Chicago Cubs: Did last winter cost the team a chance at success?

By most measures all five Chicago Cubs free agent signings from last offseason constituted failures – and the blame lies at the feet of Theo Epstein.

Last offseason, the Chicago Cubs signed free agents Yu Darvish, Brandon Morrow, Tyler Chatwood, Brian Duensing and Chris Gimenez. At the time, these moves seemed solid, with the potential to turn out well. However, all five of those free agent signings turned out to be a disaster – at least in the short-term.

The front office had a lot of work that it needed to do last season. Two-fifths of the starting rotation needed to be replaced or re-signed. For the third year in a row, the closer’s situation needed attention. There was a whole host of decisions to be made with the rest of the bullpen. And a veteran backup catcher was definitely on the shopping list too.

This time around, there are very few moves the front office has to make. In theory, next year’s position players and starting pitching rotation could be composed of players who are already on the Cubs roster.

The likeliest focal point of Theo Epstein and Jed Hoyer? The bullpen. But after a disappointing finish to the 2018 season and Epstein’s end of year press conference where he said that the Cubs needed to shift their focus from talent to production, the Cubs may make more moves than just the ones that have to be made.

Let’s hope the front office learned some lesson’s from the last go-round and gets some better results.

Chicago Cubs: Did the team miss with Yu Darvish?

After the 2017 season, Jake Arrieta and John Lackey hit free agency. Arrieta wanted a lot of money and more years than the Cubs were comfortable giving him. John Lackey appeared to be at the end of a long career.

A lot of experts thought that Alex Cobb would reunite with his old manager and pitching coach in Joe Maddon and Jim Hickey. Reportedly, the Cubs made an early offer which Cobb was willing to accept until his agent jumped in. Cobb ended up signing with the Baltimore Orioles and was part of their terrible season.

More from Cubbies Crib

• Cubs starting pitching has been thriving on the North Side
• Make no mistake: the Cubs are very much about power hitters
• Cubs are giving pitcher Javier Assad a deserved shot
• Cubs: It’s time to start thinking about potential September call-ups
• Cubs: P.J. Higgins deserves to be in the lineup on a daily basis

Due to the strange offseason, Darvish did not get an early big money offer. As the Cubs waited out the free agent market his price began to approach reasonable levels for them. Reportedly there was a last phone call to Arrieta before the Cubs signed Darvish.

Should the Cubs have re-signed the 2015 NL Cy Young winner instead? Well, Arrieta had last year’s strange offseason impact his eventual contract, too. His deal pays him a lot of money, but it has all kinds of options and opt-outs. Arrieta’s crossfire delivery invites control issues. The results of Arrieta’s last two seasons seem to suggest that his Cy Young days are behind him.

However, the right-hander was healthy for the whole 2018 season. The Cubs know Arrieta is a fitness enthusiast without any history of arm injuries. The same can not be said of Darvish. He has already had Tommy John surgery once and was on the disabled list twice this season. The Japanese right-hander only made eight starts for the Cubs in 2018.

It is difficult to predict who will age better: Darvish or Arrieta. Arrieta might be wild, but will Darvish be healthy? It is also difficult to see which one might end up costing their team during the rest of their careers. Will either one of them will pitch well enough that they will want to opt out of their current contracts?

Chicago Cubs: Trying to ‘buy low’ not going so well

The last couple of years, the Cubs have tried to find an undervalued pitcher to be their fifth starter. In 2017, Brett Anderson and Mike Montgomery competed for the job in spring training. This year, the Cubs had several options. Montgomery publicly stated his desire to be a starter. There were some rumors that the Cubs might be interested in Miles Mikolas. Jhoulys Chacin had some interesting upside. All three of them ended up pitching well.

But the Cubs went with Tyler Chatwood. There was a lot to like about his numbers away from Coors Field. Reports noted a lot of nasty movement on his pitches. So Chatwood could have turned out to be a free agent steal.

Instead, he wound up experiencing historic levels of wildness. Clearly he did not work out in 2018. The question now is how do the Cubs pick up the pieces and move on from here. They can’t count on Chatwood to hold a spot in the rotation.

Should they even allow him to hold a roster spot on Opening Day? Do they end up dumping him? If so, the Cubs will have to pay Chatwood $25.5 million over the next two years not to pitch for them. Could they find a team to take a chunk of his contract?

Clearly in 2018 Montgomery, Mikolas or Chacin would have been a better fifth starter. However, if Montgomery began the season in the rotation, who would have filled in when Darvish was injured?

Chicago Cubs: Can the team depend on Brandon Morrow?

During this competitive window and the rebuild that preceded,  there has been more turnover at closer than perhaps any other spot on the roster. Carlos Mármol, Kevin Gregg, José Veras, Hector Rondon, Aroldis Chapman, Wade Davis, Brandon Morrow and Pedro Strop have all been the closer since Theo Epstein took over the front office. And that doesn’t even count Justin Wilson, who was the Detroit Tigers’ closer when the Cubs paid a high price to trade for him.

Last offseason, the Cubs could have spent tens of millions of dollars to re-sign Davis or they could have looked for a more creative approach. Davis was going into his age 32 season. He eventually signed a three-year, $52 million contract with the Colorado Rockies. That marked the highest annual salary ever for a relief pitcher.

The right-hander struggled at times during the 2018 season. His 4.13 ERA was almost twice as high as it had been the year before with the Cubs (2.30). But Davis finished with 43 saves and helped the Rockies defeat the Cubs in the National League Wild Card game.

