February 23rd, 2024: Snell, Rotation, Extensions, Mailbag

Self-promotion: I wrote a thing at CBS looking at Gerrit Cole’s contract and his upcoming opt out. I think the most likely outcome is Cole uses his opt out and the Yankees pick up their club option to void it, but it’s not the only possible outcome. I ran through a few other scenarios. Check that out if you want, or just click the link and slowly scroll to the bottom. Either works for me. Let’s now get to today’s post. (If you haven’t yet, make sure you vote in the leadoff hitter poll. It closes at 12pm ET Friday.)

1. The latest on Blake Snell. Opening Day is four weeks and six days away and yet Cody Bellinger, Matt Chapman, Jordan Montgomery, and Blake Snell remain unsigned. The Yankees reportedly touched base with all four over the winter, though the connection to Snell is most persistent. Here’s the latest on the Yankees and the reigning NL Cy Young winner:

• Last weekend it was reported the Yankees still have “serious interest” in Snell, and Mark Feinsand then added the Yankees have an offer on the table.
• Andy Martino says there is no momentum toward a deal and one source told Randy Miller that the Yankees having an offer on the table is “BS.” Alrighty.
• The original offer to Snell – $150M several weeks ago – did not include any opt outs, and was made before the Yankees signed Marcus Stroman, per Brendan Kuty.
• Earlier this month it was reported the Yankees pulled that $150M offer and have “moved on.”

Seems to me there is some negotiating through the media going on, and given the tone of these rumors, it sounds like Snell’s camp (i.e. Scott Boras) is trying to drum up interest. The Angels and Giants are said to be in the mix for Snell and Boras could be looping the Yankees in to try to get those two teams to up their offer. If the Yankees are interested, quickly and forcefully shooting down these reports is a weird way to show it.

Aaron Judge piqued some interest the other day when he said “I definitely feel like there might be another move on the way,” though that was one line in a longer quote. Here’s the full answer Judge gave when asked if he thinks the Yankees have another move in them (you can see it at the 20:00 mark here):

"I hope so. They're always working. The thing that's amazing about being here with the Yankees is they're always trying to improve, they're always trying to make moves. If it's via trade, if it's via free agency. So I definitely feel like there might be another move on the way. But you never know. We'll see."

I dunno, that doesn’t sound like a guy hinting at another move being in the works. That sounds like a player who has been media trained to the nth degree saying his team always tries to get better. Ultimately, this is all just noise. The rumors and reports and quotes and whatnot. The Yankees made Snell an offer at one point and I am sure they’re willing to go back to the table and hear him out. I doubt the door is closed.

As it stands, the rotation is potentially excellent, though it comes with a fair bit of injury risk. More than the usual amount of injury risk, I’d say. Snell can be a chore to watch, but he’s really good even when he’s not winning Cy Youngs. He’s become underrated, somehow. He’s a top tier bat-misser who limits hard contact because he rarely makes mistakes in the zone. Snell walks a lot of guys, but he also doesn’t allow many hits.

It’s funny too, because the future of baseball is Blake Snell. Go look through the top 100 prospect lists and read those scouting reports and look at the stats. So many top pitching prospects are guys with big strikeout rates who walk a few too many, and won’t be allowed to go through a lineup a third time. Kyle Harrison, Jacob Misiorowski, Ricky Tiedemann, even Chase Hampton and Will Warren. Snell is the archetype. Teams are developing little Blake Snells and don’t want to pay the actual Blake Snell.

Anyway, the Yankees could use another starter and a literal Cy Young winner is available, so the Yankees should sign Snell (or Montgomery, if that’s who they prefer) and pay the 110% tax rate to make it happen, because that’s what it’ll take to field the best possible team given the decision-making losing streak they’ve been on the last few years. What Snell would mean for keeping Juan Soto is something to worry about later. The Yankees can sign and re-sign everyone. They just like to pretend they can’t.

