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If Yankees don't get Cole, they could target ...
Nov. 14: By all accounts, the Yankees are seeking starting pitching this offseason, and it just so happens that Gerrit Cole -- arguably the top starter in the sport and the one who twice got away from GM Brian Cashman -- is a free agent. If the Yankees want to pony up the big bucks for Cole, they could go that route, finally land him and more or less solve their rotation issues in one fell swoop.
But what if that doesn't happen? What if Cashman and Co. really are focused on payroll (and staying under the Competitive Balance Tax), an approach that has become more of a priority for the Yankees in recent years?
MLB Network insider Joel Sherman took a look in a column for the New York Post at some more cost-efficient arms the Yankees might consider. Of the four names, only Rick Porcello -- who has been more durable than effective in his five seasons in the AL East with the Red Sox and lacks the upside to put near the front of the Yankees' rotation -- currently is a free agent.
The other pitchers Sherman suggests fall into the trade category: Johnny Cueto of the Giants, Yu Darvish of the Cubs and Mike Clevinger of the Indians. Cueto and Darvish have hefty salaries, however, meaning the Yankees might need to offset the cost by including Jacoby Ellsbury (who would have to waive his no-trade clause) in a deal, as well as a package of prospects to entice San Francisco or Chicago.
Clevinger, on the other hand, would come cheapest in terms of salary -- he's eligible for arbitration for the first time this year and projected to earn about $5 million in 2020 -- but his remaining years of control (through 2022) and performance (2.96 ERA, 1.15 WHIP, 10.3 K/9 since the start of 2017) would make the 28-year-old righty the most expensive in terms of a trade package.
Yanks 'definitely' will check in on Bumgarner; Phils already have
Nov. 13: We know the Braves have been linked to Bumgarner early and often this offseason, but what about the Phillies?
MLB Network insider Ken Rosenthal reports in his Thursday column for The Athletic (subscription required) that Philadelphia has checked in on the free-agent lefty as it casts "a wide net" for starting pitching.
Rosenthal speculates that the Phillies could be motivated to keep Bumgarner from signing with the reigning National League East champion Braves, and adds that Philadelphia could be in the market for multiple veteran starters (for example, a combination of Bumgarner and fellow free-agent lefty Cole Hamels). However, Rosenthal believes that Bumgarner is a "more natural fit" for the Braves than the Phillies.
The Yankees, another team expected to consider a wide range of starting-pitcher options, have interest in Bumgarner as well. According to John Shea of the San Francisco Chronicle, general manager Brian Cashman said he hasn't reached out to Bumgarner's agency yet but "definitely" will.
Yankees not expected to pursue Didi 'very aggressively'
Nov. 13: The Yankees opted not to extend a one-year, $17.8 million qualifying offer to Gregorius last week, and it doesn't appear as though re-signing the shortstop is high on the team's list of priorities. Citing talks with industry people, SNY's Andy Martino reports that New York is not expected to pursue Gregorius "very aggressively."
Martino was previously told by a source that it was "a very close call" whether Gregorius would be back in the Bronx because the 29-year-old's camp does not think he needs to sign a one-year "pillow contract" to re-establish his value.
The Yankees are keeping a close eye on the $208 million Competitive Balance Tax threshold, and choosing to move on from Gregorius would give the team more flexibility to pursue upgrades elsewhere.
If Gregorius walks, the club has the option of moving Gleyber Torres to short and using DJ LeMahieu at second base on a permanent basis after he filled a utility role in 2019. The Yanks would still have Gio Urshela and the returning Miguel Andújar at third base and Luke Voit at first.
Cashman: 'We're going to talk' to Cole, Strasburg
Nov. 11: The Yankees are interested in both premier free-agent starting pitchers, Gerrit Cole and Stephen Strasburg.
General manager Brian Cashman said it himself Monday at the GM Meetings.
"Of course we're going to talk to Strasburg. We'll talk to Cole," Cashman said. He added that "anybody would have interest in players like that."
With Cole, the Yankees will likely face stiff competition from the teams in Cole's native Southern California, like the Angels.
Cashman also said Monday that he's had conversations with the agents of the Yankees' own free agents -- Brett Gardner, Didi Gregorius and Dellin Betances. The Yankees could try to retain any of the three this offseason, although Gardner seems like he might be the most likely with center fielder Aaron Hicks recovering from Tommy John surgery.
