February 8th, 2022: Freeman, Worst Decisions Since 2017

Lockout, Day 69 (not nice): The quarterly owners meetings begin today in Orlando and Rob Manfred will speak to the media later this week (I think). That a) could be when he’ll announce Spring Training will not start on time, and b) should be a hoot. It is cringy anytime Manfred opens his mouth in an unscripted setting. Put him on the spot and he tends to say dumb things. I hope he puts his foot in his mouth again later this week. If we have to suffer through this lockout, we should at least get to make fun of the guy who started it. Anyway, let’s get to today’s post.

1. The latest Freeman rumor. A wild hot stove rumor has appeared. Over the weekend Jon Heyman reported the Yankees are “expected to take a run” at Freddie Freeman whenever this cursed lockout ends. We heard the Yankees loosely connected to Freeman before the lockout and it’s possible (likely?) his camp is just using the Yankees as leverage.

What if they’re not though? What if Freeman feels disrespected and the Braves push him away with lowball offers, the Yankees have sincere interest, and Hal Steinbrenner decides to open the wallet? I don’t expect it to happen but it’s not completely crazy, right? Freeman’s a great player with championship pedigree, and by all accounts he’s great in the clubhouse. It fits.

There’s nothing else going on right now, so let’s have some fun with a hypothetical. Let’s say the lockout ends and the Yankees sign Freeman the next day. He’s fed up with Atlanta and Hal’s tired of getting knocked out in the postseason and hearing he’s cheap. Freeman ends up in pinstripes. What happens next? Let’s go through the hypothetical domino effect.

The Yankees get a lot better

Obvious statement is obvious, but it needs to be said. Freeman is an upgrade over Luke Voit on both sides of the ball, and he fits the lineup much better as a lower strikeout lefty. The guy hit .300/.393/.503 (135 wRC+) with a 15.4% strikeout last year and he hasn’t had a sub-130 wRC+ since 2012. Freeman’s what, 75% of the way to the Hall of Fame? Imagine the lineup:

1. 3B DJ LeMahieu
2. RF Aaron Judge
3. 1B Freddie Freeman
4. DH Giancarlo Stanton
5. LF Joey Gallo
6. 2B Gleyber Torres
7. CF Aaron Hicks
8. SS Gio Urshela
9. C Gary Sanchez

There’s some work to do on the infield there, but it looks pretty good overall, no? That 2-3-4 is as good as any in the game, plus you’d have to contend with LeMahieu contact-bombing pitchers in the leadoff spot and Gallo hitting tanks onto the 4 train platform from the No. 5 spot. The bottom of the lineup is no pushover either. Those guys can hurt you too.

We can get so caught up in discussing value and team control and all that stuff that sometimes we just need to take a step back and say yes, this move makes the Yankees a lot better. Forget about the money, forget about the luxury tax, forget about 3-4 years down the line. The priority is winning the World Series right now, in 2022, and Freeman would help the cause considerably.

The Yankees would go with a stopgap shortstop

There is no chance – zero – the Yankees would splurge for Freeman and Carlos Correa. Maybe Trevor Story would take a high-priced one-year deal and Hal would okay that, but eh, I think that's pushing it. In all likelihood Freeman means a stopgap shortstop because that’s all Hal’s budget will allow. Here are the available stopgap shortstops by ZiPS projected 2022 WAR:

1. Isiah Kiner-Falefa: +2.8 WAR (trade candidate)
2. Paul DeJong: +2.6 WAR (trade candidate)
3. Jose Iglesias: +1.9 WAR (free agent)
4. Andrelton Simmons: +1.5 WAR (free agent)
5. Elvis Andrus: +1.1 WAR (trade candidate)

(All five of those guys are projected to have negative offensive value paired with okay to very good defense. They’re no-bat/all-glove types.)

After signing Freeman it would be tempting to say “Freeman allows the Yankees to go with a defense-first shortstop” and reader, we need to be better than that. Get the best player at as many positions as possible. The Yankees were maybe the best team ever in 1998, then they traded for the reigning two-time Cy Young winner, just because they could. More of that, please.

Chances are the Yankees will go with a stopgap shortstop with or without Freeman. Correa and Story are the only non-stopgap quality shortstops out there and I need to see Hal okay a signing like that to believe it. If he agrees to spend big on Freeman, it all but guarantees the Yankees would go cheap at short. Two big outlays is not in the plans this winter.

Voit’s a goner

Luke Voit might be a goner even without Freeman. With Freeman? Forget it, Voit’s definitely gone in that case. Maybe not right away, the Yankees could hang onto Voit through Spring Training and even early in the regular season until the right deal comes along, but they’d trade him at some point. You can only tie up so many roster spots in first base/DH types. This seems pretty cut and dried. Hello Freddie means goodbye Luke.

