Chicago Cubs

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Overview (Present Rank: 1st | Future Rank: 1st)

Over a century has passed since the Chicago Cubs were last celebrating a World Series championship. To put that in perspective, two World Wars, a great depression, the creation of the internet, and the rise and fall of disco music have all occurred since the Cubs’ last championship banner. That doesn’t mean Chicago has been stuck in the cellar over those 100+ years. The Cubs have added seven National League pennants to their collection, but have come up short in the Fall Classic each and every time since 1908.

Once Theo Epstein was hired as the team’s President of Baseball Operations in 2011, the team started building from the ground up. The front office accumulated an abundance of dynamic young players on the roster during the three-year rebuilding period. After putting five consecutive losing seasons in the rearview mirror, the Chicago Cubs came close to validating the prediction made in “Back to the Future II” by winning the World Series in 2015.

Daniel Murphy’s legendary postseason performance proved it wasn’t meant to be last year, but 2015 was just the beginning for these Cubbies. With the most talented roster in the league, Chicago has the best chance of any team to win the Commissioner's trophy in 2016 and beyond. As long as Theo Epstein and manager Joe Maddon are calling the shots, the Cubs will be the presumed World Series favorites on an annual basis.


*Detailed analysis conducted April 4, 2016; rankings and charts updated throughout the season.

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Catcher (Present Rank: 7th | Future Rank: 2nd)

Miguel Montero will return as the team’s starting catcher in 2016 after another solid season in his 10-year career. Montero was the only starting position player in Chicago that was older than 29 years old for the entire 2015 season. His maturity and wisdom is his most valuable asset in a clubhouse full of rookies and young professionals. Performance-wise, Montero is an average catcher whose age might push him into the fringe starter area after a couple of years. Good thing for Chicago, they are only on the hook for two more years of Montero’s 5yr/$60MM contract.

By the time Montero’s contract is set to expire, Chicago will be ready for the No. 2 catching prospect in the game (according to Baseball America) to take the reigns. Willson Contreras was acquired in 2009, before Epstein was in charge, but it wasn’t until his breakout campaign in 2015 that baseball evaluators began recognizing Contreras for his sweet stroke and overall skill-set behind the plate. Praise must also be sent Desi Wilson’s way. The hitting coach for Chicago’s Double-A team not only helped elevate Contreras into a top-100 prospect, but he also played a part in Kyle Scwarber’s emergence as a dominant hitter.

Victor Caratini will never be a top-100 prospect or a dominant hitter, but if he continues on the path he’s on, he could eventually claim a bench role as a backup catcher. David Ross has made a career (and over 20 million dollars) out of doing just that.

Future Outlook: The missing piece of the puzzle

As far as positional players go, Theo Epstein had everything figured out for the future. With Anthony Rizzo at first base, Javier Baez and Addison Russell in the middle infield, Kris Bryant at third, and some combination of Kyle Schwarber, Albert Almora, Jorge Soler, and Billy McKinney in the outfield, the future lineup was almost complete. With an exorbitant amount of young players, Epstein was thinking he would eventually trade for a franchise catcher like he did with Miguel Montero to a lesser degree. After working with Double-A hitting coach Desi Wilson, Willson Contreras has emerged as a potential franchise catcher himself. He might not have been acquired by Epstein, but Theo has no problem with Joe Maddon inserting him into the lineup as the missing piece of the offensive puzzle.

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First Base (Present Rank: 3rd | Future Rank: 2nd)

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With a multitude of players capable of being the best hitter on this team, nobody has a better chance of achieving that distinction in 2016 than Anthony Rizzo. Only 26 years-old, Rizzo already has two top-10 MVP finishes and two All-Star appearances on his resume. Theo Epstein and GM Jed Hoyer have been fans of Rizzo for a long time. While the two were working in Boston, they drafted Anthony Rizzo in 2007. Once Hoyer became the General Manager of the San Diego Padres, he re-acquired the 6’3” first baseman in his first blockbuster trade that also involved Adrian Gonzalez landing in Boston. Finally, after the front office duo reunited in northern Chicago, they traded away Andrew Cashner to get their hands on Rizzo once again. While Cashner is struggling to maintain a spot in San Diego’s lackluster rotation, Rizzo has emerged as a franchise first baseman for a team bound for greatness.

