Was Moises Alou the Cubs’ Best Free Agent Signing, or Was it Someone More Recent?

Which was the best free agent signing in Chicago Cubs history?

At first, this question didn’t seem like it would be a difficult one to answer, but the more I thought about it, the more difficult it became.

I pose that question to you, of course, because MLB recently asked each of it’s 30 beat writers to identify and discuss the best free agent deal in their team’s history.

The results – which were limited to deals longer than a year and limited to true free agent signings – include names like Vladimir Guerrero, Nolan Ryan, Greg Maddux, Randy Johnson, and Ichiro Suzuki. But unlike the current or future Hall of Famers that made selections easy for many teams, Carrie Muskat’s choice for the Cubs, Moises Alou, was a bit more difficult to land on (particularly because one-year deals – like the initial Andre Dawson signing – were excluded).

At Cubs.com, she discusses her selection with a fairly convincing argument.

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A little background on the Cubs signing Alou, and what they got out of him:

In the winter between the 2001 and 2002 seasons, the Chicago Cubs signed a 35-year-old Moises Alou to a relatively significant three-year, $27 million deal to play in left field for the Cubs. The top average annual values in baseball that year were in the mid-teens, so Alou’s $9 million/season was rather steep.

However, his first season didn’t quite go as well as the Cubs had hoped: .275/.337/.419; 1.4 WAR. But, he bounced back in 2003 (.280/.357/.462; 3.4 WAR) and helped the Cubs reach and prolong their stay in the postseason (10-for-20 in the NLDS against the Braves and 9-for-29 with two homers in the NLCS against the Marlins).

And all of that was before he absolutely exploded in 2004 with a .293/.361/.557 slash line, 39 home runs, and much improved defense all around. In his final season with the Cubs (age 37), Alou was an All-Star, worth 5.9 WAR, and even received down the ballot MVP votes.

In total, this is what the Cubs got out of Alou for three years and $27 million:

Slash Line: .283/.353/.484
Home Runs: 76
Walk Rate: 9.6%
Strikeout Rate: 11.3%
wOBA: .359
wRC+: 117
WAR: 10.7
Postseason: .388/.423/.551; 2 HRs

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In terms of raw contract value, Alou’s 10.7 WAR across his three years was certainly worth the $27 million cost. The price of a win has obviously gone up since then, but even in 2002 dollars, I’m sure you’d gladly pay $2.5 million/win. The fantastic postseason numbers also help his case.

Muskat also listed four honorable mentions, in addition to Andre Dawson, and each is definitely worthy of the distinction:

1. Jon Lester: Six years, $155 million
2. Ben Zobrist: Four years, $56 million
3. Ted Lilly: Four years, $40 million
4. Ryan Dempster: 1 year, $300K

Although value is going to ding him slightly, I think Jon Lester may have already proven to be one of (if not) the best free agent signing in Cubs history. Sure, he’s played in only two seasons with the Cubs – 1/3 of his contract – but I believe both his regular season statistics, postseason numbers, meaningful participation in breaking the Cubs’ championship-less streak, and future out-look more than make up for the cost of his contract. He’d probably be at the top of my list at this point.

Here’s what the Cubs have already gotten out of Lester:

Starts: 64
Innings: 407.2
ERA: 2.89
FIP: 3.16
Wins: 30
K-rate: 24.9%
BB-rate: 6.1%

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And although the Cubs may have lost both of his 2015 postseason starts, Lester absolutely dominated as one of the Cubs’ heroes this past October, finishing with a 2.02 ERA and a 0.93 WHIP over 35.2 innings pitched. He even came into Game 7 of the World Series (his third appearance in the seven-game set), and pitched three innings in relief of Kyle Hendricks.

But let’s break it down to numbers only: In two seasons with the Cubs so far, Lester has been worth 9.3 WAR (via FanGraphs). If you value the cost of a win at roughly $8 million, that means he’s already been worth $74.4 million in first two seasons – that’s just about half of what his contract cost overall ($155 million). That doesn’t consider his postseason value, which is more nebulous, but certainly far more than zero.

So, with four years remaining on his deal, Lester need be only half as valuable (at most) as he has been in each of his first two years with the Cubs in order to make his contract worth it on value alone. If he ends up being better than half as good as 2015 or 2016 (which is a fairly safe bet in the near term), he can far exceed that cost. And all of that, of course, is to ignore the fact that the Cubs signed him – in large part – due to the expectation that he’d be the type of pitcher to age gracefully.

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Maybe this will look foolish in a few years, but I doubt it. In my opinion, Jon Lester has been the best free agent signing in Cubs history. His early Cubs numbers have been stellar, he projects to be very good going forward (even though he only needs to be about half as good as he’s been), and he’s already inarguably one of the biggest postseason heroes in the history of one of the oldest baseball franchises.

To be sure, the case for Moisies Alou is fair and reasonable. For me, though, it’s Jon Lester.

What do you think? Who would you pick?

[Brett: I know you weren’t asking me, specifically, Michael, but I’ll answer: I’d probably go with Lester as well, but Alou would be very close. Though I’ve gotta say I’ve always been fond of that Ted Lilly signing (which then GM Jim Hendry reportedly finalized while in the hospital). Lilly was worth 10.3 WAR through the first three years of his deal, far exceeding in value the cost of the signing ($40 million over four years). He was traded with Ryan Theriot to the Dodgers at the deadline in his final year, netting the Cubs Blake DeWitt, Kyle Smit, and Brett Wallach. I guess we can’t hold that one against Lilly.]

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