Judge might be a goner too

A few months ago Bob Nightengale reported Freeman turned down Atlanta’s five-year offer worth $135M, which is Paul Goldschmidt’s contract plus $1M a year (Freeman is the same age now as Goldschmidt was when he signed his deal). He’s seeking six years and $180M or so, according to Heyman. That’s a gap of $3M a year and one year. Seems bridgeable, but who knows?

Let’s assume the Yankees and Freeman land close to the middle at six years and $160M. That is a little more than George Springer’s contract (six years and $150M), and Springer signed his deal when he was a year younger than Freeman is now. The $26.7M average annual value would be the second richest ever for a first baseman, behind Miguel Cabrera’s current $31M a year deal.

With Freeman signed, the Yankees would have these contracts on the books for the foreseeable future (these are luxury tax hits, not actual salary):

• Gerrit Cole: $36M per year through 2028
• Freddie Freeman: $26.7M per year through 2027
• Giancarlo Stanton: $22M per year through 2027
• DJ LeMahieu: $15M per year through 2026
• Aaron Hicks: $10M per year through 2025

That’s $109.7M per year for five players – five! – for at least the next four seasons. The first base and DH spots are locked up several times over. So where does Aaron Judge fit? Do the Yankees still give Judge a big extension next offseason (I think $200M is the magic number) and commit something like $135M a year to six players? All of whom are on the wrong side of 30? I dunno. 

I think a Freeman signing would signal the intention to let Judge leave after the season. It wouldn’t be the first time the Yankees let their best player leave, and hell, who knows? Maybe the Yankees pivot to Freeman because extension talks with Judge are going nowhere and they know he's dead set on testing free agency, and taking nothing other than the largest offer.

The Yankees should sign Freeman and Judge and Correa and pay whatever luxury tax they have to pay to build a contending roster around them. They make enough money. Time to put some of it back into the roster. Realistically though, it won’t happen, and any big ticket signing this winter would create questions about Judge’s long-term future in pinstripes.

Wells becomes trade bait?

There’s a good chance Austin Wells is the Yankees’ first baseman of the future. As good a chance as any prospect who has yet to play above Single-A has to be the anything of the future, anyway. Wells can hit, but he’s a poor defender behind the plate, and moving to first base is the logical next step. Maybe Wells can be what we hoped Greg Bird would be.

With Freeman and Stanton locked up, the first base and DH jobs are accounted for, leaving no obvious spot for Wells. Maybe he really can catch (the automatic strike zone would eliminate his framing issues) or handle a corner outfield spot, and the Yankees can get him in the lineup. More likely, Wells is a future first baseman who would be capital-B Blocked with the Freeman era Yankees.

In that case, Wells becomes a trade chip, and that’s perfectly fine. Prospects are there to be plugged into the roster or traded. Wells would have heightened trade value once the new Collective Bargaining Agreement makes the universal DH a thing, and the Yankees could use him to add pitching, a shortstop, whatever. Signing Freeman and keeping Wells would be kinda silly. It would tough for those two and Stanton to coexist on the same roster long-term.

* * *

Like I said, I’m not sold on the Yankees seriously pursuing Freeman, let alone signing him. I think he’ll wind up back with the Braves (some players should spend their entire career with a single team and I think Freeman’s one of ‘em), even if it seems like he’ll land elsewhere before it gets done. If the Yankees sign him, it would be great! Freeman’s awesome. The domino effect would be wide-ranging too, extending to Judge, Voit, Wells, and the 2022 (and beyond?) shortstop.

2. Five worst decisions of the last five years. Our little two-part series looking at the best and worst decisions since 2017 (i.e. the Aaron Judge era) concludes today with the worst decisions the Yankees have made these last five years. Here are the best decisions. As you can imagine, this list is highly subjective. One person’s dumb idea is another person’s masterstroke.

Two quick things before we get to the five worst decisions. First, I’m going with “decision” instead of “move” here because non-moves are important too, and at some point a decision was made to make that non-move. And second, we don’t always know what goes into a decision. Who’s to say the free agent the Yankees didn’t sign even wanted to sign with the Yankees? We’ll just do the best we can with the information we have.

We’re evaluating these decisions in hindsight with help from the information we had at the time. I could rip the Yankees for not doing more to sign Shohei Ohtani, but he wouldn’t even listen to their pitch. I don’t blame them for that. Ultimately, results matter. Good process, bad results means you have to refine your process. Here are the five worst decisions of the Judge era.

5. The Gray trade(s)

On paper, it made a world of sense. The up-and-coming 2017 Yankees traded three prospects for 2.5 years of a 27-year-old starter who was one season removed from finishing third in the Cy Young voting. Not only that, but two of three prospects were early in their rehab from major injuries (James Kaprielian’s Tommy John surgery and Dustin Fowler’s knee surgery), and the third had seen his stock drop over the previous year (Jorge Mateo). They weren’t even top prospects!

