The Cubs enter the 2014-15 offseason with the highest expectations since Theo Epstein took over as club president in October 2011. Starting pitching should be the team’s main focus this winter.

Guaranteed Contracts

Arbitration Eligible Players (service time in parentheses; projections via Matt Swartz)

Contract Options

Kyuji Fujikawa , RP: $5.5MM club option with a $500K buyout

, RP: $5.5MM club option with a $500K buyout Tsuyoshi Wada , SP: $5MM club option (no buyout)

, SP: $5MM club option (no buyout) Jacob Turner, SP: $1MM club option (no buyout)

Free Agents

For a last-place team that finished 16 games under .500, the 2014 Cubs had several positive developments. 25-year-old Anthony Rizzo emerged as one of the best first basemen in baseball. 24-year-old shortstop Starlin Castro bounced back to his 2011-12 form. 22-year-old right fielder Jorge Soler battled hamstring injuries but still tore through Double and Triple-A and saw his success carry over for a month in the Majors. On the pitching side, Jake Arrieta emerged as a potential ace with a 2.53 ERA in 25 starts and Hector Rondon had a successful run as the team’s closer. A lot of building blocks fell into place under new manager Rick Renteria.

In March, I questioned the Cubs’ choices of position players Rizzo and Kris Bryant over power arms Andrew Cashner and Jon Gray. The Rizzo and Bryant choices, plus this summer’s acquisition of Addison Russell and drafting of Kyle Schwarber, suggest president Theo Epstein and GM Jed Hoyer have implemented a strategy favoring the stability of position players to begin their rebuild. The plan has come up smelling like roses so far, as the team’s collection of young hitters is the envy of baseball.

Rizzo has first base locked down for the Cubs potentially through 2021, on what’s become one of the game’s most team-friendly contracts. Though Luis Valbuena did an admirable job at the hot corner in 2014, third base belongs to Baseball America Minor League Player of the Year Kris Bryant. If the Cubs wait a few weeks into April to select Bryant’s contract, they’ll control him through 2021 as well.

The Cubs’ middle infield logjam represents a good kind of problem. Castro, signed potentially through 2020, was one of the game’s ten best shortstops in 2014 despite missing most of the season’s final month. Powerful 21-year-old Javier Baez made his big league debut in August, playing second base and then switching to shortstop when Castro went down. Baez struggled at his new level, as many prospects do, but has the second base job entering 2015. Then there’s Addison Russell, the key piece in the deal that sent Jeff Samardzija and Jason Hammel to Oakland. The 20-year-old Russell raked at Double-A and is knocking on the door to the Majors himself.

Valbuena, 28, had his first full season as a regular, posting a solid .249/.341/.435 line while playing third base and a bit at second. If we pencil in Rizzo, Castro, and Bryant at their respective positions for 2015, only second base is available for three players ranging from good (Valbuena) to potential All-Star (Russell and Baez).

Trading Castro, Russell, or Baez this offseason could be jumping the gun, since Baez has yet to succeed at the big league level and Russell has yet to reach Triple-A. A safe plan would be to begin 2015 with a Castro-Baez middle infield, and if Baez hits and Russell is knocking down the door come July, the team can more seriously consider trades at that point or even move someone to the outfield. Trading Valbuena this winter could make sense, though he’d be a good backup plan at second base. The Cubs need a backup plan for Baez, who struck out in 41.5% of his plate appearances as a rookie. Among players with 200 or more plate appearances, that’s easily the worst strikeout rate in baseball history.

Valbuena was one of the ten best offensive third basemen in the game this year and is under control through 2016; a team like the Red Sox could have interest. He could also be marketed as a second baseman, especially since the free agent market is weak at that position.

Soler should have the right field job locked down heading into 2015, but last year’s 86 games marked a career high. We won’t know if Soler’s hamstrings can hold up for 130+ games in the Majors until he does it. Over in left field, former 2009 Rookie of the Year Chris Coghlan had a resurgent year and should have the job heading into next season. The 2014 Cubs used a host of center fielders, the most interesting of whom is 22-year-old Arismendy Alcantara. A very good prospect in his own right, Alcantara took his first reps at the position this year after previously working as an infielder. As with Baez, Alcantara should get first crack at the 2015 job despite rookie growing pains.

The Cubs’ outfield has enough uncertainty that keeping veterans Sweeney and Ruggiano around makes sense. The team would be justified entering Spring Training with their current outfield pieces, though I’d consider an offseason run at Colby Rasmus on a one-year deal. Rasmus would bring power and upside with no long-term risk, and Alcantara could get further acquainted with center field at Triple-A or be an oft-used super-utility player in the Majors. Another outfielder who could fit is Yasmany Tomas, if the Cubs see star potential in the Cuban free agent, consider him worth a potential $100MM contract, and don’t mind creating something of a long-term surplus in the outfield.