How will Yanks address their lineup imbalance?
Nov. 9: The Yankees have a powerful lineup, but it's heavily right-handed, and according to the New York Post's Joel Sherman, that could become a problem in the postseason.
"This feels like an area in which the six-month season and October differ," Sherman writes. "Over six months, against poor teams or against foes who can’t use the same top relievers over and over in a three-game series in June, the Yanks will feast. But in the playoffs, the bad teams are gone and the good clubs are using their best options each game."
Sherman suggests several left-handed hitter options beyond the big splash, which would be trading for Indians star shortstop Francisco Lindor. He lists Didi Gregorius -- though he also writes he's "more likely gone," Orioles infielder Jonathan Villar (whom Baltimore might want to part with given how much he might earn in arbitration), Reds shortstop Freddy Galvis (whom the Reds may part with if they sign Gregorius or another shortstop), and catchers Jason Castro (free agent) and Tucker Barnhart (also potentially a Reds trade candidate with Cincinnati reportedly interested in Yasmani Grandal).
Sherman added that the Yankees "tried hard" to trade for reliever Mychal Givens at the Trade Deadline. That raises the question of whether the Yanks might try to trade for both Villar and Givens, which would relieve Baltimore of significant payroll obligations while potentially stocking the rebuilding club with more prospects.
Are the Yankees willing to exceed the luxury tax in 2020?
Nov. 9: With the GM Meetings set to begin Monday, SNY's Danny Abriano has some questions he'd like to see Yankees general manager Brian Cashman answer. Three of the questions are closely linked:
1. What's the level of interest in Gerrit Cole and other top free-agent starting pitchers?
2. Is the club willing to exceed the Competitive Balance Tax (aka the "luxury tax") threshold?
3. Will the team look to re-sign Didi Gregorius?
Factoring in projected arbitration raises and players signed to Major League contracts, the Yankees' CBT figure for 2020 is already closing in on $190 million, according to Cot's Baseball Contracts. The first CBT threshold is $208 million.
That doesn't take into account new contracts for Gregorius and fellow free agent Brett Gardner. While Gregorius' future in the Bronx is still up in the air, the Yankees and Gardner have opened negotiations on a new contract, a source told MLB.com's Mark Feinsand. Gardner, who earned $7.5 million in 2019, may be looking for a raise after posting career highs in homers (28) and OPS (.829).
Cot's puts the Yankees' 2019 CBT number at $234 million, $28 million over last season's threshold of $206 million, which means the team would be a repeat offender -- and thus, would face a steeper tax rate -- if it exceeds it again in 2020.
Furthermore, as a CBT payor in 2019, the Yankees will need to forfeit their second- and fifth-highest selections in 2020 Draft as well $1 million from their international bonus pool if they sign any free agent who rejected a qualifying offer. The list of QO players this year includes five of the top starting pitchers: Cole, Stephen Strasburg, Zack Wheeler, Madison Bumgarner and Jake Odorizzi.
Cashman is highly unlikely to name specific targets the Yankees are planning to pursue, but he might indirectly reveal whether any of those pitchers are realistic options if he sheds some light on the team's luxury-tax stance at the GM Meetings.
Stanton: Yanks "can never have too many superstars"
Nov. 7: Is there a timeline where the Yankees sign Gerrit Cole and Stephen Strasburg? If New York slugger Giancarlo Stanton had his druthers, both aces would be in pinstripes next season.
Stanton told TMZ Sports that a team "can never go wrong with Cole and Strasburg," adding that the Bronx Bombers "can never have too many" superstars on their roster. It's no secret that the Yankees are looking for an impact starting pitcher to join Luis Severino, James Paxton and Masahiro Tanaka in their rotation, and signing either Cole or Strasburg -- the market's two best free-agent starters -- would qualify as a major splash.
"I'm pretty sure Gerrit grew up a Yankees fan, so he'd always like to do that," said Stanton. "And, Stras, we debuted together, so he'd like that."
Stanton and Strasburg both debuted in 2010, though not for the same team of course; they played for division rivals in Miami and Washington. Still, phenoms that come up with other teams are always linked to the Yankees eventually, and Stanton and Strasburg were no different when they took the National League by storm at the beginning of the decade. If Stanton gets his wish, those whispers regarding Strasburg and Cole could come true in the coming months.
Yanks-Gardy reunion in the works?
