Cubs: Wheeling, Dealing Means Everything is for Sale

We Are Regal Radio co-founder and former Los Angeles Dodger scouting personnel member Sean Terry breaks down the Cubs momentum out of 2015 and sizes up their ability to capitalize while building a stronger club for 2016. Read part 1 of this post here.

The talk of the second half of the Chicago Cubs’ 2015 season centered on changes made to the middle infield by skipper Joe Maddon and his decision to usurp Starlin Castro from his shortstop position to usher in the supremely skilled hands of Addison Russell to the position.

To Castro’s credit, the move was taken in stride – seen first as a benching, then later deemed a necessary position move that would lead to his resurgence at the plate AND a comfortable new fit in the field at second base.

Following the move, gone were the mental gaffes and flimsy dribblers back to the pitcher that filled his early 2015 campaign, replaced by solid glove work and a stout sample size of 200 at-bats that salvaged his season and confidence.

Castro’s name has been tossed about frequently in prospective trade scenario’s since mid-season last year, with the most recent rumor having him shipped to the New York Yankees in exchange for Brett Gardner, though Mark Feinsand of the New York Daily News most recently has Castro not being in the Yanks’ price range for Gardner.

A trade of this ilk would help the Cubs address a sizeable hole in combination: center field/lead-off batter, as the forgone conclusion at this point is that 2015 signee Dexter Fowler earned himself a huge payday in someone else’s uniform.

The Theo Epstein-led Cubs front office seized on Castro’s early production and projected future worth by resigning him to a very friendly club extension back in 2012 when his numbers were on the same trajectory as Alex Rodriguez in his earlier years. Subsequent years’ saw a slip in production cooling Castro’s value on the open market somewhat, but the fact remains he’s a 1000-plus hit big leaguer with a multi-year $38 million deal still on the books.

Decisions, Decisions

An alternative move up the middle would be to keep Castro comfortably in a Cubs uniform at second base and potentially shop Javier Baez to suiters seeking a young infield with high upside.

Baez is still a bit unrefined at the plate, but his progress at the major league level last year proved two things: firstly, Baez is capable of making adjustments at the plate and consequently capable of reducing his alarming strikeout totals and secondly, Baez is a plus-plus defender whose glove work is good enough to start him at second base, shortstop or third base.

If the Cubs decide to shop Baez, the later point would provide the Cubs with much more flexibility and a greater base of suitors to canvass. Last season’s attempt to turn Baez into an every-day starter folded largely due to Baez’s mid-season injuries, but the fact remains if the Padres were still open to moving young stud hurler Tyson Ross, the Cubs would jump all over such a move.

If The Price Is Right

As it pertains to Cubs expected activity in free agency, the broad assumption is the Cubs will make another huge splash to bolster the rotation. The prevailing notion for a time was that a David Price and Joe Maddon reunion is all but a done deal, though Price staying in Toronto could be what the sought-after pitcher really wants.

Price is on record having spoke fondly of a potential future with the North Siders prior to his mid-season change of address to the land of OVO — and the aforementioned relationship between Price and Maddon does bode well for introductory conversations with the Cubs — the fact remains that free agency is a roller coaster process with no guaranteed results.

Furthermore, while Price is a proven star on the mound, his production over the course of his career (lifetime .650 win-loss% & 3.09 ERA) could be the undoing of this consummation. To put things in perspective, Price’s agent (Bo McKinnis) will likely start negotiations using Max Scherzer’s record breaking seven-year, $210M contract as a baseline.

$30M per year is a ton of money to spend on a starting pitcher with ample miles and modest playoff numbers, so I expect Theo to tread lightly and evaluate all options before diving blindly into the deep end.

Getty Images Jeff Samardzija, once the Cubs ace, could return to the club unexpectedly but at a very opportune time.

Getty Images
Jeff Samardzija, once the Cubs ace, could return to the club unexpectedly but at a very opportune time.

If anything is an indicator of such, this week’s sit down between Cubs brass and former Cub Jeff Samardzija should be enough evidence to temper those Price assumptions just a bit. A return to Wrigley Field by Samardzija would be a moderately priced alternative, allowing the Cubs to roll the dice on acquisition depth over singular star power.