The Cubs don’t need to worry about any other first baseman with Rizzo under team control for six more seasons if the club exercises both $14.5MM options in 2020-21. However, it never hurts to have a Plan B. For most teams, Dan Vogelbach’s excellent approach at the plate and raw power would be accepted as a viable Plan A. However, the 23 year-old’s conditioning (250 lbs), awful speed, and poor defensive abilities concern some in the organization and should lead to him getting traded to an American League team where he can thrive as a regular designated hitter. With Rizzo locked up for at least the next four years, Vogelbach heading elsewhere seems all but inevitable at this point.

(EDIT: The Cubs have officially traded Dan Vogelbach to the Seattle Mariners with Paul Blackburn for LHP Mike Montgomery and Jordan Pries to solidify the team's bullpen. Click here to read more about what Mike Montgomery will bring to the Cubs [7/20/16]).

Future Outlook: In Rizzo, we trust

Every Cubs fan is probably impressed with what Theo Epstein has been able to do in his four short years as President of Baseball Operations. What makes Epstein so successful is because he trusts his gut. His gut has always told him Anthony Rizzo would be an All-Star some day. From drafting him in 2007 to re-acquiring his services for his new team in Chicago, Epstein has always had faith in Anthony Rizzo becoming a marquee name. If fans trust Epstein (which they should), they should also believe in the player Epstein has gone out of his way to acquire multiple times. After the 26 year-old proved Epstein right by making it to the All-Star game in back-to-back years, fans should be saying “In Rizzo, we trust.”

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Second Base (Present Rank: 18th | Future Rank: 2nd)

With a strong nucleus of young talent already in place, the Cubs knew the only way to acquire impact players without giving up anything in return is through the draft and free agency. Considering players don’t make an impact for 4-5 years after being drafted, Epstein and company pursued the free agency route as a way to acquire a starting second baseman.

There wasn’t a better player on the market than Ben Zobrist. The “Super-Utility Man” was a favorite of Joe Maddons during their time in Tampa Bay together. While they fell short of winning a championship for the Rays, they're both now focused on getting Chicago it’s first ring in over 100 years. Zobrist finally tasted that coveted feeling of winning it all with the Royals last year. His pride in winning that ring after only a half-season in Kansas City would pale in comparison to being a key contributor for a perennial winner like Chicago is constructed to become.

The amount of humans that can swing a bat as fast as Javier Baez are slim to none. His bat speed is what enticed Chicago to select the 23 year-old ninth overall in the 2011 MLB Draft. However, that bat speed doesn’t mean anything if he can’t connect the bat with the ball. His 38.5% strikeout rate is easily the worst in the league over the last two years. Baez has all the tools to be an All-Star caliber player with a rare ability to play all over the infield. If he can improve his contact abilities, there will be nothing stopping Baez from joining Rizzo and Bryant as lethal cogs in the lineup. Joe Maddon just has to figure out a place he can regularly play him with Zobrist, Russell, and Bryant already under team control for at least four more years.

The team could have relied on Tommy La Stella to hold things down at second base, but without an extensive MLB track record or the tools to set himself apart, Epstein invested $56MM to acquire a proven commodity in Zobrist. The 27 year-old La Stella won’t have a starting role on this team anytime soon, but with injuries inevitably taking its toll on the roster, La Stella should find enough opportunities in 2016 to prove he still belongs. If he produces well, the Cubs can include him in a trade for a quality pitcher. If he doesn’t produce well, the Cubs will likely place him on waivers leaving him vulnerable to any team being able to pick him up once he runs out of options. Either way, La Stella is likely on his way out of the windy city now that Zobrist is firmly entrenched on the roster.

