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Free Agency, Trade, or Both: Nobody Pitches for Free—Assessing the Cubs’ Pitching Situation

“Regarding our starting pitching, the topic sentence is: we would like to add more quality pitching.”

—Theo Epstein (October 22, 2015)

There are four guarantees in life: death, taxes, people overusing “death and taxes” to make their points, and the need for starting pitching depth.

No matter the era, teams—especially contending teams—crave starting pitching. In the 1940s, columnists wrote poems about pitching depth, or lack thereof (e.g. “Spahn, Sain, and pray for rain”).

In 2003, Sports Illustrated splashed it across the cover:


So when Theo Epstein kicked off his end-of-season press conference with that “topic sentence,” it should not have come as a surprise. Like all major-league teams, the Cubs covet starting pitching. Unlike most major-league teams, though, the Cubs are (a) a legitimate World Series contender, and (b) dealing from a position of strength. Be it their cash flow or plethora of young, desirable bats, the team can play out the offseason just about any way they want. And Epstein’s history suggests that anything and everything is on the table, from small, low-cost moves, to opening the wallet for one of the big names in free agency.

A Pitcher’s Guide to Theo’s Galaxy

Before we delve into the Cubs pitching needs, let’s briefly consider a few moments in the history Epstein and Jed Hoyer. Following the 2004 season, baseball’s two biggest free-agent pitching prizes were Pedro Martinez and Derek Lowe—both of whom had just excelled in the postseason for the World Champion Boston Red Sox. However, both were over 30 and looking for deals of at least four years. The Red Sox elected not to pursue either, and spent a fraction of the resources those two pitchers would have commanded on Matt Clement, Wade Miller, and David Wells. How’d it turn out? Well, while Clement and Wells had decent seasons, and the Red Sox reached the postseason again, it was not on the strength of their starting pitching.

Now, the 2005 Red Sox and 2016 Cubs are not perfect comparisons. Coming off their World Series title, the Red Sox had the luxury of not feeling too pressured to invest heavily in frontline (but aging) starting pitchers. They were also waiting on the development of homegrown talent in Jon Lester, Jonathan Papelbon, and Clay Buchholz.

Like the Cubs, though, the Red Sox still possessed an explosive offensive core that had them in “win-now” mode, and virtually unlimited resources to devote to their starting pitching—and they chose to go with short-term deals. I’m not here to judge Epstein’s methodology, merely to point out that when addressing his team’s pitching needs, Epstein (and Hoyer) have a record of passing on long-term commitments to pitchers on the other side of 30.

In fact, other than signing Daisuke Matsuzaka in 2007 and John Lackey in 2009, most of the Epstein regime’s starting pitching acquisitions in Boston came via trade (Curt Schilling, Josh Beckett, Andrew Miller), short-term signings (John Burkett and Brad Penny), or waivers (Bronson Arroyo).

However, Matsuzaka (27) and Lackey (31) were both responses to Red Sox teams whose lack of pitching depth the previous season were either exposed in the postseason (in Lackey’s case), or was so poor they did not reach the postseason (in Matsuzaka’s). When the team fell short in 2002, Theo tried to go all-in on Cuban stud Jose Contreras to place alongside Pedro and Lowe, who had finished first and second in the ERA in the AL that year. Schilling’s arrival in Boston after the 2003 ALCS created an unprecedented fervor among the team and fanbase that mirrors the Cubs’ current situation.

So often, Epstein has favored short-term investments or trades. There is a track record, however, of going all-in (or at least attempting to do so) on aces in response to how the previous season ended. Like I said, with Epstein, anything is possible. Now, with the history lesson complete, let’s turn our attention 2015, 2016, and beyond. 

Where The Cubs Were In 2015

“The last data is always sort of the freshest in people’s minds. Sometimes coming out of the playoffs, you lose the bigger picture of the whole season. We were third in ERA as a starting staff. We were third in ERA as a pitching staff. If you want to get all nerdy and all geeky on it, we we first in FIP and first in WAR.”