For whatever reason(s), Sonny Gray did not work out in New York. He threw 195.2 innings with a 4.51 ERA (4.40 FIP) in a year and a half with the Yankees and was passed over in favor of an aging CC Sabathia in Game 5 of the 2017 ALDS. With their season on the line, the Yankees trusted 36-year-old Sabathia with one good knee over their prized deadline addition. And it was the right move! Gray had not earned anyone’s trust after the trade.

The Yankees tried everything with Gray. They suggested all sorts of pitch mix and delivery tweaks, then let him do whatever he wanted, gave him a personal catcher, used him in relief, on and on. The Yankees tried hard to make it work with Gray, and by the end of 2018, they were exasperated. The frustration was palpable anytime someone (Brian Cashman, Aaron Boone, Larry Rothschild, etc.) was asked about him.

“We are going to move him if we get the right deal because I don’t think it is going to work out in the Bronx. I don’t feel like we can go through the same exercise and expect different results,” Cashman told Joel Sherman in Nov. 2018. “... Until someone walks through your door and lives (life as a Yankee), it is hard to know. You try to vet every aspect. You plan and work at it and sometimes it pays off and sometimes it doesn’t.”

Gray’s value was way down not only because he pitched poorly, but because the Yankees were going to move him and everyone knew it. They eventually sent him to the Reds for a prospect and a competitive balance draft pick (the only draft picks that can be traded). The prospect was outfielder Josh Stowers, who didn’t stand out while in the system and was part of the Rougned Odor trade, and the draft pick turned into lefty T.J. Sikkema, who hasn’t pitched in two years due to the pandemic and an injury. Oof.

UPDATE: Small correction. Infielder Shed Long was technically the prospect in the trade, not Stowers. The Yankees got Long from the Reds, then immediately flipped him to the Mariners for Stowers.

At the time, the trade looked great! Gray appeared to be exactly what the Yankees needed. In hindsight, wow was it bad. It was bad even though the Yankees gave up very little to get Gray. Fowler and Mateo are spare part big leaguers who are on their third teams since the trade. Kaprielian had more injuries with the Athletics and is a member of the “the foreign substance crackdown hurt him until he seemingly found another way to use sticky stuff” club.

What was the mistake here? Did the Yankees not get a good enough read on Gray’s makeup and coachability? The guy excelled in the postseason and in big games with the A’s. It wasn’t like he’d never experienced pressure before. Was it Rothschild? Was it the organization’s hard lean on analytics and the lack of an individualized plan? Something else entirely?

Whatever it was, the decision backfired horribly, and the Gray trades (plural) are close to total losses for the Yankees. Sikkema returning with a vengeance is their only chance to recoup value. The Yankees didn’t give up much to get Gray, but there’s an opportunity cost associated with the traded prospects (i.e. they couldn’t be traded for someone else), then he pitched poorly and brought back little in the second trade. This seemingly good decision proved to be bad, and the decision tree has several other bad branches too. Just brutal.

4. The Hicks and Severino extensions

It’s almost comical how quickly these went south. The Yankees gave Luis Severino a four-year, $40M extension on Feb. 15th, 2019, and he was shut down with a sore shoulder on March 5th. 18 days between extension and injury. Severino has thrown 27.2 big league innings in the three years since signing his contract, postseason included. Dare I call it Pavano-esque?

The weird thing is Severino’s deal wasn’t below market (i.e. it didn’t come with a discount like most pre-free agency extensions) and the only real upside for the Yankees was the fifth year club option worth $15M. The option buys out what would be Severino’s first free agent year (2023). The four guaranteed years cover his four years of arbitration as a Super Two.

James Paxton and Marcus Stroman, two above-average starters when healthy, went through arbitration as Super Twos in recent years, and they made $28.325M and $29.3M during their four arbitration years, respectively. David Price made $45.45M through arbitration as a Super Two and that was with a Cy Young and a Cy Young runner-up on his resume. Hmmm.

Severino’s contract paid him as if he would remain a Cy Young contender through his arbitration seasons without a discount and without wiggle room for injury or performance. Good for him! And maybe the Yankees gave Severino all that money as a goodwill gesture. He was a great pitcher for us from 2017-18 and he was a small bonus international signing ($225,000), so we’re going to take care of our guy. Maybe that’s what happened. Maybe.

Overall though, the Severino extension was a relatively low upside move given the guaranteed money (again, look at Paxton, Stroman, and even Price as contemporary Super Twos), and it’s worked out about as poorly as possible. The only way it could be worse is a catastrophic injury and zero innings pitched. 27.2 innings in three years is only one small step up from that.

As for Hicks, he signed his seven-year, $70M extension on Feb. 25th, 2019, and was shut down with a back issue on March 11th, so 14 days between extension and injury. Hicks had Tommy John surgery later that year and wrist surgery last year. Since signing the extension, he’s played 157 of 401 possible regular season* and postseason games, or 39%.

* Hicks played 54 games during the 60-game season two years ago, though he would’ve missed most of the first half with Tommy John surgery rehab had it been a normal 162-game season.