Future Outlook: Joe Maddon can play with his favorite toy again

Before Joe Maddon was managing the Cubs, he was a two-time AL Manager of the Year for the Tampa Bay Rays. After adding a NL Manager of the Year plaque to his resume last year, he became just the seventh manager in MLB history to win the prestigious award in both the American League and National League. Maddon has become such a great manager because of his exceptional ability to put players in a position to succeed.

Some players deliver the results expected of them no matter where they’re placed in the lineup or in the field. Ben Zobrist is one of those players. There aren’t many players with the versatility to handle multiple positions defensively. The list of players that can be a solid defender at more than two positions while also being a consistent threat on offense is down to one so it’s not a surprise he’s Joe Maddon’s favorite toy to play with.

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Shortstop (Present Rank: 14th | Future Rank: 6th)

During the team’s rebuilding days in the beginning of the 2010’s, Starlin Castro was the team’s star player. Castro started hot by earning two All-Star nominations right after his rookie season, but ultimately became a disappointment in Chicago by concluding his Cubs career with a .688 OPS over his final three seasons. With two players already capable of taking over Castro’s starting duties at shortstop, the Cubs shipped him off to the Bronx instead of waiting for the 26 year-old to turn things around

The player most likely to take over at shortstop is Addison Russell. The 22 year-old spent the 2015 season splitting reps between second base and short, but with Castro no longer in the picture, Russell can claim shortstop as all his. Russell is yet another great addition under Epstein’s belt as President of the Chicago Cubs. Jeff Samardzija and Jason Hammel were good pitchers for Chicago in 2014, but the potential of Russell and OF Billy McKinney was too much to pass up. Plus the team re-signed Hammel once he reached free agency at the end of that season. As Russell continues to fill out his 6’0” frame, he could become a staple in Chicago’s lineup as a top-5 shortstop in the league.

After Russell and Baez’ recently graduated to the big leagues, one would think Chicago would be thin on shortstop talent in the minor leagues. In reality Chicago isn’t thin on talent at any position in the organization. The Cubs actually have their No. 1 prospect (according to Baseball America) listed as a shortstop. Gleyber Torres has an all-around exceptional profile with a smooth, line drive swing that should help him hit above .300 numerous times in his Major League career. Chicago is being aggressive with the 19 year-old and he’s responded well to the promotions. If he continues on this path, he should be ready for the bigs by 2018.

(EDIT: The Cubs traded Gleyber Torres along with Billy McKinney, Adam Warren, and Rashad Crawford to the New York Yankees for Aroldis Chapman. Click here to see how the package of players will fit in with the Yankes' new youth movement [7/25/16]).

Future Outlook: Two’s company, three’s a crowd

The Cubs have been shuffling between multiple middle infielders for the better part of the last two years. Now that Starlin Castro is out of the equation, that opens up a starting spot for Addison Russell. However, Javier Baez is still left without a starting position now that Ben Zobrist was brought into the organization. As Chicago learned over the past two years, two’s a company, but three’s a crowd. Having two stout middle infielders is great for the team, but possessing a third one creates the problem of having two positions with three players qualified to play. If Gleyber Torres gets called up with all three of these players still in the windy city, all bets are off.

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Third Base (Present Rank: 2nd | Future Rank: 1st)

Taking the league by storm, Kris Bryant powered his way into winning the 2015 National League Rookie of the Year award unanimously. Considering 2015 featured an historically good rookie class, that’s truly incredible. The 24 year-old was Baseball America’s No. 1 prospect heading into the 2015 season and he didn’t disappoint. Controversy surrounding his initial demotion to Triple-A became a non-factor after Bryant forced his way onto the big league roster with a 1.042 OPS over seven minor league games. Now that he’s established himself as a force in Chicago’s lineup, nobody has to worry about him being sent down again. With one of the highest ceilings out of all position players, Bryant’s ‘Rookie of the Year’ award is just the beginning.

Behind Bryant in the organization are two players that could potentially fill a starting role, but will never reach the pinnacle of success Bryant achieved in his rookie season alone. Christian Villanueva should get his chance to play at the big league level this season while Jeimer Candelario could be ready in 2017. Candelario has the higher ceiling of the two and has a realistic chance at being a starting third baseman one day. With Kris Bryant under team control for the next five years, that will likely be for another team.

