Jason Ross

They're not using this as a bridge year. I'm not overly enthused by what we have heard so far, but they're not just getting a bunch of 1 year deals here. Especially to bridge to: - Guy on 2nd TJS in under half a decade - Guy who had neck surgery and hasn't been healthy enough to finish a year in the rotation - Guy who was objectively not good last year and hasn't pitched in MLB. Also who has injury history galore. - Guy who hasn't thrown professional pitch. They are all interesting prospects and dart throws. But all four are massive, massive risks. Anything you get out of them (as of today) in the rotation-of-the-future is great but absolutely can not and will not be counted on in 2028 (yet - maybe that changes in the summer). And an off-season plan this year that centers around them building out the next rotation is suicidal.

Yeah, I don't think it's a great market to do that, either. My hope was that where Jed really excels is with "deadlines" and that with multiple deadlines (CBA and whatever "Spring Training" will be) would give him multiple times to flex his muscles there. Initial reports don't make me feel comfortable with what the team feels like they're going to do in November, though, because it's been almost "we're out" talk and nothing that would even indicate the Cubs "in" on anything. And it'd be one thing if they were just out on a few guys, but it seems like every player they're out on right now and I'm not sure where that leads me to think they'll get much done in November. Hope it's posturing but they rarely posture in the media.

I've thought about that. But we have seen a handful of articles that suggest teams will be aggressive before the lockout too. My hope is that we're seeing Ricketts play poor here pre-lockout in the thought of "we are going to be ownership-strong" and that is why we're hearing all of the "we are out" stuff. But I also know that's kind of the rosy-way to look at this. The Cubs deciding to get back under the LT, whatever the LT is, feels like it's equally a possibility. As does the Cubs thinking a bit that their model is right and they're going to outsmart everyone to a degree. Brendan Miller mentioned the other day elsewhere that he had a fear that the Cubs' internal model is what keeps the ceiling a bit low and that they sometimes underestimate what bigger additions can do (re; Skubal) and I can see that playing a factor here.

The Athletic ran another article today. Source, For those who don't have access, a few hitters: - The Cubs are highly unlikely to resign Suzuki - Reunion with Happ possible on short term deal if his market is light - The Cubs will check in on Sato but that will get too high for their comfort - They won't involve themselves on Arozarena - A "veteran" in the OF who will take 1 or 2 years is possible - Team likes Shaw and Ramirez in the COF - Bullpen is not a priority - but maybe another Maton level deal. - Catcher is not a priority - team likes Ayers "at the start of the season" - Maybe "budget will be there" for Kelly or another veteran So far the reporting has been mostly "Debbie Downer" stuff, to be honest. I can't tell if the Cubs are playing a game where they are going to cry poor until a new CBA is in place as a negotiation tactic or the budget just really isn't there. But I'm not overly jazzed with what we're hearing so far.

They don't have the guns to get that done. The ask was absurd this deadline, they don't really have a baseball OPs guy either and their owner wants to make them a destination team. Detmers isn't happening.

To be fair, I wouldn't sign Michael King, either.

What I also like about the list is that there are at least 8 or 9 guys on this list who have a lot in ways of "ceiling". It's a low ranked system but there's upside here. I'm okay with that.

Anything from Crane is from Tom, sadly.

Exactly this. And I think with how Sharma reports, you can guess who this is coming from. The Cubs want to temper your expectations right out of the gate. I'd also guess that's coming from beyond Hoyer. And that's a particular point of paint for me. This isn't how you approach a second 90-win season with the gaps you have, IMO. And we can "yadda yadda" all we want about what we expect, but I'm frankly fed up with having to accept and expect less from the ownership. And I'll get pissed off every time it happens.

The Athletic wouldn't rule it out but suggested the Cubs weren't going to go massive on either. The QO will keep them away from Morejon.

I would be very surprised if they make an offer to Morejon.

In their defense, after 2017 they went out and signed Yu Darvish to a massive deal just a few years after they signed Lester to a massive deal. I kind of wish the Cubs acted like it was that time a bit more often.

Outside of Skubal, there really isn't a "splash" to be made, however. That doesn't mean "aren't good players" but there isn't anything else on the entire market I'd consider "splashy". The splashy names are some of the guys I'd stay away from (King, Peralta) and the others who might be pretty solid (Rogers, Holmes) probably aren't overly exciting on their own, even if they're solid arms.