Hicks was entering his walk year when he signed his contract and, historically, players who sign extensions the year before free agency get free agent deals. There’s no discount, and that was the case with Hicks. The market for 30-ish-year-old center fielders was in the five-year, $80M range at the time. That’s roughly what Dexter Fowler and Lorenzo Cain received.

The Yankees gave Hicks seven years and $70M, and it kinda looks like five years and $70M with two years tacked on for luxury tax purposes, no? DJ LeMahieu’s six-year, $90M deal is basically the Josh Donaldson contract (four years, $92M) with two extra years tacked on to lower the luxury tax hit. Seems to me like the Yankees did that with Hicks and his contract in 2019.

Anyway, the Yankees have signed only two members of their Judge era core to extensions and both went bad immediately. Both deals went bad in less than a month. What can you do other than laugh? Hicks and Severino have amounted to $20M in dead money the last few years (not entirely dead because both guys played some, but close to dead), which is close to what I gave the Yankees props for avoiding with Patrick Corbin.

To make matters worse, the Yankees seemingly passed up other moves because Hicks and in particular Severino were due to return. They didn’t trade for a pitcher at the 2019 deadline because Severino was coming back, for example. Severino did make it back late in the season and was in the postseason rotation, but even then the Yankees needed another starter (Chad Green started Game 6 of the ALCS that year). Passing up other moves is a Yankees problem, not a Hicks and Severino problem, but it is all part of the bad decision tree.

In hindsight, the better decisions would have been to go year-to-year with Severino through arbitration (i.e. the Chien-Ming Wang route)*, and to let Hicks play out his free agent year, then reevaluate after the season. Worst case was what, Hicks has a great 2019 season and the Yankees re-sign him to a contract that looks a lot like the contract he signed?

* The Yankees and Severino were minutes away from an arbitration hearing when they agreed to the extension. He was seeking $5.25M and the team countered with $4.4M. Even if he’d won the hearing, he would have received tiny raises in the following years because of the injuries, putting his four-year arbitration earnings in the $22M range (assuming he didn’t non-tendered).

Did the Hicks and Severino contracts immediately going bad stop the Yankees from handing out other extensions? Like to Judge? I’m inclined to say no. Cashman & Co. are smarter than that. If a bad deal or two are reason enough to avoid similar deals, you’d run out of ways to build a team real quick. That these are the only extensions the Yankees gave out doesn’t factor into my ranking here. They’re just two deals that went real bad, real quick, and ostensibly prevented the austerity era Yankees from doing other things because they eat up roughly 10% of the team's available luxury tax payroll space.

3. Hiring Boone

I am of the belief that a good manager can only help so much, but a bad manager can cost you a lot of games through bad decisions and unhappy players. I don’t get the sense Yankees players are unhappy (they all seem to genuinely like Aaron Boone) though I’ve yet to see evidence Boone can elevate his team and get the most out of his players. If anything, the last two years are evidence of the opposite. That the whole is less than the sum of the parts.

“He was a dark horse candidate. He was introduced to me from people I respect in the game, so I threw him on the list of, ‘Okay, I'll at least look under the hood and see what's there.’ And I was blown away,” Cashman told Bryan Hoch about hiring Boone in 2019. “There was a lot of risk there, but our process was designed to lead us to the best candidate.”

The meticulous almost to a fault Yankees deviated from that process to hire Boone. Their stated process was going to involve interviewing several candidates, then bringing back the finalists for a second interview with ownership. The second round of interviews never happened. The Yankees were “blown away” by Boone (Cashman’s words), skipped the second round of interviews, and hired him. They won’t trade a slightly better prospect to get the help they need, but they’ll forgo an entire round of interviews to put someone in charge of their players. I mean, what?

Cashman said the goal was to hire a manager with “the ability to fully engage, communicate, and connect with the playing personnel,” particularly the young core that thrust the Yankees back in contention in 2017. And since then, every young player on the roster other than Judge (and Jordan Montgomery, who’s come back well from Tommy John surgery) has gone backwards. If Boone possesses this ability to “fully engage, communicate, and connect” with young players, it has not translated to results on the field, and results on the field are all that matter.

Boone is an unremarkable on-field manager who often gets boxed into poor matchups by more skilled managers, and whatever he does in the clubhouse hasn’t moved the needle. At best, he’s a mediocre manager, and at worse, he’s straight up bad. Putting a non-player this high on a bad decisions list should tell you where I fall on that spectrum. Boone isn’t the problem with the Yankees, but after four years, I can’t say I see him as part of the solution either.

2. Passing on Harper

I’m also willing to accept passing on Manny Machado here, but I was a Bryce Harper over Machado guy, so I’m going with Harper. Point is, Harper and Machado were only 26 (!) when they became free agents. They were in-their-prime stars, and the Yankees straight up said no thanks. At least they wined and dined Machado. They did no such thing with Harper.