Future Outlook: Kris Bryant, Most Valuable Player?

It’s difficult to predict a player winning the Most Valuable Player award with so many talented players in the league. While many don't believe Bryant will be MVP candidate so early in his career, the 24 year-old has a legitimate chance of winning the award multiple times in his career. After all, Bryant was the No. 1 prospect in America last year before winning the Rookie of the Year unanimously. Considering the last National League hitter to unanimously receive the same honor (Albert Pujols; 2001) ended up adding three MVP’s to his Hall of Fame resume, Bryant must be feeling good about his odds.

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Outfield (Present Rank: 9th | Future Rank: 5th)

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Adding Ben Zobrist will certainly improve the club in 2016, but the biggest move in Chicago’s offseason was the signing of Jason Heyward to a 8yr/$184MM contract. With a plethora of options to choose from, Heyward took less money to sign with the Cubs because of the young nucleus Theo Epstein was building in Northern Chicago.

Even with viable options in place, the Cubs now have one of the best two-way players in the game manning one of their outfield spots. If Heyward had played in more than 104 games during the 2013 season, he could have been named a Gold Glover in each of the last four seasons. Regardless, he’s an outstanding defensive outfielder with 20-20 potential on offense. He even eclipsed the 20-20 mark in 2011 by belting 27 homers to pair with 21 stolen bases. At only 26 years old, the future is bright for Heyward, and the Cubs alike.

After Heyward was brought in to man one of the outfield positions, it was assumed center field would be his main position in 2016 with Dexter Fowler taking offers on the free agent market. After conflicting reports regarding Fowler’s deal with the Orioles, the 30 year-old decided to return to Chicago on what is essentially a one-year deal worth $13MM. Fowler brings a speedy presence atop the lineup that can also cover all the gaps in Wrigley Field. Fowler’s return can allow Joe Maddon to keep Heyward in his natural position in right field as well. After betting on himself with a one-year “prove it” deal, Fowler could have a career year batting leadoff in the best lineup he’s ever been a part of.

With Heyward in right and Fowler in center, Kyle Schwarber is ready to emerge as one of the league’s top-5 left fielders. Developed as a catcher, Schwarber had just as good of a chance at sticking behind the plate as Bryce Harper did when he was coming up through the ranks. Still, Schwarber’s dynamic bat will benefit from playing everyday in left field as opposed to getting the occasional rest catchers need on a consistent basis. His lack of speed could hurt his overall defensive value, but his offensive potential remains sky-high.

The 2014 fourth overall pick cruised through the minors before unveiling his power stroke in the majors. Schwarber’s 16 homers down the stretch as a rookie would have translated to 38 bombs over a 162-game span. Traditionally, as he gets older he’ll only improve his offensive production. The 24 year-old is yet another young hitter for Chicago with the potential of being a top-5 player at his position.

(EDIT: Kyle Schwarber tore his ACL in the third game of the season, and will miss the entire 2016 season. His future outlook is still bright assuming he makes a full recovery [4/8/16]).

Before Dexter Fowler re-signed with Chicago, it was assumed Jorge Soler would be handed one of the coveted starting jobs in the outfield. Soler is another player in the Cubs’ organization with a top prospect pedigree. The No. 12 prospect in the game had a mediocre rookie season last year. While none of his numbers jump off the page, it’s important to note he was only 23 years old facing major league pitchers in a full-time gig for the first time in his career. Now that he has some experience under his belt, Chicago is hoping Soler’s natural tools will start to kick in, and he can begin to decimate major league pitchers like he did in the minors. Soler must prove he’s worthy of a starting role in 2017 for the team to not go after another free agent, or even bring Fowler back on another short-term deal (if he doesn’t earn himself a multi-year pact elsewhere).

After trading Chris Coghlan away to the Oakland A’s once Spring Training got underway, the team is left without a reserve outfielder capable of playing in case any two of the three starters get injured in 2016. (EDIT: The Cubs re-acquired Chris Coghlan to be the team's reserve outfielder in 2016 [6/9/16]). As long as the Cubs can make it through the 2016 campaign with three of those four players healthy, they should be in good shape with Albert Almora primed to make an impact come Opening Day 2017.