Nov. 7: Brett Gardner is the Yankees' longest-tenured player, and he might stay that way after one of the best seasons of his career. MLB.com's Mark Feinsand reports that New York is already talking to the free agent and his camp about a deal that would bring the popular outfielder back to the Bronx for 2020.
Gardner, 36, finished with a career-best 28 homers and .829 OPS while suiting up in 141 games for the injury-ravaged Yankees in 2019. He was the American League's eighth most valuable player this decade according to Baseball-Reference WAR, and excelled on a one-year, $7.5 million deal with New York this past season.
Sabathia: I've talked to Cole 'at length' about playing in NY
Nov. 6: Eleven years ago, the Yankees made one of the most successful free-agent signings in franchise history, bringing in CC Sabathia on a seven-year, $161 million contract. At the time, the big lefty, a California native, was unsure if he wanted to play in New York, but the Yanks significantly outbid the Angels and everyone else for his services. The recently retired Sabathia thinks the Yankees could do the same with Gerrit Cole this offseason, even if he has his own reservations about the Big Apple.
It has been widely assumed that Cole, another California native, wants to play on the West Coast, though he quashed that speculation the day after the World Series ended. "I never said that," the right-hander told the Houston Chronicle.
Even if Cole does privately have his heart set on a West Coast team, Sabathia thinks the Yankees could sway him with the right offer. He also revealed that the two have spoken on multiple occasions about Sabathia's experience in New York. More >
Could Wheeler be the Yankees' fallback option for Cole?
Nov. 6: The Yankees' decision to sign DJ LeMahieu to a two-year, $24 million contract instead of paying up for Manny Machado last offseason worked out incredibly well. LeMahieu was arguably the team's MVP, and New York had more resources to spend elsewhere.
The team will likely pursue free agent Gerrit Cole this year, but if the ace right-hander signs elsewhere or his asking price is too lofty, Ken Davidoff of the New York Post thinks signing a lower-cost alternative could work out well for the Yankees again.
If the Yankees miss out on Cole, Davidoff suggests they should do what it takes to get Zack Wheeler to jump from one New York team to another, even though it would cost the Yankees two Draft picks in addition to Wheeler's salary. More >
What does not extending a qualifying offer to Didi mean for Yankees' offseason plans?
Nov. 4: The Yankees did not extend a qualifying offer to Didi Gregorius ahead of Monday's deadline, but could he remain the club's starting shortstop in 2020?
The possibility certainly exists that New York could work out a new deal with Gregorius, but it's far from a guarantee -- especially considering the Yankees already have a potential in-house replacement. The club could simply shift Gleyber Torres to shortstop and have DJ LeMahieu return to second base, a position where he won three Gold Gloves during his time with the Rockies.
Along with Gregorius New York had six other players -- Dellin Betances, Brett Gardner, Cory Gearrin, Cameron Maybin, Austin Romine and retired left-hander CC Sabathia -- hit free agency following the season. The Yankees also declined a $20 million option on first baseman Edwin Encarnación, instead paying him a $5 million buyout.
Given New York's alternatives to Gregorius up the middle, the club might focus its priorities elsewhere. In fact, MLB.com's Bryan Hoch suggests that Gardner could be the free agent most likely to return to the Yankees next season in the wake of Aaron Hicks' Tommy John surgery.
How will luxury-tax concerns affect Yankees' plans?
Nov. 3: Aroldis Chapman's reworked contract keeps the Yankees' payroll situation relatively neutral in comparison to his former deal, but New York's competitive balance tax (CBT) considerations could still affect how they attack this offseason's Hot Stove.
Writing for the New York Post on Sunday, MLB Network insider Joel Sherman estimates that Chapman's $48 million salary over the next three seasons will cost the Yanks roughly $17.5 million annually toward the CBT payroll. Adding that figure to the Yankees' signed players, arbitration-eligible players and handful of non-arbitration-eligible players that the club needs to sign to fill out the roster, Sherman estimates that New York will be right up against the $208 million threshold for the first CBT penalty (20% tax on all overages for first-time offenders). That means the Yankees would have roughly $20 million to spend before triggering the second CBT penalty (additional 12% surtax), and roughly $40 million before triggering the third and final penalty (42.5% tax).