“At no time at all – all winter – did I say I’m looking for an outfielder. So the Harper stuff, I’m surprised you’re still asking,” Cashman told Billy Witz at the 2018 Winter Meetings. “... It’s not something that we would play on at that level and that type of money.”

The outfield at the time was Judge, Hicks, Brett Gardner, and Giancarlo Stanton. Judge is amazing. Hicks was a year away from free agency though, and Gardner was 35 and coming off his worst offensive season (91 wRC+ in 2018). Also, Stanton spent more time at DH (86 games) than in the outfield (72 games) in 2018. The Yankees had to anticipate that would continue moving forward.

Cashman may have said he wasn't looking for an outfielder that offseason, but the Yankees pretty clearly could have fit one. Judge in right, Hicks in center, Harper in left, Stanton at DH, and Gardner on the bench as a fourth outfielder/defensive replacement. See? Easy. In that scenario Harper would effectively replace Andrew McCutchen, who finished 2018 as the starting left fielder.

Also, the Yankees badly needed a lefty bat during the 2018-19 offseason. This was the regular lineup at the end of the 2018 regular season and into the postseason:

1. LF Andrew McCutchen
2. RF Aaron Judge
3. CF Aaron Hicks
4. DH Giancarlo Stanton
5. 1B Luke Voit
6. SS Didi Gregorius
7. C Gary Sanchez
8. 3B Miguel Andujar
9. SS Gleyber Torres

Seven righties, one lefty, one switch-hitter. And the one lefty had Tommy John surgery right after the postseason. It was known Gregorius would miss the start of 2019. It was plainly obvious the Yankees needed another lefty bat during the 2018-19 offseason and Harper was right there. He was right there. As a Scott Boras client, make him the biggest offer* and you’d get him, full stop.

* The Yankees stayed under the luxury tax threshold in 2018 and would have only surrendered their second highest draft pick in 2019 (the Sikkema pick) and $500,000 in international bonus money to sign Harper. The 2019-20 international class was the Jasson Dominguez class, though I assume the Yankees would have traded for additional pool space. That $500,000 would not have come out of Dominguez's pocket.

The Yankees replaced Gregorius with Troy Tulowitzki (lol), another righty, and also brought in DJ LeMahieu, yet another righty. LeMahieu was amazing! Tulowitzki only lasted a week though. The lineup was again imbalanced in 2019. And it’s still imbalanced. Joey Gallo helps, and of course the Yankees wouldn’t have needed Gallo had they signed Harper.

Harper, the reigning NL MVP, carries the 15th highest luxury tax hit in baseball and will play the entire 2022 season at age 29. He’s hit .281/.402/.556 (146 wRC+) with the Phillies. Yankees left fielders have been pretty good the last three years (.253/.348/.450 and 116 wRC+), though that’s tied up almost entirely in the out of nowhere Cameron Maybin and Mike Tauchman contributions in 2019. Since 2020, the left fielders have hit .229/.331/.400 (103 wRC+). Woof.

The excuses we got for passing on Harper didn’t pass muster at the time and seem only sillier in hindsight. They can’t sign Harper because they have to lock up their core! (Judge is a year away from free agency.) They don’t want Harper because they want Nolan Arenado next offseason! (Arenado signed an extension and the Yankees were nowhere to be found when the Rockies gave him away.) His defense is slipping! (lol have you seen this team’s defense?) They can’t pay Harper because they’re paying Stanton! (Weird how they were able to pay Gerrit Cole and are reportedly planning to pay Judge, huh?)

Give Judge an eight-year extension next offseason (that might be what it takes) and he will be the same age in Year 8 that Harper will be in Year 13 of his 13-year contract. You almost never get a chance to sign a free agent as good and as young as Harper, and the Yankees passed. And you know what makes it worse? They’re poised to do it again this offseason with Carlos Correa and Corey Seager. Since when do the Yankees let prime-aged stars slip through their fingers?

Harper would have been a legend in pinstripes. He would have mashed (the guy has averaged 38 homers per 600 plate appearances since 2015 without the benefit of the short porch) and fans would have loved him. Retired number, plaque in Monument Park, the works. Well, maybe not on the Monument Park stuff, but who knows? Either way, I have a very hard time believing the Yankees would be/would have been worse off with Harper than they are without him.

1. Staying under the luxury tax threshold in 2018 (and 2021)

It is completely insane and, frankly, indefensible that the Yankees went to Game 7 of the ALCS in 2017, then chopped more than $30M off payroll in 2018. They spent $224.1M on player payroll in 2017 ($208.4M in salaries plus a $15.7M luxury tax bill) and $192.3M in 2018 (all salary). We were told getting under the luxury tax threshold would allow the Yankees to do more in the future. Hah.

