Obsessive Jon Lester Watch: The Red Sox Have Made an Offer

jon lester feature red soxAlthough the Chicago Cubs reportedly had him into town yesterday for some discussions, some wooing, some wining, and some dining, we don’t know if the other big thing took place while Jon Lester visited: some negotiating.

Did the Cubs talk numbers? Did Lester or his reps? Did the Cubs make Lester an offer?

And did Lester tell the Cubs about the offer that he may have already had at that point?

In the wee hours of the morning – you are dedicated, Gordon Edes – here’s what Edes tweeted out:

Edes must have just found out about the offer – perhaps in the middle of the night – because he had written about Lester and the Red Sox just shy of midnight last night in a post about how nothing was doing on the Lester and Pablo Sandoval fronts, although meetings had taken place. That ESPN Boston piece has now been updated to clip out the Lester part (though you can see in the URL that it used to be there), and a new Lester-specific piece is up from Edes, which essentially says that the Red Sox made the offer at some point earlier in the week, before Lester met with the Cubs.

I am belaboring this a little because I’m intrigued that Edes appears to have found out about the offer to Lester in the middle of the night, perhaps a day or two after the Red Sox made it, but only a few hours after Lester’s visit with the Cubs concluded. I’m really not drawing any conclusions there, I just think it’s interesting to think about the timeline. Did the Red Sox try to get Lester to pull the trigger before meeting with the Cubs? Was the Red Sox’s offer coming through around the same time as those new rumors about the Braves and Cardinals were getting out? Were those rumors actually a response to the Red Sox’s offer?

In any case, Lester now has an offer in-hand from the Red Sox, and the negotiations – with every interested team, really – are underway. Edes says a quick decision is not forthcoming, which means that Lester will take the time to hear from other teams. What you never know for sure with free agents is whether they’re truly open to being convinced by each and every team with whom they speak, or if they’ve got a clear preference for one team, and then speak with other teams as a means to get the most money out of the team they want.

Hopefully we catch wind of the Red Sox’s offer. It’s a pretty safe guess that it’s six years and a touch more than $20 million annually. Everyone knew that was going to be the minimum required to land Lester, and, given the relationships involved (and Lester’s repeated statements that money won’t be the deciding factor for him), I wouldn’t fault the Red Sox for trying very hard to get Lester at the very minimum it takes.

That said, when it comes to top tier free agency in the last five years, it always seems like the contract the guy eventually gets is at least one year longer, and about 10 to 20% higher in AAV than folks expect. For Lester, that would mean something like a seven-year, $175 million deal is what it’s going to take. I know. That seems borderline insane. But when was the last time a top tier free agent signed a deal and you didn’t think it was a little insane?

***

I remain excited about the chance that the Cubs could land Lester, and I know that they are very sincere in their efforts to get him. But I do want to make sure I’m appropriately bracing you for the possibility that the Red Sox have always had the inside track, given the relationships and comfort in play here, and the likelihood that the money is going to be very close on any serious offer. From the outside, it looks like this: the Red Sox made a mistake in lowballing Lester before the season with their $70 million extension offer, they then had a down year, have obvious rotation needs, and now have ownership directly involved in trying to get Lester back. Doesn’t that seem like the story of a team that’s going to do whatever it takes to get this particular pitcher?

And, if they do, there will be some serious gnashing of the teeth by Cubs fans who feel like it’s a here-we-go-again situation. I won’t be among them, first because of everything I just wrote, and second because there seriously is so freaking much quality pitching available over the next 15 months. It’s the refrain Theo Epstein and Jed Hoyer keep saying again and again. There’s a reason, and it’s not just to brace fans for the possibility that the big name won’t drop this offseason. It’s because it’s overwhelmingly true. After Lester, there are still Scherzer and Shields, and some great second tier guys. And there’s Yang. And there might be Maeda and Kaneko. And then there’s a possible Hamels trade. Or a Mets trade. Or a Padres trade. And that’s all pre-2015. From there, you’ve got Price. And Zimmermann. And Cueto. And Latos. And Fister. And Samardzija. And Porcello. And so on and so forth.

Hopefully the Cubs do land Lester, and hopefully it’s on a not-insane contract (though, at this level, as I said, they’re always a little insane). But, if they don’t, and especially if Lester goes to the Red Sox, I’m not going to be surprised, and I’m not going to be able to dwell in disappointment for too long.

written by

Brett Taylor is the Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and on LinkedIn here. Brett is also the founder of Bleacher Nation, which opened up shop in 2008 as an independent blog about the Chicago Cubs. Later growing to incorporate coverage of other Chicago sports, Bleacher Nation is now one of the largest regional sports blogs on the web.

more cubs news

Now We Know Why Ian Happ Was Removed Mid-game

In the top of the seventh inning of today's 8-3 win over the Miami Marlins, Alexander Canario trotted out to left field in place of Ian Happ. At first, we thought (or maybe just hoped) that Craig Counsell was giving...

Enhanced Box Score: Cubs 8, Marlins 3 – April 19, 2024

And just like that the Chicago Cubs are the first team in the NL Central to reach 12 wins! They're not technically in first place yet because the Brewers (11-6) have played fewer games, but we're talking about a matter...

Nico Hoerner and Dansby Swanson with Back-to-Back Slick Defensive Plays

With a lefty Marlins starter on the mound this afternoon, Nico Hoerner lead off today's game for the Chicago Cubs. And he did it in style, ripping a leadoff double to the left-center field wall, before coming into score a...