More from Chicago Cubs News

• Cubs starting pitching has been thriving on the North Side
• Make no mistake: the Cubs are very much about power hitters
• Cubs: It’s time to start thinking about potential September call-ups
• Cubs: P.J. Higgins deserves to be in the lineup on a daily basis
• Cubs might start to limit Justin Steele’s workload soon

Greg Holland was the other proven closer on the free agent market. He had recorded 41 saves and a 3.41 ERA in 2017. However, there were some concerns with his peripheral statistics including a high flyball rate. Holland ended up being one of the victims of last year’s strange offseason. He ended up signing a one-year, $14 million contract after passing on higher offers earlier in the season. Holland also had a disastrous season for the Cardinals

Brandon Morrow appeared to be the perfect solution. He was dominant as Kenley Jansen‘s primary setup man in 2017. Unfortunately the Cubs got to see just how dominate as he gave up no runs and just one hit in 4 2/3  innings while striking out 7 Cubs during last year’s NLCS.

Morrow ended up signing a two-year, $18 million deal with the Cubs. When he pitched, he did what we expected (1.47 ERA, 22 saves). But Morrow, like Darvish, has a history of arm injuries. The Cubs closer went on the disabled list. He only pitched 30 2/3 innings over 35 games this year. And most importantly he wasn’t available for the Cubs down the stretch and during the postseason.

So was it a mistake to sign Morrow? Well, when you sign pitchers with a history of arm injuries you shouldn’t be surprised when they hit the shelf. But the other free agent closers were going to cost a lot more and neither one of them had a great season. Davis’s multi-year contract might be a financial burden in the future.

The Cubs planned on being careful with how they used Morrow. However, between May 29 and June 2, he pitched four times in five days including last three days in a row. Knowing they had perhaps pushed Morrow too far, the Cubs didn’t use him again until June 6.

Unfortunately he gave up two runs that day and only recorded one out. Some people point to that series of days as the place where the Cubs may have used Morrow too much. Perhaps if the Cubs do stick to using him more carefully in 2019, he will both pitch well for them and be available when they need their closer the most.

Chicago Cubs: A mixed bag in offseason bullpen moves

There were a lot of decisions made regarding the bullpen last offseason. The Cubs initially went with Eddie Butler over Justin Grimm on Opening Day. Pedro Strop avoided his final year of arbitration by signing a two-year contract extension.

Hector Rondon was non-tendered and the Cubs signed Steve Cishek as a free agent. Cishek had by far had the best season of all of the free agents the Cubs signed last year. But after the closer, the second-biggest transaction with the bullpen was Brian Duensing.

Duensing signed a two-year, $7 million contract before the 2018 season after a successful 2017 season with the Cubs. His end of year numbers look terrible (ERA 7.65 in 37 2/3 innings). However, Duensing didn’t give up a run in his first 17 games and he only gave up one run through his first 23 appearances.

So Duensing didn’t have a terrible season. He had a terrible injury-filled second half or so. That’s not nearly as bad a story. Duensing may be able to bounce back and be more of the pitcher he was in 2017 and the beginning of 2018.

However, there is a possible warning here. Veteran pitchers who suddenly turn things around might not keep things turned around for long. So when the Cubs are considering re-signing Jesse Chavez and Jorge De la Rosa this winter, they should have some evidence that they can continue to pitch at or near the high level that they did at the end of last season.

Chicago Cubs: Team opted to go with what they knew

Last offseason was more about what they didn’t do than what they did when it came to position players. The Cubs did not re-sign Jon Jay. They did not trade for Manny Machado. Nor did they trade away Addison Russell or any of their other young bats. The Cubs did not sign any big name free agent hitters. However, they did closely follow Lorenzo Cain‘s free agency.

There was a lot of talk about the possibility of the Cubs trading for Machado. At the time a lot of the debate came down to is one year of Machado worth multiple years of inexpensive team control of players such as Russell. If the Cubs had traded for Machado that would have given them the inside track to either sign him to an extension or re-sign him as a free agent now.

What was the right thing to do about Machado is still not clear. However, I am now wondering if the Cubs had enough of a hint about Russell’s off-the-field issues last off season that they should have been working to trade him away. Now, Russell still has to serve 29 games of his 40-game suspension to open 2019.

If they had traded the young infielder away then, the Cubs wouldn’t be faced with the messy decisions they have to deal with now. If not for Machado, maybe they could have traded him for pitching or to restock their depleted farm system. The Pirates didn’t get much for Gerrit Cole.

As for Cain, I think there were two possibilities there. One, the front office was closely monitoring his situation in case his contract situation turned into Dexter Fowler‘s contract from 2016. Two, the front office was going to sign Cain if they traded away a young outfielder or two.

With Epstein’s comments about valuing production over talent perhaps Andrew McCutchen is the Cain of 2018. Of course there is another free agent outfielder you may have heard about.

Last year’s free agents did not help the Cubs in 2018. However, with the exception of Gimenez, all of those free agents signed multi-year contracts and will be back next season. Imagine how much better the Cubs could be in 2019 if those free agents play the way we thought they would when they signed their contracts.

With 2018 being one of the best free agent classes in recent history, the Cubs have a chance to significantly improve upon an already playoff-worthy roster. Hopefully, the front office has learned some lessons from the last off season.