted a large majority of this rant/article could be worthless if the Sox and Lester have worked a backdoor deal to reunite at the end of the year. After all, Lester did say that he would be understanding of a trade, but wouldn’t rule out returning to Boston in the offseason. Maybe trying to just show Red Sox Nation a last huzzah of respect, or maybe this is something that could seriously happen. I mean we’ve seen returns in baseball before. Just ask Cliff Lee.

For better or worse the MLB does not have a hard salary cap, which means teams are allowed to spend the money they’ve got, and if that exceeds the ‘cap’, they pay something called a luxury tax, which is paid out to the rest of the league. Unlike your NFL, NBA, and NHL headlines, the Red Sox are not in a cap situation where they are legitimately unable to sign Jon Lester to a contact he’s worthy of, they’re just not interested in writing the check. Owner John Henry has been verbal with his displeasure of large contracts to players over 30.

“virtually all of the underpaid players are under 30 and virtually all the overpaid players are over 30”

This lack of a hard cap does seemingly cause a bit of a talent disparity, as the major market teams who have the money to spend will pay top free agents much more than small market teams are capable of doing so. It makes small market teams have to focus largely on home-grown talent, and finding that gem of a free agent who isn’t necessarily worth the big bucks, but can contribute to a winning roster. Causing teams to typically have to trade their best players when they’re about due for a big payday. Well as it stands though, the Red Sox are not one of those team, and this approach is a new and uneasy one for the fan base to swallow.

The Sox have been burned by big contracts before, sparking another blockbuster trade that served to mainly dump Josh Beckett’s contract after he single handily turned the clubhouse into a circus back in 2012. Seemingly afraid to have a similar situation occur after Lester gets his deal, Henry seems intent on building a World Series worthy, and Fenway worthy team of cheap contract guys under 30. Not exactly the message you want sent out to the league, nor the players in your system as one of largest baseball markets in America.

It’s one thing to not want to pay big money for a free agent who might not adapt well to the Boston pressure -we’ve seen it happen before- but it’s another to deny a worthy paycheck to a guy who came through your system, wants to stick around, and has proven his dominance. What’s a five-year deal to a guy who’s on the now officially labeled John Henry line of 30 years old. John Lackey is surely showing you can pitch lights out at 35, even after Tommy John Surgery. Although he’d also be playing for the veterans minimum if he sticks around next season. It sends a new message to guys in the system that if you go looking for a large paycheck, your time in Boston has an expiration.

There is no fear about the possibility of lack of talent, it just all boils down to money. And what’s frustrating is the Red Sox have 99 problems, but money ain’t one. Unless of course dear old John Henry is addicted to Filipino massage therapists and is in desperate need of the money elsewhere. Perhaps he is single handily attempting to slow the upward curve of the MLB contract, saying we’re a big market team, but we’re not gonna pay the money. A standoff I can only see being so useful as the Yankees and now Dodgers will never follow suit.

However, when you trade the best pitcher you have, and one the league would agree is probably top three or four in next year’s free agent pool of pitchers, yet tell fans you’re not expecting a long rebuild but are looking at 2015 ready to win, it doesn’t add up. After trading Felix Doubront to the Cubs, Jon Lester is the single left-handed pitcher in your pool of MLB ready pitchers. He’s an innings eater who limits the use of bullpens, a guy who can consistently pitch well into the 7th inning and beyond. He collects strikeouts in respectable volume, and he keeps the score within range for even the worst of offenses to compete for wins. A career 110-63 record with a 3.64 ERA, 1386 strikeouts, and a WHIP of 1.287 through nine years all in a Red Sox uniform. How can you tell the fan base you want to win, with your best pitcher willing to take a discount to stay around and you don’t oblige. My biggest question to John Henry, Larry Lucchino, and Ben Cherington would be if not him, who else?

Boston has a wealth of decent prospects to keep an eye on pitching wise, we’ve seen growth from Brandon Workman and Rubby De La Rosa this season, but most still can’t help but feel they might benefit from not being permanent fixtures in the rotation and certainly not your expected 2nd or 3rd pitchers. Not to mention who’s there to mentor them now? Do you really want the only vet left in the dugout (with John Lackey being dealt to the Cardinals) AKA Clay Buchholz, to be mentoring your youth? God no. Not after the headcase he’s turned out to be. Beyond that you’re potential starters are Allen Webster (again not ready to even be a member of the 25 man roster consistently), then you’ve got your next top prospect and first lefty in Henry Owens, but he’s playing double-A ball as I write this, so that’s not happening anytime soon.