I would have no issues if the Cubs went into the Skubal thing, offered him a very lucrative offer that matched market rate and he chose another organization. You cannot force someone to sign. What I have issues with however is not trying and telling the world you're not trying. It's pathetic. And if Sharma is reporting it, the Cubs are almost assuredly not trying. It isn't like this is even coming from notable debbie downer Jesse Rogers. Sharma doesn't miss.

The Cubs are not going to spend like the Dodgers and Mets., they are sitting out Skubal. Team will look at groundball pitchers.

Zero interest in Will Warren unless you have a real developmental plan there. He has zero feel for anything that moves. None. His sweeper sucks and is routinely bashed. He's a low-arm slot guy so "sweeper?" is usually a go-to pitch there and this thing doesn't work. Below average whiff, he leaves it over the plate constantly and guys crush it. Matt Shaw has warts, sure, but you're going into next year at least confident he's good defensively at multiple positions and a solid weak-side platoon hitter. I have zero confident in Will Warren. And it isn't like the Yankees are some bad pitching developmental organization. They can keep Warren.

I'm sorry, I gave them too much credit. The Athletic and Sharma reports the Cubs will not be involved in Skubal. And listen, you can say a fine offseason can be had or whatever, but this is horsefeathers behavior from a big market team to declare yourself out on November 9th. Sell the horsefeathers team if you have no aspirations, Tom. Considering this comes from Sharma and so close to the Passan article last week, I'd assume the Cubs have set their budget. And I'm not particularly feeling very strong about said-budget considering.

Last time we had a CBA increase, it went up $20m. If we assume the LT line, it'll be close to the final 2026 payroll. They could realistically spend over that line. But I'm not entirely sure where the line will be.

I apologize to the world early: *if* Kentucky wins, I'm going to be real insufferable for a while.

Yeah, I think the rotation is in just a bad place right now. And you can probably build out a decent enough rotation from the other parts. Like a Clay Holmes, Sonny Gray, David Peterson, Edward Cabrera, Justin Steele rotation has the chance to have a lot of low end #2s across most of it. But you're still missing a hoss, there's significant risk in the final two and then I wonder "what the real upside here? Is that good enough?" And then I just come back to this idea where they just sign the best player.

Every time I look at the permeations of this offseason I keep coming back to "but why not?" on Skubal. Most every argument I have against him is generally me giving into the whims of an owner who doesn't spend enough and I just can't allow that this time. If the CBA goes up another $20m, this organization has roughly $100m to spend. If you give me $100m, I can get: Skubal (43), Taira (15), Peterson (15), Sanchez (5), Butler (9) Conforto (7), Cleavanger (5) and still have spare change (and I might even be a little high here or there). This is a lot of rough napkin math so we can quibble on some numbers and some names but it leaves you with a full rotation, two LHH platoon guys to pair with Shaw, Ramirez, and Alcantara, a backup C who can DH/1b and a LHP with velo. Maybe you swap out a name; lets say you like Grisham more than Butler or Varsho, but you get the point. I like that team, mostly. There's probably some mix-and-match DFA guys who slide into places too. I'll admit that this plan probably banks on the Cubs figuring out someone from the Steele, Brown, Cabrera, Taira group to fit as a "decent second best option" and one of them as a "decent bottom end guy" but I also feel like I have the best foundation in the rotation with Skubal to offset some of that (he's a stabilizing force for some risk) and there's a reason Zombro and Hottovy are here; to help bridge that gap. And I think somewhere you're going to have to take a little bit of a gamble on something. But that's me. I think I'm very hard in the camp of "Just go get me Skubal and stop horsefeathers around". You get so few chances at 6 win pitchers. And I just cannot get behind a "Well Tom didn't want to". Nah, horsefeathers that horsefeathers. Enough excuses. Just go be the Cubs one time.

