Give the Yankees credit for their strong push for Gerrit Cole and Stephen Strasburg this week, despite the likelihood that neither will end up in New York. A large swath of Yankees fans have turned against Hal Steinbrenner, somehow deciding he's a cheapskate, but the club's face-to-face meetings with both mega free agents say otherwise. The Yankees are all-in; there's no reason to think they're bluffing.
Why else would general manager Brian Cashman have flown to the West Coast and back in two days if he wasn't sincere about selling the Yankees' brand? He pitched all the accessories that come with baseball in the Bronx—big-market energy, the American League's top-drawing team, defending AL East champs, no losing seasons since 1992 and the current core that's increased its win total three straight years, topping out at 103 in 2019.
Those are sweet-sounding perks, but what really matters to Cole and Strasburg—both Scott Boras clients—is how much Steinbrenner, the principal owner, is willing to pay. According to those familiar with the talks, no dollar amount was discussed by either side. It's too early for that. But the Yankees wanted to let both pitchers know the summit wasn't gratuitous.
The Yankees need to change the narrative, to upgrade from contenders to finishers. To do that they need Cole or Strasburg in a way that's larger than the sum of their existing parts. Because the roster is already good. Heck, it's great. But it's time for Steinbrenner to make a serious splash and, just as significantly, convince the ticket buyers that 2020 will be the year the barrier is finally crossed.
The Steinbrenner family is willing to pay whatever it takes, although that's a dangerous promise to make to Boras in any negotiation, let alone to the two most sought-after pitchers in the game.
Remember, Zack Wheeler, who has no postseason track record, just pulled down $118 million in a five-year deal with the Phillies. The windfall will be exponential for Boras, who can use the Yankees' interest to drive up the price for the Nationals, who are believed to have the inside track on Strasburg, and the West Coast teams, who offer Cole the opportunity to return to his Southern California roots.
It's entirely possible that the Yankees will whiff, despite being willing to offer Cole a "record-setting deal," as ESPN's Jeff Passan is reporting. In that case, they'll almost certainly turn their attention to Madison Bumgarner. It'll be a much smaller deal, but make no mistake, the former Giants lefty has enough October cred to be a difference-maker to the Yankees, even if he's in his late prime/early decline phase.
Bumgarner is leaving San Francisco on a down note—the Giants finished 29 games behind the Dodgers in the NL West and 12 games out of the wild-card race, which means the Yankees' sales pitch will likely have greater traction for Bumgarner. He'd very much like to return to the playoffs. That's where he's done his best work over an 11-year career. That's his legacy: World Series beast.
Trouble is, the Yankees haven't won a pennant since 2009, and the drought has created an alternative narrative among some (many?) elements of the fanbase. They dismiss the $204 million payroll and instead focus on what Steinbrenner and Cashman haven't spent on: the kind of ace they're only now pursuing. Cashman didn't help matters in his post-playoffs press conference, coolly telling reporters he didn't regard the 2019 season as a failure despite the heartbreaking loss to the Astros in Game 6 of the ALCS.
He was technically right. The Yankees are a smart, well-run organization that spends money wisely. They've turned into perennial contenders without ever having to rebuild. Unlike the Red Sox, who finished last in the East in 2014 and '15 before winning a championship in 2018, the Yankees have never needed to bottom out.
But that argument sounds less compelling today than it did three years ago when the Yankees started their minisurge. For the first time since 2016, it feels like the club has stalled. Aaron Judge said as much in the clubhouse after the season-ending loss to the Astros.
"No matter how many games we won, or whatever else we did, this season is a failure," he muttered. "We'll be thinking about this for a while. I'll be thinking about it all offseason. Every single day."
For all their triumphs, the Yankees need a championship in 2020 to validate their progress. Otherwise, the "brand" that Cashman is selling will morph into the modern-day version of the Braves, who made it to the NLCS eight years in a row in the '90s with only one World Series conquest to show for it in 1995.
Ironically, the Yankees are doing plenty under the radar. They spend more on analytics and player development than any team in the majors. One club executive put it bluntly, saying, "Pretty much whatever we need, Hal almost always says 'yes.'"
Even the salaries the Yankees minor leaguers earn sets them apart. One American League official said: "The Yankees can pay their Triple-A guys $10,000 a month, which is significantly higher than what other teams pay. That's one reason why their system is so successful—because of their investment."
Another executive, addressing that same point, said: "The only team in the East that could've competed with the Yankees last year was their Triple-A club. And I'm actually not kidding."
One other point: Unlike the Astros, who are facing serious penalties from the commissioner's office for alleged sign-stealing dating back to 2017, the Yankees can say they've built an honest contender. "We Don't Cheat" might as well be the motto for 2020.
But this isn't the NCAA. Rob Manfred doesn't have the power to strip the Astros of their 2017 championship. The Yankees will have to live with falling short that year. And in 2018. And in 2019. It's finally starting to hurt.