Obsessive Jon Lester Watch: Cubs Believe He’s Going Back to Red Sox? Phillies Scouting Red Sox?

We’re starting early today, I guess.

Peter Gammons was just on CBS Sports Radio and apparently said this (I didn’t catch the interview):

Gammons was then on the Dennis and Callahan show in Boston, and he phrased it this way:

I wish I’d heard the interviews live, because you can sense a fair bit more context that way. In print, however, the best we can discern from this is that Cubs sources may have told Gammons that they believe Lester will return to the Red Sox. What does that actually mean? Well, it doesn’t mean that Lester to the Sox is a done deal, otherwise the Cubs wouldn’t be going through the rigamarole of meeting with Lester and his reps today, as they are reportedly doing.

Instead, it means that, based on conversations he’s had with people who probably are in a position to know, Gammons has gotten the sense that some Cubs sources, if they are guessing, believe that Lester will ultimately decide to sign with the Red Sox. That could mean those Cubs sources do not feel confident about their potential offer(s) to Lester. It could mean that those Cubs sources believe Lester wants to return to Boston. Or it could mean some kind of combination of those things that, on a gut level, suggests a most likely outcome. Or it could be a little gamesmanship playing out between two teams competing for the same player.

And then you have to add a layer of processing, because Gammons says that this is all a “feeling” he’s gotten, as opposed to something definitive he’s been told. Of course, it could be something definitive that he’s been told, because nothing in “feeling” precludes that possibility.

That is all to say, while Gammons’ comments don’t seem to look too good for the Cubs, and you can certainly add them to your repository of information, I’d caution you against going too far with it at this stage. There are so many things these comments could mean, all possibly true, and not all of them end with Lester actually signing with the Red Sox. Remember: on Sunday, folks involved in the bidding thought Russell Martin was going to the Cubs. By Monday morning, he was going to a different team involved in the bidding. In sum, I take from Gammons’ comments only this: people in a position to know some things about the Lester pursuit believe the Red Sox are very serious about trying to bring him back. We already knew that, I suppose, but this gives it a little more oomph.

Let’s be very clear about something so that you don’t get your headspace all screwed up: once it became clear that the Red Sox were very serious about bringing Lester back, I think it was very hard to believe the Cubs could remain the favorites to land Lester. Yes, he has familiarity with the front office, but he also has familiarity with many folks in Boston. And that’s the city where he lived for almost a decade. That’s the team that drafted and developed him. And it’s a team with a ton of money, and a resolve to un-make the mistake they made when they lowballed him earlier this year. I still think the Cubs have a shot here, but I’m also keeping things in perspective.

Also: Yankees, eh? That was well-timed, given this morning’s report on the Yankees and Max Scherzer. Maybe Lester is genuinely interested in the Yankees, or maybe he’s hoping they’ll come in to push the price up on the Red Sox or Cubs. And frankly, if you’re the Yankees, wouldn’t you want to at least try and push the price up on the Red Sox? I guess maybe that won’t be possible without going so far that you risk Lester accepting a deal with which you’re not comfortable, but you’re the Yankees. If the Lester bidding is about to get bananas, it’s going to be because the Yankees started sniffing around.

Separately, but relatedly …

It’s worth pointing out the persistent rumors about the Phillies engaging the Red Sox in trade talks about Cole Hamels. Just this morning, Ken Rosenthal reports that the Phillies have been doing “background work” on the makeup of Red Sox youngsters/prospects Mookie Betts, Matt Barnes, and Christian Vazquez. While I can’t envision a scenario where the Red Sox would include Betts in a Hamels deal, it’s pretty clear that the work the Phillies are doing is in anticipation of a possible trade. Would the Phillies still be doing that work if they knew that the Red Sox were confident they would land Lester? Or is Boston preparing for the possibility of trying to add both Lester and Hamels this offseason?

I don’t think we can rule that out, and, in that regard, the two stories may not actually have anything to do with each other.

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

Enhanced Box Score: Cubs 4, Astros 3 – April 24, 2024

The Cubs did all their scoring in the first, and made it stand up for the win with generally good pitching and generally good defense. Jameson Taillon looked solid again in his second start, locating well, giving up no barrels,...

Dansby Swanson with a First Inning Three-Run Homer

For the second straight night, the Cubs are jumping all over the Astros in the first inning. After a couple hits from Nico Hoerner and Ian Happ to get things going, Michael Busch hit a sac fly, Christopher Morel walked,...

Welcome Back to Iowa, Brennen Davis: Rocket Homer in His First Game Post-Rehab

What a road it's been - continues to be - for Cubs outfield prospect Brennen Davis. The former top prospect was on a rocket ship to Triple-A in 2021, and then mostly lost the last two years to various injuries....

CRAAAAAP: Cody Bellinger to the Injured List (UPDATES)

So much for all those words of optimism and negative X-rays. After colliding with the outfield wall last night, Cody Bellinger fractured his rib (Update: It's actually TWO fractured right ribs) and will hit the injured list today. Chicago Cubs...

Chicago Cubs Lineup: What is it, June 2023?

