1_PROPOSED_MARQUEE_VIEWTwenty-two years ago to the day Jon Lester chose the Cubs last week, Greg Maddux – number 31 – left the Chicago Cubs in free agency for the Atlanta Braves. I won’t say today’s signing – also number 31 – makes up for that colossal screw-up back then, but it’s certainly nice to be on the other side of things this time.

Today is Lester Day, with the Cubs’ new lefty being introduced officially at a 1pm CT press conference. You’ll be able to follow that press conference on an MLB.com live stream, on ESPN Radio 1000, and on CSN Chicago. For those of you who can’t watch or listen, I’ll have a live blog going here at the site.

Some more on the Cubs’ biggest signing ever, and on the future for the Cubs in light of the Lester deal …

  • We discussed the particulars of the contract at length last week in a couple posts, so I won’t rehash that stuff here. One new item is a little more detail on the $30 million signing bonus (an MLB record), per the AP: $15 million is paid up front, $2.5 million is paid in 2018, $2.5 million is paid in 2019, and $10 million is paid in 2020. Setting aside the accounting implications for the Cubs that I discussed last week, which I suspect is the primary reason for the huge bonus, this structure gives the contract the odd distinction of being both frontloaded and backloaded. The frontloading potentially helps the Cubs for their unique financial situation – and is a nice incentive for Lester, because $1 today is worth more than $1 tomorrow – and the backloading helps in the way that it helps all institutions that would rather pay tomorrow for a hamburger today.


  • With $40 million of the $155 million guarantee in the contract, then, taking the form of signing bonus plus the 2021 option buyout ($10M), there’s $115 million in salary to be spread out over the six years of the deal, assuming the option isn’t picked up/doesn’t vest, or just under $20 million per year. I look forward to a half decade of folks debating and mis-describing the structure of Lester’s contract, and misapprehending the difference between what he’s paid in a given year (that sub-$20 million figure) and what the AAV for his deal is in a given year ($25.83 million for ever year of the deal).
  • Speaking of the number 31 up there in the opening, since Lester can’t keep wearing 31 (it’s retired both for Fergie Jenkins and Greg Maddux), he’ll have to swap it out. If you troll around the web, you can find instances of Lester being listed as number 33 on the Cubs, but I’d wait for an announcement before you order your shirsey.
  • A great write-up on the signing and the Cubs’ window of contention from Jeff Sullivan at FanGraphs. To Sullivan, Lester is a great fit for the Cubs not only because he provides something they need – impact pitching – but also because he’ll be aging right alongside the Cubs’ youngsters getting better. Lester projects by many to age relatively well (given his pitch mix, and lefties seem to age a little better than power righties for some reason), and the Cubs project to have a long possible window of contention. That’s a nice fit if you’re going to dive in on a huge contract for a pitcher in his 30s.
  • Therein, Sullivan includes this tweet from Dan Szymborski, which makes me happy:



  • Granted, there’s a ton of play in doing those valuation projections (where does the WAR figure start, how much does it decline, when does it start to decline, what’s the value of a free agent win, what’s the inflation rate for that value, etc.), but, if memory serves, it’s fairly rare that these top-of-the-market free agent contracts actually project to provide value. Usually, they project to be $10s of millions too high right off the bat (which, I know, is simply a reminder that top-tier free agency is not going to provide “value” – the winner will always “overpay” – but it’s also nice to see this particular deal actually projecting as, like, fair).
  • Friend of the program Sahadev Sharma handled the transaction analysis for Baseball Prospectus, and he mentions the Cubs as a team on the rise. The best part? The Cubs were already a team on the rise before they signed Lester.
  • I enjoy reading opposing fans’ reactions in times like this. No, not for the woe-is-me you might find in there, but for an outside, passionate perspective on what they’re seeing from the Cubs. This write-up from Viva El Birdos (a Cardinals blog) is a good read about what’s coming for the Cubs, and what it means for the Cardinals. The conclusion: “The Cubs are about to make this rivalry exciting again. Tickets will be tougher to get in Chicago, and a full Wrigley Field will add to the already full Busch Stadium to give the rivalry more weight. As a Cardinals’ fan, perhaps the most intriguing question is not whether the Cubs are contenders or the number one competition for the division. The most interesting question is probably, do the Cubs make me nervous in 2015 and beyond. Yeah. They do.”
  • Patrick Mooney reminds folks of something very important as we get excited about the Lester deal and what’s coming: these giant contracts pretty much always come with a downside. It’s totally fine to be all buzzy today and look forward to the future. Just remember this feeling when, a few years from now, you probably start having the other feeling: oh God, why are the Cubs saddled with this horrible contract?!? Hopefully, after the Alfonso Soriano situation, Cubs fans will be better prepared to accept the way these big contracts go – they provide great value early on (as Soriano did, and the Cubs made the playoffs twice), they trail off in the middle years (Soriano had some good, but not great, years after the first two), and then you’re ready to be unburdened in the final couple years. That doesn’t mean the contract wasn’t worth signing, or didn’t provide a good return overall.


  • When the Cubs beat out the Red Sox for Lester, I was reminded of the series last year in which the Cubs swept the Red Sox in Boston, which, in an exaggerated way, felt like the death of the 2014 Red Sox (indeed, they never recovered), and the birth of the 2015 Cubs as a plausible contender (indeed, here we are). I thought it was fun to look back on that now, many months later and after last week.
  • Being that it’s Lester Day, here’s the Lesterday song, if you haven’t already heard it.
  • Speaking of which, very well done:




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