Albert Almora was the first player drafted in the Theo Epstein era in Chicago. He was viewed as an advanced high school hitter that could quickly reach the big leagues. Ironically, both of Epstein’s first round picks after Almora (Bryant, 2013; Schwarber, 2014) are already impact players on the big league roster while Almora is still working on fixing the kinks in his swing. Of course, Bryant and Schwarber were taken out of college with the intention of getting to the bigs in a hurry. The Cubs are being more patient with Almora and for good reason. If they let him completely develop his game, he could become a solid offensive contributor for the club, but his true value lies on the defensive side of the ball where his wheels help him rank as a plus defender.

Later on in 2017, the team could be calling up three of their other premium outfield prospects. Mark Zagunis and Billy McKinney should be in Triple-A by the end of the year while Ian Happ is likely to begin his 2017 season there as well. McKinney and Happ are both former first round picks with the potential of being impact players while Zagunis projects to be more of a low-end starter or fourth outfielder. Donnie Dewees and Matt Szczur could also be formidable fourth outfielders for Chicago in the future with Szczur potentially filling that role this season.

The Cubs front office knew it needed to take a young pitcher with their first round pick, but Epstein has always stuck with “take the best player available” policy, and toolsy outfielders have always found a way to fall right into Chicago’s lap. In Ian Happ’s instance, he was the No. 9 overall pick last year and immediately showcased the kind of hitting, running, and fielding the Cubs were expecting from the 21 year-old. McKinney came over along with Addison Russell in the Jeff Samardzija deal which is proving to look better and better for Chicago everyday. McKinney has a great swing, but lacks the other tools to be an All-Star caliber player. Both players should be above-average starting outfielders once they establish themselves in the majors.

(EDIT: The Cubs have traded Billy McKinney along with Gleyber Torres, Adam Warren, and Rashad Crawford to the New York Yankees for Aroldis Chapman [7/25/16]).

Eloy Jimenez is another name to keep an eye on. The 19 year-old was signed out of the Dominican Republic a couple years ago and is already impressing some executives in the organization. Jimenez’ real test will come as he faces more advanced pitchers. If he can keep hitting successfully in Double-A or Triple-A, the Cubs could have found themselves something special in the strong-armed Jimenez.

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Future Outlook: The rich get richer

The Chicago Cubs have been setting themselves up for one of the best outfield situations in the league, not only in 2016, but for the next 5-10 years. Despite all the homegrown talent in-house, the Cubs inked Jason Heyward to a lucrative 8yr/$184MM contract. With Fowler back and Schwarber a year older, the Cubs have an excellent outfield in 2016. Even though Fowler could depart in a year, the team has Jorge Soler and Albert Almora ready to pick up right where he'll leave off. If neither of them work out, the team also has Ian Happ, Billy McKinney, Mark Zagunis, and Eloy Jimenez in their farm system. The Cubs were wealthy with outfielders before, but adding Heyward to the mix is just another example of the rich getting richer.

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Left-Handed Starting Pitchers (Present Rank: 8th | Future Rank: 22nd)

With an opportunity to end the curse in Chicago, Jon Lester had to say goodbye to the team that drafted him, the same team he won two World Series’ with. Theo Epstein didn’t draft Lester in 2002, but he refused to trade him in various deals once he emerged as a top prospect for the Boston Red Sox. Epstein’s infatuation with Lester helped the Cubs win the bidding war last offseason that culminated in a 6yr/$155MM deal for the now 32 year-old. Lester’s Chicago debut was fantastic as the southpaw finished the season with a 3.32 ERA while adding 207 strikeouts over 205 innings. The Cubs are hoping Lester’s postseason brilliance in 2013 was no fluke, and he can repeat that kind of production as Chicago goes on their own World Series run.

