Yankees Deadline Pitching Needs

by Cary Greene

July 6, 2022

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Baseball fans everywhere are now counting down to the 2022 MLB Trade Deadline which strikes 6pm on August 2nd this year.

MLB expanded the playoffs this year so that twelve teams will now qualify, instead of the ten teams in previous seasons. which could make this year’s Deadline especially competitive. The two extra playoffs spots means even more teams may go all out to make the playoffs and this could easily create a frenzy of trades, the likes of which could be unprecedented. This means that the players that Yankees fans may have their eye on are likely similarly coveted by even more teams than is usual during the month of July.

The 2022 Yankees will certainly be one of the 12 MLB playoffs teams. Fangraphs not only has the Yankees as a lock to qualify for the postseason, but they also have the Yankees chances of clinching a first-round bye in the playoffs at 96.7%.

Since the Yankees are already in the postseason and likely already have a first round bye locked up, the main goal from now until the postseason starts will be to keep key players healthy and to put the best possible postseason roster in place so that ending the twelve-year championship drought and winning a World Series is made all-the-more likely to happen.

Therefore, who the Yankees face in the playoffs matters a great deal because the Yankees will want to favorably match up with those teams. Brain Cashman should have an eye on those likely matchups as he navigates the waters approaching this year’s Trade Deadline.

It is very possible that the Yankees would host the five-game Division Series, against either the Red Sox or the Twins with the Astros likely hosting the other Division Series against the winner between the Blue Jays and Rays/Guardians

In the National League, the Dodgers would also likely get a first-round bye and host the Division Series against either the Braves or the Brewers, with the Mets hosting either the Padres or the Cardinals/Giants.

The below table illustrates the strengths and weaknesses of each contender. It’s likely that there may be several changes to each team's exact position as the season moves through the dog-days of summer and into the stretch run.

If the Yankees wind up hosting the Red Sox in the Division Series, the Yankees would be wise to exploit the Red Sox biggest weakness, which is their vulnerability to tough right-handed pitching and hitting.

The Yankee bullpen would be a huge key to containing the potent Red Sox offense which is especially tough on left-handed pitching. Therefore, pitchers with good splits against right-handed hitters but who can also handle lefties would be crucially important for Aaron Boone to be able to call on. Suppressing the likes Jarren Duran, Boston’s rookie sensation (a center fielder who bats from the right side) and stalwarts Xander Bogaerts and J.D Martinez (two of the toughest right-handed hitters in the game) would be key. The Yankees will also have to deal with Boston’s lethal lefty, Raphael Devers.

The Yankees would probably lead with Gerrit Cole and Luis Severino to start the first two-games of a Division Series against the Red Sox. Depending on how that goes, Nestor Cortes might be the starter in a pivotal Game Three because his splits are outstanding against right-handed hitting, even though he’s a lefty. Jameson Taillon might be held in reserve in a series like this and the Yankees might hand him the ball for Game Four and come back with Cole in a decisive Game Five, should there be one.

I would expect the Yankees to also load the bullpen with the relievers that have the best splits against right-handed hitting, so Ron Marinaccio (if healthy) , Clay Holmes, and Mike King might be key relievers to feature, reinforced by Clarke Schmidt, possibly J.P. Sears, along with Wandy Peralta and Miguel Castro.

Jonathan Loaisiga, if he’s in peak form, could also help because he’s usually tough on right-handed hitting, but it feels like Loaisiga is far from a certainty at this point, given that he’s struggled all season long. It seems like the Yankees have a true opportunity to bolster an already good bullpen, by adding a high leverage righty (or two). Looking past a potential series with the Red Sox only serves to reinforce the importance of doing this.

It’s very clear that this single priority is the Yankees greatest need. The Yankees bullpen has been extremely resilient thus far considering all of the losses they’ve endured. Considering that glue-guy Chad Green was lost for the season and Domingo German, Jonathan Loaisiga, and Zack Britton have all battled serious injuries and now, the promising Ron Marinaccio is on the 15-Day Injured List with shoulder pain and/or “dead arm,” as Yankee Manager Aaron Boone put it when explaining the injury to the media - exactly how the Yankee bullpen hasn’t missed a beat is pretty remarkable. On top of all this, the Yankees lost their closer, Aroldis Chapman and though he’s returned, he looks like he’s suffering from age-related diminished velocity and and may also be having pitching-related mental issues or mechanical problems as his control has all but vanished. Chapman doesn’t exactly invoke the kind of high-level confidence that he once did.

