Theo Epstein has served as the Cubs’ President of Baseball Operations for nine offseasons now. With an eye on contending beginning in 2015, the club committed at least $191MM in three of four offseasons. The Cubs were able to avoid paying the luxury tax in 2018, resetting their penalty percentages for 2019. Under the designation of a first-time payor, the club received a $7.6MM luxury tax bill for ’19. For 2020, it appears Cubs ownership under the Ricketts family is again treating the base tax threshold – $208MM for 2020 – as something of a salary cap. Based on the team’s quiet offseason, it appears that the Ricketts aren’t willing to go much beyond that point.

Had the Cubs brushed up against the second surcharge threshold of $248MM, they would have been subject to a tax bill in the neighborhood of $14MM, and could have potentially reset in 2021 with Jon Lester, Jose Quintana, and Tyler Chatwood coming off the books. Given that relatively modest one-time penalty, the question must be asked: is there more at play in the Ricketts’ unwillingness to spend? For example, could ownership’s reluctance to spend be a function of Epstein’s track record in free agency? In other words, can the Cubs’ top exec be trusted with the checkbook?

To answer that question, I’ve assigned a letter grade to each of Epstein’s 15 Cubs free agent signings of $10MM or more. Aside from the grades, this will also provide context on how the Cubs got to their present situation. Note that this analysis omits some effective bargain contracts, such as the Cubs’ 2012 signing of pitcher Scott Feldman. That signing netted the Cubs Jake Arrieta and Pedro Strop in a trade months later, which turned out to be a masterstroke. Still, that’s more a testament to Epstein’s trading ability than a measure of his track record in signing significant free agents.

The Rebuilding Years

David DeJesus – signed on 11/30/11 for two years, $10MM. Grade: B

What we said at the time: Given the lack of offense he provided the Athletics, DeJesus didn’t come at a bargain price for the Cubs. Still, the 32-year-old will be worth the money if he bounces back in his first extended National League exposure.

DeJesus was Epstein’s first free agent signing of his Cubs tenure. This signing worked out fine. At the time, the Cubs were still running out the clock on left fielder Alfonso Soriano’s deal, while they had little to speak of in right or center field. DeJesus wound up leading the team in defensive innings at both of those positions in 2012, and served as a classic second-division regular. In August of the second year of DeJesus’ contract, the Cubs essentially gave him away to the Nationals to avoid paying his remaining $2.5MM.

Edwin Jackson – signed on 12/20/12 for four years, $52MM. Grade: F

What we said at the time: They paid about market value for Jackson, which could net a profit if he improves. The contract will make more sense to me if the Cubs aim to contend in 2014. Otherwise, they won’t get a lot out of the first half of the contract, when Jackson is closest to his prime. A contract of this nature might have been a better move during the 2013-14 offseason, when the team will be presumably closer to winning.

Jackson was Epstein’s first major free agent signing for the Cubs, and at the time the move had a “this money is burning a hole in our pocket” vibe. The Cubs had run parallel pursuits of the second and third-best free agent starters that winter, Jackson and Anibal Sanchez. You probably don’t remember it this way because Sanchez’s deal ended poorly, but his first two seasons of that five-year, $80MM deal with the Tigers were good enough to pay for almost the entire contract.

Jackson’s selling point was taking the ball every fifth day and putting up an ERA around 4.00, perhaps with a little bit of upside to unlock. Cubs GM Jed Hoyer said at the time, “He pitched all of last year at 28 years old, he’s been incredibly durable, had some really excellent seasons during his time in the big leagues, and we actually think his best days are ahead of him.” That position was a reasonable one, although Jackson still seemed unnecessary for a team with two rebuilding seasons ahead of it. More sensible were the Cubs’ smaller rotation depth deals that winter, for Scott Feldman, Scott Baker, and Carlos Villanueva.

Ultimately, Jackson bombed in Chicago, making 58 starts with a 5.58 ERA over the first two seasons. By June of the third year, the righty was released. The lesson, perhaps, was not to spend significant money on non-star free agents.

Carlos Villanueva – signed on 12/20/12 for two years, $10MM. Grade: B

What we said at the time: He’ll be a useful swingman.

Villanueva was indeed able to serve as a useful swingman for the 2013-14 Cubs, providing 20 starts due to a Matt Garza injury and the Feldman, Jeff Samardzija/Jason Hammel trades. But it wasn’t hard to move him back to the bullpen when the Cubs needed a spot for Arrieta.

There’s a gap here, as the Cubs had a quiet 2013-14 offseason. It wasn’t for lack of trying, however, as they made a $120MM bid for Masahiro Tanaka.