If Jon Lester had not signed with Chicago, the Cubs would have absolutely no lefty in their system capable of being a quality starting pitcher. Bryan Hudson has a chance to be an valuable starter as a third round pick out of last year’s draft. However, the 6’7” lefty is all over the place with his command, and will really have to show improvements this year to get back on track.

Future Outlook: Jon Lester’s one of a kind

Nobody in Chicago’s organization can come close to matching Jon Lester’s production from the left side. While Jake Arrieta may be the best right-handed pitcher in baseball, every scout knows a quality lefty is more rare and valuable. Jon Lester has delivered ace-caliber production for the better part of the last eight years, and it earned him a lucrative $155MM contract. Jon Lester is getting into his 30’s now, but he's showed no signs of slowing down. He is as motivated as ever with a World Series ring being the only thing on his mind.

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Right-Handed Starting Pitchers (Present Rank: 2nd | Future Rank: 21st)

While Jon Lester is one of the league's better left-handed pitchers, Jake Arrieta can argue he’s the best pitcher in the game period. Regardless of Lester’s presence, the Cubs never feel more confident of winning a game than when Arrieta takes the hill. A historically good final two months of the season led to Chicago winning its last 13 games with Arrieta on the hill while also earning him his first Cy Young award in his six-year career. It looked like Arrieta would never reach that pinnacle of success during his tumultuous run with the Baltimore Orioles. Arrieta admits to almost retiring before the Cubs were able to revive his career. Now the 30 year-old looks to put two more dominant campaigns on his resume before hitting the free agent market after the 2017 season with a chance of beating David Price’s record-breaking contract.

With a need for another frontline starter, the Cubs continued their spending spree in the offseason by taking another player away from their division rival in St. Louis. In addition to Jason Heyward (who spent the entire 2015 season with the Cardinals), the Cubs also signed John Lackey away from their biggest competitor in the division. Lackey also has a similarity with Chicago’s other free agent signee Ben Zobrist in the fact that both players contributed to a World Series championship in the last three years. Lackey had his own postseason success as a rookie during the Angels’ World Series run in 2002 and during Boston’s memorable playoff run in 2013. As Lackey gets closer to retirement (37 years old), he’ll hope to add at least one more ring to his collection.

Kyle Hendricks and Jason Hammel complete the rest of the rotation as formidable back-end options. The way both pitchers were acquired might make some fans laugh at just how good Theo Epstein is. Hendricks was included in a deal along with Christian Villanueva (future bench third baseman) from the Texas Rangers for the aging Ryan Dempster in 2012. Dempster pitched 69 awful innings for the Rangers before leaving the Rangers and ultimately retiring after the 2013 season while Hendricks is already a reliable mid-rotation starter while flashing ace-caliber stuff at just 26 years old.  

Meanwhile, Jason Hammel was sent to the A's along with Jeff Samardzija as a rental pitcher in 2014. After Oakland’s meltdown from the best team in the American League to the losers of the Wild-Card game, the Cubs signed both Jon Lester and Jason Hammel away from Billy Beane’s club that effectively ended their careers in Oakland. While the A’s were able to get some value for Samardzija in a separate deal with the White Sox, the Cubs are the clear winners of their 2014 mid-season trade. Now Chicago will benefit from having Hammel and Hendricks in their rotation while Dempster isn’t even in Major League Baseball anymore and Samardzija just signed a $90MM contract to produce similar results Chicago is receiving from Lackey for a fraction of the price.

In the minor leagues, the Cubs have a number of intriguing righties. Duane Underwood stands above the rest as the No. 1 pitching prospect in the organization. His mid-90’s fastball and explosive curveball gives him a high floor. If he can continue developing his changeup, Underwood could reach his ceiling as a mid-rotation starter. The Cubs could see what they have in the 21 year-old as soon as next year as he’s starting this season in Double-A.

Dylan Cease is another pitcher that has the potential to be more than a back-end starter. Cease would have been a first round pick in 2014 if it wasn’t for Tommy John surgery during his senior year in high school. Now Cease has completely revamped his approach with a more smooth, repeatable delivery that has allowed him to significantly improve his command. His arm injuries could get in the way of maxing out his potential, but if he can stay healthy, Cease has the stuff of a No. 3 starter. However, overcoming multiple elbow injuries, a lack of experience, and an ineffective changeup will be easier said than done for the 20 year-old.