On paper, the Cubs seem to have little to improve on from 2015. Their starters ranked at or near the top of the National League in most statistical categories:

Statistic NL Rank
Innings Pitched 6th
ERA 3rd
FIP 1st
DRA 2nd
WHIP 1st
K% 1st
BB% 3rd
GB% 6th

That’s an impressive record, and the Cubs’ top three starters will all return in 2016. However, despite the rotation’s stellar numbers, a closer examination reveals a team which, if it is to be a true World Series contender, has work to do.

By any measure, Jake Arrieta’s 2015 season was the best by a Cubs pitcher in a quarter-century, and must be included in the conversation of the team’s best seasons of the last century. His second half  (0.75 ERA and 0.72 WHIP) ranks among the greatest in baseball history. Arrieta will be 30 next season, but appears to be in the prime of his career. That said, counting on Arrieta to replicate his historic numbers is foolhardy, especially a season after he threw more pitches than anybody in baseball.

As we covered in Jon Lester’s end-of-season player profile, he showed little sign of regression in 2015, aside from a slight drop in velocity. The fact remains, however, he will play next season at 32, and eight consecutive regular seasons of at least 191 2/3 innings pitched (along with 14 postseason starts) for a pitcher who throws 80 percent fastballs will eventually show in wear and tear.

This is not to denigrate Arrieta and Lester. The Cubs still have a formidable a 1-2 combination at the top of their rotation that would be the envy of most teams. But given their age and high-level performances in 2015, some regression is to be expected.

Kyle Hendricks, 26, had a solid breakout season, and seems like a prototypical number three or four starter on a contending team.

Jason Hammel, 33, remains a wild card. In the second half, his strikeout to walk ratio decreased by nearly half and batters posted a .230 ISO against him. His fastballs, long used to set up his slider, imploded from the All-Star break through the postseason. Batters slugged .625 against his fourseamer and .894 against his sinker. If he’s here in 2016, it figures to be as a fifth starter or long-man out of the bullpen.

Dan Haren has retired, and did so with a typically perfect Tweet:

While he may provide some depth to the staff, Travis Wood was a revelation out of the bullpen in both the regular season (2.95 ERA and 2.53 FIP) and postseason (0.91 WHIP and 41.3 percent strikeout rate). Wood’s newfound versatility as a long reliever and spot starter made him an invaluable piece, but relying on him as a part of the rotation certainly isn’t something this front office is planning upon.

Wood’s fellow relievers Trevor Cahill, Tommy Hunter, Jason Motte, Clayton Richard, and Fernando Rodney are all free agents. Some will be bid adieu without so much as a second thought, but some will leave a sizable void.

The 2015 staff was phenomenal, and the Cubs will bring back their no. 1 and 1A starters, a young, promising no. 3 starter, and a dominant closer (in Hector Rondon). Beyond that, though, there are questions about both quality and quantity. As the Kansas City Royals demonstrated this season, or the Red Sox in 2013, it’s not always necessarily a top-heavy staff that wins in October, but rather a deep and flexible staff. So, who will the Cubs pursue this offseason?

The Big Names

Alright, you didn’t come here for the monologue or to watch lip-sync battles. You want to hear about the A-list star and their new movie.

On Tuesday morning, less than 36 hours after the end of the World Series, ESPN’s Tim Kurkjian predicted that the Cubs would end up with either David Price, Johnny Cueto, Jordan Zimmermann, or Zack Greinke—in other words, one of the big four free-agent arms. There seems to be a prevailing notion across baseball that the Cubs, flush with cash and a young, low-cost offensive core, will go all-in on one of those big four.

By now, you know their respective resumes and makeup.

Price’s 2015 velocity with his four-seam and sinker—the pitches he goes to with more than 50 percent frequency—were his highest since 2012. Cueto just hurled a few postseason masterpieces. Greinke just completed one of the great seasons in baseball history. Zimmermann, the least-heralded of the group, has a lower WHIP than Gerrit Cole, Sonny Gray, and Justin Verlander since 2011, and a better FIP than Arrieta, Lester, and Chris Archer.