“I’ve been saying you can have a world championship caliber team and not have a $200-plus-million payroll. And I think we’re finally getting to a point where that’s coming true for us,” Hal Steinbrenner told Witz in Nov. 2017. Scott Boras gave a response that still resonates:

“The fact that their payroll is going to be under what it was 10 or 15 years ago is something that everyone in the game has to look at and consider as to what are their goals,” Boras said. “What’s their principle? Again, we all know, when you have a choice, what do you do with your success? What do you do with the greatness of your business operation? And how do you reward the fans that allowed that to happen?”

The Yankees shed Alex Rodriguez’s contract after 2017 and CC Sabathia’s big money years came to an end. Chase Headley was salary dumped and a few pricey short-term commitments expired as well (Matt Holliday, Michael Pineda, etc.). The Yankees had so much money come off the books that they were able to trade for Stanton and still cut payroll significantly.

Rather than use all those expiring contracts and their cheap pre-arbitration core to load up the roster with short-term deals to boost the World Series odds, the Yankees slashed payroll. And because keeping payroll down was a priority, the Yankees refused to trade their top prospects (i.e. cheap players for the roster), which limited their trade opportunities as well. It was a masterclass in not taking advantage of an opportunity.

The 2017-18 offseason amounted to the Stanton trade, re-signing Sabathia, the Headley salary dump, the Brandon Drury trade, and signing Neil Walker. Getting the reigning NL MVP was great! But that’s it? Gerrit Cole got traded that offseason, Carlos Santana signed that offseason (Tyler Austin started at first base on Opening Day 2018!), and so much other stuff that would have made sense for the Yankees didn’t happen because they bowed at the altar of the luxury tax.

Staying under the luxury tax threshold in 2021 was dumb as well, though not as dumb as it was in 2018, when the Yankees had so much flexibility. By last season, the cheap young core wasn’t so cheap anymore, and not as core-y anymore either. Last year was more like trying to prop the window open for one more run. In 2018, the Yankees had a chance to smash through the window and assert their dominance on the rest of the sport, but passed.

2017-19 was always going to be the best chance to win with the Judge-led core because that’s when the core players were cheap, giving the team the flexibility to do other stuff. The Yankees kinda snuck up on everyone in 2017, and rather than use that flexibility to improve the roster in 2018, the Yankees used it to duck under the luxury tax, which has benefited the team in no discernible way on the field (unless you’re one of those folks who believes they couldn’t possibly afford Cole without it). I feel wasting that window the way the Yankees did is unforgivable, and an air of complacency continues to hang over the organization.

“I don’t believe we need to abandon the successful, organized, detailed process because now we’re knocking on the door. It doesn’t mean all of the sudden you become haphazard, or just reactive or emotional. I think, again, we’re keeping it simple,” Cashman told Witz in 2018. “... It’s convenient and an easy story to write about us being different than the Boss’s Yankees, but the game is completely different, too. I think we’ve been operating in a different capacity (because of the luxury tax) because it’s a whole new world order.”

Dishonorable Mentions

I will say this: I had a tougher time coming up with bad decisions than good decisions for this little exercise. For all my bitching and moaning and the Yankees’ lack of postseason success, they do go to the postseason every year, and their 419-289 (.592) record since Opening Day 2017 is the third best in baseball, behind only the Dodgers (451-258, .636) and Astros (435-273, .614). We are so very spoiled. Here are a few other decisions on my bad list, in no particular order.

Letting Gregorius walk. Once it was reported Didi Gregorius would take a one-year deal during the 2019-20 offseason, I thought the Yankees should be all over it. Multi-year deal? No, but a one year post-Tommy John surgery “prove yourself” deal was a-okay with me. Sir Didi went to the Phillies and hit .284/.339/.488 (116 wRC+) in 2020, then signed what is now a disastrous two-year contract. Gregorius would have given the Yankees more depth and an alternative to what proved to be an underwhelming Gleyber Torres in 2020. Alas.

Leaving Whitlock exposed. This is a pure hindsight criticism because almost no one batted an eye when the Yankees left Garrett Whitlock exposed in the 2020 Rule 5 Draft. He was rehabbing from Tommy John surgery and hadn’t actually pitched since 2019. Then the Red Sox took him and Whitlock became one of the best relievers in the game. This would have been merely bad had, say, the Pirates or Rockies taken Whitlock. Going to Boston is salt in the wound.

The Ottavino trade. In a vacuum, trading Adam Ottavino was fine, even within the context of the Yankees being cheap and adhering to a fake salary cap. But trading him to the Red Sox (!) and then watching him pitch well most of the year, and Boston edging out the Yankees for homefield advantage in the Wild Card Game by one game? Oof. To make matters worse, the Yankees used a chunk of the savings on Justin Wilson and Darren O’Day, who were at best non-factors.

