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Winter Report Card: Chicago Cubs

Buoyed by the big signing of Jon Lester, the Cubs have nailed their winter and look ready to push their way up the NL Central standings.

With little more than five weeks before pitchers and catchers report, we're checking in on how each team has fared in conducting its offseason business while acknowledging that there's still time for its prognosis to change. Teams will be presented in reverse order of finish from 2014.

Chicago Cubs

2014 Results: 73-89 (.451), fifth place in NL Central (Hot Stove Preview)

Key Departures: C John Baker, RHP Kyuji Fujikawa, MGR Rick Renteria, OF Justin Ruggiano, RHP Carlos Villanueva*, RHP Arodys Vizcaino, LHP Wesley Wright

Key Arrivals: OF Chris Denorfia, RHP Jason Hammel, 2B Tommy La Stella LHP Jon Lester, MGR Joe Maddon, C Miguel Montero, RHP Jason Motte, C David Ross

Theo Epstein's vision is beginning to take shape. En route to their fifth straight losing season and their third under the Epstein/Jed Hoyer regime, the Cubs showed significant progress in 2014. They improved by seven wins over 2013; took the wraps off top prospects Arismendy Alcantara, Javier Baez and Jorge Soler; swapped Jeff Samardzija and Jason Hammel for prospects Addison Russell and Billy McKinney; and enjoyed strong rebounds from Starlin Castro and Anthony Rizzo. They've continued to take steps forward this winter, bringing in some big names to slot alongside the young talent and setting the stage for a push up the division standings, toward .500 and beyond.

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At the helm will be a new manager in Joe Maddon, who opted out of his job in Tampa Bay after a nine-year run that included five seasons of at least 90 wins, four postseason appearances and the first pennant in franchise history — all on a shoestring budget. Predecessor Rick Renteria did nothing glaringly wrong during his lone year at the helm, but he was simply a victim of not being as famous or accomplished as his successor, whose sudden availability caught the baseball world by surprise. The change wasn't pretty — in some quarters, it was viewed as unseemly — but Maddon's experience in molding a young core of talent into a contender and in working with an analytically-inclined front office makes him the ideal man for the job. This time, he'll get to do it with a much bigger budget, one that includes the ability to nab a marquee free agent when it fits the team's purposes.

Jon Lester buys into dream of helping Cubs end World Series drought

That's what the Cubs did in signing Jon Lester to a six-year, $155 million deal, one whose average annual value of $25.83 million currently ranks second among pitchers behind only Clayton Kershaw's $30.7 million, though Max Scherzer is likely to wind up somewhere between the two. The 31-year-old lefty is coming off a season in which he set career bests in innings (219 2/3), ERA (2.46, more than a run below his 3.58 career mark), FIP (2.80), walk rate (2.0 per nine) and strikeout-to-walk ratio (4.6) in pitching for the Red Sox and Athletics, who acquired him via trade on July 31 — a wrinkle that kept the Cubs from losing a top draft pick, since the A's were ineligible to make Lester a qualifying offer. The signing reunites Epstein with a key pitcher who, on his watch with the Red Sox, broke into the majors in 2006 and helped the team win a World Series the following year; Lester also served as staff ace for the 2013 champions under Epstein's successor, Ben Cherington.

Lester also significantly fortifies the Cubs' rotation, for while they are neck-deep in position prospects, particularly in the infield, they're short on the pitching front. That group includes 2014 breakout Jake Arrieta and Kyle Hendricks, either Tsuyoshi Wada or Travis Wood, and another free-agent fortification in Hammel, who returned to the Cubs via a two-year, $20 million deal (and a $12 million option for a third year). Hammel pitched to a 3.47 ERA and 3.92 FIP in 176 1/3 innings last year, his largest workload since 2010. If not the most durable hurler around — he's averaged 25 starts and 151 innings of league-average work (100 ERA+) over the past four seasons — he's at least affordable and capable of delivering above-average value, with two seasons of at least 3.0 WAR in the past three.

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That rotation will throw to a significantly upgraded catching corps. The Cubs traded a pair of low-level pitching prospects (Zack Godfrey and Jeferson Mejia) to the Diamondbacks for Miguel Montero, who has three years and $40 million remaining on his contract. Though he earned All-Star honors for just the second time in his career, the the 31-year-old backstop may be wearing down. He hit just .243/.329/.370 with 13 homers for a 95 OPS+, his second straight year of below-average offense, and has been worth just 1.2 WAR over the past two seasons, compared to 8.2 WAR over the previous two. None of those figures account for his above-average pitch framing, which via Baseball Prospectus' metrics ranked 10th in the majors at 14.2 runs and has been in double digits in five of the past six seasons.

