Obsessive Jon Lester Watch: Some Possible Negative Signals for the Cubs

jon lester feature red soxJust about anything about Jon Lester right now begins with a note that there are some big do-ins in Boston, and they’ll absolutely impact the Lester pursuit one way or another. I don’t think we can accurately predict how just yet, but I wanted to make sure to offer it up front. Suffice it to say that it’s plausible that adding two top bats to the team could make the Red Sox all the more attractive to Lester right now.

Another possible impact of the Boston offensive maneuvering? Maybe the Yankees now see the Red Sox as an even bigger threat in the AL East, and what better way to kill two birds with one stone than to try and grab Lester? Yes, yes, we’ve heard the rumors about the Yankees not spending on any top tier free agents this offseason, but we didn’t buy it then, and we’re not buying it now. Indeed, Peter Gammons, who has recently suggested the Yankees could be lurking on the Lester periphery, said just this morning that he wonders whether the Red Sox’s Sandoval/Ramirez moves could push the Yankees into a hotter pursuit of Lester.

Even before these potential Boston signings broke, Nick Cafardo was writing yesterday that the Red Sox were worried not about the Cubs signing Lester, but the Yankees.

And then you’ve got the Giants, having possibly missed out on Pablo Sandoval, possibly ready to use the savings there to go after someone like Lester, according to Ken Rosenthal (and here, too).

On the balance, it’s hard to see how any of this is good news for the Cubs’ pursuit. And then there’s this Gordon Wittenmyer report, noting in part, “Cubs insiders did not express confidence as the season ended that they would be successful in their pursuit of top free-agent pitching target Jon Lester. And sources said they’re not especially optimistic after their meeting in the last week.”

Not to get too parse-y, but, for what it’s worth, “did not express confidence” is technically a neutral statement, not an affirmatively negative one (the opposite is “did express confidence” – would you really expect the Cubs to express confidence that they’d get Lester when the season ended? Or at any time?). Further, “not especially optimistic” is not the same as “affirmatively pessimistic.” Again, it would be a bit odd for the Cubs to have met with Lester and immediately be “especially optimistic” about their chances of landing him, especially when everyone seems to be on board with the idea that the Red Sox are the most likely destination right now.

Still, it’s probably not a great sign, all things considered. Throw in the possibility that the Yankees could now become seriously involved, too?

It will be very interesting to see how the Lester pursuit is clarified in the coming days by whatever the Red Sox are able to finalize with respect to Ramirez and Sandoval. Remember: Lester is reportedly meeting with two additional teams this week, so we’re very likely to hear some more on his market in the coming days either way. This Red Sox news probably brings it even more to the fore.

Lastly, a funny anecdote making the rounds today with word on the Red Sox agreeing to sign Hanley Ramirez. This is from a USA Today piece four years ago:

A fluffy question was posed to Lester: had he and Ramirez, back when they were in the minors, perhaps gone out for a pizza one night and talked about someday playing in the All-Star Game?

“I’d have a better chance of being struck by lightning than me and him getting a pizza together,” Lester said. “You can take that for what it’s worth. But there was no chance on God’s green earth that I was getting a pizza with him.”

So, maybe there’s not a very good relationship there between Lester and Ramirez. Or maybe Lester just hates pizza. Either way, I wouldn’t take this as any meaningful reason for Lester to avoid the Red Sox now. These guys are all pros, and I highly doubt Lester would not sign with the Red Sox solely – or even partially – because there was a guy on the team with whom he didn’t want to go get pizza.

In any case, it’s a funny story. Hopefully the Cubs don’t emphasize their Giordano’s pizza partnership too heavily in the Lester sales pitch. Or, wait a minute! Maybe the reason Lester didn’t want to get pizza back then is because he wasn’t in Chicago, and he refuses to eat any pizza that isn’t authentic Chicago deep-dish pizza!

We’re through the looking glass here, people.

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

The Mini-Break Pays Off: Ian Happ with a ROCKET Home Run!

After a red-hot first ten games of the season (172 wRC+), Ian Happ had gone ice cold offensively. Aside from continuing to take his walks (he always does), his overall production plummeted to the point where Craig Counsell game him...

Kevin Alcantara Doubles, Matt Shaw Singles, and Moises Ballesteros HOMERS THEM ALL IN!

Brennen Davis isn't the only hot Cubs prospect. In fact, Moises Ballesteros is basically THE hot Cubs prospect of the season so far. And tonight, after two of the Cubs top prospects — Kevin Alcantara (on a double) and Matt...

Pre-Gamin’: Pirates at Cubs (6:40 CT) – Lineups, Broadcast Info, Game Thread

CUBS LINEUP — The Chicago Cubs are back at Wrigley Field tonight against the Pirates, facing a 22-year-old fireballer who threw six strong innings against them last weekend, Jared Jones. Here's a look at the Cubs lineup for the rematch...

Brennen Davis Just Homered AGAIN

For a moment, it seemed like we were in for another round of terrible Brennen Davis luck. Just as the Cubs outfield prospect was heating back up, this happened: https://twitter.com/thats_so_cub/status/1791239496777760989 Davis is just a magnet for HBPs, even when it's...

