The Cubs Land Jon Lester, and Their Master Plan Proceeds As Foreseen

Michael Ivins/Boston Red Sox/Getty Images

In October, we dwell on baseball’s unpredictability, searching for creative ways to say “crapshoot.” But few of that month’s columns mention that baseball becomes less predictable when the offseason starts. Baseball Prospectus, a company that makes its bones by forecasting player performance, team standings, and even the outcome of individual playoff games, implicitly concedes that there’s no model sophisticated enough to touch the hot stove. In its annual free-agent rankings, BP includes a predicted destination for every free agent from “Randy,” a random-number generator. Of course, free-agent signings aren’t really random: In the long run, free agents gravitate toward big-market clubs with a history of having high payrolls, just as the teams with the better regular-season records win a higher percentage of postseason series. But Randy reminds us that in any given winter, anyone can go anywhere.1

We can’t appeal to authority to improve on Randy’s predictions, because there are no authorities on the offseason. Only three of 28 team executives surveyed last month foresaw Pablo Sandoval leaving San Francisco. Only five thought the Marlins would extend Giancarlo Stanton. We’re bad at this, and the insiders aren’t any better. So it’s worth taking note when an offseason sequence unfolds the way we thought it would.

The White Sox completed a Monday trade and signing that briefly made them the leaders in the clubhouse for biggest offseason upgrade. Tuesday was the Cubs’ turn: After trading for Diamondbacks catcher Miguel Montero earlier in the day, they landed Jon Lester late Tuesday night, ending an almost comical sequence of reports, refutations, and uninformative updates as the lefty fielded competing offers from the Red Sox, Dodgers, and Giants. To acquire Lester, Montero, and starter Jason Hammel, a 2014 trade-deadline departure whom they brought back on Monday for two years and $20 million, the Cubs spent way more money and added more wins than the White Sox. But nothing they did took anyone in the industry by surprise.

On Monday morning, GM Jed Hoyer said, “We’re going to add multiple starting pitchers.” By Tuesday night, he’d made good on his vow. The Cubs’ path to contention has always been too clear for the team to be cagey: trade veterans for prospects and salary relief, make the most of high draft picks, spend on the international market, and supplement with trades and free agents to fill whatever needs the farm system couldn’t supply.

We knew this would be the winter when the Cubs entered that final phase, and that Lester, who turns 31 in January, would be part of their plan. Other events have also proceeded as we have foreseen: When manager Joe Maddon opted out of the final year of his contract with the Rays, Chicago was the rumored destination. It was obvious, also, that the Cubs would want a better starting catcher than Welington Castillo. Initial speculation centered on Russell Martin, the best free agent available, but as soon as Martin signed with Toronto, Montero became the best candidate. The Cubs are making every highly paid pundit and barely read blogger sound prescient. More than that, they’re making climbing out of the cellar seem as simple as a spammer’s prescription for earning a fortune from home.

It takes talent to be this predictable, though: The Cubs’ winter was easier to anticipate than the White Sox’s because the Cubs had fewer holes. There are so many ways in which a rebuild can run off the rails before it reaches this point: veterans who don’t bring back the expected return, prospects who get injured or exposed at Double-A, free agents who don’t arrive right on schedule or who refuse to sign. While it would be premature to declare their mission accomplished before they top 73 wins, the Cubs have avoided every pitfall so far. Their blueprint has been visible, yet they still haven’t been stopped.