Backing Montero up will be David Ross, who signed a two-year, $5 million deal. The going-on-38-year-old hit just .184/.260/.368 with seven homers in 171 PA in 2014, his second straight subpar season with the bat amid injuries, namely a 2013 concussion and plantar fasciitis last year. But he, too, has been consistently above-average as a pitch-framer (+6.8 runs in 2014). By comparison, nontendered backup John Baker was 1.2 runs below average, that while hitting an even thinner .192/.273/.231. Starter Welington Castillo, meanwhile, was 9.2 runs below average, the majors' fourth-worst showing. More on him below.

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As for the other comings and goings among the pitchers: Tommy John surgery limited reliever Kyuki Fujikawa to 25 innings during his two-year, $9.5 million deal; he signed with the Rangers. Lefty specialist Wesley Wright, who gave the team a solid 48 1/3 innings in 2014, was nontendered and signed with the Orioles. Utility pitcher Carlos Villanueva, who provided the team with 69 relief appearances, 20 starts and 206 1/3 innings en route to 1.3 WAR during his two-year, $10 million deal, remains a free agent. Former Cardinals closer Jason Motte, who pitched 25 innings in his return from May 2013 Tommy John surgery, signed a one-year, $4.5 million deal to provide depth in the bullpen.

Among the position payers, reserve outfielder Justin Ruggiano, who hit .281/.337/.429 with six homers in 250 PA, was dealt to the Mariners for righty Matt Brazis, a 25-year-old reliever who put up a 2.36 ERA with 10.5 strikeouts per nine in 72 1/3 innings split between High A and Double A. Ruggiano essentially switched places with 34-year-old Chris Denorfia, who after four strong seasons for the Padres slumped to .230/.284/.318 with three homers in 358 PA split between San Diego and Seattle. He signed a one-year, $2.6 million deal that includes additional incentives starting at the 400 PA level and could serve as a righty complement to starting leftfielder Chris Coghlan.

Tommy La Stella, who hit .251/.328/.317 in 360 PA as a rookie for the Braves last year, was acquired in exchange for oft-injured pitching prospect Arodys Vizcaino, who after missing two years due to Tommy John surgery pitched 46 innings across four levels in 2014, including five innings with the Cubs. La Stella will likely serve as a backup/insurance policy in case Baez, who hit .169/.227/.324 with nine homers in 229 PA as a rookie, needs a minor league refresher course.

Unfinished Business: Unloading

Winter Report Card: Boston Red Sox

The Cubs have done a very good job of filling their top needs — namely starting pitching and catching — this winter without trading any of their key prospects. In doing so, they've created surpluses that suggest future deals ahead. The going-on-28-year-old Castillo is just a year removed from a 4.5-WAR season and entering his first year of arbitration eligibility. His pitch framing may be subpar, but his arm, offense (career 98 OPS+) and price tag should appeal to somebody. The Diamondbacks, who have Tuffy Gosewisch atop their depth chart in the wake of the Montero trade, are an obvious target, as are the Orioles, who could possibly use some insurance as Matt Wieters works his way back from Tommy John surgery, and the Rangers, who need a complement to Robinson Chirinos. The A's (Stephen Vogt and Josh Phegley) and White Sox (Tyler Flowers and Adrian Nieto or Rob Brantly) have unimposing tandems that could stand an upgrade.

There's far less value to be had in dealing Edwin Jackson, who pitched to a 6.33 ERA last year and has a 5.58 mark in 316 innings for the Cubs over the last two years. He's still owed $26 million over the next two seasons and probably needs a fresh start elsewhere.

Another player who could be dealt is Luis Valbuena, who's holding down the hot corner until the arrival of Kris Bryant. Twenty-six-year-old Mike Olt had a miserable rookie season (160/.248/.356 in 258 PA) but could serve as a placeholder until Bryant is ready. That said, the team could try Olt in the outfield, and Bryant may wind up there long-term if Castro is shifted to third to make room for Russell. In all, it's an enviable surplus to have, one that doesn't need to be broken up just yet.

Preliminary Grade: A-

Few teams have had as strong an offseason as the Cubs, who have made big splashes and filled their major needs. Dealing Castillo to fill another need and finding a better use for Jackson's roster spot are still on the to-do list and could take them to a full A grade, but all in all, this has been an impressive winter.