Yankees will meet with Gerrit Cole and Stephen Strasburg this week

According to Ken Rosenthal of The Athletic, the Yankees will send a delegation to Southern California within the next two days to meet with the most prized free-agent pitchers on the market, Gerrit Cole and Stephen Strasburg.

Over the past few offseasons, the Yankees have been notoriously delayed in their approach when it comes to big-name free agents. Whether or not it’s a tactic that GM Brian Cashman uses to gauge the open market before extending what he and Hal Steinbrenner feel is a fair offer, this winter could mark a turning point for the future of the Bombers.

With many of their young stars either still outside the window of arbitration or just now entering it, there will soon come a time when the Yanks are forced to extend the likes of Aaron Judge, Gary Sanchez and Gleyber Torres — each for enormous paydays.

Therefore, the time is now for the organization to add a top-flight No. 1 ace that not only makes them American League favorites but isn’t completely abandoned because of the ever-important luxury tax threshold.

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Entering season 11 without a World Series championship, the Yankees will need to replicate much of the success they experienced in 2019 while avoiding having to place 30 different players on the injured list.

While starting pitchers always come with a hint of risk, considering the massive amount of strain they put on their arms every five days, the Yanks have avoided making a significant splash in free agency for a pitcher since they signed Masahiro Tanaka back in 2014.

And while Masa has been up and down as of late during the regular season, there’s no doubt he’s been the club’s best postseason pitcher since coming over from Japan.

Because every team has a window of opportunity to win championships (yes, plural), New York must blow every other offer that Cole, 29, and Strasburg, 31, have been or will be extended, out of the water.

We now know they’ll get their first, and perhaps, last chance to make a lasting impression as the Yanks are set to sit down with both Cole and Strasburg in Southern California this week. 

No, the Yankees won’t sign both, but the pair of recent World Series right-handers share the same super-agent, Scott Boras.

While many within baseball expect Cole to sign with the Angels, seeing that he’s from Newport Beach, CA (reports that Cole denies) — Angels’ brass is already on record stating they will spend whatever it takes to sign Cole.

So if Cashman and company truly desire a player they drafted out of high school in the first round of the 2008 draft, now will be their final attempt to get him in pinstripes.

As for Strasburg, who is from San Diego, CA — home of this year’s Winter Meetings which run from Dec 8-12, a return to Washington D.C. seems most likely unless someone offers “stupid money.”

Hal Steinbrenner recently told Meredith Marakovits that he likes the Yankees’ rotation — and if the season started today, he’d be more comfortable with it than he was a year ago; however, it still lacks a consistent shut-down ace.

While Luis Severino has the stuff to get back to the level he displayed in 2017 and ’18 — and James Paxton won 10 consecutive games down the stretch, injuries struck both this past season.

Even with the luxury tax being in play, Steinbrenner says it won’t be a hindrance to signing a starting pitcher.

"“(The luxury-tax thresholds are) a big deal,’ he said. “It’s something we’d certainly prefer not to do, because there are June draft ramifications. There are numerous ramifications. But (going over all three thresholds) is something that I would consider."