Samardzija pulled a Jimmy Butler back in 2013, passing on a contract extension offer from the Cubs, an event that eventually led the Shark into being flipped Addison Russell with the club’s infamous white flag clearinghouse trade.

The Shark later smelled blood in the water when he ventured to the South Side last year, but his inability to get consistent movement on his fastball and command of his hard sinker led to him having an underwhelming season where he gave up long balls with alarming regularity in hitter-friendly US Cellular Field.

Nonetheless, should he make himself into a Prodigal Son for the Cubs it could become a win-win for both the Cubs and Samardzija, as he pitched the best baseball of his career under the tutelage of Cubs pitching coach, Chris Bosio. A signing of Samardzija would likely be in the range of 4 years for $65M to 5 years for $80M, which if our original spending projections hold true, would put the Cubs in position to add several other serviceable parts as well this offseason.

The list of available free agents runs deep,  probably too deep for us to list in entirety here. I’ll do my best to whittle it down and highlight a few other complimentary names while providing their 2014 splits as reason or not for the Cubs to keep an eye on them.


With a still relatively young infield, the Cubs may look to acquire a veteran utility infielder capable of playing multiple positions and blending in well with the laid-back culture of the Cubs locker room.

  1. Emilio Bonifacio: lifetime .259 hitter and utility glove man with previous ties to the North Side, having played there in 2014 prior to being traded mid-season. Spent the 2015 season with the White Sox. Bonifacio’s ability to mentor for Castro/Baez and Soler could be an X-factor.
  2. Howie Kendrick: lifetime .293 avg./.336 OBP hitter fits the mold of the type approach the Cubs wants to instill in the organization’s philosophy. Prior to last year, Kendrick funneled his way thru the Anaheim Angels organization where a similar brand of baseball was played. Just two seasons ago, he finished in the top 20 in American League MVP voting.


With a defensively challenged Kyle Schwarber and chronically injured Jorge Soler both slated to start at the corner outfield positions, the Cubs will be seeking to acquire a fourth outfielder type with defensive flexibility and proven ability to provide speed and small ball dimension to the Cubs lineup.

  1. Denard Span: lifetime .287 avg/.352 speedster with plus-plus defensive ability. Span was a little banged up last year and spent time in and out the lineup of a dysfunctional Nationals team, he could come cheap and benefit from a fresh start on the North Side.
  2. Austin Jackson: lifetime .273 avg/.333 hitter capable of playing all three outfield positions. Jackson contributed and managed to fit in well with the Cubs in a small sample size during the postseason run last season. A team-friendly deal in a return could be a simple solution for the Cubs.

Starting Pitching:

Whether they sign Price or Samardzija the Cubs will still need more than three starters (Jake Arrieta, Jon Lester + free agent) to get to the World Series next year.

Ultimately, the front office’s confidence in the ability of Jason Hammel to resuscitate his stuff may factor into how many acquisitions the Cubs make; however, general manager Jed Hoyer has spoken of needing depth on the mound so there are a few other names to consider to bolster the back end of the rotation.

  1. Yovani Gallardo: a lifetime .576 win/loss % with a proven ceiling to near 20 wins. Gallardo has been a durable innings eater throughout his career, and has also amassed some solid experience with playoff exposure.
  2. Scott Kazmir: a lifetime .521 win/loss % with a sub 4.00 ERA over an 11 year career. Kazmir has suffered from injuries in recent years, but his earliest and most successful efforts came under the watchful eye of Joe Maddon in Tampa Bay. Perhaps a Rays reunion of lessor magnitude could be just what the doctor ordered, allowing the Cubs to catch lightning in a bottle for a season.
  3. Justin Masterson: a lifetime .464 win/loss % doesn’t jump off the page, but at one point Masterson was a highly touted arm with significant upside. Still relatively young (30), perhaps Masterson can still realize his potential in a Cubs uniform and bring some good karma in the process. Who better than the Kingston, Jamaica native to help the Cubs concoct a ‘lil seasoning for the expected (curried) Billy goat this year.

Follow Regal Radio on Twitter @regalradio1 and on Facebook under Regal Radio; Sean Terry is a co-founder of We Are Regal Radio and host of WARR’s The Varsity Show

4 responses to “Cubs: Wheeling, Dealing Means Everything is for Sale

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