Nothing that happened this week, be it those rumors or Judge’s quote, leads me to believe the Yankees are any closer to signing Snell than they were 3-4 weeks ago. If it happens, great. The Yankees will be a better and deeper team, but I would be surprised. It’s been a good long while since the Yankees went above and beyond and made that one last unexpected big move. The last was … Mark Teixeira?

"I'm not going to get into free agents. I'm just going to tell you that we continue to look at a lot of different options,” Hal Steinbrenner told Bryan Hoch on Thursday. “Given where we are payroll-wise, any addition to the club is going to be a costly one, but I'm still willing to consider anything that comes my way. Anything (Brian Cashman) and his team bring my way. I'll leave it at that. But we are not done trying to improve this team."

2. Rotation order takes shape. The Yankees begin their Grapefruit League season Saturday and, alas, the spring opener will not be televised. They open on the road against the Tigers, and Bally Sports is not airing that game. We’ll get two games Sunday though. Both split squad games will be televised. A Reddit user put together a helpful spreadsheet with the spring’s broadcast info, so there’s everything you need to know. No game Saturday but two games Sunday. I guess it’ll have to do.

I thought about recapping some Spring Training news and notes here today, but gosh, there’s nothing worth writing about until the games begin. I don’t have anything to say about how slimmed down Carlos Rodón and Giancarlo Stanton look in live batting practice. Those are “best shape of his life” stories without saying the magic words. You’re smart. You know we need to see it in games to believe it (and not just in spring games either). Games are coming soon and we can circle back then.

For now, I just want to quickly note the starting rotation order is taking shape. Nestor Cortes and Marcus Stroman were told they are starting the exhibition games in Mexico City on March 24th and 25th, according to Bryan Hoch. The Yankees give their starters an extra day of rest going into their regular season debut, which means Cortes and Stroman are lined up to start the third and fourth games of the regular season.

Also, Stroman threw live batting practice Monday and Cortes did it on Tuesday (here he is striking out Juan Soto on three pitches), indicating it’ll be Stroman in the third game of the season and Cortes in the fourth. Rodón also threw live batting practice Monday, so he and Stroman are on the same schedule. Obviously that’ll change at some point in these next five weeks, but their schedules are close enough to know Rodón is lined up to start the second game of the season, not the fifth.

Gerrit Cole will of course start Opening Day, and the process of elimination says Clarke Schmidt will start the fifth game. Nothing surprising there. The Yankees begin the season with seven games in seven days, so they won’t be able to skip their fifth starter the first time through the rotation or anything like that. The Yankees usually don’t do that anyway. They really ease their guys into things early in the season.

Right now it’s Cole, Rodón, Stroman, Cortes, Schmidt in that order to begin the regular season, pending the entire Grapefruit League schedule. It doesn’t take much to throw things out of whack. Remember who started the second game of the regular season last year? It was Schmidt. Remember who started the third game? It was Jhony Brito. This is all tentative. Also tentative, this weekend’s rotation:

• Saturday vs. Tigers: Luis Gil (no TV)
• Sunday vs. Blue Jays: Carlos Rodón (YES)
• Sunday at Phillies: Marcus Stroman (Phillies TV)

Monday’s a home game against the Twins and Nestor Cortes lines up to pitch that day. Tuesday is a road game against the Rays. That feels like a “send a bunch of non-roster guys on the road to face a division rival” game. Bally Sports is airing Tuesday’s game. I hope we get some Chase Hampton and Will Warren action, among others. Wednesday’s an off-day, the first of the spring for the Yankees.

(Hampton and Warren both threw live batting practice Wednesday. That lines them up nicely for Tuesday. Whenever they get into an actual game, I hope it’s televised.)

It’s too bad Saturday’s game won’t be televised. I was hoping to get eyes on Gil and see what he looks like post-Tommy John surgery (he is so trim now I didn’t even recognize him). I’ll have to wait a bit to see Gil in action. For now, the rotation order has begun to take shape, and with any luck, the Yankees will make it through camp in one piece, and no adjustments will have to be made to that rotation order.

