With Jon Lester's Suitors Lining Up, Where Is the Best Fit for Him?
Jon Lester hasn't found a contract just yet, but it's clear he has found one thing on the open market:
Options.
Yes, lots and lots of options.
Last week, Rob Bradford of WEEI.com reported that there were six teams with "legitimate interest" in Lester. No surprise, given that the 30-year-old left-hander is coming off a career year and, unlike fellow free-agent aces Max Scherzer and James Shields, isn't tied to draft-pick compensation.
Equally unsurprising is that the Boston Red Sox are among the six teams interested in Lester, according to Bradford. As for the other five, it seems those might be:
- Chicago Cubs: They've been linked to Lester for weeks and, according to Mark Gonzales of the Chicago Tribune, met with him Tuesday.
- Kansas City Royals: As Jeffrey Flanagan of Fox Sports Kansas City reported, they've at least had "preliminary talks" with Lester's agents.
- Toronto Blue Jays: According to Bradford, they're interested in signing Lester even after inking Russell Martin to an $82 million contract.
- Atlanta Braves: ESPN's Buster Olney has reported that they're meeting with Lester this week.
- St. Louis Cardinals: ESPN's Jim Bowden says they've joined the hunt for Lester as well.
As for which is the best place for Lester, that's where we can be so bold as to offer our opinion. Let's run through Lester's six rumored suitors one by one (in alphabetical order by city) and narrow down the best fit for him.
Atlanta Braves
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The Braves' best hope of luring Lester to Atlanta might be appealing to his desire to be close to home.
Lester may be a Washington native, but the word (via ESPN.com) is that he keeps an offseason home in Atlanta. Were he to sign with the Braves, that would presumably become his in-season home.
That's not all the Braves can offer Lester. They can also offer a chance to pitch at a dandy of a pitcher's park in Turner Field in the next two seasons and then at their brand-new stadium starting in 2017.
Accompanying Lester along the way would be a core of talented young players who are in it for the long haul, namely first baseman Freddie Freeman, shortstop Andrelton Simmons, closer Craig Kimbrel, left-hander Alex Wood, right-hander Julio Teheran and newly acquired righty Shelby Miller.
Whether the Braves can make a competitive offer for Lester, however, is a good question.
With over $79 million on the books for 2015 and, per Jeff Todd of MLB Trade Rumors, possibly another $20 million to be paid out through arbitration, there's not much space between where the Braves are now and their $112 million Opening Day payroll from 2014.
The Braves therefore might have to deal Justin Upton to squeeze in Lester, which would be filling one hole while creating another. And even if they were to keep Upton, Lester could be forced to get used to organizational penny-pinching as a fact of life in Atlanta.
Verdict: Lester in Atlanta is a good fit from a personal and baseball perspective, but maybe not so much from a financial perspective.
Boston Red Sox
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To a certain extent, it's silly to discuss how Lester fits in Boston. He knows how he fits there.
Lester made his major league debut with the Red Sox in 2006 and stuck with the organization right up until it traded him to the Oakland A's this past July. He won two World Series and racked up a 3.64 ERA along the way, and he managed to pull off the rare feat of leaving the Red Sox on good terms.
Lester told Sean McAdam of CSNNE.com before getting traded that he would be open to a reunion, and Boston manager John Farrell echoed that sentiment in a WEEI interview in August.
"I think we would all love to see Jon Lester back in a Red Sox uniform," Farrell said, adding, "He's durable, he's productive, he's done it in Boston, there's a great comfort level with everyone here."
The financials sure aren't a concern. The Red Sox are only projected for a little less than $120 million in expenditures for 2015, leaving them well short of the $150 million to $160 million range they opened at in 2013 and 2014.
The Red Sox are also short on long-term commitments, so there's plenty of payroll room for the Red Sox to lock up youngsters such as Mookie Betts, Xander Bogaerts, Blake Swihart and Henry Owens around Lester in the long run. If he goes back to Boston, he could soon find himself a part of a powerhouse once again.
At the same time, there is an element of uncertainty with Boston's future. David Ortiz is nearing the end of his career. Dustin Pedroia appears to be declining. And after 2015, Mike Napoli, Shane Victorino and Yoenis Cespedes are all slated to hit free agency.
Verdict: Going back to the Red Sox would mean accepting a huge payday from a club Lester knows he fits with, but it would also mean banking on a future that has equal parts upside and downside.
Chicago Cubs
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The Chicago Cubs certainly have room for Lester on their payroll. They're a big-name, big-market team that has less than $40 million committed for 2015.
Beyond the money, the Cubs can offer Lester a chance to be a part of what could be a dynasty.
As you might have heard, the Cubs have more young hitters with tremendous upside—Anthony Rizzo, Javier Baez, Jorge Soler and Kris Bryant, to name a few—than anyone. They also made an ace out of Jake Arrieta in 2014 and now have one of the best managers in the game after their hiring of Joe Maddon.
Running the Cubs is Theo Epstein, who of course is a familiar face where Lester is concerned. If he joins the Cubs, it'll be partially for the same reason Epstein jumped ship from the Red Sox to the Cubs: to go down in history as a guy who helped them end their more-than-century-old championship drought.
If so, Lester could go into the books as a figure who was just as important as Epstein. Patrick Mooney of CSNChicago.com is not wrong about the role he would fill, writing, "The Cubs understand they need someone to set the tone for their pitching staff, help establish a clubhouse culture and take the ball for Game 1 of a playoff series. That's what Lester could do on the North Side."
