Jon Lester to Sign With the Cubs

Jon Lester will be signing with the Chicago Cubs, according to Ken Rosenthal. Jeff Passan has the details, noting that the Cubs will be paying $155 M for six years.

Two thoughts on this deal that are Pirates-related. The first thought is the obvious one, that this isn’t the best news seeing the Cubs landing a top starting pitcher. They have been loading up on top young hitting talent, and just need the pitching. They also have a lot of money to spend on pitching, as shown by giving Lester almost $26 M per year over six years. They could probably sign another top starter next year as well. That’s going to make them a dangerous team in the future, and will only make the NL Central that much more difficult.

The second thought is that Lester signed for about $26 M per year, while Francisco Liriano is signing for about $13 M per year and three years less of a commitment. Here are the comparisons of the two pitchers over the last two seasons.

Liriano: 3.20 ERA, 3.26 xFIP, 323.1 IP

Lester: 3.10 ERA, 3.49 xFIP, 433 IP

The innings pitched are very significant. Lester averaged about 55 innings more per season than Liriano. But the two pitched about on the same level the last two seasons, with Liriano having the edge in xFIP. If they’re both pitching the same when healthy, then is Lester’s extra 55 innings worth an extra $13 M, plus an extra commitment of about $78 M over three additional years? Looking at the two deals, and that one key difference, it seems that either the Cubs are paying a premium for Lester, or the Pirates are getting a huge value with Liriano.

Either way, it’s good that Liriano is in the mix already, since the starting pitching market is about to heat up with Lester off the board.

Tim started Pirates Prospects in 2009 from his home in Virginia, which was 40 minutes from where Pedro Alvarez made his pro debut in Lynchburg. That year, the Lynchburg Hillcats won the Carolina League championship, and Pirates Prospects was born from Tim's reporting along the way. The site has grown over the years to include many more writers, and Tim has gone on to become a credentialed MLB reporter, producing Pirates Prospects each year, and will publish his 11th Prospect Guide this offseason. He has also served as the Pittsburgh Pirates correspondent for Baseball America since 2019. Behind the scenes, Tim is an avid music lover, and most of the money he gets paid to run this site goes to vinyl records.

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William Wallace

I think Lester is a great pitcher but this deal will haunt the Cubs in three years and be an albatross around their neck. Look at these pitchers with years and dollars start breaking down. Lester will not make this deal pan out for the Cubs. He will probably be a huge difference the first two years in but after that it is a crap shot.


I originally had Shields going to Boston, but with Cubs adding Lester and Reds knowing they have to either go all-in this year or start selling assets while they still have value, I’m now thinking RedSox will make an aggressive play for Cueto.

Ian Rothermund

I’m confident the Cubs will still find a way to suck.

Will Sanchez

not with Madden there..


No,it’s not like the Rays didn’t suck last season. Madden is a miracle worker ? Get real. Smizikstan needs a new citizen like you.


Except that Lester pitched in the AL in a hitter’s park.


Yes, the raw stat lines match up but when you consider park and league a bit of gap emerges.

Pitcher: ERA- / FIP- / xFIP- from 2013-14
Lester: 77 / 80 / 90
Liriano: 88 / 90/ 87


Shaping up to be a difficult division. Cubs are still probably a year away from playoffs, but no longer a team Bucs can just expect to roll 11-12 wins against. With Reds expected to have some bounceback from an unexpectedly awful 2014, Pirates are going to have to beat up on Milwaukee this year.


Does anyone realize that the Cardinals also play the Cubs, not just the Pirates ? And they have a lot more problems with LH pitchers.


Somewhat immaterial. If the Cubs ascension means every other NLC suffers, then it’s probably just sending one team to playoffs, no WC. So it’s still Bucs vs Cards for the division again.

Will Sanchez

like i have been saying all along..the “window” is closing after 2016 it will be cubbies and cards…the BUCS will become “also rans” THIS IS LAST YEAR that we can actually “go for it” since money wise our owners won’t compete with the rest..


Not really. The OF is set through 2018. Taillon and Glasnow should both be pretty good, and Cole will still be here along with three years of Liriano, so starting pitching should be OK. Bucs will have to replace Walker and Pedro (the latter probably with Josh Bell, but asking Hanson to replace Walker’s offense might be asking too much.) All in all, Bucs will still have a lot of cost control over next 4-5 years and money to add what they need.


Stupid statement.


Good for the cubbies, however until proven otherwise 1908 is still a long time ago in a galaxy far,far away.


pb: Yep, I like to see any of our NL Central competitors increase their team payroll by almost $40 mil/yr with only 2 players. The White Sox applied the pressure with their signings, and were looking to corral the fan support for the city. Lester was a must for Epstein, but SIX YEARS of $25 mil/yr beginning at age 31? The guy has been superhuman in today’s MLB with 8 straight years averaging 200 innings pitched per year without even a slight injury, but that is a big gamble.

Will Sanchez

the cubbies can afford to add 4 or 5 pitchers at @)-25 mill…since Most of their position players could be earning around the 500 k mark


Theo ended Boston’s 86 years of WS futility. No reason to think he can’t end Cubbies’ 107 years.

Cubs are finally acting like a big market team. Too bad for their fans they haven’t done so recently. A lot of goats have died in the past decade on behalf of the Cubs.


Perfect, now lets get Welington Castillo for some real competition in spring training for Cervelli and Stewart.

Lukas Sutton

Not seeing any reason for the Cubs to move him. Montero has seen very “meh” offense in recent years and is likely in CHC due to his pitch framing, which Castillo is relatively awful at. Castillo still gives them a decent bench bat and a quality backup catcher, with a lack of needs elsewhere on offense that we could provide. Their only glaring needs are possibly another decent SP (which we cant really afford to give away) and experience for their rookies. Trading Castillo would actually create a large hole at backup catcher for the Cubs and force Montero to start a ton of games. I’d put good money on the Cubs liking having 2 decent options at catcher.


Supposedly the Cubs are looking at Ross. If they acquire him, obviously Castillo is on the block. The question is, will they trade him to a division rival who obviously needs a C? I like Cervelli but odds are he’s going to be hurt.


Yeah, saw they were shopping Castillo on MLBTR yesterday. I’m a bit surprised at that. But Theo really likes Ross. Probably because Lester really likes Ross.

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