Oscar De La Cruz, Ryan Williams, and Jake Stinnett could also make an impact for the Cubs rotation in a few years. De La Cruz has the highest ceiling of the three as a 6’2” 21 year-old with a mid-90’s fastball. Improving his offspeed pitches will be the key to his development. Williams on the other hand already has solid mix of offspeed pitches, but he doesn’t blow it by anyone. While Williams is more of a contact-inducing pitcher, Stinnett has the stuff that could put hitters away. Holding Stinnett back is a significant lack of experience (started pitching as a junior in college) so all of his pitches will likely improve as he gets more experience, but struggling in Single-A ball as a 23 year-old doesn’t bode well for any pitcher’s future outlook.

Pierce Johnson, Trevor Clifton, Jen-Ho Tseng, and Paul Blackburn all have a chance to crack the rotation some day. However, each of them are held back by a lack of command and/or velocity. They could have a shot at sticking around as middle relievers, but Blackburn is really the only one out of the four that could realistically make that work with his solid mix of pitches.

(EDIT: After performing well again in 2016, Chicago traded Paul Blackburn to the Seattle Mariners with Dan Vogelbach for LHP Mike Montgomery and Jordan Pries to solidify the team's bullpen. Click here to read more about what Mike Montgomery will bring to the Cubs [7/20/16]).

Future Outlook: Arrieta’s contract could be one more record he breaks

Last year was a record-breaking year for Jake Arrieta. The 0.41 ERA he owned over his final 12 starts was the lowest ERA in MLB history over the final two months of the season. Arrieta cashed in with the first Cy Young Award of his career. As he approaches free agency in two years, Arrieta is looking to cash in once again.

Chicago could let him walk, but considering the unimpressive group of pitchers in the farm system, the Cubs would be wise to keep Arrieta no matter how expensive he gets. The only reason Epstein would allow Arrieta to wear a different uniform in 2018 would be if Epstein already has a replacement in mind. It might not be Arrieta, but some pitcher will be leading this staff into the 2020’s, and only Hendricks is still young enough for the team to think that future ace is currently on the roster.

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Bullpen (Present Rank: 14th | Future Rank: 26th)


Hector Rondon may not be a household name (yet), but he’s establishing himself as one of the elite closing pitchers in today’s game. Rondon was one of only two pitchers to save at least 20 games while maintaining an ERA below 1.85 (Aroldis Chapman being the other) in 2015. His 59 saves over the last two years highlight his consistency since stepping into the closer role. Chicago will rely on the 28 year-old to shut things down once again in 2016. If he keeps pitching like he has been recently, he could earn a very lucrative contract once he hits free agency after the 2018 season at 30 years old.

Setting up games for Rondon in 2016 will be a job left for Pedro Strop and Travis Wood. Strop was brought over in the Jake Arrieta deal that might end up as one of the most lopsided trades in MLB history. Strop has been an effective high-leverage reliever for Chicago while Arrieta is arguably the best right-handed pitcher in baseball. Wood’s results have been much less consistent, but they’ve mostly been as a starter. Once the Cubs converted the 29 year-old to a relieving role, he owned a 2.95 ERA over 58 innings showcasing his potential in the 'pen.

Trevor Cahill and Justin Grimm are also converted starters that relieve games for Chicago now. Neither pitcher has much experience in a major league bullpen, but the Cubs are more confident in Grimm than Cahill after Grimm’s spectacular 2015 season. Cahill’s fallen off by a large margin since being an All-Star starting pitcher in 2010 as a 22 year-old, but he can still be an effective reliever going forward.

Adam Warren, Neil Ramirez, and Carl Edwards will fill out the rest of the bullpen. Warren was acquired from the Yankees for Starlin Castro over the last offseason. Warren’s role was undefined in 2015 as he was both a starter and a reliever, but he was effective in any situation the Yankees put him in last year. Ramirez and Edwards were both brought over along with Justin Grimm in the Matt Garza trade from 2013. Edwards has closing potential in the future while Ramirez is more of a wild card.