3. Rapid fire thoughts. A few quick extension updates (or non-updates, really). Brian Cashman told Greg Joyce the Yankees haven’t had any talks about a long-term deal with Gleyber Torres – “He’s our second baseman for this year. Haven’t had any conversations about anything past that,” Cashman said – and Clay Holmes told Joel Sherman he’s had no extension talks with the Yankees yet. Torres has said several times he wants to remain with the Yankees – “I don’t want to leave here. I want to be a Yankee for life,” he told Erik Boland earlier this week – while Holmes said he’s focused on the season, yadda yadda yadda. Also, Cashman told Bryan Hoch he doesn’t “see too many things stopping (Juan Soto) from reaching free agency.” Not a shock there. The Yankees knew going in that keeping Soto beyond 2024 will require winning a free agent bidding war. Locking him into an extension before then just isn’t gonna happen. So, that’s the latest on the extension front. The Yankees aren’t pursuing any. Here’s what I wrote about possible extensions a few weeks ago … The Pirates signed Mitch Keller to a five-year, $77M extension earlier this week. He was two years away from free agency. I answered a mailbag question about Keller last month and noted he could be a trade deadline target if an extension didn’t get done, so scratch that idea. Keller is no longer a deadline possibility … Hyun-Jin Ryu, one of my favorite non-Yankees, is heading back to the KBO. The 36-year-old turned down MLB offers to return to the Hanwha Eagles on an eight-year (!), $12.7M contract that is the richest contract in KBO history (it’s a four-year contract stretched out over eight years to lower the luxury tax hit). Ryu’s rookie year with the Eagles was insane: 2.23 ERA in 201.2 innings as a 19-year-old, which earned him Rookie of the Year and MVP honors (and a lot of arm problems throughout his career). I signed Ryu as part of my 2018-19 Offseason Plan and I wish he would’ve found his way to the Yankees at some point. That guy had major David Wells vibes as a hefty lefty who seemed like he could roll out of bed in December and paint the corners. Farewell, Hyun-Jin. I hope there are no snakes back home …

… And finally, this flew under my radar last week, but Rob Manfred told Jon Morosi he would like the expansion wheels to be in motion when he retires in Jan. 2029. That doesn’t necessarily mean having awarded franchises – a committee has to review applications and whatnot, and that takes time – it just means starting down the road toward 31st and 32nd franchises. It’s fair to question whether there’s enough pitching talent to support two additional teams (there’s barely enough pitching for 30 teams), but who knows what the game will look like in 5-10 years? As someone who covers the game, an expansion draft would be very fun. Does the league really need to further water itself down? No, but it’ll happen anyway.

Mailbag Questions of the Week

Sandeep asks: It can’t be this simple, but does G’s setup at the plate have something to do with him not being able to catch up to high velocity? Seems to me that because of the angle of his body in his extreme closed stance, his bat setup position must be further away from the back of then plate than if he stood straight on.

A hitter’s setup at the plate can absolutely have something to do with his ability to catch up to velocity, and not a little something either. It can make a huge difference. I couldn’t tell you the best stance for handling velocity, though it’s probably different for every player. For what it’s worth, Giancarlo Stanton told Chris Kirschner he made some swing changes over the winter, but wouldn’t provide any details.

Here’s Stanton hitting against Dennis Santana earlier this week. If you can see a difference from last year based on that one swing from that angle, you’re way better at this than me. Grapefruit League games start this weekend and we’ll get a better look at Giancarlo (and everyone else) then. And even then, swing changes can be so small that they’re almost impossible to see with an untrained eye.

Stanton’s extremely closed stance has long been a hot topic because it looks weird, but the guy did hit 59 homers and win an MVP with that stance. Can you blame him for sticking with it? Now that he’s 34 and coming off two poor years, it’s time to adjust. And he might not even adjust his stance. Stanton said he’s made changes to his swing, which is not necessarily the same thing as adjusting his stance. We’ll see.