Creating a Winner

Jason Hammel – signed on 12/12/14 for two years, $20MM. Grade: B

What we said at the time: Signing Hammel would help them stabilize the middle of their rotation, but presumably would not preclude them from continuing to pursue an ace like Lester. The reported terms make for an attractive price for Chicago.

The Cubs had included Hammel with Samardzija in the trade that netted them Addison Russell from Oakland in the summer of 2014, and then they brought Hammel back as a free agent in December. The team was able to avoid a three-year commitment and add a secondary rotation piece as Epstein made his first real push for contention. Though Hammel failed to make an impact in the playoffs in his time with the Cubs, he provided solid regular season work with a 3.79 ERA across 61 regular season starts.

Jon Lester – signed on 12/13/14 for six years, $155MM. Grade: A

What we said at the time: The lofty $155MM price tag matched expectations, and after years of conserving payroll, the Cubs can certainly afford it. The Cubs need their new ace to be a workhorse, a trait that’s missing from the team’s other projected starters. Any deal of this magnitude and length for a starting pitcher carries a lot of risk, but the Lester signing addressed the team’s biggest need without sacrificing young cornerstone players or a draft pick.

The Cubs put a monumental effort into their pursuit of Lester, convincing him that the team was ready to contend. His signing marked a turning point for the franchise. Lester delivered, especially on the front end of the deal with 9.1 WAR in the first two seasons and 35 2/3 superb, crucial frames in their 2016 postseason run. The Cubs don’t win the World Series without Lester, cementing his status as a franchise legend. Even as Lester transitions into more of a back-rotation arm, he’s continued to provide the Cubs with solid innings, meaning the Cubs will likely get an even-money return on their investment.

The Cubs signed Lester in the 2014-15 offseason, and also pursued free agents Russell Martin and James Shields that winter. After the 2015 club surprisingly reached the NLCS, the Cubs pushed in more chips on their heaviest-spending offseason to date.

John Lackey – signed on 12/4/15 for two years, $32MM. Grade: B

What we said at the time: I thought Lackey would command a three-year deal even at his advanced age and with a qualifying offer attached, so plucking him from the Cardinals on a two-year term was a big win.

After entering the offseason seeking impact starting pitching, the Cubs finished a “distant third” to the Red Sox in the bidding for David Price, according to Epstein. That led him to a much more modest commitment with Lackey. Lackey’s tenure with the Cubs was similar to that of Hammel: good value in his first season with the team, and minimal postseason impact.

Ben Zobrist – signed on 12/8/15 for four years, $56MM. Grade: A

What we said at the time: I was surprised by the Cubs’ plan to move Castro to make room for a second baseman from outside the organization. Instead of plugging Baez in at second base, the Cubs went with veteran Ben Zobrist, who turns 35 in May. Zobrist served as Joe Maddon’s Swiss Army knife for six seasons after establishing himself in the Majors with the Rays. While Zobrist may not be the defensive asset he once was, he’s still an excellent high-contact hitter and potential three-win player. The Cubs should get good value with Zobrist at $14MM a year, despite the riskiness of signing a player through age 38. He’s a clear improvement over Castro, and with the Yankees taking on Castro’s contract, two-thirds of Zobrist’s deal is covered.

Like Lester, Zobrist became an integral part of the Cubs’ 2016 championship team, winning World Series MVP. The distribution of his regular season value to the Cubs was uneven, with two seasons of around 4 WAR and two that were close to zero. Ultimately, Zobrist gave the Cubs much more than $56MM worth of value.

Jason Heyward – signed on 12/11/2015 for eight years, $184MM. Grade: D

What we said at the time: I was surprised to see the Cubs aggressively pursuing Jason Heyward, because right field didn’t seem like a primary need for the club. Nonetheless, they signed the offseason’s best position player to an eight-year deal guaranteeing $184MM. That the Cubs will effectively be signing Heyward away from the Cardinals only sweetens the deal for the club. Including an opt-out clause was a prerequisite to signing Heyward, who was an unusually young free agent at 26 years old. Now that the Cubs have Heyward and this contract, they have to hope he does opt out after 2018, making this a three-year, $78MM deal. If Heyward’s 2018 season is good enough to compel him to opt out (to which Matt Swartz assigns a 50% likelihood), then it likely means the Cubs got more than their money’s worth.

The best available free agent that winter – David Price – matched the Cubs’ desire for an impact starting pitcher. Once Price signed with the Red Sox, the Cubs pivoted to the second-best available free agent in Heyward, much like the Angels signing Anthony Rendon after missing out on Gerrit Cole this winter. The plan was for Heyward to serve as the Cubs’ center fielder, a position he had rarely played in the past but was thought to be able to handle due to his stellar right field defense.