Re-signing Happ. Despite their obsession with data, the Yankees ignored all the red flags (declining velocity, declining spin, fewer whiffs, more homers, etc.) and re-signed J.A. Happ to a two-year, $34M contract during the 2018-19 offseason. In return the Yankees received two good nonconsecutive months in two years, though to be fair, the second year of the contract was cut short by the pandemic. They also had to jump through hoops to avoid a) the third year vesting option, and b) starting Happ in the postseason. Also, the Yankees had to re-sign Happ because the Gray trade flopped and they needed a starter, so this is another ding we can kinda sorta attribute to the Sonny deal going bad.

The Odor trade. The Yankees trading prospects (fringe prospects, but still prospects) for one of the worst players in baseball one week into the regular season was a clear sign they didn’t do as much as they needed to do during the offseason. A week into the season and you’re trading for Rougned Odor for depth? Yikes. Also, the Yankees designated Thairo Estrada to clear a 40-man roster spot for Odor, and Thairo hit .273/.333/.479 (119 wRC+) in an up-and-down part-time role with the Giants after being traded for cash. Should’ve just kept him. I said so at the time.

The Heaney trade. What does it say that most of these bad decisions are recent? Maybe it’s recently bias? Well, whatever. Heaney was homer prone with the Angels (1.53 HR/9 and 15.4 HR/FB%) and even more homer prone with the Yankees (3.28 HR/9 and 23.2 HR/FB%), which is no surprise given the change in ballparks and divisions. Heaney was picked up to be an inventory arm and he was so bad the Yankees had to designate him for assignment before the end of the season because Jameson Taillon on one good ankle gave them a better chance to win.

3. Remembering a random Yankee: Jeff Francis. By request, this week’s random Yankee is another member of the 2013-14 bullpen revolving door. Here’s the random Yankee archive. You can find links back to everyone we've covered there.

Francis grew up outside Vancouver in North Delta, British Columbia, and the Rockies selected him with the No. 9 pick in the 2002 draft. At the time that made him the second highest drafted Canadian in baseball history*, behind Adam Loewen (another Vancouver area guy), who went No. 4 overall to the Orioles the same year.

* The highest drafted Canadian is technically Jameson Taillon (No. 2 overall in 2010). He was born in Florida and grew up in Texas, but both his parents are Canadian, so Taillon has dual citizenship. Loewen is the highest drafted Canadian among players actually born in Canada.

Francis appeared on several top 100 prospects lists over the years – Baseball America (subs. req’d) ranked him the game’s No. 23 prospect in 2005, one spot ahead of Nick Swisher – and he made his big league debut late in 2004. He was a rotation mainstay from there, notably throwing 414.1 innings with a 4.19 ERA from 2006-07. That’s a 116 ERA+ once adjusted for Coors Field.

The Rockies went to the World Series in 2007 and Francis was their Game 1 starter in all three postseason rounds. He was great in the NLDS and NLCS (three runs in 12.2 innings combined) and not so great against the Red Sox in the World Series (six runs in four innings). Francis had shoulder trouble in 2008 and surgery sidelined him all of 2009. When he returned in 2010, he allowed 61 runs in 104.1 innings, and his stuff was greatly diminished.

Francis pitched to a 4.77 ERA (100 ERA+) in almost 900 innings with the Rockies from 2004-10. He became a free agent after 2010 and bounced from the Rockies to the Royals to the Reds back to the Rockies back to the Reds to the Athletics from 2011-14. Francis started 2014 with Cincinnati, was claimed off waivers by Oakland in May, then was traded to the Yankees in July.

The Yankees were hanging around the postseason race in July 2014, though they were short on arms. Knee surgery ended CC Sabathia’s season in May, then Masahiro Tanaka’s elbow sent him to the injured list in early July. The rotation at the time of Tanaka’s injury was Tanaka, Hiroki Kuroda, David Phelps, Chase Whitley, and Vidal Nuno. Sheesh.

On July 6th, the Yankees swapped Nuno for random Yankee Brandon McCarthy, but that didn’t add an arm. It just replaced one pitcher with a better pitcher. Five days later the Yankees acquired Francis from the A’s with cash for cash or a player to be named later*. He had been designated for assignment a few days earlier, when Oakland needed 40-man roster space following the Jeff Samardzija trade with the Cubs (that sent former Yankee Billy McKinney to Chicago).

* The Yankees eventually settled the trade with cash. So officially, it was Francis and cash for cash. I wonder which side received more cash?

“You’d like to think it’s an opportunity for someone to really step up and show what they’ve got,” Joe Girardi told David Waldstein about the Francis trade and the team’s pitching shortage. “For a lot of us, that’s how we get our start in the big leagues. Someone gets hurt and you get an opportunity to play, and then you prove that you can play and you stick. There are certain people that are difficult to replace.”

The Yankees did not put Francis, then 33, in the rotation. They called up Shane Greene to replace Tanaka and acquired Chris Capuano later that month. Francis had allowed 12 runs in 18.1 innings with the Reds and A’s earlier in the season (including four runs in one inning against the Yankees on June 16th), so the Yankees put him in the bullpen as their long man. He joined the team on July 11th. His first appearance in pinstripes came on July 22nd.