"The Chicago Cubs should sign the best player on the market" feels like a pretty obvious statement. "Yeah, no [duh], Sherlock" may go through your head when you read that, and it's a fair thought, On the surface, it isn't really much of a hot take. But give me a little space here, because I think there will be a lot of people who will find reasons to push back on me saying that about Skubal. They'll point to the cost of the contract (Skubal will set the record for AAV for a starting pitcher this offseason), the agent (Skubal is represented by Scott Boras, which really just reinforces the first point), or starting pitchers and their injuries (the Cubs had the fourth-most days missed due to time spent on the IL in 2026, so we're well acquainted with how things can go belly-up) to argue why the money should be spent elsewhere. I'm here to tell you this: the Cubs should ignore that noise and just sign the best damn pitcher on the market. Tarik Skubal is Awesome, and the Cubs' Rotation Isn't Let's start with the stuff we all agree upon: Skubal is awesome. From 2024 through 2026, Skubal led the world in starting pitcher fWAR, at 18.0. That's more than Cristopher Sánchez, Chris Sale, Paul Skenes, or Zach Wheeler (or anyone else, but you get my point). In the same span, he ranks second in ERA, second in expected ERA, second in xFIP, and fourth in strikeout rate, and he has the second-lowest walk rate among qualifying hurlers. It doesn't matter what statistic you look at; he's awesome. And one more thing: Skubal has the fourth-most innings pitched over those three seasons; he's available. It's one thing to have all the talent in the world, it's another to be able to use it. Outside of a small blip this season, Skubal has been a better combination of dominant and durable than anyone. The Cubs' starting rotation is decidedly not awesome. The team has a massive need for starting pitching, making the initial fit an easy argument. Last season, the Cubs were a bottom-10 team in almost any category you can name, including fWAR (28th), xERA (24th), K% (23rd), and homers (29th). The team attempted to address this issue at the deadline, but due to the prices of controllable pitching, they were left trading for Clay Holmes, David Peterson and Kevin Gausman, all of whom are free agents. To make that happen, the team had to once again unload useful prospects. This time, that meant Jefferson Rojas, Cole Mathis and Mason McGwire. As of this writing, the Cubs' 2027 rotation is quite murky, too. It's a mixed bag of injured pitchers who have massive question marks surrounding their future (Justin Steele, Cade Horton and Ben Brown) and players who have talent but have been ineffective (Edward Cabrera). Behind them in the farm system, there are no clear-cut candidates to step into a top-of-the-rotation role. The team hopes first-round pick Cade Townsend will be "that guy", but he hasn't thrown a professional pitch yet, so it's best to hold off on the coronation. Jaxon Wiggins has flashed the stuff, but last year was a year, he dealt with his own issues of ineffectiveness and injury. Solving the issue internally doesn't feel like a very likely scenario in the interim, so the help has to come from outside. Starting Pitchers Get Hurt Sometimes, But They Age Better Than Hitters If you're feeling snakebitten by starting pitchers, I wouldn't blame you. Last year was a particularly rough season for the Cubs on this front. Horton and Steele combined for under eight innings. Brown looked like a possible rotation anchor for a short time, but spent the second half on the injured list. Matthew Boyd had knee issues stemming from playing basketball with his kid. The Cubs weren't alone in this regard, of course. Pitchers get hurt all the time, and more often recently than ever before. Major League Baseball has looked into it themselves. Stints on the shelf for pitchers rose sharply from 2017-2024, with the vast majority of them happening early in the year. There is an injury crisis affecting pitchers right now, and we'd be fools to ignore it. Obviously, though, keeping it in mind can't mean allowing it to dissuade you from all investment in hurlers. Yes, pitchers are getting hurt more often, and yes, teams are more cautious than ever with starting pitchers. As a result, however, pitchers who don't break age better than their position-playing counterparts. Hitters, not pitchers, decline earlier. Hitters over the age of 35 are becoming vanishingly rare. In 2024, just 4.1% of all plate appearances in the majors went to hitters in the back half of their 30s. We have plenty of data that shows that by the age of 32, bat speed begins a fairly rapid decline. This year, only three hitters aged 35 or older had a wRC+ over 105: Freddie Freeman, Nolan Arenado and Max Muncy. They're also the only three players to hit 2.0 fWAR at that age. Not one player aged 37 even got enough playing time to qualify for the batting title. Compare that to pitchers aged 35 and up. The number of 35+-year-olds who got to the 2.0-WAR bench mark was more than double that of their hitting counterparts, with seven. One of those was Nick Martinez. Two pitchers over the age of 37 posted 4+ fWAR, and but for Jacob Misiorwski's unbelievable season, Chris Sale would have had a good argument for the NL Cy Young Award. It's not a one year thing either. There were eight pitchers who had more than 2.0 fWAR in 2025 over the age of 35, compared to just three hitters. Pitchers age better, in every sense except that their careers are more likely to be permanently and substantially diminished (or even ended) by injuries. Signing a starting pitcher to the kind of deal Skubal will require probably means absorbing a year lost to injury at some point. But you can make up for that. While a hitter signed to a 10-year deal can become a multi-year albatross, pitchers have a better aging curve. Zack Wheeler, who had a deep-vein thrombosis in August 2025, proved this year that you can come back from a nasty surgery and thrive again even in your late 30s. The best pitchers tend to last, and Skubal is that kind of pitcher. Repeating History; The Jon Lester Story Jed Hoyer has been around the Cubs organization since he was brought on by Theo Epstein upon Epstein's arrival in 2011. He was there when the Cubs made a massive statement in the winter of 2014-15, bringing in proven winner Jon Lester. He saw the fruits of that contract, as Lester helped lead the Cubs to a 2016 World Series title and was worth 16.8 fWAR during his time on the North Side, being useful through his age-35 season. Lester brought a winning mentality. He was an absolute bulldog on the mound, who already had a playoff starter's résumé. Jon Lester was a dude in the World Series. You may remember him in Game 7, but let's not forget what he did just two games earlier. Game 5 of the 2016 World Series is sometimes overshadowed by the more climactic games that followed in Cleveland, but