It all sounds good...until you get to the big "what if": What if the Cubs continue to be the Cubs?
Verdict: The Cubs can pay a handsome sum to bring Lester aboard as a sort of final puzzle piece, but it would mean going all-in on the franchise's big gamble.
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Kansas City Royals
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If you can't beat 'em, join 'em?
That's more or less what Lester would be doing if he joined the Kansas City Royals, as he was last seen letting a sizable lead slip away against them late in the American League Wild Card Game. That the Royals made it as far as the seventh game of the World Series after that could be what strikes Lester's fancy.
The Royals are set to return pretty much everyone from the roster that just won the AL pennant, including the big names: Alex Gordon, Eric Hosmer, Lorenzo Cain, Mike Moustakas, Salvador Perez, Kelvin Herrera, Wade Davis and Greg Holland. James Shields is the big exception, but Lester would take his spot and could end up being a considerable upgrade.
Beyond him simply being the better pitcher, you shudder to think how good Lester could be at Kauffman Stadium and in front of Kansas City's defenders. The K is one of the most pitcher-friendly parks in existence, and it doesn't get much better than the Royals defense.
But like with the Braves, there's a financial question mark here. After opening at a little over $90 million in 2014, the Royals are already projected for over $80 million in expenditures in 2015. Signing Lester would either require him taking a discount or them making a lot of room.
And that's just for 2015. With their homegrown products only due to get more expensive going forward, building around Lester would be a yearly challenge for the Royals.
Verdict: Lester in Kansas City is an intriguing fit from a baseball perspective, but making the financials work won't be easy.
St. Louis Cardinals
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If winning is Lester's priority, it's hard to ask for any more of a sure thing than a team that's been to the National League Championship Series four years in a row.
And the St. Louis Cardinals could easily do so again if they sign Lester.
He'd join a starting rotation that already consists of Adam Wainwright, Lance Lynn, John Lackey and Michael Wacha, and he'd be pitching to Yadier Molina. Offensively, he'd be back by the newly acquired Jason Heyward, Matt Holliday, Jhonny Peralta, Matt Carpenter, Matt Adams, Kolten Wong and Jon Jay.
In the long term, Lester would be able to have faith in a Cardinals development system that seemingly never stops running out of talent. That has a lot to do with how, as Carpenter and Adams go to show, they have a knack for turning nobodies into somebodies.
But once again, there's a financial question mark. There's less than a $20 million gap between the Cardinals' 2015 commitment and the mark set by their Opening Day payroll in 2014, and it'll be a while before they get any real payroll relief. Fitting Lester in will be tough.
Besides which, I'm asking myself this if I'm Lester: With Holliday getting older, Heyward only signed through 2015 and Wainwright and Molina both showing signs of mortality in 2014, are the Cardinals a trap?
Verdict: The rich would seemingly get richer if Lester were to join the Cardinals, but the financials and the question marks on some notable stars are possible deal-breakers.
Toronto Blue Jays
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At the least, joining the Blue Jays would mean Lester wouldn't have to worry about facing an offense that placed in the top five in runs scored in 2014.
Indeed, being backed by that offense instead sounds a lot better. And its newest addition is far more than just a hitter. Russell Martin is a guy whom Lester could really like working with.
Among Martin's many defensive talents is pitch-framing, as Baseball Prospectus' figures says he was among the elites at stealing strikes in 2014. That makes him not unlike David Ross, who was Lester's personal catcher in Boston and who, as FanGraphs' Jeff Sullivan noted, was a big part of his success.
That's not the only reason Martin and Lester could be a fearsome duo. Between the two of them, they know the AL East very well. As such, they alone could help the Blue Jays improve on a modest 39-37 record against AL East competition in 2014.
The questions begin, however, when you get into whether the Jays can even afford Lester after signing Martin. Then you wonder how willing he is at pitch at Rogers Centre, a notorious hitters' park. And though the Blue Jays have a solid lineup wrapped around Martin, Jose Bautista and Edwin Encarnacion, it currently has holes in center field and left field and at second base.
Verdict: Lester joining forces with Martin would mean a huge boost for Toronto's rotation, but signing him would take some effort and wouldn't erase the club's other question marks.
Best Fit: Chicago Cubs
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Of the six teams we've discussed, the Cubs and Red Sox look like the best bets to sign Lester for one key reason:
They're the ones who can offer him the most money.
Assuming Lester is just like every other free-agent/normal human being, that's what matters the most.
Beyond that, the question is whether joining the Cubs' quest to end the Curse of the Billy Goat is worth Lester turning his back on the comfort and solid foundation that await in Boston. And as attractive as those things are, Lester hopping on board with the Cubs would just be too perfect.
The Cubs aren't far off from being ready to contend. They showed promise in a 33-35 second half in 2014. With Bryant due to arrive soon, their offense could make the leap from "promising" to "elite" in a hurry. Add in a Lester-Arrieta one-two punch, a solid bullpen and Maddon's presence and you're looking at a team that could absolutely be playoff-bound in 2015.
And once the Cubs are playoff-bound, they're going to stay playoff-bound. The machine they're building is one that will stay functioning for a while once it's complete. And if it produces a World Series title or two, the big cogs are going to be remembered as heroes.
The Red Sox can offer Lester fortune and familiarity. The Cubs can offer him fortune and glory. A hard combination to pass up.
Note: Stats courtesy of Baseball-Reference.com unless otherwise noted/linked. Payroll information courtesy of Cot's Baseball Contracts.
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