Francis’ Yankees debut was a memorable game. That was Chase Headley’s first game with the Yankees, when he arrived in the middle innings and provided the walk-off single in the 14th inning. Also in that game Derek Jeter doubled to pass Lou Gehrig and take over as the franchise doubles leader. Francis was the game’s winning pitcher. He tossed a scoreless top of the 14th against the Rangers (video), then Headley won it in the bottom half. Here’s a video recap of the game.

"Jeff Francis hasn't thrown in I don't know how long. 14, 15 days maybe. Maybe even more than that," Girardi told Chad Jennings after the game (it was Francis’ first game action in 20 days). “He comes in to throw strikes, gets a big three outs for us, and we win the game.”

Four days after his Yankees debut, Francis made his second and ultimately final appearance with the team. He was brought in to get the left-on-left matchup against Dan Johnson with the Yankees down 3-2 in the ninth inning against the Blue Jays. Johnson hit Francis’ fourth pitch into the short porch for a three-run homer to break the game open (video). Francis stayed in to finish the inning and was charged with one run while getting two outs.

The Yankees designated Francis for assignment four days later. The move cleared a roster spot for Zoilo Almonte and got the Yankees back to what was at the time a normal seven-man bullpen and four-man bench. Francis cleared waivers and was released a week later. He did not pitch the rest of the season, then split 2015 between Triple-A and the big leagues with the Blue Jays (16 runs in 22 innings with the MLB team).

Francis spent 17 days on the Yankees roster, pitched twice, and retired five of the seven batters he faced. Not including position player pitcher (and random Yankee) Dean Anna, Francis’ seven batters faced were tied with Wade LeBlanc for the fewest among the 33 (!) pitchers the Yankees used in 2014. Francis and LeBlanc huh? The 2014 Yankees were a trip, man.

Anyway, Francis announced his retirement on Dec. 15th, 2015 – “It was time,” he told Patrick Saunders – and in 2018, he told Kyle Newman retirement consists of being a dad and serving as assistant pitching coach for the Canadian Junior National Team. Francis signed more than $17M in contracts as a player and he was elected to the Canadian Baseball Hall of Fame last week, which is pretty cool.

4. Rapid fire thoughts. Baseball is underway! The Yankees (and several other teams) opened a minicamp for non-40-man roster minor leaguers at their Spring Training complex this week. If you’re interested, Kristie Ackert tweeted out some photos from Tampa and Bryan Hoch has a few details on the minicamp. Minor league Spring Training starts sometime next week and Joel Sherman says veterans on minor league deals with invitations to big league camp (like Ender Inciarte) can attend minor league camp, but are not required to. I assume those guys will sit out as erstwhile union members. Anyway, minicamp is underway and minor league camp is a week away. Non-40-man roster baseball is back … Ron Blum reports MLB is not testing for banned substances under the Joint Drug Agreement during the lockout. That was a bit of an unknown because the JDA is technically separate from the Collective Bargaining Agreement, but I guess they're treating it as one and the same. That means no performance-enhancing drug testing for more than two months now (players are tested randomly during the offseason). The stars who try to become superstars get all the attention, but the fringe roster guys just trying to stick in the big leagues have the most to gain from PEDs. I wonder if we'll see some random relievers with added velocity and bench guys with a little more exit velocity come Spring Training. Hmmm. Maybe we'll get a bunch of monster PED dingers this season and the lockout will be worth it ... And finally, the great Elliotte Friedman has the details on the NHL’s and NHLPA’s new agreement regarding gambling endorsements. Players are free to sign endorsement deals with gambling entities, with a few caveats:

On Oct. 22, the NHLPA informed players and agents that it had reached a deal with the NHL for “participation” in the world of legal sports betting. It cleared players to participate in advertising “related to” betting and “can endorse or have a promotional involvement with Sports Books,” provided that: single-sport betting is legal where the betting entity operates; the endorsement is legal in that jurisdiction; the “endorsement activity” does not promote betting on NHL games; the player is not shown betting; and it “is not intended to establish or advance a relationship between the betting entity and a club unless the club already has a relationship with the entity.”

Auston Matthews, one of the best and most high-profile hockey players in the world, was the first NHL player to land a gambling-related endorsement. I bring this up only to say I imagine MLB and the MLBPA will come up with a similar agreement soon, maybe even during CBA talks. MLB can’t be all-in on gambling the way it is (the Nationals recently became the first MLB team to open a sportsbook at their ballpark) then turn around and say sorry Aaron Judge, you can’t sign an endorsement deal and accept money from DraftKings or MGM or whatever. Like it or not, it’s going to happen. There need to be guidelines, but it’s going to happen.

(Send your requests for Tuesday's random Yankee series and questions for Friday's mailbag to RABmailbag at gmail dot com.)