Chicago Cubs: Which free agent signing will they regret?

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For every Andre Dawson, there’s a Todd Hundley. For each Moises Alou, there’s a Milton Bradley. For each free agent gem that the Chicago Cubs sign, they have a signing that doesn’t work out so great due to under-performance by the player, over-payment on contract, or just a bad fit for the team.

The Cubs went on a bit of spending spree this off-season, paying out fairly large contracts to Jason Heyward, Ben Zobrist and John Lackey. The Laws of Cubbie-dom suggest that at least one of these signings will not work out as hoped. This is not to suggest that we’re hoping any one of these guys fail–it would be wonderful if all three enjoyed career years. But, history suggests that someone will disappoint.

Who?

Perhaps we can compare each one to similar past signings to forecast which free agent signing the Cubs might regret.

Next: The utility guys

Credit: Anthony Gruppuso-USA TODAY Sports /

Baseball-reference.com offers a cool tool called a “Similarity Score”, a concept they lifted from Bill James. Particularly helpful for suggesting the value of our free agents is the “Age Based Similarity Score”. Essentially, it shows us who has posted similar numbers to a player up this time in their careers, and we can then look at those players’ subsequent seasons as predictors for a free agent’s future performance.

The Cubs handed utility man Ben Zobrist a four-year, $56 million deal in December. For 2016, they’ll pay Zobrist just over $10 million (according the baseball-reference.com). Position players being paid similarly in 2016 are James Loney, Edwin Encarnacion, Martin Prado and Nick Markakis (as reported by sportrac.com). That suggests the Cubs are getting good value for Zobrist, who is certainly capable of putting numbers competitive with Prado, Loney and Markakis–though we should not expect him to play up to Encarnacion’s levels, at least offensively.

Now if we look at Zobrist’s Similarity Scores, we see that his career, up to this point, has been most similar to former Cub Bill Mueller and a couple of former Yankees in Hector Lopez and Aaron Boone. This isn’t good news if we use Similarity Score for future predictions. Zobrist will play most of the season at age 35. Mueller only had 126 plate appearances after turning 35. Lopez had a little more than 400 plate appearances. And Boone had only 269. The model doesn’t bode well for Zobrist’s longevity. But who can really predict the future health of a player?

The last time the Cubs spent some serious money on a utility-type player may have been back in 2004 when they signed Todd Walker. Walker did just what the Cubs expected him to do: provide them with a bit of pop offensively while being able to play all over the diamond. Walkers OPS while with the Cubs was over .820 while he played first base, third base, second base and left field.

As long as our expectations are kept in perspective of other player’s in Zobrist’s pay scale and what he was signed to do (provide a bit of pop from several different defensive positions), we should feel OK with the Zobrist signing–assuming he can stay healthy.

Next: The aging aces

It wasn’t so long ago that the Cubs gave a contract to an aging star pitcher, hoping to squeeze enough gas out of the tank to cruise into a pennant. That pitcher was Greg Maddux. The Cubs brought back their one-time ace for his age 38 season on 2004. It was a safe move because Maddux was a fan favorite and showed he still had the ability to eat innings and get outs.

This off-season, the Cubs signed John Lackey with similar hopes. Lackey had great success last season with the Cardinals, and the Cubs are hoping there’s enough gas left in the 37-year old’s tank to provide good rotation depth behind Jake Arrieta and Jon Lester.

The Maddux deal worked out well for the Cubs. They got two full years of 200+ innings and several more quality starts through part of the third season before the then-playoff-irrelevant Cubs traded him to the contending Dodgers.

It’s reasonable for the Lackey to produce similar results for the Cubs. And it doesn’t hurt that Lackey is signed to just a two-year deal. So even if the aging star does not produce at a $16 million-level, the Cubs will not long be bogged down in paying Lackey.

Due to the short-term length of the contract, it will be hard for the Cubs to regret signing John Lackey.

Next: The 8-year guys

In December, the Cubs signed outfielder Jason Heyward to an eight-year, $184 million contract. The last time the Cubs handed out an eight-year contract it was to Alfonso Soriano. The year was 2006 and the Cubs inked Soriano for $136 million.

How did that work out?

Well, initially it worked out wonderfully. Soriano hit 62 home runs, had an OPS close to .900 and made the All-Star game in his first two seasons as a Cub. Not coincidentally, the Cubs made the playoffs in those two seasons, as well.

Playing in his age 33 season in 2009, Soriano’s production began to slip. He missed significant playing time and never quite got on track offensively. He finished the season with just 20 home runs while hitting .241 and slashing his way to a .726 OPS.

Soriano’s overall production increased over his remaining three and a half seasons with the Cubs, though his batting average was never higher than .262 and his defense was always a bit suspect.

Overall, Soriano was never not a good player for the Cubs. The problem was that the Cubs were paying him to be a great player–at least as great as he had been playing previously for the Yankees, Rangers and Nationals.

The Cubs are paying Heyward to be great player (no pressure). They handed over an eight-year contract averaging over $20 million per year for Heyward to play at an elite level.

The good news is Heyward’s age 33 season–the season where Soriano’s production began to drop off–will be Heyward’s final year in the contract. It’s unlikely his age will cause a decline in production.

But what level of production can we expect? Soriano hit 41 home runs the season before he signed his deal with the Cubs. Heyward’s highest single season was 27 back in 2012 while playing for the Braves. It’s clear the Cubs are not paying Heyward for past production, but rather are playing him based on potential.

Heyward is just entering his age 26 season–which coincidentally is the season when Soriano found his power stroke and hit 39 home runs (in 2002 while playing for the Yankees). If we see similar numbers from Heyward from his age 26 to 33 seasons as we did from Soriano, the Cubs (and all of us fans) should be well-pleased with the investment.

Perhaps, though, the greatest lesson we learn from the Soriano contract is that eight years is a long time. It is tough and rare for a player to play at an elite level for eight years. Those who do generally end up in the Hall of Fame–and we’ve yet to see Heyward post up HoF numbers.

So here’s my bold prediction: due to the length of contract, the Heyward deal will be the one the Cubs live to regret.

This is purely speculative and argumentative, so please voice your opinions in the comments!

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Chicago Cubs: Which signing will they regret?

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