The Chicago Cubs have pushed their rebuilding project into overdrive this offseason by first signing renowned manager Joe Maddon, and now bringing lefty ace Jon Lester into the fold on a six year, $155 million contract. 

Make no mistake, the deal was a coup for the Cubs, and they will finally win a title by the time Lester’s deal has expired. 

Of course, it’s jarring to imagine the Cubbies actually winning the World Series. The drought is currently at 104 years and counting, and the organization has become synonymous with losing. 

But if not now, then when? All of the necessary pieces are in place to make it happen. 

The front office is under the steady hand of former Red Sox wiz kid Theo Epstein, who has done a remarkable job of acquiring top prospects in return for established veterans. The latest example was Epstein prying the third ranked prospect in baseball, Addison Russell, away from the A’s in exchange for Jeff Samardzija and Jason Hammel this past summer.  

Maddon is one of the top three managers in baseball, and he showed in Tampa Bay his perpetually optimistic leadership worked with a team of talented young players. Now at the helm of a franchise with deep pockets, his genius should become even more apparent. 

Most importantly, though, the franchise is littered with top prospects that are primed for multiple all-star appearances -- many of which have already shown they are ready for The Show. 

25-year-old first baseman Anthony Rizzo sported a .385 on base percentage and belted 32 dingers in 2014, and Starlin Castro is a solid option at shortstop. And despite hitting below the Mendoza Line when he was called up at the end of the season, nine home runs in 52 games showed Javier Baez is another potent bat to keep an eye on.

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Their natural improvement, coupled with the eventual additions of Russell and Cuban slugger Jorge Soler, will make the Cubs’ batting order one of the most feared in baseball.   

Still, the pitching staff is a patchwork collection of unproven mid-tier prospects and journeymen. This was largely by design, as Epstein has made it a priority to find premier hitting prospects and fill in the pitching staff afterwards. 

That’s where Lester comes in. 

His career 3.58 ERA will translate well to the National League, especially when you consider he spent nearly a decade in the suboptimal pitching conditions of Fenway Park.   

While being on the wrong side of 30, the lefty from Tacoma, Washington isn’t as beaten up as some would expect. Lester has only pitched 200 more innings than Clayton Kershaw, who is four years his junior. 

Lester’s Fly Ball Percentage may not be ideal for the “friendly confines of Wrigley Field,” but he will be savvy enough to know how to pitch around guys and milk pitchers hitting in the NL. 

And if the Cubs’ bats can carry them through the regular season, the playoffs will be where Lester shows what the Cubs really paid for. In 84 postseason innings, Lester has a 2.57 ERA, and on the way to his second World Series ring in 2013 he was especially remarkable, allowing only one earned run in more than 15 innings. 

If Lester can maintain his level of play over the next few seasons as the Cubs’ continue to develop, he will have another look at a ring. 

In "Back to the Future Part II", it was hard for Marty McFly to process the Cubs having gone all the way in 2015 – and that was filmed in 1989. But taking inventory of the pedigree on the roster and the leadership of Maddon and Epstein, it isn’t too crazy to think about putting some money on the Cubbies. 

Reach Staff Contributor Sean Burch here.