This is the point in the season where the Yankees bullpen situation has reached critical mass and as the importance of elite postseason pitching cannot be understated, Brian Cashman will absolutely look to bolster the Yankee bullpen at the Trade Deadline. For his part, Cashman truly does understand how important a bullpen is in the postseason. Not only has he put a priority on the bullpen in season’s past, but given that the Yankees have been squelched numerous times in recent postseason history by teams whose bullpens played huge roles in the Yankees ensuing demise.

Projecting the bullpen in the playoffs involves a number of key “ifs.” If presently rehabbing Zack Britton can return to peak form, he could become a huge x-factor for the Yankees, but it seems unlikely that he’d be his old self. Counting on Chapman to regain his old form also seems like a stretch at this point. It all adds up to the Yankees undoubtedly probably being in the market for both righty and lefty relievers that could serve as reinforcements in order to shape a World Series winning roster.

Boston’s Chaim Bloom is reportedly looking to add outfield help and may also be looking to upgrade the rotation and the bullpen at the Deadline. Pitchers of interest to Bloom are rumored to be Luis Castillo and David Robertson and he’s inquired on Bryan Reynolds, Ian Happ, and Andrew Benintendi.

The Red Sox meanwhile would hope that Chris Sale is available to start Game One and perhaps James Paxton might also be back to start a game in this potential series. Countering these possibilities, the current Yankees can roll out eight players with an OPS against lefties of .783 or higher, which means that Nick Pivetta would be Boston’s best-bet against the Yankee lineup. Nathan Eovaldi has proven to be a big-game pitcher and he usually elevates his performance in the postseason, so along with Sale and Pivetta, the Red Sox would be very formidable in a five-game series. If Bloom adds Luis Castillo to the rotation, that gives Boston a big boost because his splits against right-handed hitting are very good. A trio of Pivetta, Eovaldi, and Castillo following Sale in a five-game series would make Boston very difficult to beat.

What if the unthinkable happened?

What if Minnesota were to beat Boston, on the strength of their ability to hit right handed pitching? This amounts to being the only hope the Twins have of beating the Red Sox in a short series. Should this occur, the Yankees strategy would really flip-flop. Personally I think the Twins will be soundly out-pitched by the Red Sox in a five-game series, Boston presently has the fourth best pitching in MLB and it seems it will be even better by the time the postseason starts.

In the unlikely event that the Yankees do face the Twins, the Bombers would need to leverage their left-handed starters and relievers. I’d expect Nestor Cortes to possibly start Game One in a Yankees-Twins Series, followed by Gerrit Cole in a Game Two and then possibly Jordan Montgomery in Game Three. In a series with the Twins, hopefully Chapman and Britton would play big roles and J.P. Sears could be very important as well. Wandy Peralta and Lucas Leutge would both also need to be leaned on to handle the Twins explosive lineup that is lethal against right-handed pitching.

Meanwhile, Minnesota struggles with left-handed hitting so the path to a Yankees victory in a series such as this would be to stack lineups with plenty of left-handed hitting, something the team has presently but probably needs more of. Certainly Matt Carpenter, Anthony Rizzo, and Marwin Gonzalez would all need to get plenty of at bats. The Yankees could probably use at least one more left-handed hitter to provide balance and it looks like trading for someone who fits the bill is also a priority of Cashman’s.

Advancing deeper into the playoffs and World Series, will require the Yankees to likely face the Astros and the Dodgers. Boston’s pitching will be formidable, but things will only get more difficult if the Yankees are fortunate enough to advance to the World Series. How many times have Yankees fans seen the narrative where the Yankees face stifling pitching in the postseason play out in recent years? This year, more than ever, elite pitching awaits the Bombers.