Steve asks: If the Yankees sign Juan Soto to some 15 year contract, aren't you kind of worried he'll be a DH or have to move to 1B in 5-6 years? I know RF is tiny in Yankee Stadium but his defense is already rough at 25. I would still sign him, but unless he's a 140-150 wRC+ guy his contract will be a massive albatross since he doesn't give you anything else outside of his bat. Would signing someone like Alex Bregman (obviously a bad fit as a RHH, but this is just an example) who provides value on both sides of the ball be a better long term fit? Someone like Bregman would also require less AAV and fewer years on his contract. Obviously I'd still sign Juan Soto and worry about everything else later, but I'd like to hear your thoughts.

I answered a similar question in December and my answer hasn’t changed. Soto is a generational hitter, so buy the bat and figure out the defense later. The obvious comp is Miguel Cabrera, a similarly precocious talent who was immediately one of the best hitters in the game when he was called up. The Tigers signed Cabrera long-term and let him ride the bat to the Hall of Fame. The contract became an albatross, but not until he was at the very end of the line.

To use Steve’s example, Bregman is a nice player, but he’s been closer to All-Star level than MVP level since hurting his wrist (and the Astros got caught stealing signs), and he’ll be 31 in the first year of his free agent contract. Bregman has a pretty good chance to turn into an albatross too. Next offseason’s other top position player free agents are Pete Alonso and Gleyber Torres. Good players, both of them, but neither is particularly close to Soto’s age and production, and expected production moving forward.

We went through the “but his defense is bad” thing with Bryce Harper years ago. The Yankees passed on Harper and so many other prime-aged stars (Manny Machado, Corey Seager, etc.) and those decisions have proven to be disastrous. Franchise-altering levels of bad. Soto is not a good defender, but he’s not late career Bobby Abreu either. You can always put a poor defender at DH. It’s a heck of a lot easier to do that than to have one of the best hitters in the game on your roster in his prime.

Darren asks: Reading the comments from Boone and everyone else in the Yankees organization about how Carlos Rodon is in great shape and how “it’s like night and day from last year“ are somewhat infuriating. After signing a $162 million contract, it’s pretty incredible that Rodon apparently didn’t put any effort into showing up healthy or in shape last year. It’s obvious it wasn’t just injuries. It was effort that he lacked. Am I supposed to be happy now? Or trust him over the long-haul? Has any player in your memory started out a big long-term contract so terribly in year 1 and then actually rebounded to have a good few years?

It’s a bad, bad look for Rodón, yeah. A player’s weight is the kinda thing no one cares about until he’s not performing (unless it’s Bartolo Colon, who was treated like a lovable mascot at the end of his career even while throwing batting practice). CC Sabathia’s weight was a non-issue until he began to decline. Same with Pablo Sandoval when he stopped being one of the greatest postseason hitters ever.

Was Rodón hurt and bad last year because he was not in the best shape? Or did he get hurt because he’s gotten hurt plenty throughout his career, and the injuries took away from his preparation and effectiveness? I don’t know. The folks in Tampa say Rodón is in noticeably better shape and that’s great. Whether it leads to results remains to be seen, and Rodón has not earned the benefit of the doubt. He has a lot to prove moving forward, both performance-wise and just in overall commitment.

As for the last question, I can’t think of anyone who signed a big money long-term deal and had as bad a Year 1 as Rodón, and later bounced back. Francisco Lindor’s first year with the Mets wasn’t great, though he was still healthy and a league average shortstop. Zack Greinke’s first year with the Diamondbacks was pretty meh, but it was worlds better than Rodón’s first year with the Yankees. We’re hoping for a reverse Patrick Corbin here. Going from the worst pitcher in baseball in Year 1 to great thereafter.

C.J. asks: Based on some public comments, Aaron Judge seems to be a constant presence in Cashman’s ear about personnel. By comparison, I don’t recall Jeter expressing such an interest in personnel. I’m wondering if you’ve noticed this too/have any thoughts or reactions to it?