The Yankees have been hesitant to cross the CBT threshold in past years (the Red Sox notably did so while assembling their 2018 World Series champion roster), but the pressure to spend might be heightened in the Bronx after New York finished the 2010s without a single American League pennant. They have internal decisions to make on whether to extend the one-year, $17.8 million qualifying offer to shortstop Didi Gregorius, and whether to re-sign reliever Dellin Betances, who tore his left Achilles tendon in September. The pinstripes are also expected to be players in the sweepstakes for free-agent aces Gerrit Cole and Stephen Strasburg.
Source: Chapman staying with Yankees
Nov. 3: Aroldis Chapman will remain with the Yankees through 2022 after reworking his contract, a source told MLB.com's Mark Feinsand. The deal was first reported by ESPN's Jeff Passan. The club has not confirmed the agreement.
Chapman had until 12:01 a.m. ET on Sunday to opt out of the two years and $30 million remaining on the five-year, $86 million pact he signed with New York after the 2016 season. Instead, the Yankees added an additional year for $18 million to the deal, per Feinsand, which means Chapman will earn $48 million over the next three seasons. More >
Yanks mum on Didi, but indicate he could be back
Nov. 1: According to SNY's Andy Martino, the Yankees are keeping their intentions regarding free agent shortstop Didi Gregorius quiet, but do "like him as a person and see him as a bounce-back candidate as a player."
Gregorius was hurt for much of last season, and over 82 games, struggled to a .238/.276/.441 slash line, though he did hit 16 home runs. But he's still 29, and a season removed from career highs in homers (27) and OPS (.829).
With Gregorius a free agent, New York does have an infielder who can play shortstop in Gleyber Torres, who filled in for him at the position while he was sidelined last season.
Does Yankees' buyout of EE contract make Cole acquisition more likely?
Oct. 31: The Yankees declined to exercise their $20 million buyout on veteran slugger Edwin Encarnación, instead opting to pay him a $5 million buyout that makes him a free agent. New York acquired Encarnación in a trade with the Mariners last June. After being traded, he hit .249/.325/.531 with 13 home runs in 44 games for the Yankees. Overall, he slashed .244/.344/.531 with 34 homers in his age-36 season.
The buyout of Encarnación's contract frees up $15 million that would otherwise have gone to keep him in the fold. The Yankees have long been connected to Cy Young Award candidate Gerrit Cole, whose contract with Houston expired following the Astros' loss to the Nationals in World Series Game 7 on Wednesday night.
New York drafted Cole in the first round out of high school before he chose to go to UCLA, and has tried to trade for Cole in the past. The right-hander could set records for a pitcher contract in both overall and annual average value, and the Yankees have been conscious of bumping up against or breaking through the luxury tax threshold. But the Encarnación buyout perhaps makes it more likely that New York goes all in on bringing Cole to the Bronx.
The Yankees lost to the Astros in a six-game American League Championship Series and have starting rotation questions heading into 2020. Rotation stalwart CC Sabathia has retired, creating a vacancy that needs to be filled, not that the acquisition of Cole would be barred if there hadn't been an opening.
Does Stanton stand in the way of Yanks signing Cole?
Oct. 29: If it wasn't for Giancarlo Stanton's big contract on the books, the Yankees would be certain to pursue free-agent-to-be Gerrit Cole, according to Joel Sherman in an article for the New York Post. Cole, the most dominant pitcher of the postseason and a strong American League Cy Young Award candidate, has been on New York's radar from the start -- the Yankees drafted him out of high school in 2008 before he decided to go to UCLA, and then tried to trade for him but weren't willing to offer prospect Miguel Andujar in return. Will the club still go after Cole aggressively even if it means creating a luxury tax problem? More >
Is Cole to Yankees a long shot?
Oct. 25: Meeting with reporters on Thursday, Yankees general manager Brian Cashman balked at the idea that he had passed on some of the top available starters in recent years. Even though Justin Verlander, Gerrit Cole and Patrick Corbin ended up elsewhere, Cashman said he doesn't regret the team's decision-making process.
New York will have another chance to acquire Cole this offseason, but given the club's recent modus operandi, that may be a long shot.
The team is expected to engage on the 29-year-old, but as SNY's Andy Martino notes, the industry assumption is that the Southern California native prefers a West Coast club. For the Yankees to land Cole, they may need to significantly outbid other teams.
In a recent article for ESPN+ (subscription required), Buster Olney compared Cole's situation to that of CC Sabathia in the 2008-09 offseason. The Yankees were interested in Sabathia at that time, but the big left-hander wasn't sure he wanted to play or live in New York. The Yankees offered him $161 million over seven years to the Angels' $100M, and the rest is history.
