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New Chicago Cubs Offseason Checklist Following Joe Maddon Hire

Jason Catania@@JayCat11MLB Lead WriterNovember 4, 2014

Spencer Green/AP Images

The Chicago Cubs got their man and their manager. By hiring skipper Joe Maddon, a move that became a reality with Monday's introductory press conference, the franchise kicked off what looks to be a busy and productive offseason as the club embarks on the next stage of a long rebuilding process and return to relevance—and perhaps even the postseason—sooner than later.

Just ask Maddon himself.

"For me, I'm going to be talking playoffs next year," Maddon said via Joey Nowak of MLB.com. "We're going to set our mark high, and I'm going to talk playoffs and World Series this year, and I'm going to believe it."

That's a big statement from someone who's new to a team that hasn't reached the postseason since 2008 or the World Series since 1945—let alone won it all since 1908. Now it's up to Maddon, as well as Cubs president Theo Epstein and general manager Jed Hoyer, to back that up.

Carrie Muskat @CarrieMuskat

Maddon's deal with #Cubs is 5 years, $25 million

In signing Maddon, who opted out of the final year of his contract with the Tampa Bay Rays last month, to a five-year deal that runs through the 2019 season, the Cubs are hoping a man widely regarded as one of the very best managers and tacticians in the sport can do for his new organization what he did for his old one.

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That is, turn a cellar dweller into a perennial power.

But having Maddon take the place of Rick Renteria, who was abruptly dismissed late last week after just one season on the job, is far from the only big move Epstein and Hoyer will have to pull off to achieve that objective.

Remember, in addition to needing some skipper stability—Maddon checks in as the fifth manager since the beginning of the 2010 campaign—this is a franchise desperately requiring a return to relevance after five straight losing seasons.

With Maddon now officially in the fold and soon to be on the bench, here's a rundown of what else the Cubs need to get done this offseason.

There's plenty still to do if Maddon and Company really are aiming for the playoffs in 2015.

Spend on a Starter...

The Cubs need an arm or three, and it's no secret that appears to be their priority this winter.

"We need to add impact pitching, from outside the organization," Epstein said, according to Bruce Miles of the Chicago Daily Herald. "We fully acknowledge that. That's a primary goal going forward. Certainly over the next 15 months, I'll be disappointed if we don't add impact pitching from outside the organization."

The current rotation candidates include 2014 breakout pitcher Jake Arrieta, the regression-victimized Travis Wood and second-year arm Kyle Hendricks, who has made all of 13 starts with Chicago.

Beyond that trio, there's veteran Edwin Jackson, who owns a nasty 5.58 ERA in his two years as a Cub, scrapheap projects Jacob Turner and Felix Doubront as well as Tsuyoshi Wada, who re-signed on Monday for one year, per Muskat, in a move that understandably received much less fanfare.

Signing free agent Jon Lester would give the Cubs a front-of-the-rotation starter they so badly need.
Signing free agent Jon Lester would give the Cubs a front-of-the-rotation starter they so badly need.Marcio Jose Sanchez/Associated Press

Lucky for the Cubs, the top two free agents on the market this year happen to be starting pitchers, left-hander Jon Lester and right-hander Max Scherzer.

Between those two, there has been more speculation, per Gordon Wittenmyer of the Chicago Sun-Times, that Lester could be the primary target given the left-hander's potentially slightly lower price tag and lack of draft-pick compensation for being traded midseason. Not to mention, Lester has ties to Epstein from their Boston Red Sox days.

The other big name that has been rumored as a good fit is righty James Shields, as Wittenmyer writes, with whom Maddon is plenty familiar from their time in Tampa Bay together.

The front office should continue its bargain-bin shopping to unearth the next Arrieta, Scott Feldman or Jason Hammel, but it's about time to pony up for a stud starter.

...and Maybe Trade for One Too

Again, this team needs arms—as in plural.

Considering how overloaded Chicago is on the position-player front, particularly in the infield, it might make sense for the club to at least dangle some of that potential excess to see what sort of offers come in.

Depending on how aggressive Epstein and Hoyer want to get, they have the goods to acquire just about any pitcher made available on the trade market, including aces like the Philadelphia Phillies' Cole Hamels or the Cincinnati Reds' Johnny Cueto, as well as solid mid-rotation arms like Mat Latos of the Reds or Tyson Ross of the San Diego Padres.

Heck, even old buddy Jeff Samardzija, whom they traded to the Oakland Athletics for top shortstop prospect Addison Russell last July, could be an option.

Chicago has the pieces to trade for a stud starter, like Cole Hamels, if they so choose.
Chicago has the pieces to trade for a stud starter, like Cole Hamels, if they so choose.Matt Slocum/Associated Press

Find a Leader on the Field

Epstein, Hoyer and Maddon form quite a triumvirate of savvy, experienced decision-makers. The Cubs, however, are lacking that element on the diamond, in large part because the vast majority of the 25-man roster is so young.

Remarkably, only four players on the current 25-man roster have an age that begins with a "three" and not a "two": 33-year-old Wada, 33-year-old John Baker, 31-year-old Jackson and 30-year-old Carlos Villanueva. None of that quartet, by the way, is anything close to a cog going forward.

As for the longest-tenured Cub? Why, that'd be shortstop Starlin Castro, who has played in 740 games since debuting as a 20-year-old in 2010.

"We need to add some reliable performance from veterans from whom we know what we'll get because young players' performance is so volatile early in their careers," Epstein told Miles.

At the top of that list should be Russell Martin. Not only is the 31-year-old, nine-year veteran a leader, he also would address the need for a strong, all-around backstop.

In addition to his .402 on-base percentage in 2014, Martin has been a key component of a Pittsburgh club that went from 20 consecutive losing seasons—the most ever in America's four professional sports—to two straight postseasons. Think the Cubs would value that kind of impact?

Although the Pirates just tendered a qualifying offer to Martin, per Bill Brink of the Pittsburgh Post-Gazette, the Cubs' top draft pick—one of the first 10—is protected.

Get All that Young Talent to Maddon

Among his many strong suits with the Rays, one of Maddon's best traits was his ability to incorporate, develop and work with young players.

The Cubs possess arguably the top farm system in all of baseball, thanks to outfielder Albert Almora, right-hander C.J. Edwards and consensus top prospect Kris Bryant, among others.

But they also have a number of players in the nascent stages of their big league careers, including right fielder Jorge Soler, center fielder Arismendy Alcantara and infielder Javier Baez.

And although first baseman Anthony Rizzo and Castro have been around for a while, both will be only 25 entering 2015, so they're more or less MLB adolescents still.

It behooves the Cubs to get all this young, still-maleable, on-the-verge talent to Maddon so they can have time to be molded, sculpted and brought along by him.

If that means not worrying so much about trivialities like the Super Two arbitration deadline, then so be it.

The first to-do item of the Cubs' offseason—get Joe Maddon—has been taken care of. There's still a lot to get done, but the plan is in place to get this franchise back to the playoffs soon. And if Maddon gets his way, perhaps it'll be even as soon as next year.

Statistics are accurate through the 2014 season and courtesy of MLB.comBaseball-Reference.com and FanGraphs unless otherwise noted.

To talk baseball or fantasy baseball, check in with me on Twitter: @JayCat11.

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