You can probably also guess their price tags: five to seven seasons, and $25-30 million per season.

You might also know that Price (30), Cueto (30), Zimmerman (30), and Greinke (32) will all be at least 30 next season. As can be expected for stud pitchers at their ages, there are a lot innings on those arms. Since the start of 2009, Greinke ranks seventh in innings pitched and Price ranks ninth. The Cubs already employ both Lester (sixth in innings pitched since 2009) and Arrieta (more pitches thrown than any pitcher in baseball since the start of 2014). For the money it’ll take, would the front office really add another arm with so many miles on it?

As our own Rian Watt wrote last week, “it would be extremely out of character for this front office to lock up, for a half-decade or more, $50 million a year in the fragile arms of just two starting pitchers, both of whom would be playing the entirety of their contracts after age 30.” 

As we detailed above, though, Theo and his front offices have been known to go out of character on occasion.

Make no mistake, the Cubs can afford any one of the big arms. But should they? With Arrieta and Lester at their peak, or at least in the vicinity of their peak, a compelling case can be made to go for it this offseason. That is, sign one of the elite pitchers, hope you win the whole thing the next two seasons with your trio of aces, and worry about the future when it arrives. That’s unlikely, but certainly possible. Which leads me to the next Epstein quote:

“We’re going to trust ourselves to build effective pitching staffs each year.”

Take those words as you want to, but the mention of building each year has me believing the Cubs are thinking of some short-term investments this year. With that, we look at the other free agents:

John Lackey: Lackey is 37, but since sitting out all of 2012 after Tommy John surgery, he’s quietly been among the best right-handed pitchers in baseball. In the past three seasons, he’s posted very good numbers: 202 innings pitched per season, 3.35 ERA, 3.73 FIP, 5.6 percent walk rate, and a 46 percent groundball rate. Lackey’s velocity with his four-seam and sinker has also increased since the surgery, and he’s throwing harder now than he was at age 30.

He is also a consummate big-game pitcher, posting a 3.11 ERA in 23 postseason appearances, and he dominated the Cubs in Game One of the NLDS before being forced back on short rest in Game Four. In short, Lackey is showing no signs of slowing down, and ranked among the NL’s top five in fewest pitches per inning and fewest pitches per plate appearance. The Cubs should feel comfortable (and in fact excited) to go for two years with Lackey, but will another team come along with three years, or even four?

Ian Kennedy: Maybe it’s just me, but I’m amazed Ian Kennedy will be playing next season at just 31. I would have guessed he was 33, 34, or 35, easily. Kennedy would be the ultimate low-risk, high-reward investment on a one-year deal. There are some intriguing peripherals (for example, a 24.4 percent strikeout rate since the start of 2014), but he has not posted a DRA below 4.24 since 2011, and despite pitching his home games at Petco Park, surrendered 31 home runs last season. Kennedy feels more like the Cubs third- or fourth-choice acquisition. 

The Groundball Guys

If the Cubs staff had a weakness in 2015, it was with power at Wrigley Field. Among NL staffs at home, Cubs pitchers surrendered the eighth-most home runs and owned the sixth-highest home run to fly ball ratio. This offseason, the market just happens to be rich in pitchers who keep the ball on the ground. Lackey fits the bill, but who else does?

Brett Anderson, aside from being one of the game’s best Twitter followsis perhaps the most intriguing option at the back of the rotation. His second-half struggles (1.382 WHIP and .768 OPS) masked a solid season overall (3.69 ERA and 4.34 DRA), which included his major-league best 67 percent groundball rate. 

Anderson fits the profile of a free-agent pitcher who would interest the Cubs and their desire for flexibility. He is young (28), produces groundballs at a remarkable rate, and has some peripherals (17.8 percent strikeout rate and 1.298 WHIP) that could cause him to fly under the radar. This means Anderson could possibly be available on a one-year or two-year deal, shine for a contending Cubs team, and hit the market again at age 29 or 30. 