Defense and baserunning made up a large part of Heyward’s value, but he was still a 116 wRC+ hitter over the three previous seasons. Heyward was, in essence, a younger version of Carl Crawford: a low-power corner outfielder known for great defense and baserunning and a decent bat. Crawford, signed by Epstein in Boston five years prior, became an epic bust. Halfway through Heyward’s contract with the Cubs, the results have been similarly disappointing. Heyward has managed to climb his way up to league average offense in the past two seasons, resulting in a pair of 2 WAR campaigns. It’s not nearly enough for a player earning $23MM a year. Barring a return to form, Heyward’s contract could wind up more than $100MM underwater for the Cubs.

A Cubs fan might be inclined to say, “Hey, it’s not my money, and you can’t put a dollar value on the rousing speech Heyward delivered in Cleveland during the rain delay of Game 7 of the World Series.” Those things are true. We can’t know whether Kyle Schwarber, Ben Zobrist, and Miguel Montero would have gotten those hits without the speech or if Carl Edwards and Mike Montgomery would have held onto the lead in the bottom of the inning. But we do know that Heyward has failed to live up to his contract on the field, and that he’s a large part of the payroll crunch that has kept the Cubs from improving the team the past two winters. Long thought to be of interest to the Cubs, Bryce Harper inked a contract with the Phillies with an average annual value only $2MM beyond that of Heyward.

Dexter Fowler – signed on 2/25/16 for one year, $13MM. Grade: A

What we said at the time: Fowler’s talks with the Orioles fell apart when they wouldn’t give him an opt-out clause, and the Cubs swooped in with a low-risk one-year deal. While it’s true the Cubs sacrificed another potential draft pick, Fowler basically fell into their laps.

From a team perspective, when a low-risk free agent opportunity comes along, even after Spring Training starts, the payoff can be huge if you can find a few coins in the couch cushions and snag the player. The Cubs had all but moved on from Fowler, but when he became available for one year and $13MM, they found the money and moved Heyward back to his natural position. The unexpected contract became critical to the Cubs’ 2016 championship, as Fowler put up 4.6 WAR in the regular season and led off Game 7 of the World Series with a home run.

Attempting To Add Pitching

Tyler Chatwood – signed on 12/7/17 for three years, $38MM. Grade: D-

What we said at the time: After coming up short on returning expat Miles Mikolas, the Cubs signed former Rockie Tyler Chatwood to a surprisingly large contract for a pitcher coming off a 4.69 ERA. Now that he’s out of Colorado, Chatwood has several things going for him: his age (28), his ability to induce groundballs, and a fastball approaching 95 miles per hour. Though it was surprising to see Chatwood land at nearly $13MM a year, he’s a solid upside choice to replace Lackey.

The Cubs were unwilling to go beyond $15.5MM for Mikolas – who ended up having a spectacular 2018 season – and instead set the market for Chatwood. You might be noticing a trend here: when Epstein has won the bidding for a youthful free agent the Cubs perceive to have upside – Edwin Jackson, Jason Heyward, and Tyler Chatwood – the contracts have gone terribly. Chatwood’s longstanding problem with the Rockies had been a lack of control, and the Cubs weren’t able to fix that. In fact, in 2018, Chatwood walked nearly 20% of batters faced, by far the worst in the game among those with 100 innings. Chatwood’s contract seems likely to land him the Cubs’ fifth starter job out of camp in 2020. It’s another case of the Ricketts’ recent fiscal conservatism preventing the team from making upgrades – obviously the free agent and trade markets offered better alternatives for the Cubs’ rotation this winter.

Brandon Morrow – signed on 12/10/17 for two years, $21MM. Grade: D-

What we said at the time: While his contract is reasonable, the risk comes in the Cubs’ reliance upon a pitcher with Morrow’s lengthy injury history and heavy 2017 postseason workload. Given the volatility of relievers, the contract itself is no riskier than those given to Wade Davis, Mike Minor, Jake McGee, Bryan Shaw, Tommy Hunter, Juan Nicasio, and others.

In 2017, Morrow emerged from a minor league deal and a long injury history to serve a key role in the Dodgers’ World Series run. Though he may have been burned out pitching 13 2/3 postseason innings, Morrow’s only real blemish was a four-run drubbing in Houston at the hands of George Springer, Alex Bregman, Jose Altuve, and Carlos Correa that cost the Dodgers Game 5 of the World Series. HMMMM.

It wasn’t trash can banging that did Morrow in with the Cubs, however. He made it only to mid-July of the contract’s first season and hasn’t appeared in the Majors since due to injuries, though Morrow is currently healthy and in camp with the Cubs on a minor league deal. To be fair, the 2017-18 offseason is so littered with free agent reliever busts that it’s difficult to say Epstein should have known better and signed, say, Craig Stammen.