Behind the plate, 27-year-old Welington Castillo played acceptably but saw his batting average and walk rate decline from 2013. The Cubs don’t have to make a long-term decision on Castillo, who is entering arbitration for the first time. The team does have a potential star catcher in the pipeline in 2014 first-rounder Kyle Schwarber, but he needs to prove he can stick at the position. In the spirit of adding position player talent now and worrying about a potential surplus later, the Cubs could make a run at the best free agent catcher, Russell Martin. Signing Martin would signal the Cubs intend to take a leap forward into contention in 2015, though he could require upwards of $50MM as well as the forfeiture of the Cubs’ second-round draft pick.

Epstein whiffed on the biggest expenditure thus far in his Cubs tenure, Edwin Jackson. Jackson now has two years and $22MM left on his contract. According to a late August report from Bob Nightengale of USA Today, the Cubs and Braves engaged in talks in July to swap Jackson and B.J. Upton. That could be revisited, but it’s not the best match since Upton has more than twice as much money remaining on his contract. Other disappointing contracts with between $16-30MM remaining include Cameron Maybin, Chris Johnson, Aaron Hill, Allen Craig, Michael Bourn, Nick Swisher, and Carlos Beltran. While those players have been letdowns, their teams may not be as close to the breaking point as the Cubs seem to be with Jackson.

Regardless of Jackson, the Cubs will need to explore adding starting pitching from all angles. The 2014-15 free agent class is rife with options for all parts of a rotation. The Big Three are Max Scherzer, Jon Lester, and James Shields. Lester is the most obvious fit for the Cubs, as a player who joined the Red Sox around the same time Epstein did and was a big part of the executive’s success there. That he isn’t eligible for a qualifying offer is helpful, but Lester’s price tag will probably exceed $150MM. If they prefer the trade market, the Cubs could try to swing a deal for the Phillies’ Cole Hamels, who is owed $96MM through 2018.

One big name starter alone probably wouldn’t be enough to push the Cubs into contention. Arrieta looked like an ace this year, but his 176 2/3 pro innings marked a career-high, and he missed the season’s first month recovering from a shoulder injury. Kyle Hendricks posted a sparkling 2.46 ERA in 80 1/3 innings as a rookie, but his scouting report and lack of strikeouts suggest a back of the rotation starter. Though his ERA bounced around in his three years with the Cubs, Travis Wood profiles at the back end of a rotation as well and could be non-tendered or traded. The other immediate options are projects who once showed potential: Jacob Turner, Felix Doubront, and Dan Straily. If the Cubs want to keep Turner they’ll pick up his $1MM club option, as renewing him would cost at least 80% of his 2014 salary, which comes to more than $1.5MM.

The Cubs would do well to add one or two mid-tier starting pitchers even if they sign one of the Big Three. Wada could be in that mix after a successful 13-start run, though the Cubs would probably want him for less than his $5MM club option. The Cubs will likely set their sights higher and go for Kenta Maeda, Brandon McCarthy, Francisco Liriano, or Justin Masterson. Masterson comes with the Epstein connection plus other helpful factors such as the lack of a qualifying offer and a likely short-term deal. Epstein has succeeded in the free agent starting pitcher bargain bin over the years, finding Hammel, Wada, Scott Feldman, and Paul Maholm on the cheap.

The Cubs’ bullpen has talent. Rondon is the incumbent closer, while Justin Grimm, Neil Ramirez, and Pedro Strop also pitched well. The Cubs could cut Wesley Wright loose and pursue a better option from the left side, with Andrew Miller profiling as the top southpaw reliever on the free agent market. Right-hander Kyuji Fujikawa is likely to have his option bought out after missing most of his two-year term with the Cubs due to Tommy John surgery. The 2014 Cubs led the NL in relief innings, and the ten pitchers who tossed 14 or fewer innings apiece accounted for a 6.91 ERA. The nine hurlers who had 21 or more relief innings tallied a cumulative 3.04 mark. Better starting pitching could have a significant trickle-down effect on the bullpen in 2015.

Alfonso Soriano is finally off the books for the Cubs, who owe $25.5MM to five players under contract for 2015. They could spend another $17MM or so on arbitration eligible players, bringing total commitments to around $43MM. What is an appropriate payroll for the 2015 Cubs? It seems they could reasonably sit around the middle of the pack with a $110MM payroll, and they could also roll over unspent money from 2014. A $70MM war chest would be more than enough money to add the players necessary to compete next season.

In the longer-term, the Cubs should raise their payroll to be top five in baseball, befitting of their status as a major market team. Though their short-term television rights are an open question, the Cubs’ potential TV deal for all their games following the 2019 season will be what Epstein called a “paradigm shifter” for club revenue, according to Gordon Wittenmyer of the Chicago Sun-Times. Improvements to Wrigley Field, which are now underway, will “move the needle,” according to Epstein. The Cubs have begun their renovation project despite a pending lawsuit between rooftop owners and the city of Chicago regarding the team’s plans to erect signs that will affect the rooftop view.

Regular season winning percentages in the Theo Epstein/Jed Hoyer Cubs era have increased from .377 to .407 to .451. Though he could sign an extension, Epstein only has two years left on his contract. Aggressive acquisition of starting pitching this offseason should mark the end of his three-year rebuilding plan.