Derek Jeter definitely wasn’t as publicly vocal about improving the team as Judge, but Jeter also won four World Series titles in his first five seasons, which changes the calculus. Judge is still seeking his first World Series and he’s watching his prime years tick away. Jeter also didn’t have an owner who cut payroll multiple times during his prime. That infuriated me as a fan. Imagine being on the roster, going to Game 7 of the ALCS in 2017, and then ownership rewards you by cutting payroll the next year? I’d be furious.

Judge has been outspoken about improving the team. We also haven’t seen much evidence suggesting the front office and ownership are listening to him. Was Judge the reason the Yankees traded for Juan Soto? Or was that just a no-brainer baseball move? Should we blame Judge for Carlos Rodón? My biggest takeaway is Judge is frustrated, and he’s comfortable voicing his opinion now that he’s locked up and been named captain. Whether his words have actually spurred any action is unclear.

Anthony asks: Do you think there’s anything fishy going on with the lack of interest in some of these FAs? Snell is a 2 time CYA winner and it seems no team has interest. Montgomery? Chapman? Even Bellinger is risky but nobody biting? And now MLB says they would love to add a signing period to the offseason. There has to be some level of collusion going on here, right? It just seems quite concerning for non elite free agents going forward.

I don’t think teams are colluding, at least not intentionally. I think it mostly has to do with the bar to get into the postseason being so low. Why spend an extra $20M to go from 88 wins to 92 wins when 88 wins can get you a Wild Card spot? The four Scott Boras clients – Cody Bellinger, Matt Chapman, Jordan Montgomery, Blake Snell – get all the attention and that’s understandable, but others like Brandon Belt, Adam Duvall, Michael Lorenzen, Tommy Pham, Donovan Solano, and Michael A. Taylor are unsigned too. They’re not stars but they are legitimate Major Leaguers who can help a team. The stars will get theirs. They always do. The non-elite free agents feel the biggest squeeze. If a guy like Lorenzen, who signed one-year contracts worth no more than $8.5M in each of the last two offseasons, can’t get a job in this pitching landscape (i.e. there’s not enough of it), you have to question the teams and their commitment to winning, not the player and his agent.

(I keep seeing it suggested the top free agents will have to sign one-year “prove yourself” contracts, but a) Snell just won the Cy Young, how is he supposed to raise his free agent stock in 2024?, and b) Bellinger just did the prove yourself thing and had a tremendous season. Why should he take another one?)

Jon asks: It seems taken for granted that Verdugo will be starting in the outfield and Grisham will be on the bench. Maybe this is wishful thinking because Grisham slots so much more nicely into the outfield alignment alongside Soto and Judge, but what would it take for him to beat out Verdugo to be treated as a starting outfielder, with Grisham playing in center?

I think it’s simple: Trent Grisham has to out-hit Alex Verdugo. Grisham is an excellent defender, but the guy hit .191/.300/.347 (82 wRC+) in over 1,000 plate appearances the last two years. We just sat through a year of Harrison Bader hitting basically that (76 wRC+ with the Yankees in 2023) while playing great defense, and it was not fun. And it’s not like Verdugo is a slouch in the field. He’s not great, but he’s not bad either. I touched on this a bit when ZiPS projected Grisham better than Verdugo. The Yankees need offense more than they need outfield defense, so play Verdugo. And if Grisham forces his way into the lineup, great. My guess is he’ll wind up playing way more than we expect anyway. It always seems to work out like that.

Jason asks: There have been some recent rumors that the NYY are still interested in Dylan Cease, but have balked at the White Sox’s demand for Spencer Jones as the headline return. Am I crazy to think that this should be a no-brainer trade for the Yankees to make? Aside from the high variability in outcomes for a guy like Jones, it seems like the Yankees have other outfield prospects both near and longer term. Plus the time is now to take advantage of the Soto/Judge/Cole window, and Jones probably won’t be fully ready for another couple of years.