Drew Smyly – signed on 12/12/17 for two years, $10MM. Grade: D

What we said at the time: The Cubs quietly made a different free agent signing with a Maddon/Hickey connection, lefty Drew Smyly. Smyly had undergone Tommy John surgery in June of 2017, and was signed with an eye toward the 2019 rotation. If Smyly returns to full health and ability for 2019, the Cubs will have a good kind of problem on their hands in that they’ll have six established starting pitchers under control for that season.

Though it’s only been two years, the Cubs seem far removed from a time when they would throw $10MM at a pitcher in hopes that he could provide depth a full season into the future. Smyly was a luxury and a depth stash, and while he did return to a Major League mound in 2019, it wasn’t for the Cubs. In the first omen of the club’s clamping down on payroll, Smyly was shipped to the Rangers as a pure salary dump so that the Cubs could “afford” Cole Hamels’ club option. That the Cubs unloaded $7MM of Smyly’s contract and he was subsequently terrible for most of 2019 saves this from an F grade, but it’s hard to say whether Epstein got lucky or actually expected the lefty to struggle.

Steve Cishek – signed on 12/14/17 for two years, $13MM. Grade: B

What we said at the time: Cishek, 31, has had a few ups and downs at times in recent years and has played with four organizations in the past three seasons. For the most part, though, he has continued to function as a quality setup option. The sidearming Cishek will offer a different look out of a re-worked Cubs pen.

It’s hard to complain about the results the Cubs got out of Cishek, who posted a 2.55 ERA across 134 1/3 innings in his two seasons. Though he was generous with free passes, hitters generally couldn’t square him up.

Yu Darvish – signed on 2/10/18 for six years, $126MM. Grade: C

What we said at the time: Darvish’s $21MM average annual value was surprisingly low. Like other big market teams, the Cubs are intent on staying below the $197MM competitive balance tax threshold, and the sixth year given to Darvish helped accomplish that. With Darvish in the fold alongside Jon Lester, Jose Quintana, Kyle Hendricks and Tyler Chatwood, the reigning NL Central champs will have one of the more complete (and formidable) rotations in all of baseball.

Darvish’s debut season with the Cubs in 2018 was a disaster, as he made only eight starts due to injuries. At that point, his contract looked like quite the albatross. Even as late as July 3rd of the 2019 season, the righty’s ERA sat at 5.01. Then, he reeled off a 13-start run with a 2.76 ERA, 118 strikeouts, and a mere seven walks in 81 2/3 innings. A pitcher who had exhibited lousy control for the Cubs suddenly had the best control in baseball. Darvish’s turnaround and the potential for strong work in the final four years of his contract means this contract could become a win for the Cubs. Of course, Darvish is 33 now, so it could easily go south as well.

Craig Kimbrel – signed on 6/5/19 for three years, $43MM. Grade: F

What we said at the time: With a career 1.91 ERA, 14.7 K/9, and 4.23 K/BB rate over nine seasons and 532 2/3 career innings, Kimbrel’s resume could very well eventually land him in Cooperstown down the road. While 2018 wasn’t as dominant as some of his past years, Kimbrel still seemed to have a viable platform year with a 2.74 ERA, 13.86 K/9, and 3.10 K/BB over 62 1/3 frames for the World Series-champion Red Sox. Beyond the surface numbers, however, there were some red flags. It was hard to ignore Kimbrel’s increased struggles in the second half of last season, and then through Boston’s playoff run.

It could be a win-win situation for Chicago, as the team looks to both avoid the top tax threshold while also getting a closer to bolster a bullpen that has generally been around the middle of the pack this season. The looming question could concern Kimbrel’s effectiveness, as other players whose qualifying offer-induced long waits in free agency (Stephen Drew and Kendrys Morales in 2014) both struggled badly after sitting out months of the season.

That concern from MLBTR’s Mark Polishuk proved prescient, as Kimbrel posted a 6.53 ERA while allowing nine home runs, more than a hit per inning, and a 12.5 BB% in his 20 2/3 innings. Kimbrel has two more seasons with the Cubs to turn the contract around, with the possibility of an additional season vesting. You can see how one bad signing begat another. Morrow was unable to serve as the team’s closer in 2019 as planned, pushing the Cubs to use the money they saved from Ben Zobrist’s leave of absence on Kimbrel. Now, due to Kimbrel’s presence and contract, the biggest addition to a questionable bullpen this winter was Jeremy Jeffress.

Of these 15 free agent contracts, Darvish, Heyward, Lester, Kimbrel, and Chatwood remain on the books for 2020. For luxury tax purposes, that’s just under $97MM. Epstein was able to win a World Series in Chicago in part due to free agent contracts for Lester, Zobrist, Fowler, and Lackey, but missteps on other players have led to the Ricketts family turning off the spigot – perhaps even at the expense of contention.