CUBS LINEUP — The Chicago Cubs took Game 1 against the Houston Astros in convincing fashion last night. So tonight, they'll go for the quick series win against Spencer Arrighetti at Wrigley Field (it'd be a good idea to win...

Bellinger Optimistic Post-Injury, Busch’s Defense, Almonte Stock Rising, Tauchman Slugging, and Other Cubs Bullets

Ed. Note: Since this article was published, a CT scan revealed a rib fracture for Cody Bellinger, who is now on the Injured List. You can find all the details of that news in our most recent article right here....

Cubs Outfield Prospect Pete Crow-Armstrong Coming Up

With Cody Bellinger headed to the Injured List with a rib fracture, the Cubs are in need of another outfielder: center field prospect Pete Crow-Armstrong is coming back up to the big leagues for the second time. https://twitter.com/670TheScore/status/1783217891195625709 Crow-Armstrong, 22,...

Is Mike Tauchman the Best Player in Baseball? An Exploration

Hey, we're just having some early-season fun. So allow me to present the 'Mike Tauchman Is Clearly Better Than' list. As of this moment, Mike Tauchman has ... ... a higher wRC+ (151) than Pete Alonso, Fernando Tatis Jr., and...

Cubs Farm Report | April 24, 2024: Kevin Alcántara Cannot Miss Right Now

Name a player hotter than Kevin Alcántara right now. Go ahead, I'll wait. (He's already raking again today. Literally as I type this.) More on Alcántara's big day and the Smokies home run parade last night in today's Cubs Farm...

Oof: Blake Snell to the Injured List Just Three Horrible Starts into His Giants Career

Just three starts into his San Francisco Giants career, Blake Snell is heading to the injured list with a left-adductor strain. Oof. You hate to even say it — and who really knows if this was related — but early...

Latest News

Dodgers vs. Nationals Prediction: Expert Picks, Odds, Stats & Best Bets – Thursday, April 25, 2024

The Los Angeles Dodgers (15-11) and Will Smith (four hits last time out) are favored (-199) on the moneyline for their matchup with the Washington Nationals (10-13) on Thursday at 4:05 PM ET on MLB Network.Los Angeles' Yoshinobu Yamamoto and...

Enhanced Box Score: Cubs 4, Astros 3 – April 24, 2024

The Cubs did all their scoring in the first, and made it stand up for the win with generally good pitching and generally good defense. Jameson Taillon looked solid again in his second start, locating well, giving up no barrels,...

Mariners vs. Rangers Prediction: Expert Picks, Odds, Stats & Best Bets – Thursday, April 25, 2024

The Seattle Mariners (12-12) visit the Texas Rangers (13-12) at 2:35 PM ET Thursday for a sluggers' duel between two of the best home-run hitters in baseball. Caleb Raleigh has racked up six homers this season (No. 9 in the...

Padres vs. Rockies Prediction: Expert Picks, Odds, Stats & Best Bets – Thursday, April 25, 2024

The San Diego Padres (14-13) are favorites (-150) on the moneyline when they take on the Colorado Rockies (6-19) Thursday at 3:10 PM ET, live on SDPA.Randy Vasquez will get the ball for San Diego while Colorado will counter with...

Dodgers vs. Nationals Probable Starting Pitchers – April 25

After winning three games in a row, the Los Angeles Dodgers (15-11) play on the road against the Washington Nationals (10-13) at 4:05 PM ET on Thursday.The probable starters are Yoshinobu Yamamoto (1-1) for the Dodgers and MacKenzie Gore (2-1)...

Royals vs. Blue Jays Prediction: Expert Picks, Odds, Stats & Best Bets – Thursday, April 25, 2024

The Kansas City Royals (15-10) are favored on the moneyline (-121) in Thursday's contest versus the Toronto Blue Jays (13-12). Game time is at 2:10 PM ET on SNET. The Blue Jays, with +168 odds, are favored against the spread...

Astros vs. Cubs Prediction: Expert Picks, Odds, Stats & Best Bets – Thursday, April 25, 2024

The Houston Astros (7-18) visit the Chicago Cubs (15-9) at 2:20 PM ET Thursday for a sluggers' duel between two of the best home-run hitters in baseball. Jose Altuve has racked up six homers this season (No. 9 in the...

Best MLB Prop Bets Today, April 25, 2024

The Boston Red Sox versus the Cleveland Guardians is a game to see on a Thursday MLB schedule that features 10 competitive contests.There are typically plenty of MLB player prop bets available for each and every matchup. Scroll down to...

Padres vs. Rockies Probable Starting Pitchers – April 25

The Colorado Rockies (6-19) face off against the San Diego Padres (14-13) at home on Thursday beginning at 3:10 PM ET.The probable starters are Randy Vasquez (0-1) for the Padres and Dakota Hudson (0-4) for the Rockies.Padres vs. Rockies Pitcher...

Brewers vs. Pirates Prediction: Expert Picks, Odds, Stats & Best Bets – Thursday, April 25, 2024

The Milwaukee Brewers (15-8) are set to take on the Pittsburgh Pirates (13-12) Thursday at 12:35 PM ET, airing on BSWI. The Brewers are listed as -128 favorites by sportsbooks, while the underdog Pirates have +107 odds for the contest.Freddy...

more cubs news