I don't think you're crazy and I agree with you fully, though I suspect we’re in the minority. A lot of people are very high on Spencer Jones, including FanGraphs, which ranked him as the 15th best prospect in the game earlier this month. Others, like Keith Law (subs. req’d) had Jones outside their top 100 prospects entirely (but in the 101-110 range). Other sites have Jones in the back half of their top 100 and that’s where I see him. Upside so great it can’t be ignored, but real flaws that must be corrected to reach that ceiling.

Jones, my No. 2 prospect, struck out a lot for a college guy in High-A last year and he has issues with spin. I don’t buy the “left-handed Aaron Judge” thing that is being forced down our throats. Judge is incredible at making adjustments, and for such a big guy, his swing is pretty short. Jones’ swing is not, and we don’t know whether he can make adjustments at the level Judge can. Most likely not, because few can. And even if he can, Jones is what, two years away from helping the Yankees? Probably three?

There are three ways to acquire top of the rotation pitching:

1. Develop it yourself.
2. Trade top prospects for it.
3. Spend big money to sign it in free agency.

The Yankees have not done No. 1 in a long time. Their last homegrown starter with three consecutive +3 WAR seasons is Andy Pettitte. There’s been a Chien-Ming Wang here and a Luis Severino there, but just about every team develops a guy who burns bright for 2-3 years before flaming out now and then. It says a lot that the best starter the Yankees have developed in the last five years might be Mike King.

The Yankees have certainly spent on top of the rotation starters. Mike Mussina, CC Sabathia, Masahiro Tanaka, Gerrit Cole, etc. Yoshinobu Yamamoto tells us they have a line somewhere, but the Yankees are willing to open the wallet for the right guy at the right time. Trade top prospects for an ace though? It’s been a while since the Yankees did that, unless you put Frankie Montas in that bucket, and I don’t.

Jesus Montero for Michael Pineda might’ve been the last such trade, and even then Pineda only had one year in the big leagues. The Yankees typically don’t trade for aces, in part because aces do not become available in trades often. They also don’t develop many legitimately above-average starters, so they’re left having to spend on a Sabathia or Cole when they become available. That’s their only avenue for frontline pitching and has been for a while now.

I’m rambling here. I have enough questions and concerns about Jones that I’m willing to trade him right now for an impact starter. Corbin Burnes would have been ideal. Even with one fewer year of control than Dylan Cease, that guy is an ace and a workhorse, and would’ve given the 2024 Yankees a much better chance to win a title. Cease, as talented as he is, is a bit of a project. You have to help him make some tweaks to bring out the 2022 version again. I’d trade Jones for him. He’s hardly a sure thing himself.

Emiliano asks: Sorry for the dumb question: Maybe I pay too much attention to this because I work in advertising but, IMHumbleO the Yankees are really bad at social media (specially on Sunday games or games that the team came from behind amazingly). But this spring they seem to be more active than ever and I was wondering: do you pay attention to that stuff? Do you get mad like me seeing them act like they're too cool for school even on the internet? What teams think are good at this?

I do not follow every team on social media and I don’t pay much attention to which teams are good at it and which teams aren’t. The Yankees seem better than most? The “question of the day” gimmick is fun, if not a little played out after like two years, and we get Tommy Kahnle mic’d up and things like that. And when the Yankees post game highlights, they’ll occasionally do so from cool angles, like this one. The Dodgers are noticeable on social media. They post a lot of fun stuff, such as Teoscar Hernández teaching Shohei Ohtani Spanish. The Cubs are pretty good too. There was a time not that long ago, maybe 3-4 years ago, when the Yankees went through the motions on social media. You got the lineup, the final score, and maybe a highlight or two each day. That was it. There appears to have been a concerted effort to be more engaging the last few years (and this spring), and it’s important. It’s a way to reach young fans and build a fan base.