Lester was the centerpiece of this preordained offseason: Even the terms weren’t unexpected. In a profile of Lester last month, MLB Trade Rumors’s Steve Adams came within $2 million of predicting the guaranteed total: $155 million over six seasons,2 which gives Lester the second-highest average annual salary ($25.8 million) for a pitcher, behind Clayton Kershaw’s $30.7 million. There’s nothing complicated about the contract. Lester is one of the best pitchers in baseball, and the Cubs, who’ve developed more hitting prospects than they have open positions, needed better pitching than they could promote from within. Aside from the factor that applies to every player — TV-contract-accelerated salary inflation — there are a few reasons why Lester received a record salary for a free-agent arm:

He’s Already Adjusted: When they enter the league, pitchers (as a group) are at the peak of their powers. Projecting any individual arm beyond that requires teams to estimate when the inevitable descent will start and how steep it will be. Prior to 2014, Lester’s strikeout rate had declined by more than 25 percent relative to its 2009 high. And this year, his velocity was down more than a mile and a half per hour compared to its peak in that same 2009 season. Nonetheless, Lester recorded a career-best walk rate, a big rebound in strikeout rate, and, thanks to his increased efficiency, a new high in innings pitched.

Lester recovered his former dominance by doing a better job of repeating his delivery, as measured by the spread in his release points. He also altered his pitch mix to emphasize his cutter and curve. And as Jeff Sullivan observed, he improved against righties by pitching farther inside. Those adjustments would seem to suggest that as Lester’s stuff tails off further, he can compensate with command, smarts, and a deep arsenal that makes him less reliant on the fastball than a starter with fewer options available. However, he might want to work on his pickoff move.

Draft-Pick Compensation Cost Not Included: Because Boston traded Lester in July, he was ineligible for a qualifying offer, unlike Max Scherzer and James Shields. As a result, his suitors knew that they wouldn’t have to sacrifice a compensation pick to sign him. Thanks to their losing seasons, the Red Sox and Cubs will pick seventh and ninth, respectively, in next year’s amateur draft. The first 10 picks are protected, so both teams were aware that they’d have to surrender only a second-round pick to sign a player carrying a compensation sentence.3 Still, teams place some value on those selections, and if Lester hadn’t been exempt from the qualifying offer, his eventual deal might have been for less money. By trading Lester away during the season, the Red Sox indirectly made it less costly for their competition to sign him this winter.

He’s Not an Obvious Health Risk: Lester has made at least 31 starts in seven straight seasons. The best indication of a pitcher’s future health is his injury history, and Lester’s isn’t long: Since his recovery from cancer, only a short 2011 DL stint and a few day-to-day injuries mar his perfect record. Yet despite his durability and frequent postseason appearances, Lester’s highest-workload seasons can’t compare to those of Justin Verlander, CC Sabathia, or, more recently, Shields and Madison Bumgarner. Nor did he rack up innings at an early age, reaching 200 innings for the first time at 24. Plus, Lester’s easy motion looks less worrisome than Scherzer’s high-effort release. Unlike major league teams, which can base studies on archived scouting reports, we can’t say whether a wonky delivery is a reliable indicator of early decline, but many evaluators believe it is. And of course, it couldn’t have hurt that Lester has a slightly stronger postseason record than Scherzer and an agent given to less lofty demands.

jon-lester-triJim Davis/The Boston Globe via Getty Images

To the extent that it’s possible for a free-agent pitcher, Lester is free of red flags. According to Baseball-Reference, the lefty with the most similar stats through age 30 is Andy Pettitte. It’s a tantalizing comparison: Not only did the two post near-identical innings totals (Lester 1,596; Pettitte 1,584.1) and career ERA+ marks (Lester 121; Pettitte 117) through age 30, they have mirror-image builds and identical five-pitch repertoires highlighted by signature cutters. Pettitte’s slow decline phase is a tough act to follow, but the Cubs can accept the risk that Lester won’t replicate the best-case outcome because they’ve minimized their exposure in other areas. By developing position players and importing proven pitchers, they’ve avoided the injury nexus, the dangerous early-twenties period when pitcher attrition rates reach their pinnacle. And with most of their roster years away from arbitration, let alone free agency — only the White Sox, Marlins, and Astros entered the winter with less cash committed to 2015 — they’ll have plenty of payroll to play with even if Lester goes south.

