Yankees: Five moves they should make during the Winter Meetings

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The Winter Meetings are officially here and there’s a good chance the Yankees will be very active over the course of the next four days.

The offseason hot stove is starting to heat up and the expectation is that this year’s Winter Meetings will feature a lot more action than it did a year ago. The Yankees are one of the many teams who will be looking to make a big splash and according to reports they will not be denied in their pursuit of a certain ace right-hander.

Signing Gerrit Cole is the number one objective the Yankees will try to get done this week in San Diego, but even if they do there’s still more work to be done. Including signing Cole here are five moves the Yankee front office should try to make before they head back east to the Bronx.

Sign Gerrit Cole

We’ll start with the obvious first because signing Gerrit Cole is the Yankees top priority this offseason. Their main focus right now is on landing this year’s AL Cy Young runner-up and rightfully so. There isn’t a free agent available who the Yankees need more this offseason than Cole if they’re going to get over the hump and win a championship in 2020.

He’s everything they’re looking for to improve their starting rotation and it would be a failure in the eyes of the fans if they didn’t land him before the offseason is all said and done with. According to Bob Klapisch of The New York Times, the Yanks already have an offer on the table for Cole that would make him the highest-paid pitcher in major league history.

I'm told #Yankees have a seven-year, $245 million offer on the table for Gerrit Cole. Would be a record-setting contract for a pitcher, surpassing Greinke’s $34.4 million AAV. Question is whether #Dodgers or #Angels will go to 8-9 or even 10 years.
— Bob Klapisch (@BobKlap) December 8, 2019

This would be a great first offer from the Yanks who are considered one of the three favorites to get Cole along with the Angels and the Dodgers. However, a seven-year offer might not be enough to convince him to sign on the dotted line so they’re probably going to have to add another year and another $35M.

Coming into the offseason there was talk that Cole would sign a deal worth at least $280M and if the Yankees and Hal Steinbrenner are willing to commit that amount of money to him you have to like their chances. During their meeting with Cole last week he reassured the Yanks he’ll have no west coast bias when making his final decision. He wants to go where he can win consistently and build his legacy as one of the greatest starting pitchers of his era. There’d be no better place for him to do both o than in New York.

NEW YORK, NEW YORK – APRIL 17: Brett Gardner #11 of the New York Yankees reacts after he hit a grand slam in the seventh inning against the Boston Red Sox at Yankee Stadium on April 17, 2019 in New York City. (Photo by Elsa/Getty Images) /

Re-sign Brett Gardner

It seems like the Yankees are solely focused on Gerrit Cole right now but once he makes his free-agent decision more moves will follow from New York. One of those moves will likely be re-signing Brett Gardner to return for a 13th straight season in pinstripes. A reunion between Gardy and the Yanks makes all the sense in the world especially with Aaron Hicks now expected to miss a large chunk of next season recovering from Tommy John surgery.

Not only do they need someone to fill in for Hicks in center field but they also need a power lefty bat and Gardner was their best a season ago. Mike Tauchman will also be back which helps but he’s only played in one big-league season and might be better off serving as the fourth outfielder to start the season and split some of the reps in left field with Giancarlo Stanton.

Last offseason the Yanks brought Gardy back on a one-year deal worth 7.5M but after he posted a career-high 28 HR and 74 RBI in 2019 he should be in line for a nice pay raise this offseason. A one-year deal worth $10M is a fair offer for Gardner and maybe the Yanks add on a second-year with a club option. Either way, I’d be shocked if the 36-year-old isn’t back in the Bronx next season to help this group chase another championship.

NEW YORK, NEW YORK – SEPTEMBER 17: Didi Gregorius #18 of the New York Yankees follows through on his fourth inning two run double against the Los Angeles Angels of Anaheim at Yankee Stadium on September 17, 2019 in the Bronx borough of New York City. (Photo by Jim McIsaac/Getty Images) /

Re-sign Didi Gregorius or trade for a left-handed hitter

The Yankees haven’t closed the book on re-signing Didi just yet but it’s not looking very likely that he’ll be back in 2020. Even after an injury-plagued down year in 2019, the 29-year-old shortstop should still be able to cash in on a multi-year deal with a club looking for middle infield help.

Didi struggled offensively last season, but a lot of that can be attributed to him coming back to soon from TJ surgery. As long as he stays healthy he’s going to have a more productive season on both sides of the ball in 2020 and the Yankees and every other team interested in signing him knows that.

There will probably be teams that offer Didi a deal for three or four years, but if he wants to return to New York it would probably only be on a one-year deal. The Yanks declined to give him the qualifying offer of $17.8M earlier this offseason because they were afraid he would accept it but I think they’d still love to have him back for another year just for less money. They’re not going to outbid another club to bring him back but there’s still a need for Didi on this roster.