Chase asks: I am not a huge what if guy, but just for Mailbag giggles, how does the Yankees last ten years of look if the Astros stayed in the NL?

Was it really only a decade ago that the Astros moved to the AL? Well, 11 years and 11 seasons ago now, but it feels like it happened so long ago, like in the early 2000s. Jose Altuve debuted in 2011, two years before the Astros switched leagues. Carlos Correa, the No. 1 pick in the 2012 draft, was drafted by an NL Central team. Sheesh.

The Astros were well into their hard tanking era when they switched leagues and, had they stayed in the NL Central, those 2015-18 battles with the Cubs would’ve been something else. Houston’s toughest competition in the AL West for much of their reign was the Athletics, who were fighting an unfair fight payroll-wise. The Kris Bryant/Anthony Rizzo era Cubs had talent and money. Those Astros-Cubs battles would’ve been a blast.

As for the Yankees, getting the Astros out of the AL certainly would have improved their odds at winning a pennant these last seven years. At least in the regular season, the Yankees likely would have been the league’s dominant team. Heck, they had the league’s best record from 2017-23 even with the Astros in the AL. Here are the top winning percentages from 2017-23:

1. Dodgers: 350-167 (.677)
2. Yankees: 328-189 (.634)
3. Astros: 319-195 (.621)
4. Rays: 317-198 (.616)
5. Brewers: 301-217 (.581)

The Yankees did enough losing to non-Astros teams in the postseason those years (Rays in 2020, Red Sox in 2018 and 2021) that I don’t think we can simply assume they would have won a World Series along the way. Where’s the fun in that though? Here’s an alternate universe in which the Astros stay in the NL Central.

2015: Yankees lose to Angels in Wild Card Game

Let’s be real here, that 2015 Yankees team was dragging leading into the postseason. They went 30-33 in their final 63 games and they scored three or fewer runs 11 times in their last 19 games. By the end of the season they looked old (because they were). An offense led by Carlos Beltrán, Brian McCann, and Alex Rodriguez got shut down by Dallas Keuchel in the Wild Card Game. The Angels were the first team on the outside looking in that year and I have no reason to think the Yankees would’ve hit Garrett Richards (3.65 ERA and 3.86 FIP in 207.1 innings in 2015). No change here. The Yankees go home in the Wild Card Game in 2015.

2016: Yankees still miss the postseason
2017: Yankees lose to Astros in the World Series

Look, I totally get feeling that the Yankees were robbed in 2017. The Astros cheated that season, we know that, and the Yankees lost two one-run games in the ALCS. They also scored only three runs in four games at Minute Maid Park. That was the real problem. But with the Astros in the NL Central, that is not an issue. The Yankees outscored the Red Sox by 23 runs in head-to-head games that year and I think they would’ve beaten them in the ALCS.

Beating the Dodgers in the World Series though? That part I have a hard time getting on board with, and it seems like a lot of folks assume it would’ve happened. Yes, the Yankees were cheated out of a pennant by the Astros, but I don’t feel comfortable assuming they would have beaten the Dodgers. That Dodgers team was so good. With the Astros in the NL, I think the Yankees win the pennant in 2017 … and then run into the Astros in the World Series.

The Astros beat the Dodgers in the actual World Series that year, so they beat them in the NLCS in my alternate universe, and we know how Yankees vs. Astros goes in the postseason. Even with the Astros in the NL, the Yankees lose to them anyway in my alternate universe in 2017, just a round later. Would getting to the World Series have changed the offseason? The Yankees cut about $30M off payroll to get under the luxury tax in 2018, remember. Maybe they don’t do that coming off a pennant. Hmmm.

2018: Yankees still lose to Red Sox in ALDS
2019: Yankees win the World Series!

The Yankees didn’t face the Astros in the 2018 postseason and they still would have gotten stomped pretty good by the Red Sox. As for 2019, I believe that was the Yankees’ best chance to win a World Series in the Aaron Judge era. That team got hammered by injuries, but they were mostly healthy come October. Remember their lineup that postseason?