Where did the patience go with this team too? The Red Sox have always been a team that keeps prospects in the minors until they’re 100% sure they’re ready to come up. Now that philosophy has seemingly gone out the window. It can be damaging for the growth of youthful players to come up too fast, and get into irreversible funks against the best players in the world. Yet the organization seems entirely ready to hand the reigns over to the young. And being over-confident in your youth has never come back to bite them in the ass….hello 2014.

So where the hell is this all going? Surely there has to be a bigger plan…….right?

Granted this is already a long-winded article, let’s put the passionate Red Sox fan within me to the side for now. If Boston really wasn’t going to sign Lester, without a doubt the only sensible thing to do was to trade him, especially without anything worthwhile to play for this year. And let’s just keep that glimmer of hope that Lester is serious about coming back as well, and the team would actually pay him.

Trading Lester for Yoenis Cespedes might have been an ok thing after all. Lester’s trade value might not have truly been what he is worth. He’s essentially a 2-3 month loan before he either attempts to get back to Boston, or goes out looking for the biggest paycheck. You can’t sell the farm knowing that, so the deal might seem a little light, but Boston came out ok.

Billy Beane is throwing out his book -something John Henry might have picked up in the trash at the coincidentally same time and forced upon Ben Cherington- and has shifted to a win now mode. He’s made moves to acquire pitchers to solidify a playoff ready rotation that can finally hopefully break through into the later rounds of the playoffs, ultimately with the eyes set on a World Series. Giving up a decent bat, and a outstanding fielder, Oakland clearly believes they have the offense to win, but needed the arms. It’s a smart and extremely aggressive move coming from a guy like Beane, and one that should pay dividends, despite losing a solid player like Cespedes. I know who I will be rooting for the rest of the year to win it all.

Cespedes is the current two-time defending home run champion and has a slash line of .256/.303/.464 with 17 HRs and 67 RBIs this season. He immediately provides offense to an otherwise lackluster outfield for Boston. And while is glove and speed can leave a little more to be desired, he more than makes up for it with the cannon of an arm he has.

The only big question will be where to play him in Fenway. Jackie Bradley Jr. has done a smashing job covering the expansive center field, and has proven he’s got a cannon of his own. Shane Victorino (when healthy) plays the also decently hard to play right field extremely well. Do you keep things as they are, putting Cespedes at the base of the wall? With an arm like that, and how shallow left field is, good luck with the routine doubles off the wall, and don’t you think about taking any extra bases or scoring lightly with balls played on the wall if that ends up the case. Either way it’s something John Farrell will have to play around with.

Contractually speaking, he also fits the bill for the direction Boston hopes to stick towards. Although he has just one more year on his contract, he is only going to be making $10.5 million next season. So comparing him to the similarly priced Stephen Drew this year, this looks like hitting the jackpot.

Even though on paper it doesn’t quite feel like a win, losing Jon Lester & Jonny Gomes, for Cespedes for at least one year, and a competitive balance pick, this trade has more value to it than just that though.

Had Boston traded Lester to a team like the Dodgers who have no personal standard of money management and gone on to win a World Series or damn close, there is no chance in hell he comes back. *Remember you’ve got have a sliver of hope that this have some legitimacy to it.* By sending Lester to the A’s who live by very strict cap standards, there is no way he’s re-signing there. Even with a World Series victory, Oakland would just not give what he’s looking for. Despite it also being closer to his birthplace in Washington, Lester would still set out with the goal of either being a Red Sox again, or finding that big contract.

Now whether this all makes sense during the offseason when Lester is donning that Red B once more or Ben Cherington (possibly by the hands of the owners) really did just go full idiot and let the best pitcher this team has had in a long time walk without paying him what he’s worth, will ultimately not be unknown until the offseason. Because technically Lester and the Sox have to act like they have no agreement to reunite (if there are such plans) until he is once again a free agent.

Only time will tell if this was one of the biggest regrets in Red Sox history, or just all part of a bigger plan. Either way, it’s tough to swallow here today. Thanks Jon, and good luck!

Author: Tyler Arnold

My name is Tyler Arnold, I am the founder, a co-owner, and editor-in-chief of The Runner Sports. Sports have been my life since I was young, so here I am doing the only sensible thing, making a career of it. I love it all, and will watch any and every game I possibly can. Thanks for your readership.

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