One of the things I always found amusing about Lester was that he was SUCH a bad hitter. He was fairly athletic and when he got in the box he looked the part. Nice stance, bat ready to go, every thing looked right up until the moment he swung when he looked like a 4 year old on a sugar high. That 0 for 66 to start his career was earned honestly.

Some folks have pointed out that, although he was so bad to start, he worked hard and managed to become a pretty average hitter for a pitcher. From 2017-2021, he hit .153 .195 .244 with 4 HR!

I have to admit I never really warmed to Jon Lester.  He always had an A-Rodian quality of seeming fake.

I never got that sense.

Whatever I perceived of his personality that kind of thing says a hell of a lot more about him than some jackass’ opinion while sitting in his boxer shorts on his couch.

True, and also I now have a disturbing mental image. I don't think I've ever seen an uglier couch.

Of course when discussing Lester’s on field resume no discussion is complete without discussing his big game quality.  In six World Series games he was 4-1 with a 1.77 ERA and overall in the post-season he was 9-7 with a 2.51 ERA in 22 starts (26 appearances).

That's the thing that sticks with me. I don't think there was any point when I lacked confidence in the Red Sox in the playoffs when I knew he was lined up to pitch. It was great. He was great.

Nice writeup. He's one of those guys whose whole arc of prospect/majors/free agency/retirement I have "followed" with you fellas on Primer/Sox Therapy/RLRS Blog.

There is a lot of talk today about how Lester should have been on the Red Sox for his whole career, with even John Henry having admitted at one point that he thought they blew the negotiations. I'll start by saying that yes, I would have liked to have Lester on the team for his whole career. He was very good and great at times, a homegrown player, and fun to root for. But I disagree with the idea that the Red Sox somehow blew it with him.

The Red Sox initial offer was 4 years, $70 mil., which sounds ridiculously low when you consider that he eventually got 6/156. But take a look back at how Lester was pitching at the time and it doesn't seem ridiculous at all. After a stretch as a dominant starter from 2008-2011, he took a large step back. In 2012, he he was replacement level, and then with some adjustments, had settled in as a good-not-great starter in 2013 (2.7 WAR). Offering him 4/70 was essentially seeing him as a valuable starter, but not an ace going forward. A bit low, maybe, but not an insult.

Unable to sign him, they went another way and traded him for Cespedes, who they then dealt for Porcello--who they then signed to a 5/95 deal. With the benefit of hindsight, how did they fare?

Lester, 2015-20 (6 years, ~$144 mil due to shortened 2020)
1,002.1 IP, 13.2 WAR

Porcello, 2015-2019 (5 years, $95 mil)
964 IP, 9.3 WAR

Looks like Porcello was a slight overpay and Lester was a big overpay. The Sox really made the right move here, despite how painful it was.


And what of that 4/70 offer? Had he accepted it, the Red Sox would have gotten 12 WAR for $70 mil, about $6 mil/WAR. That's a very good deal for the Sox, so maybe it should have been higher. Lester has said since that he would have signed for 6/120, but a) take that with a grain of salt and b) even that would have been pricey for his production.

Porcello, 2015-2019 (5 years, $95 mil)
964 IP, 9.3 WAR

Looks like Porcello was a slight overpay and Lester was a big overpay. The Sox really made the right move here, despite how painful it was.

Shouldn't value of the 1 year of Cespedes and few years of Alex Wilson be added to the Porcello cost?

It should, but I am lazy. Also, Wilson was better than I remembered and Cespedes was good for the Sox but it was a year they were punting so I'm not sure how much value he provided there.

No I meant the value of having Cespedes for 2015 (instead of trading him for Porcello), not what he gave them in 2014.

Is he the last player from the Sox teams of the aughts that was active? Is Rich Hill from the 2010 team as far back as it goes?

edit: nope, Daniel Bard played for the '09 team and I assume he'll be active again in 2022.

Hindsight makes this exercise a lot easier, but if you look at the Porcello vs Lester choice, it turns out that there were three years where Lester was very good-to-excellent:

In 2015, he was better than Porcello, but the Red Sox were going nowhere, anyway
In 2016, where Lester finished 2nd in the NL CY Young...but Porcello won the AL Cy Young the same year
In 2018, where he was better than Porcello, but the Red Sox won the World Series and had a dominant season, so this clearly worked out for Boston.

Porcello was cheaper, and his contract was shorter, and he was generally quite durable. He won a Cy Young during the contract, and they won a World Series during the contract. It's all good.

In 2015, he was better than Porcello, but the Red Sox were going nowhere, anyway

Now, hold the phone. This came up in the other thread: https://www.baseballthinkfactory.org/sox_therapy/discussion/the_lockout_files_what_couldve_been/

FWIW in 2015 Porcello and Hanley totaled -0.2 WAR for the Red Sox, and Lester, Cespedes, and Alex Wilson combined for 10.9 WAR for other teams.

No I meant the value of having Cespedes for 2015 (instead of trading him for Porcello), not what he gave them in 2014.

I was looking at it more from the point of view of keeping Lester vs. trading Lester at the deadline and doing what followed. But you're right, if you're looking at the decision they made the following offseason, they could have kept Cespedes (and Wilson) AND signed Lester. Those two cost $36 mil in AAV for the 2015 season so there probably would have had to be other moves to allow that.

It's funny that the Lester retirement is prompting so much discussion about a squad he wasn't even on. The 2015 team is somewhat of an interesting failure, in that so many resources and so much talent was involved and they ended up a mis-aligned cluster-####. And then most of the same guys came back and won the division the next year.