it was the pivot point in that series. Down 3-1 to Cleveland, the Cubs were on life support at home. The offense had gone cold, and Cleveland smelled blood, looking to finish things off at Wrigley Field. Lester shut down that Cleveland team, limiting the visitors to just two runs over six innings as the team held on after a three-run offensive outburst early in the game. Lester was able to hold out long enough for Aroldis Chapman to get the save. The Cubs haven't had a Lester-caliber stopper in the last two years, and it's showed. In 2025, they got knocked out by the Milwaukee Brewers because they didn't have the horses to match up in the rotation. In 2026, when the Cubs went against the San Diego Padres, they got knocked around early in Game-1 and couldn't match Nick Pivetta in Game 2. Their vaunted offense went cold, and they didn't have a strong enough starter to keep them breathing until the bats could wake up. To make the Lester deal happen, the Cubs had to go well above their normal spending pattern. Before the lefty agreed to a 6-year, $155-million deal, the team had only eclipsed the $100-million mark once—way back in 2007, with outfielder Alfonso Soriano. We're now over a decade beyond the ink drying on that contract, and the Cubs have yet to go above $200 million. While the deal that Skubal will eventually sign should dwarf (as in more than double) the size of Lester's, that cannot be the excuse for not making that leap. No Time is Perfect, But Now is Close Enough The Cubs can't allow imperfections in timing or in a player's profile to be the reason they never make the big move. It's easy to think there will be a "next" or a "better" time, but there's never a better time than "now". When the Cubs signed Lester, they were fresh off a season wherein they won 73 games and finished dead last in the NL Central. That didn't stop them from breaking from their decades-long spending pattern. The current iteration of the Cubs has won more games than they lost four years running and has made the playoffs in the last two. They have the best position player on the planet, and another top-10 fWAR player on the roster. Alex Bregman and Dansby Swanson are marching into their mid-30s, and while I'd love to believe Pete Crow-Armstrong is going to remain one of the best position players on the planet, the odds are that 2026 will be his peak season, and that 2027 will be his second-best. The Cubs are better positioned to add a special pitcher than they were in 2015, and they're certainly better positioned to benefit from that kind of addition than they'll be a year or two from now. The market is shaping up for the Cubs to be a massive player here. The Los Angeles Dodgers, the equivalent of MLB's bogeyman, seem to be in an odd place financially. Mark Walter, the Dodgers' owner, is in some legal hot water at the moment. Reports are that the Dodgers may only want Skubal on a Kyle Tucker-style short-term, high-AAV deal. Walter is also currently looking to get out of his backing of a Cadillac F1 team, just one year into the project. There will be other big bidders, but if the Dodgers are less aggressive than they'd otherwise be, the Cubs have to seize the rare opportunity. To be good next year, the Cubs have to spend more than they've ever spent before, and they can't by any means stop with Skubal. But it also won't require them to become the Dodgers or the Mets. In 2019, the Cubs had the third-highest payroll in baseball at around $191 million. In 2026, the fifth-highest payroll was the Blue Jays, at $270 million. The CBA is going to play a part in this, but if recent history shows us anything, there is likely to be an increase in the luxury tax again. The last CBA saw the lowest tax threshold increase $20 million in one offseason. Another, similar bump from $244 million would put that bottom threshold around $265 million. That would give the Cubs well over $100 million to spend on 2027 alone, leaving $55-$60 million after Skubal signed—enough to fill out a good roster. As mentioned above, Skubal's agent is Scott Boras. Not everyone has a great relationship with the super agent. He can be corny and grating. He really strings things out. But the Cubs and Boras have a working relationship, which should grease the wheels. Some teams can be turned off with Boras's involvement, but the Cubs aren't one of those teams. They brought in Bregman via Boras last offseason. These two sides know each other and that gets your foot in the door. In Summary: Just Do It There are a lot of hurdles to make this happen. It's going to require the Cubs to first accept that their spending model needs an update. When the Cubs signed Lester, it was the 19th-largest contract ever; it is now not even in the top-70. FanGraphs recently put out an article looking at free-agent predictions for contract sizes. Their crowdsourced data put the predicted contract for Skubal at $335 million, which would make it a top-10 all-time contract. FanGraphs writer Ben Clemens was higher, at $380 million—the highest ever for a pitcher and fifth place all-time. But young pitchers like Cam Schlittler, Misiorowski, and Skenes will easily eclipse that deal in the future, much like others eclipsed Lester's. It doesn't feel like an impossible ask in that context. Secondly, it's going to require the Cubs to accept that this is a unique opportunity. How many times are you going to have the best position player in baseball on a nice contract? How many more good years do Bregman and Swanson have left? How often will you have a need this glaring on a team with this good a chance to be good? How much more perfect does it have to be? If this isn't the guy you're going to be irrational about, who the hell is? The good news is there is some smoke here. They looked into him at the trade deadline, but clearly that didn't go far. Jeff Passan has mentioned they "want him badly". The bad news is that in that same article, Passan mentions the Cubs may be unwilling to spend what he'd need. I'm begging them to give in and pay up, this one time. Ultimately, I have the easy task of spending someone else's money here. I'm not shelling out $380 million of my own dollars (granted, I also am not sitting on a franchise with an estimated net worth of $5 billion) to get this over the finish line. But if the Cubs want to get to a point where they don't have to trade good prospects for rentals (like they did at this deadline); if they want to get to a point where they are getting back into the conversation of a bye in the first round of the playoffs; and if they want to avoid another year "slipping away", no other player in this market seems as stable as Skubal or fits the organization's needs more neatly. What do you think the Cubs should do regarding Tarik Skubal? Should this be the player they break the bank for? Let us know in the comment section below. Image courtesy of USA TODAY Network via Reuters Connect View full article

