Yankees 2020 Shopping List: Here’s Who They Need To Return To The World Series

By Chris Melore

Major League Baseball’s offseason is already in full swing as all 30 teams are diving into the annual spending spree, better known as free agency. One of the winter’s biggest wheeling-and-dealing events kicks off Sunday night in San Diego with the Winter Meetings.

For the Yankees, a second straight 100-win season came to a sudden and crushing end in the ALCS at the hands of the Houston Astros.

MORE: So Much For ‘Savages In The Box,’ Yankees Were Strikeout Machines During ALCS Failure

Despite being let down again by their lack of clutch hitting, New York has already made it known they’re planning to spend and spend big to fix the one area that’s miles behind their biggest rivals — starting pitching.

The following is the Yankees’ version of a Christmas wish list; what they need to shop for this offseason to become champs for the first time since 2009:


New York desperately ne to hit a home run in the starting pitching market this winter — not just for their roster, but to salvage their relationship with many fans who have lost confidence in the front office’s ability to make a game-changing move.

Owner Hal Steinbrenner and GM Brian Cashman have failed in recent years to land the big name ace via free agency or trade. From Justin Verlander, to Chris Sale, to Patrick Corbin (all who have World Series rings now) — that simply can’t happen in 2020 if the Yanks are serious about winning a championship.

Astros ace Gerrit Cole dominated in the 2019 playoffs, striking out 47 in 36 innings and recording a 1.72 ERA. (Photo by Mike Stobe/Getty Images)

The name at the top of the shopping list is an obviously one: Gerrit Cole.

Cole is coming off one of the great pitching seasons in recent memory and, arguably, the best walk-year performance in baseball history.

The 29-year-old workhorse struck out a staggering 326 batters in 212.1 innings this past season. It was his second All-Star campaign in a row with the Astros, who was seemingly revived after not reaching his full potential with the Pirates.

New York has no one who can match Cole’s level of greatness currently — not even starters Luis Severino or James Paxton — and the front office would appear to know that. According to reports, ownership has given their blessing to offer the prized free agent a “record-setting” deal.

The only obstacle that should be facing the Yankees successfully signing Cole would be if the California-native makes the decision to pitch closer to home.


Did you think really think there was only going to be one pitcher on this list?

The Yanks’ bullpen-or-bust strategy blew up in their face during the 2019 ALCS. The Astros continually came through in the clutch off New York’s high-paid relievers, who were forced into games earlier and earlier by the team’s lackluster starting pitching.

Aside from Masahiro Tanaka, Severino, and Paxton, there is no reason Brian Cashman shouldn’t be looking to go overboard this winter and build a super rotation.

Giants starter Madison Bumgarner has a stunning 2.11 ERA in 16 postseason appearances. He’s also 4-0 in the World Series. (Photo by Jamie Squire/Getty Images)

This offseason’s free agent pitching crop includes a name that New York should have already traded for last year: Madison Bumgarner.

The 30-year-old lefty’s resume speaks for itself. He’s won three championships, twice pitched a shutout in the NL winner-take-all Wild Card game, and has a legendary 0.25 ERA in five World Series games.

Bumgarner has seemingly lost some of his luster among league executives due to injuries in 2017 and 2018, but he rebounded to make a league-leading 34 starts last season and struck out 203 batters — his best total since 2016. The veteran southpaw and postseason ace is the perfect answer to replace CC Sabathia, who retired after the playoffs.

Now, instead of trading prospects, that move will only cost money.


If signing two big name free agent pitchers is just too rich for the Yankees’ blood, the team ne to explore the already-active trade market this winter.

J.A. Happ has no place in the starting rotation. Re-signing the 37-year-old has already proven to be another costly pitching mistake for Cashman, who passed on making a larger offer to younger lefty Patrick Corbin and gave Happ at least $34 million guaranteed. He could earn another $17 million in 2021 if he makes at least 27 starts or throws 165 innings next year.

Rumors are already swirling New York may try to sell low on Happ — making room for a better rotation option. Perhaps Corey Kluber?

Corey Kluber won the AL Cy Young in 2014 and 2017 for the Indians. (Photo by David Maxwell/Getty Images)

The Cleveland ace is coming off a disastrous season, which was limited to just seven starts. The 33-year-old missed most of the season after having his pitching arm broken by a line drive back to the mound.

Before that though, the two-time Cy Young winner was one of the game’s premier workhorses, throwing over 200 innings and striking out over 200 batters in five straight seasons. The Indians picked up his $17.5 million option for next year, but the team has made it known they are trying to shed payroll. Cleveland is even reportedly open to trading franchise player Francisco Lindor.

New York should finally look to move their wealth of young prospects to get the dominant rotation it ne.

With outfielders Giancarlo Stanton and Aaron Hicks locked up to long-term deals — and Aaron Judge under team control — keeping talented youngsters like Clint Frazier and Estevan Florial is only damaging their trade value at this point.

Trade them and get the pieces you need to win in 2020, not 2024.


He may not have won the award, but make no mistake, DJ LeMahieu was the most “valuable” player in 2019.

FLASHBACK: 5 Undeniable Reasons Why DJ LeMahieu Is The AL MVP

DJ LeMahieu hit .325 with 3 homers during the Yankees’ 2019 playoff run. (Photo by Elsa/Getty Images)

Signed only through 2020 to a dirt cheap bargain of $12 million, the Yankees can’t allow the super utility infielder to reach free agency.

LeMahieu flashed Gold Glove defense at first, second, and third base in 2019, while having a career year at the plate. Not only did the 31-year-old drive in 102 RBI (mainly from the lead-off spot), he was the league’s most clutch performer — hitting a mind-boggling .389 with runners in scoring position.

Locking up LeMahieu now would give manager Aaron Boone supreme stability up the middle of the field, with catcher Gary Sanchez, infielder Gleyber Torres, Hicks, and LeMahieu all under contract for the next few seasons.


This deal is already reportedly in the works, but it’s something that still ne to get done and fast.

The Yankee veteran is the final member of the 2009 championship club still around and that type of experience can’t be measured in the stat columns.

The 36-year-old speter seemed like he was at the end of his career a season ago, but transformed himself into a power hitting lefty that brought a righty-heavy Bronx lineup needed balance. Gardner shocked the baseball world by slugging a career-high 28 homers and 74 RBI.

With Hicks expected to miss the first half of 2020 with Tommy John surgery, bringing back Gardner for one more run will give New York the outfield insurance they need.

columns by Chris Melore