Doug Fister: Which Fister is hitting the free-agent market? Is it the pitcher who from 2011-2014 posted a 3.11 ERA and 1.163 WHIP, with a DRA of 3.89 or better each season? Or is it the player who posted a 6.12 DRA and became a one-pitch pitcher for much of 2015? Always known for his sinker, Fister, 32, has become even more reliant on the pitch of late, going to it 63 percent of the time in 2015. Since 2013, he’s lost nearly four miles per hour (from 90 to 86 mph) and his groundball rate has dropped 10 percentage points (54 to 44). If he’s somewhere in between the two extremes, Fister could provide great depth, but due to age he might be a risk at more than one year.

Available via Trade, but at What Cost?

“We may be forced into a situation where the right move is to take away somewhat from that position player group in order to add impact pitching.“

Carlos Carrasco: Theo and company did not come out and explicitly say Carrasco is that impact pitching, but damn if he’s not an ideal fit. First off, would Cleveland consider trading a 29-year -old righty who posted a 2.84 FIP and a 1.073 WHIP in 2015? Carrasco is under Indians control through 2020, on a team-friendly deal that maxes out at about $37 million. Any one of the big four free agent arms will likely earn that in 1.5 seasons or so in their new deals.

However, Cleveland ranked in the bottom five in the AL in runs scored, home runs, slugging percentage, and ISO. The team desperately needs an impact bat, and it being the Indians, they would likely prefer a young and cost-controlled talent. They sure seem like the perfect trade target for the Cubs.

Tyson Ross: Since the start of 2013, the Padres’ 29-year-old right hander has had the second-best groundball rate among starting pitchers (another groundball guy!), while ranking 15th in strikeout rate,  and 18th in ERA and FIP. The Padres control Ross through 2017, but last winter, Padres General Manager A.J. Peller showed a willingness to make big trades. One of the subjects of those big moves—Justin Upton—is now a free agent, leaving a significant hole in a lineup that already ranked in the bottom five of most offensive categories. Are Jorge Soler or Javier Baez worth Ross in his age-29 and 30 seasons?  

Julio Teheran: Teheran, like Carrasco, is on a team-friendly deal through 2020 (about $41 million over next five seasons). He is, however, only 25, and has posted a 3.85 FIP and 1.184 in three big-league seasons to date. Despite Teheran being young, cheap, and effective, the Atlanta Braves offense is a mess, and the team is nowhere near contending. If the Cubs coming calling with their young sluggers, you would think the Braves would listen.

Who You Got?

The prospect of adding Price, or Cueto, or Greinke, or Zimmerman to a team that won 97 games and reached the NLCS is tantalizing. However, would they commit five to seven years and up to a quarter million dollars on a pitcher over 30, a year after committing six years and $155 million to Lester?

A step or two down, there are a group of veteran starters who keep the ball on the ground, or possess great strikeout numbers, and could very easily be had for one or two seasons.

Meanwhile, Atlanta, Cleveland, and San Diego all need young, inexpensive bats, and have outstanding, low-cost arms under control for the next two to five seasons.

In Boston, Epstein had a history of augmenting great offenses and his frontline starter(s) with short, low-money veterans. However, he also had a tendency to make a splash with big-name pitchers from time to time.  Which philosophy will he ascribe to this offseason?

Now, I’m not suggesting that this is an “either/or” situation. That is, perhaps the Cubs will push their chips into the middle and sign an elite pitcher, while also signing a second-tier veteran for short-money, and trading one of their stud hitters for a cheap, talented young pitcher. The Cubs front office has few limitations this offseason,  and Epstein has shown a willingness to go down every avenue to acquire pitching for contending teams. How it all unfolds remains a mystery, but damn if it won’t be fascinating to watch.

Lead photo courtesy Denny Medley—USA Today Sports.

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13 comments on “Free Agency, Trade, or Both: Nobody Pitches for Free—Assessing the Cubs’ Pitching Situation”


Great read. Love the Theo quotations and then the reading of the tea leaves. I am in the trade for a pitcher camp. Taking a chance on one free agent high priced pitcher (Lester) is probably the most ownership/management can stomach. I don’t think tying up 300-350 million dollars on two arms is a rational strategy. I think (and hope) they move players for one or more pitchers.