On top of Lester and Hammel, the Cubs added Montero for two prospects whose loss won’t be felt in a stacked farm system: 20-year-old Jefferson Mejia ranked 18th on Kiley McDaniel’s comprehensive list of Cubs prospects whom he projects to be big leaguers, while 24-year-old Zack Godley, who hasn’t advanced beyond High-A, didn’t merit a mention. Montero’s BABIP and power have dipped in the past two seasons as his stroke has produced more ground balls, and he hit only two homers during an extended post-All-Star-break slump. However, Montero’s batted-ball rates didn’t degrade further in the second half, and he walks often enough to make him at least an average offensive catcher. Although teams started calling about Castillo as soon as Montero switched teams, the younger catcher would make a perfect platoon mate if the Cubs decide to keep him: Montero, a left-handed hitter, has historically been much more productive against right-handed pitching, while the right-handed Castillo has crushed lefties. In addition, Montero is a sizable upgrade on defense. Although his caught-stealing rate has slipped some since it topped 40 percent in 2011 and 2012, he remains above average at framing, a skill that Castillo still hasn’t mastered.

The Cubs, who had the second-youngest position players of any club last season, will count on youth just as much next year, with Montero the only projected starter who’ll be more than 29 on Opening Day. The Cubs are betting that Javier Baez and Arismendy Alcantara will make more contact. They’re hoping there won’t be a book on Kris Bryant when last year’s minor league home run king arrives, and that Jorge Soler’s inexperience won’t be exposed in his first full season. They’ll have to build a bullpen out of lesser-known names, and the rotation is still one starter away from representing a strength. There are bound to be a few faltering first steps, but the clock counting down to contention is about to zero out.

So with the primary items on the Cubs’ wish list crossed off, what’s next for the teams that lost out on Lester? In the wake of Sandoval’s departure, watching Lester send a rose to somebody else has to hurt Giants GM Brian Sabean, who’ll now turn his attention back to other rumored objects of interest. For the Dodgers, who can console themselves with Kershaw and Zack Greinke, the pain is probably less acute. And for the runner-up Red Sox, who may regret not going higher with their extension offer last spring, losing Lester is a setback, but not a disaster.

The Sox offered Lester a six-year deal, which would have been the longest they’d ever awarded a free-agent pitcher. Given John Henry’s hard-line stance on contract length for over-30 players, that sixth year (plus the owner’s recruiting trip to Atlanta) is a testament to the team’s interest, but the $20 million gap between the winning bid and Boston’s — which the Red Sox must have had a chance to close — says the Sox weren’t desperate. Nor should they have been. Before Lester made his decision, Sox GM Ben Cherington cited “15 to 20 starting pitcher scenarios” that the team had considered as potential routes to the “good rotation” that he’s promised fans. In addition to pursuing remaining free agents Scherzer, Shields, and Brandon McCarthy, Boston could try to loosen Phillies GM Ruben Amaro Jr.’s death grip on Cole Hamels or package surplus position players for one of many one-year rentals remaining on the post–Jeff Samardzija market.

When the Red Sox drafted Lester in 2002, they were still two seasons away from ending their 86-year stretch without a title. Since then, they’ve won two with Lester on the staff. While the lefty was tempted to return to his roots, winning another World Series in Boston must have seemed passé compared to the prospect of breaking a second curse with the Cubs. By accepting Chicago’s offer, Lester brought Theo Epstein and Jed Hoyer, his old/new employers, significantly closer to completing a mission much like the one they undertook more than a decade ago in Boston. Whatever the sequel’s outcome, they’ll all be better paid.

Filed Under: MLB, MLB Winter Meetings, MLB Hot Stove, MLB Free Agency, MLB Free Agents, MLB Trades, MLB Contracts, Money Matters, Pitchers, Catchers, Chicago Cubs, Jon Lester, Theo Epstein, Jed Hoyer, Jason Hammel, Miguel Montero, Boston Red Sox, San Francisco Giants, Los Angeles Dodgers, MLB Stats, Baseball, Ben Lindbergh

Ben Lindbergh is a staff writer at Grantland.

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