New York's approach has been different lately. While the team has continued to spend big, it has shied away from the win-at-all-cost moves that defined the late George Steinbrenner's tenure as owner.
With Bryce Harper, Manny Machado and Corbin on the market, the Yankees avoided making a big splash in free agency last offseason, settling for depth-building transactions such as the signings of DJ LeMahieu, Adam Ottavino, Zack Britton and J.A. Happ. They also traded for James Paxton to bolster the rotation.
Cashman: Sánchez 'part of the solution'
Oct. 24: Another injury-plagued regular season and poor postseason for Gary Sánchez has led to more questions about how much the Yankees can trust the backstop as one of their team leaders. But for those wondering if New York might shop the slugger this offseason, Yankees general manager Brian Cashman's comments on Thursday likely provided an answer.
“I thought Gary Sánchez had a great season, outside of the injuries,” Cashman said. “Gary is part of the solution.”
Sánchez led all catchers with 34 homers over just 396 at-bats in the regular season, but he went 4-for-31 with 16 K's in the playoffs, bringing his career postseason slash line to .176/.225/.382 with a 36 percent strikeout rate over 111 plate appearances.
However, Cashman pointed to Sánchez’s work behind the plate as one reason why the Yankees were able to hold the Astros to 21 runs and a .179 average in the American League Championship Series.
“Gary's a big part of that,” Cashman said. “He follows the game plan, he executes the game plan. He limited the Astros to two stolen bases the whole series, and they're a very aggressive baserunning team. ... When I say our pitching did a great job during that series, Gary is a big part of the reason why in how he called those games and how he kept changing the signs to make sure that we're protecting our pitch selections. I just thought he did a remarkable job. I don't think he gets the credit that he's due.”
With Hicks undergoing TJ surgery, Gardner likely back
Oct. 24: Yankees general manager Brian Cashman announced Thursday that outfielder Aaron Hicks would be undergoing Tommy John surgery on Oct. 30, with an estimated recovery time of eight to 10 months.
MLB.com's Mark Feinsand speculates that Hicks' injury could increase the chances of free agent Brett Gardner returning to the club. Feinsand has heard that another one-year deal is likely for the Yankees' longest tenured player.
After buying out his contract option for $2 million last offseason, the Yankees re-signed Gardner to a one-year, $7.5 million deal. At the time, the expectation was that he would play a lesser role, with Hicks, Aaron Judge, Giancarlo Stanton and Clint Frazier in the fold.
But given the Yankees' myriad of injuries, Gardner ended up playing 141 games, and he produced career highs in homers (28) and OPS (.829).
If Cole signs elsewhere, will fallback option come from within?
Oct. 22: The Yankees are expected to pursue starting pitching this offseason after relying heavily on their bullpen in the postseason, but there's been some speculation that they would need to significantly outbid other teams to get Southern California native Gerrit Cole to come to New York.
If Cole proves to be too expensive, and Stephen Strasburg uses his opt-out leverage to get a longer deal from the Nationals, the Yankees would be left to consider mid-tier options such as Madison Bumgarner, Zack Wheeler, Hyun-Jin Ryu and Jake Odorizzi. Each of those hurlers will be costly in their own right, but they might not necessarily put the Yankees over the top.
While Yankees fans will be disappointed if general manager Brian Cashman doesn't address the rotation with a major move or two, there's a chance the team's Cole fallback option is already in the organization.
According to nj.com, Cashman hasn't ruled out top prospect Deivi Garcia (MLB Pipeline's No. 62 overall) making the club's Opening Day rotation in 2020, citing Jordan Montgomery's surprising ascent two years ago as proof that anything could happen.
“How would I know?” Cashman said when asked about the possibility of Garcia cracking the starting five. “Montgomery won a rotation spot, he wasn’t even on a competition list that anybody was talking about going into the spring. He wasn’t part of the depth chart and he leapfrogged everybody and the coaches were pounding the table for him.”
Garcia began last season in Class A Advanced, but he quickly moved through the ranks and finished the season in Triple-A. All told, he had a 4.28 ERA with 165 strikeouts over 111 1/3 innings. He won't turn 21 until next May.