Pre-Gamin’: Marlins at Cubs – Lineups, Broadcast Info, Game Thread

*The Cubs were rained out yesterday, but today? Today, we've got a Friday 1:20 start at Wrigley Field, and that means all is right in the world. Before you take a look at the Cubs lineup against Miami, check out...

MLBits: The White Sox Might be the Worst Team Ever, What Games I’m Watching this Weekend, More

Happy Friday! Well, for everyone except for the pilots who were supposed to be manning the Colorado Rockies flight last week but instead allowed a member of the Rockies coaching staff to hop in the pilot's seat for a fun...

Can I Interest You in a Positive Injury-Update on Justin Steele?

Justin Steele, arguably the single most irreplaceable player on the Chicago Cubs 2024 roster, went down with a hamstring injury just 4.2 innings into his Opening Day start against the Rangers on March 28. In his place, the Cubs sixth...

FAA Reportedly Investigating How a Passenger on Colorado Rockies Team Flight Was Seen Accessing the Cockpit

If you do this job long enough, it's really wild to see the range of topics that can somehow become attached to sports. That is to say, I did not envision myself at some point writing about flight safety, cockpit...

Cubs Farm Report | April 19, 2024: Kevin Alcántara is Heating Up!

The Iowa Cubs were rained out, but the rest of the farm was in action, and so was Kevin Alcántara, who picked up four hits and now has seven in his last three games as he breaks out of an...

It’s Not Kyle Hendricks Last Chance (But…), Ben Brown, Jameson Taillon, and Other Cubs Bullets

Well, the rain stole one from us yesterday, which is a blessing and a curse. On the bright side, the bullpen gets an extra day of rest (on top of the day Hayden Wesneski bought them). But on the flip...

The Chicago Cubs Are Not Stealing Bases So Far This Year

The Chicago Cubs are against theft. Of bases: https://twitter.com/codifybaseball/status/1781046629103231339 The Chicago Cubs this year have stolen just three bases, the fewest in all of baseball. Dansby Swanson has stolen two bases, Nick Madrigal has stolen one. That's it. I don't...

Latest News

Now We Know Why Ian Happ Was Removed Mid-game

In the top of the seventh inning of today's 8-3 win over the Miami Marlins, Alexander Canario trotted out to left field in place of Ian Happ. At first, we thought (or maybe just hoped) that Craig Counsell was giving...

Scottie Pippen’s Youngest Son Will Play at Michigan

A familiar last name will be in the Big Ten next season. Scottie Pippen's kid, Justin, has committed to the University of Michigan, according to Krysten Peek of Yahoo Sports. The youngest son of the Chicago Bulls legend, Pippen started...

Nico Hoerner and Dansby Swanson with Back-to-Back Slick Defensive Plays

With a lefty Marlins starter on the mound this afternoon, Nico Hoerner lead off today's game for the Chicago Cubs. And he did it in style, ripping a leadoff double to the left-center field wall, before coming into score a...

Enhanced Box Score: Cubs 8, Marlins 3 – April 19, 2024

And just like that the Chicago Cubs are the first team in the NL Central to reach 12 wins! They're not technically in first place yet because the Brewers (11-6) have played fewer games, but we're talking about a matter...

Blue Jays vs. Padres Prediction: Expert Picks, Odds, Stats & Best Bets – Friday, April 19, 2024

Following a two-homer game in a loss to the Yankees, Daulton Varsho leads the Toronto Blue Jays (10-9) into action as -112 favorites against the San Diego Padres (11-10). First pitch from PETCO Park at 9:40 PM ET on Friday,...

Diamondbacks vs. Giants Prediction: Expert Picks, Odds, Stats & Best Bets – Friday, April 19, 2024

Jung Hoo Lee will look to extend his 10-game hitting streak when the San Francisco Giants (9-11) take on the Arizona Diamondbacks (9-11). The Diamondbacks are listed as -121 favorites on the moneyline for the contest, which starts at 10:15...

Dodgers vs. Mets Prediction: Expert Picks, Odds, Stats & Best Bets – Friday, April 19, 2024

The New York Mets (10-8) will put their four-game win streak to the test when they visit the Los Angeles Dodgers (12-9) Friday at 10:10 PM ET on MLB Network. Bookmakers consider the Dodgers to be -201 favorites, while the...

Jonas Valančiūnas Player Props: Three-Pointer Props and Odds vs. the Kings – Friday, April 19, 2024

The New Orleans Pelicans face the Sacramento Kings at 9:30 PM ET on Friday, in the NBA Play-In Tournament, and one of the 3-pointer over/unders available for this matchup requires only one make from Jonas Valančiūnas.Jonas Valančiūnas' Three-Pointer Prop Odds...

Brandon Ingram Player Props: Three-Pointer Props and Odds vs. the Kings – Friday, April 19, 2024

Brandon Ingram must make two 3-pointers to beat his prop when the New Orleans Pelicans meet the Sacramento Kings on Friday at 9:30 PM ET, in the NBA Play-In Tournament.Brandon Ingram's Three-Pointer Prop Odds vs. the KingsBrandon Ingram's over/under for...

CJ McCollum Player Props: Three-Pointer Props and Odds vs. the Kings – Friday, April 19, 2024

CJ McCollum's New Orleans Pelicans play the Sacramento Kings on Friday at 9:30 PM ET in the NBA Play-In Tournament, and to beat his 3-point prop, he must make four from downtown.CJ McCollum's Three-Pointer Prop Odds vs. the KingsCJ McCollum's...

more cubs news