Chicago also has a couple of quality southpaws in their system that could make an impact for their 2017 bullpen. Gerardo Concepcion’s lack of control came into full effect last year as highlighted by an abysmal 8.2 BB/9. However, it’s important to note Concepcion was once a heralded prospect from Cuba, and is still very new to relieving. If he can keep the ball in the zone, he can still be an effective lefty specialist at the next level. Jack Leathersich is the other lefty warranting major league consideration with a great fastball/curve combo. However, Leathersich will miss the entire 2016 season due to Tommy John surgery. If he can find a way to regain his strikeout ability (15.4 K/9 in 2014), the Cubs could have an intimidating presence in their ‘pen throwing from the left side.

(EDIT: The Chicago Cubs have acquired flame-throwing reliever Aroldis Chapman from the New York Yankees for RHP Adam Warren as well as prospects SS Gleyber Torres, OF Billy McKinney, and OF Rashad Crawford. Click here to read more about what the 'Cuban Missile' will bring to the Cubs in 2016 [7/25/16]).

Future Outlook: Get the Cuban Missile locked and loaded

Weaknesses in Chicago’s roster are now few and far between after snapping a five-year losing streak. However, the bullpen could definitely benefit from another arm or two added to help shut things down in high-leverage situations. Hector Rondon has been a terrific closer, and the Cubs will have to seriously consider extending him soon before he reaches free agency after the 2018 season. Besides Rondon, there isn’t anybody on the roster that is a truly elite reliever. Adam Warren was a solid addition, but the Cubs need more.

As proven by the reigning World Champions in Kansas City, a dominant bullpen can be the difference in winning a championship or coming one out away from hoisting the Commissioner's Trophy. If Epstein can acquire a player of Aroldis Chapman’s caliber to pair with Rondon, Chicago would legitimately have no weaknesses in their roster. He certainly has the trade assets to make a deal happen. Expect the Cubs to go all-in on an elite reliever at the trade deadline as Chicago begins their World Series run down the stretch in 2016.

(EDIT: After leading the league in wins for most of the season, the Cubs are going for it all in 2016, and sent a significant package of prospects to New York for the only reliever of Chapman's caliber: Aroldis Chapman. With free agency looming, the Cubs must make sure they didn't give up Torres, McKinney, and Warren for a two-month rental. Signing Chapman to an extension will be a priority for the Cubs' front office once the final out is recorded in the Fall Classic. The Cubs have also acquired Mike Montgomery and Joe Smith to strengthen the relief corps [8/1/16]).

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OVERALL OUTLOOK: Rome wasn’t built in a day

The Boston Red Sox hired Theo Epstein to be their General Manager in 2002 and the rest is history. The team broke the curse of the Bambino in 2004, winning the team’s first championship in 86 years. After adding another World Series to his resume in 2007, the Chicago Cubs offered the Executive of the Decade, Theo Epstein over $18MM to end a curse of their own. Four years later and Epstein has turned Chicago into an offensive juggernaut with a quality pitching staff and positive reinforcements cemented all over the depth chart.

Wrigley Field is now the home to numerous young players with top prospect pedigrees. From acquiring an All-Star first baseman in Anthony Rizzo for a lackluster starting pitcher (Andrew Cashner), to translating Scott Feldman and Steve Clevenger into Pedro Strop and the reigning Cy Young winner Jake Arrieta, it’s clear Epstein has immediately improved Chicago’s roster and gotten them to where they are today. Where they are today is on the brink of something special.

Any Cubs fan is craving just one World Series victory to help forget about the last 100+ years of agony, but as Epstein proved in Boston, the greatest team builder in sports isn’t satisfied with just one World Series victory. The empire he’s building in northern Chicago is poised to become the MLB’s next great dynasty that adds multiple championship banners along the way. Great things come to those who wait and Epstein is reminding Chicago fans that Rome wasn’t built in a day.

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