“For his age, to do what he’s doing,” Cashman said. “I was just looking at Baseball America last night and he’s listed as like, Double-A All-Star and I think it opened up with him being the youngest pitcher in the Eastern League. And I was like, he was probably the youngest pitcher in the International League, and if he got here, he would have been the youngest pitcher in the big leagues. It was an incredible run. But obviously he’ll go on the roster this winter and we’ll see what we got in the spring.”
Even if Garcia needs more time in Triple-A, the Yankees will benefit from having a healthy Luis Severino alongside James Paxton and Masahiro Tanaka in 2020. Severino missed most of 2019 due to shoulder problems, but he was a Cy Young contender before that. J.A. Happ and Montgomery, who will be two years removed from Tommy John surgery in June, are options to round out the rotation.
Will Yanks need to crush field with bid to sign Cole?
Oct. 21: After relying heavily on their bullpen in their American League Championship Series loss to the Astros, the Yankees are widely expected to target Gerrit Cole this offseason to fill their need for a bona fide ace.
But even if the Yanks have the top bid, there's no guarantee that Cole, a Southern California native, will want to come to New York.
In an article for ESPN+ (subscription required), Buster Olney notes that some Astros teammates predict Cole will ultimately sign with a California team. Per Olney, the industry expectation is that he'll end up with the Angels.
Olney compares Cole's situation to that of CC Sabathia in the 2008-09 offseason. The Yankees were interested in Sabathia at that time, but the big left-hander wasn't sure he wanted to play or live in New York. The Yanks were told they needed to significantly outbid other teams to sway Sabathia. They did just that, offering him $161 million over seven years to the Angels' $100M, and the rest is history.
New York's approach has been different in recent years, with general manager Brian Cashman avoiding win-at-all-cost moves. A year ago, the Yankees weren't willing to go to six years for New York native Patrick Corbin, and as a result they were outbid by the Nationals. But after another disappointing postseason exit, the club could be more aggressive this offseason.
Whether the Yankees are involved or not, Cole could top David Price's $217 million contract with the Red Sox for the largest deal ever signed by a pitcher.
Lindor a possible target for Yanks?
Oct. 21: Fresh off a heartbreaking loss to the Astros in the American League Championship Series and a decade removed from their last World Series title, the Yankees are heading into a pivotal offseason. New York has been eliminated from the postseason by Houston in three of the past five years, and general manager Brian Cashman will be tasked with making moves that finally put the club over the top.
Ace right-hander Gerrit Cole is expected to be a target, but MLB Network insider Joel Sherman thinks the club should also look elsewhere for a big splash. In an article for the New York Post, Sherman suggests calling the Indians to see if 25-year-old shortstop Francisco Lindor is available.
"Look, the Yankees are ready to win now and Lindor is everything they need," Sherman writes. "A switch-hitting shortstop with power, speed, limited strikeouts, defensive excellence at short and proven postseason fearlessness. The Yanks’ athleticism improved from 2017 to ‘19. But on the same field, the Astros look like they’re playing fastbreak and the Yanks slow down to half-court."
Lindor can become a free agent after the 2021 season, and Indians chairman/CEO Paul Dolan has admitted that it will be a challenge to re-sign him, as he will likely command a contract north of $300 million.
The Yankees have an opening at shortstop, with Didi Gregorius headed for free agency after his worst season in pinstripes. Internally, they could turn to Gleyber Torres at short and have DJ LeMahieu take over at second base full-time. They may also try to re-sign Gregorius if the price is right, as the 29-year-old has proven to be productive on the field as well as an important clubhouse presence during his time in pinstripes. But those options could take a back seat if there's a realistic chance to get Lindor.
Pressure will be on Yanks to make big splash with Cole signing
Oct. 18: Although the Yankees' poor hitting with runners in scoring position has been their biggest problem during the American League Championship Series against the Astros, their lack of an ace hasn't helped matters.
Manager Aaron Boone has gone to the bullpen early in nearly every postseason game, leading to overtaxed arms and Houston's hitters gaining more familiarity with New York's relievers. Just one Yankees starter has lasted more than five innings in the club's seven postseason games, with Masahiro Tanaka going six scoreless in ALCS Game 1, New York's only win of the series.
The Yanks are in their third year of contention with their current core, but the club hasn't been able to break through and win the World Series -- or even get there. In fact, if New York doesn't come back from its 3-1 ALCS deficit, it will have gone the entire decade without a Fall Classic appearance, something that hasn't happened since 1910-19.