Andrew Felper

Thanks! Personally, I don’t they will sign any of the big pitchers. A trade and a two-year deal for a mid-level vet seems more likely. It maintains flexibility. However, I can’t help but think Theo’s history dictates a big deal is in the work – be it a signing or trade.


That being said- if Kenta Maeda is posted, I think the Cubs will do everything they can to sign him. His age (27) and projection might put his contract in the 80-100 million range-something I think the Cubs would happily pay.

Andrew Felper

It would be fascinating if he’s posted. It reminds me a bit of why the Yankees original Sabathia deal made so much sense.

Michael Mahon

This has been easily my biggest fear since the season ended. Dumping over $200 million into over 30 pitchers. I’ve been praying Theo plays it smart and signs a Kennedy or Gallardo and maybe does a similar trade and extension for maybe Strausburg. What are the odds on a move like that?

Andrew Felper

Kennedy has great strikeout numbers, but there’s tough to find much else to like at this point. It’s difficult to imagine the Nationals, w/ a new manager and pitching coach, trading Strausburg. I think Lackey and a young guy under control on a team in need of hitting would be my preference. But again, they can afford Price, and there’s worth things than having him in his ages 30-32 seasons with Arrieta and Lester. It’s going to be so fascinating to watch how this plays out.


“… up to a quarter million dollars.” I know this is insane, but this should read billion and not million.

allan birmantas

The problem is the fact that the Cubs have only a #1, a #2 and a #5 on their staff. They need two dependable pitchers to be their #3 and #4. I would suggest that they pass on the “star” types. and concentrate on the second tier, affordable ones which are available. Lackey on a two year contract especially intrigues me.

Andrew Felper

I think Hendricks could be a #4 a World Series team, but I don’t want to split hairs. I agree they need two starters this offseason. I think they could do both, let’s say, Price and Lackey, or Price and Ross, or Anderson/Lackey and Ross/Carrassco. I am so eager to see if their abundance of resources means they will go in on Price for those first three years, like the Yankees did with Sabathia. I agree with you on Lackey.


I’m glad you pointed out just how strong our pitching was this year–no one wins 97 games with a sub-par pitching effort. That being said, it absolutely was anomalous…It seems to me that Zimmerman is as high as we should go with a contract and I really hope we go with the “depth” approach. A trade is probably necessary too. We may have to compromise the luxury of “positional redundancy” for more pitching redundancy. Soler/Castro/Baez (all players I dread trading) have to be on the table to obtain the services of Ross/kimbrel/tehran/carrasco/etc. I personally really like the idea of carlos carrasco, signing either lackey/leake/gallardo, at least one more strong bullpen arm, and locking down a centerfielder with plus defensive coverage if schwarber is going to be in left

Andrew Felper

Thanks for reading! I think you hit the nail on the head with the ideal offseason plan. I keep thinking of the ’04 Red Sox who brought in Schilling (trade), Arroyo (waivers), and Foulke (free agent) to join Pedro, Lowe, Wakefield, Timlin, and Embree. They used multiple approaches to provide depth. I expect Theo & Jed to be very creative and unsentimental about trading positional depth, as their window with Arrieta & Lester at their peak might never be more open.

Zack Moser

I’ve been beating the drum of positional and lineup flexibility, —if not quite “redundancy”—and I think it’s possible (and preferrable) that, if the FO is to trade for pitching, then they fill the gap on the offensive side with a player who offers plus D and multi-positional possibilities.

I.E. Soler-plus for Carrasco, Zobrist/Heyward to lead off and play OF, etc. Maintains the team’s versatility advantage while adding offense, defense, and pitching, at a similar or lower cost than signing one of the Big Four pitching FAs.


On the major league side, I wonder if Wei-Yin Chen might be a reasonable fit at 4/56 or so. I’m also curious whom they they might target to populate the upper minors with some depth – it will be a good challenge for Jason Parks and the rest of a talented scouting staff.

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