MLBits: Red-Hot Rockies, Sticky Stuff Suspension, Salvy’s Patience Paying Off, More

The longest active winning streak in baseball belongs to ... the Rockies. More on the red-hot Rox and more in today's MLB Notes. The Red-Hot Rockies? A little over a week ago, the Rockies were 8-28. Since then, they've won...

The Cubs Are Coming Home to Face the Pirates

Cubs vs Pirates — There's going to be a little deja vu here for the next week, as the Cubs play seven straight games against the Pirates and Braves after just wrapping up six games against ... the Pirates and...

Cubs Farm Report | May 16, 2024: Brennan Davis Goes Yard in Iowa Loss

Brennan Davis' fifth home run of the season was not enough for the Iowa Cubs on Wednesday as they fell to the Syracuse Mets in a rain-shortened affair. That and more in today's Cubs Farm Report. Cubs Farm Report |...

Javier Assad is the Definition of Pitchability

Like his rotation-mate Shota Imanaga, Javier Assad has reached the point where, after every single start, you want to say the same thing: wow, that was awesome, this guy is good. It gets a little stale, in an extremely desirable...

Joe Buck is Returning to the Booth to Call a Cubs-Cardinals Game

I know that Joe Buck is a polarizing broadcaster. Some people love him. Some people hate him. I also know that he seems to have gone through phases in his career where there were stretches I thought he was mutably...

Pete Crow-Armstrong Put on a Show, and Continues to Make a Strong Case for Continued Playing Time

Pete Crow-Armstrong put on a show last night, which I mean in the most literal sense. It was more like a performance than a baseball game. Bases-loaded HBP while showing bunt? OK, sure. Running easily to first on a dropped...

Latest News

Red Sox vs. Cardinals: Free Live Stream, TV Channel, How to Watch

On Friday, in a series opener at Busch Stadium, Brayan Bello starts for the Boston Red Sox (22-21) against Kyle Gibson and the St. Louis Cardinals (18-25), with first pitch scheduled for 8:15 PM ET.If you're planning on watching this...

How to Watch Rangers vs. Angels: Live Stream or on TV

Marcus Semien and the Texas Rangers (23-22) host Taylor Ward and the Los Angeles Angels (16-28) on Friday in a series opener, with first pitch at 8:05 PM ET.Keep reading to find out all the details on how to watch...

Pirates vs. Cubs: Free Live Stream, TV Channel, How to Watch

The Pittsburgh Pirates (19-25), led by Connor Joe, visit Nico Hoerner and the Chicago Cubs (25-19) at 2:20 PM ET on Friday in a series opener.See how to watch the Pittsburgh-Chicago matchup below.When is Pirates vs. Cubs and when does...

The Mini-Break Pays Off: Ian Happ with a ROCKET Home Run!

After a red-hot first ten games of the season (172 wRC+), Ian Happ had gone ice cold offensively. Aside from continuing to take his walks (he always does), his overall production plummeted to the point where Craig Counsell game him...

Kevin Alcantara Doubles, Matt Shaw Singles, and Moises Ballesteros HOMERS THEM ALL IN!

Brennen Davis isn't the only hot Cubs prospect. In fact, Moises Ballesteros is basically THE hot Cubs prospect of the season so far. And tonight, after two of the Cubs top prospects — Kevin Alcantara (on a double) and Matt...

New York Yankees vs. Chicago White Sox Series May 17-19: Odds, Starting Pitchers & Predictions

The New York Yankees will be hosting the Chicago White Sox for a three-game series, with the first matchup getting underway at 7:05 PM ET on Friday, May 17.Yankees vs. White Sox Series Info White Sox @ Yankees Time: Friday,...

Baltimore Orioles vs. Seattle Mariners Series May 17-19: Odds, Starting Pitchers & Predictions

A three-game series featuring the Baltimore Orioles and the visiting Seattle Mariners will begin on Friday, May 17 at 7:05 PM ET.Orioles vs. Mariners Series Info Mariners @ Orioles Time: Friday, May 17 at 7:05 PM ET Orioles Starting Pitcher:...

Toronto Blue Jays vs. Tampa Bay Rays Series May 17-19: Odds, Starting Pitchers & Predictions

In the opener of a three-game series, on Friday, May 17 at 7:07 PM ET, the Toronto Blue Jays are hosting the Tampa Bay Rays.Blue Jays vs. Rays Series Info Rays @ Blue Jays Time: Friday, May 17 at 7:07...

Atlanta Braves vs. San Diego Padres Series May 17-20: Odds, Starting Pitchers & Predictions

The Atlanta Braves will be hosting the San Diego Padres for a four-game series, with the action getting underway at 7:20 PM ET on Friday, May 17.Braves vs. Padres Series Info Padres @ Braves Time: Friday, May 17 at 7:20...

Miami Marlins vs. New York Mets Series May 17-19: Odds, Starting Pitchers & Predictions

The New York Mets are on the road, opening a three-game set versus the Miami Marlins on Friday, May 17 at 7:10 PM ET.Marlins vs. Mets Series Info Mets @ Marlins Time: Friday, May 17 at 7:10 PM ET Marlins...

more cubs news