Gerrit Cole, meanwhile, is in the midst of one of the greatest walk-year campaigns in history. The Yankees got a first-hand look at the right-hander in ALCS Game 3, when he tossed seven scoreless innings in a pivotal win for Houston.
• Read the latest news and rumors on Gerrit Cole
After failing to sign Cole out of high school as the 28th overall pick in the 2008 MLB Draft and then missing out again two years ago, when the Pirates traded him to Houston, it's reasonable to expect the Yanks to make an all-out push to finally get him in pinstripes.
It's not a given, however, as MLB Network insider Ken Rosenthal writes in an article for The Athletic (subscription required). While the team has continued to spend big, it has shied away from the win-at-all-cost moves that defined the late George Steinbrenner's tenure as owner.
The Yankees avoided making a big splash in free agency last offseason, settling for depth-building transactions such as the signings of DJ LeMahieu, Adam Ottavino, Zack Britton and J.A. Happ. They also traded for James Paxton to bolster the rotation, though he hasn't proven to be a true No. 1 starter.
At the start of the offseason last year, the Yanks were considered the favorites to land Patrick Corbin, but they were significantly outbid by the Nationals. Corbin, who signed for $140 million over six years, has since helped Washington reach its first World Series.
And while general manager Brian Cashman aggressively explored the pitching market leading up to the Trade Deadline, the team ultimately didn't make a move on that front due to some reportedly exorbitant asking prices. That's also why they didn't acquire Cole from the Pirates, as Pittsburgh was reportedly asking for a package centered around Miguel Andújar and Clint Frazier.
The moves New York did make mostly worked out, but another postseason flameout would put the pressure on Cashman to be more aggressive at the top of the market this offseason.
Would Yanks let Didi walk to sign Cole?
Oct. 17: It's likely this offseason that the Yankees will prioritize adding the top-tier ace they lack, and Astros right-hander Gerrit Cole could be a prime target, possibly at the expense of their other free agents.
New York has most of its key players under control beyond 2020, but shortstop Didi Gregorius is set to hit the open market, alongside Dellin Betances, Brett Gardner, Austin Romine, Cameron Maybin and possibly Edwin Encarnación, who has a $20 million club option ($5 million buyout).
While Gregorius had a down year after undergoing Tommy John surgery last October, which could limit his asking price, he is still just 29 years old and produced 14.6 fWAR from 2015-18 after taking over for the legendary Derek Jeter.
The Yanks will likely look to re-sign Gregorius, but with emerging superstar Gleyber Torres showing the ability to play shortstop and DJ LeMahieu capable of stepping in as the full-time second baseman, New York does have options. As a result, ESPN's Jeff Passan suggests the team could let Gregorius walk and put that money toward signing Cole instead.
A Yankees-Dodgers battle for Cole?
Oct. 14: After a brilliant regular season, Cole has continued to dominate in the postseason, going 2-0 with a 0.57 ERA, a 0.57 WHIP and 25 strikeouts in two starts during the American League Division Series against the Rays.
The 29-year-old couldn't be heading into free agency on a higher note, and MLB Network insider Jon Heyman predicted Monday on the latest episode of the "Big Time Baseball" podcast that Cole will set multiple records this offseason by landing a seven-year, $245 million contract.
That would be the largest contract ever signed by a pitcher and would also give Cole the highest average annual value ($35 million) in MLB history, for any player.
So which teams might be in position to give Cole that deal? In Heyman's view, it could come down to two of the richest clubs in the game, the Yankees and Dodgers.
The Yankees' need for an ace starter has been well documented, and the club is going to have to lean heavily on its bullpen to defeat Cole's Astros in this year's AL Championship Series.
The Dodgers' rotation is in better shape than the Yankees', and Los Angeles has been hesitant to make a sizable expenditure on the free-agent market during Andrew Friedman's tenure as president of baseball operations. But as Heyman notes, the team could have a greater sense of urgency after a disappointing loss to the Nationals in the National League Division Series, which came on the heels of back-to-back World Series appearances and a franchise-record 106 wins in 2019.
Los Angeles hasn't won a World Series title since 1988, and the club watched the rival Giants collect three championships in the past decade despite averaging only 82 victories per season in that span.
Additionally, the Dodgers may need to replace two starting pitchers, with Hyun-Jin Ryu and Rich Hill set to join Cole on the free-agent market.