No matter what the Cubs do this Hot Stove season, last winter's failures hang over their heads like a dark cloud.
If the Cubs truly aren't able to afford the top free agents on the open market this offseason, the main reason for that is because they've had to spend so much money in free agency on pitching the last few years. It's also because they swung and missed in a major way last winter and are still feeling the effects.
The Cubs entered last winter feeling pretty good about the state of their offense but wanted to augment the pitching staff in a big way. So they went out and handed $198 million to Tyler Chatwood ($38 million), Brandon Morrow ($21 million), Steve Cishek ($13 million) and Yu Darvish ($126 million). They also paid Drew Smyly $3 million in 2018 to rehab from Tommy John surgery before he and the $7 million remaining on his deal were shipped off to the Texas Rangers last month.
The four free agent pitchers (not including Smyly, who didn't throw a single pitch) combined for 1.1 WAR (FanGraphs) across 244.2 innings in 2018.
Jesse Chavez posted a 1.0 WAR for the 2018 Cubs in 39 innings.
The Cubs paid Chavez roughly $400,000.
They paid the other four pitchers $54 million.
Of course, it's rather unfair to include Cishek in that bunch, as he was the MVP of the Cubs bullpen for the first five months of the year before a late-season fade. And Morrow was fantastic when healthy (22-of-24 in save chances, 1.47 ERA, 1.08 WHIP), though he didn't throw a pitch after the All-Star Game and came to the Cubs with a long history of injury issues.
Darvish was supposed to be the guy that put the Cubs rotation over the top and Chatwood was the under-the-radar arm the organization hoped would take a step forward getting away from Coors Field. Both guys were out of the rotation by Aug. 1.
"I think incomplete would be probably the kindest thing I could say [about last winter's moves]," Theo Epstein said, emphasizing that he meant the Cubs front office should get the "incomplete" grade, not the players. "There are a lot of talented players here that we didn't get off to great starts with in their times as Cubs. But we're digging in and working really hard - as are the players - to try and turn that around.
"...Our offseason moves should not be evaluated well at all and the in-season moves were pretty darn good. We're gonna have to try to have a much better offseason this time."
The Cubs already translated the in-season moves to the offseason, opting to bring Cole Hamels back on a $20 million option.
With Darvish's health and Chatwood's control major question marks, picking up Hamels' option became a no-brainer for the Cubs - even at that lofty price tag during a time where every penny is important.
Chatwood's contract is unmovable but he's still not even 29, so there's a chance for a rebound; it's just that the Cubs can't bank on it.
Darvish is the bigger question mark, as he wasn't very good even when he was able to take the ball - 4.95 ERA, 1.43 WHIP, fifth-inning meltdowns that became a major storyline and accounted for only 0.2 WAR in 40 innings. To put that in context - Darvish was just as valuable to the 2018 Cubs as Anthony Bass and James Norwood, who each notched 0.2 WAR despite only 15.1 and 11 innings pitched, respectively.
Now that Darvish's triceps/elbow is cleaned up, can he get back to being the pitcher he was before signing the megadeal with the Cubs?
The Cubs hope so, but that's really all they can do - hope.
"I think he's in a good place mentally to go forward next year," GM Jed Hoyer said. "First year for free agents, there are a lot of pitfalls. Hopefully post-surgery, he comes back and he's ready to go for spring training."
The Cubs couldn't move Darvish's contract even if they wanted to, so instead of going out and adding to the bullpen or signing another big hitter this winter, they may be left with making a bunch of smaller moves and praying Darvish can get back on the right track.
Then there's the whole coaching aspect of last winter. The Cubs hired new hitting coaches (Chili Davis, Andy Haines) and a new pitching coach (Jim Hickey) shortly after the 2017 season ended. Those three are all out of their post, with only Haines leaving because he took a promotion with the Milwaukee Brewers.
That's a lot of shake-up on a coaching staff when Epstein stressed the importance of continuity the day after the Cubs season ended. And there could be more unrest with manager Joe Maddon heading into the final year of his contract.
The Cubs championship window is still open, but who knows for how much longer. There's an urgency from the fanbase to go out and add to a team that finished the 2018 regular season tied for the NL lead in victories.
But last winter is a cautionary tale about the major pitfalls that come with free agency and the Cubs can't afford any more misses this winter.