1. 1B DJ LeMahieu
2. RF Aaron Judge
3. 2B Gleyber Torres
4. DH Edwin Encarnación
5. LF Giancarlo Stanton
6. CF Brett Gardner
7. C Gary Sánchez
8. SS Didi Gregorius
9. 3B Gio Urshela

Cameron Maybin replaced Stanton for defense and Luke Voit loomed on the bench as a pinch-hitter. James Paxton was on a roll heading into the postseason, Masahiro Tanaka was still the man at the time, and Luis Severino returned late in the year to rejoin the rotation. Zack Britton and Aroldis Chapman were at the height of their powers in the bullpen.

The Yankees won 103 games in 2019 and that team was at its best heading into the postseason, in terms of health. Rather than face the Astros in the ALCS, the Yankees likely would’ve gotten the Rays (Tampa lost to the Astros in the ALDS), a team they outscored by 40 runs (!) in the season series that year. That Rays team was good. The Yankees were better. They win the ALCS to clinch their second pennant in three years.

Juan Soto’s Nationals were very good in 2019. That team famously started 19-31, then went 74-38 the rest of the way, and beat the 89-win Brewers in the Wild Card Game, the 106-win Dodgers in the NLDS, and the 91-win Cardinals in the NLCS. Chances are Washington would have run into the Astros at some point, possibly instead of St. Louis, and well, we saw how the Astros vs. Nationals series played out.

What reason do I have to believe the Yankees would have beaten the Nationals in the 2019 World Series? None. This is all make believe. But looking at the last few World Series winners, the 2019 Nationals team are the biggest outlier and look the most beatable. Like half that team could’ve retired after the World Series, and it would’ve been understandable. If the Yankees were ever going to win a World Series from 2017-23, 2019 was the year to do it. I’m not saying it would have been easy. Just that 2019 was the year.

2020: Yankees still lose to Rays in ALDS
2021: Yankees still lose to Red Sox in Wild Card Game
2022: Yankees lose to Astros in the World Series again?
2023: Yankees still miss the postseason

2022 was the first year with the 12-team postseason format and does that even happen with the Astros still in the NL, and only 14 teams in the AL? Yeah, maybe. The Wild Card Game format began when the Astros were still in the NL Central. MLB didn’t seem to care about league imbalance then. Anyway, the Yankees did not see the Astros in the 2020 or 2021 postseason. No change there.

That 2022 season was a roller coaster. The Yankees started so well, finished with an extended stretch of mediocrity, and then had to fight tooth and nail to outlast Cleveland in the ALDS. The Astros quickly swept the Mariners in the other ALDS. Cleveland and Seattle is about as easy a road through the AL as you could ask for, right? No disrespect, but that’s not exactly Ivan Rodriguez’s Rangers and Pedro Martinez’s Red Sox.

The thing is, the Yankees probably just run into the Astros anyway, right? Houston’s gone to seven straight ALCSes and, from 2017-22, they played in four of six World Series. Houston kept beating great teams and getting to the World Series. In our alternate universe, maybe the Cubs or Dodgers or Braves pick them off one year. Just looking at the landscape, it seems like the Astros would have kept getting there anyway.

Losing to the Astros again in the 2022 World Series would have meant three pennants in six years for the Yankees, with one World Series win over the Nationals and two World Series losses to the Astros. It would have been a very 1995-99 Braves-esque run. Atlanta beat Cleveland in the 1995 World Series and lost to the Yankees in 1996 and 1999. So, even though the Braves were a great and successful team, they weren’t the best team of the era.

I feel like that’s how things would’ve gone for the Yankees from 2015-23 even with the Astros in the other league. There would've been a much clearer path to the World Series and I think they would’ve broken through at some point, but the Astros were still very good, and the Yankees likely would have run into them at some point anyway. That said, even one World Series would have changed so much. We’d all feel much differently about this team with a 2019 title in hand.

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