As it pertains to Morejon starting, I think it's important to remember that this is now the third offseason in a row that one of the best relievers on the market has been a "convert into SP option" with the prior two being Brad Keller (2025) and Jeff Hoffman (2024). Those two have combined for zero starts. You can argue some things like: - Brad Keller and Jeff Hoffman had already been a failed starters at the MLB level - That they're both in a different situation than Morejon And those things might be true. Yeah. But Morejon was also a starter in the minors so it's not entirely different and he moved off it for a reason. Before this, the Giants tried that with Jordan Hicks. He was terrible. He has only since found success again in the bullpen. But it's interesting we're at, yet, another "maybe we can start this relief ace" offseason and the prior two never came close to that flip. I think it's more likely that Morejon never makes another start in his MLB career than he becomes an established SP, let alone a top of the rotation guy. He's a fun gamble, but that's what he is: a gamble in the rotation. One that costs a QO.

Reverse split pitchers create interesting conundrums. And I'm all for them. When the Cubs bring in a RHP like Webb who gets LHH out well, it forces the other team to react. "Do I take out my good lefty? Or do I let him hit?" and having those kinds of options are good. But yeah, getting another lefty is probably a good thing. Greg brought up Garrett Cleavanger as a choice and I really like his velo. They could maybe find a DFA or fringe option to add, as well. You likely feel pretty good about Rollison and Webb here but a third solid option can make things a lot easier.