Gleyber Torres could easily shift over to shortstop next season and DJ LeMahieu could move back to second but Gleyber isn’t the defender Didi is at short which is a concern. Didi is also the Yankees best left-handed hitter when he’s at his best and their lineup is still going to be very right-handed heavy next season even if they bring back Brett Gardner. In addition to that Didi is one of the top leaders in the Yankee clubhouse and a true fan favorite which can’t be understated.

I hope the Yanks find a way to bring Didi back, but if they can’t they could look to add another left-handed bat via trade. A deal for switch-hitting superstar Francisco Lindor seems like a pipe dream for now, but a trade for Pirates All-Star first baseman Josh Bell is something the Yanks could potentially pull off according to Jim Bowden of The Athletic.

NEW YORK, NEW YORK – OCTOBER 15: Joe Smith #38 of the Houston Astros pitches during the eighth inning against the New York Yankees in game three of the American League Championship Series at Yankee Stadium on October 15, 2019 in New York City. (Photo by Mike Stobe/Getty Images) /

Sign Joe Smith, Dellin Betances, or Blake Treinen

It’s a safe bet that the Yankees will add another reliever to their bullpen at some point this winter. Improving the bullpen isn’t a pressing need like it has been in year’s past but you can never have too many good relief pitchers. Three names come to mind in right-handers Dellin Betances, Joe Smith, and Blake Treinen. Any one of these guys would help deepen the Yankee pen and give Aaron Boone another quality option to choose from.

Betances has spent his entire pro career with the Yankees and is a free agent for the first time. The four-time All-Star only pitched in one game last season due to shoulder issues and when he did make his season debut in early September he partially tore his Achilles. It was a brutal blow for Dellin but he should be healthy and ready to go for spring training which means he’ll still likely garner plenty of interest on the free-agent market because of his great track record.

The Yankees would love to have Dellin back, but he could be out of their price range if opposing teams offer him a multi-year deal. The only way I see him returning is if it’s on a one year deal as well and maybe with a club option for 2021.

More from Yanks Go Yard

Joe Smith is a guy I’ve wanted on the Yankees for years now just so they don’t have to face him in the playoffs. The 35-year old sidearmer has been a thorn in New York’s side two out of the last three Octobers and has always come up big on the postseason stage. His ability to shut down right-handed hitters has always been his biggest strength and is part of what makes him so valuable.

If the Yanks signed Smith he would provide a different look in a group that’s filled with power arms. He would be a great addition and the Yankee pen is so deep that he could be used at any time in a game which could increase his effectiveness.

Blake Treinen just recently became a free agent after he was surprisingly non-tendered by the A’s and should be highly sought after despite having a poor season in 2019. That’s because two years ago he was arguably the best reliever in baseball so a change of scenery could be exactly what he needs to get his career back on track.

Treinen really struggled to keep his power sinker down in the zone last season, but he still has plus stuff and the ability to dominate as he did in 2018. He could be a great reclamation project for new pitching coach Matt Blake to work with.

HOUSTON, TEXAS – OCTOBER 13: J.A. Happ #34 of the New York Yankees pitches during the tenth inning against the Houston Astros in game two of the American League Championship Series at Minute Maid Park on October 13, 2019 in Houston, Texas. (Photo by Bob Levey/Getty Images) /

Trade J.A. Happ

If the Yankees sign Gerrit Cole or add another starting pitcher this week they could look to trade J.A. Happ for a couple of reasons. The first would be to clear up some cap space. Happ is owed $17M in 2020 and has a vesting option for the same amount in 2021. If he stays with the Yanks next season he probably won’t be allowed to reach the 27 starts or 165 innings he needs to for his contract to vest but he could with another club in need of a veteran starter.

The second reason he could be dealt is to open up a spot in the starting rotation for Jordan Montgomery. The soon to be 27-year-old southpaw missed the first five months of the season last year recovering from Tommy John surgery, but he’ll be ready to go in 2020. In 2018, Montgomery had a terrific rookie season for the Yanks and still figures to be a big part of the team’s rotation for years to come.

Whether it’s Cole or someone else the Yankees are going to add another starter and if Happ remains on the roster Montgomery could be relegated to the bullpen. It’s important to have starting pitching depth but clearing up cap space and securing a spot for Montgomery on the starting staff is more important for this Yankee team. And it’s not as if they’d have a lack of depth after trading Happ because Mike King and top prospect Deivi Garcia could both crack the rotation at some point next season. (Don’t forget about Domingo German either).

The Rangers are interested in trading for Miguel Andujar. dark. Next

Even if it means the Yanks have to attach a high-end prospect to get another team to take Happ they should still do it. Knowing their willingness to sign Cole to a record-breaking contract, they should really try to clear up some cap space and outside of trading Giancarlo Stanton (which isn’t happening) the best way to do it would be by trading Happ.

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