The Yankees chose not to bolster their rotation with a trade, but Brian Cashman should sign one of these 5 starters in free agency next winter.
General manager Brian Cashman is being skewered on social media for his failure to strengthen the team’s starting rotation via a trade this month. That’s certainly a disappointment for Yankees fans at the moment, but the offseason will present the franchise with another opportunity to add a big-name starter.
That’s really all Yankees fans can look forward to at the moment. This year’s chance of winning a World Series look to be on thin ice due to the inconsistency of Aaron Boone’s starting rotation. Anything can happen if the team’s arms get hot at the right time, but New York will not head into October as the favorite.
That makes it a prudent time to look ahead at what the Yankees might be able to do in the offseason. The hope is that Luis Severino will return to full health to replace CC Sabathia, but upgrades will still be required. Signing one of the following five starters would give the Yankees a big boost in free agency.
5. Hyun-Jin Ryu
Thirty-two-year-old southpaw Hyun-Jin Ryu is enjoying the best season of his career with the Dodgers. He’s a huge reason why fans in Los Angeles think they’re destined to appear in this year’s World Series. Having an ace with an ERA of 1.74 in 20 starts is a major factor as to why the Dodgers are riding high in the NL West.
It’s unlikely Ryu will repeat that level of brilliance next season, but he’s still going to be in line for a big-money contract in free agency. The only reason he checks in so low on the list is because of his likelihood to stay in Los Angeles. He’s comfortable with life on the West Coast and a move to New York might be more than he’s willing to take on. Look for the Yankees to make him a strong offer, but ultimately he’ll probably re-sign another lucrative deal with the Dodgers.

4. Wade Miley
No one will call Wade Miley the ace of the Astros staff, but he might be accurately named as the biggest bargain of the bunch. The one-year, $4.5 million deal he signed last offseason looks like an absolute steal for Houston.
The only mistake the Astros’ front office seems to have made with Miley is failing to get him to agree to a multi-year deal. They’re going to pay the price for that error in the offseason. Even at 32 years of age, Miley is still going to be in line to receive lucrative, multi-year offers when free agency begins.
Miley doesn’t feature overpowering stuff, but his excellent command allows him to get hitters out at a high level. He’s already managed to pitch 126.2 innings this season and has amassed an impressive WAR of 3.2. A number of contenders, including the Yankees, would be more than happy for him to repeat that performance in their uniform during the 2020 campaign.
The danger with Miley’s next contract will be the number of years required rather than the dollars per season. If the Yankees can get him on a three-year contract similar to the deal JA Happ signed this offseason he could be a terrific addition. Don’t look for Miley to be Cashman’s top target, but he could easily end up in pinstripes if a few pitchers choose to go elsewhere early in free agency.

3. Jake Odorizzi
Jake Odorizzi hasn’t been as good as either Ryu or Miley this season, but he does have age on his side. He’ll hit free agency just after the completion of his age-29 season. The Yankees may see his future as a bit brighter due to the lack of years on his right arm.
He’s made solid money with the Twins this year, but he’ll have the chance to eclipse his current salary of $9.5 million when he hits the open market. It’s possible he will emerge as a pitcher that the Yankees are willing to offer a four or five-year deal.
He’s been a real weapon for Minnesota this season. Odorizzi doesn’t have ace-level stuff, but he’s a solid No. 2 or 3 starter on a good team. In particular, New York will be attracted to his consistency. The Twins know what they’re going to get from him every time he takes the mound. There aren’t many pitchers in New York’s current rotation who share that quality.
Predictably, it’s expected that Minnesota will make a sizable offer to keep him. The Yankees will likely express interest, but Cashman will establish a limit to what he’s comfortable offering Odorizzi before negotiations really begin. The Twins can keep him if they’re willing to pay a premium, but if they’re not, pinstripes could be in his future.

2. Zack Wheeler
The Yankees showed some interest in Zack Wheeler ahead of this year’s trade deadline, but the Mets elected to hang on to the talented right hander. That decision will pressure the Mets to keep him away from the Bronx when free agency arrives.
That may prove to be a difficult task for New York’s National League franchise. They certainly have the money to keep Wheeler, but it’s hard to imagine them outbidding the Yankees if Cashman really sees Wheeler as a top-end starter.
When you watch Wheeler run his fastball up to the plate at close to 100 miles per hour it’s easy to convince yourself that he has ace stuff. His 4.71 ERA on the season doesn’t back that opinion up, but it’s worth noting that his FIP is a much more palatable 3.65. His ability to strike out hitters at a prodigious clip will make him a very attractive target for the Yankees in free agency.
Wheeler is making just under $6 million this year, which means he’ll be looking to hit it big on the open market. He’s one player on this list who will almost certainly sign with the highest bidder. Again, if the Yankees want to make him their big pitching acquisition of the offseason, they have a great chance to land him.

1. Gerrit Cole
There is no arguing about who the Yankees’ top free agency target will be this winter. Gerrit Cole is the ace the team desperately needs. Even if it means overpaying for him, there is a real expectation that he’s a signing Cashman must and will make.
Cole will be 29 next season, but the fact that he’s an unquestioned No. 1 starter means that he’s going to be in line for a five or six-year contract at the very least. It’s also very likely that he’ll be looking for a salary in excess of $20 million per season. That might be a tough contract for Cashman to swallow, but it shouldn’t be a deal breaker.
The talented hurler has already provided the Astros with a WAR of 3.7 with a healthy portion of the season still in front of him. The fact that he’s also gone over the 200 innings mark in his last two seasons in Houston also should add to his value. Cole is not a five-inning guy. He likes to work deep into games and that has a great effect on his team’s bullpen.
In the eyes of many Yankee fans, this offseason is going to be all about Cole. It’s hard to argue with that line of thinking given the struggles of the team’s rotation to date. Cole is the one pitcher who’s scheduled to hit the open market who can immediately become the team’s ace. It will be difficult to pry him away from the Astros, but Cashman should make him an offer he can’t refuse.