Both the Astros and the Dodgers feature pitching that is extremely tough on right-handed hitting. In the case of the Astros, who would potentially meet the Yankees in a bitterly contested American League Championship series that very likely could go the distance, their pitching is also equally good against left-handed hitting. Yankee fans got a chance recently to observe how elite pitching can stifle even the most explosive of offenses as Houston no-hit the Yankees for 15-straight innings when they recently visited the Bronx.

Assuming the Yankees can get past Chris Sale and the Red Sox, the Astros have the indomitable, ageless lefty Justin Verlander, who would likely open a series against the Yankees. Verlander might also start the fourth or fifth game in the series and he might also be available for a Game Seven, with the right to go to the World Series hanging in the balance. Dusty Baker will do whatever it takes for Houston to maximize their chances of getting the job done.

The Yankees will need every ounce of offense they can muster to get past Houston and the Yankees own left-handed pitching will be the key to beating Houston - as the Astros are susceptible to tough lefties. For this reason, the Yankees would be wise to pitch Cortes in Game One, Cole in Game Two and Montgomery in Game Three. This way, Cortes could pitch Game Six if needed and Cole might be available for a decisive Game Seven.

The Yankees left-handed relievers could be a massive advantage in a seven game series against the Astros and between Chapman, Britton, Peralta, Luetge, and Sears, the Yankees will hopefully have a lot of options. The Yankees also have a number of other relievers with very good splits against right-handed hitting and the Yankee bullpen might wind up being the difference if the series does go seven games.

A World Series against the Dodgers would pit the Yankees against an even better overall pitching staff, one that is easily the best in baseball. The Dodgers are far more susceptible to left-handed pitching so for this reason, it would probably be a strategic mistake to open the Series with Cole and then start Severino in Game Two. Instead, Cortes should start the second game followed by Montgomery - who may wind up also starting a Game Seven. Severino would be held in reserve to start Game Four and then the Yankees could line things up from there, probably going back to Cole for Game Five, Cortes for Game Six and Monty for Game Seven.

I’m not sure Jameson Taillon starts a single game against the Dodgers, they simply match up too well against him to risk it.

Possible Yankee Trade Targets - Relievers:

I’ll start by saying that I whole-heartedly believe that Brian Cashman will look to add to the Yankees bullpen at the Trade Deadline. Though the Yankee bullpen has been extremely good, it’s not quite built for a true World Series run. The Yankees are likely in need of both a lefty and a righty reliever and both need to absolutely be high-leverage types who might even put wind up putting the Yankees over the top against teams like the Red Sox, Astros and Dodgers.

We’ll start with the righty-relievers Cashman might target. He’ll probably will look to add at least one fairly dominant right-handed reliever. David Robertson was a name I floated this winter, but not many here on SSTN liked the idea. Perhaps now those grasshoppers might be willing to aqueous to the notion! He’s sporting a 1.86 ERA for the Cubs this year, with mostly great peripherals.

Competition will be fierce for him as the Red Sox, Blue Jays, and Rays are all rumored to be interested in acquiring him. Acquiring Robertson would be pretty painless, it would take a single prospect like Josh Breaux or Brandon Lockridge. This is the kind of trade Cashman would ideally like to make and I’m sure the last thing he wants is for the Yankees to have to face Robertson in the playoffs again. Robertson is a gutsy, multiple innings-capable reliever with postseason pedigree. He’d be a perfect fit for the Yankees to acquire.

There are a number of other relievers that may be available as well. Seranthony Dominguez is having a great season with the Phillies and they are a team to monitor as the month of July wears on. Presently, the Phillies are fighting for their lives for the last playoff spot, so if they can stay in contention, any deals for Dominguez would be squarely off-the-table. Dominguez is a righty that is so tough on right-handed hitters, they virtually have no chance against him. Dominguez would exact a pretty painful price in terms of prospects, along the lines of Hayden Wesneski or even Roderick Arias, the latter of whom I’m certain the Yankees wouldn’t part with for Dominguez.

Now for the intriguing lefties! Another reliever that Cashman may want to trade for is the Diamondback’s lefty Joe Mantiply, who is very tough on right-handed hitters. He’d be just the kind of bridge-reliever that a successful postseason run would need and he’d prove quite useful to the Yankees especially, given how their path to the postseason may look. Mantiply would be extremely easy to trade for, likely costing only a single lower-tier prospect, someone along the lines of Roberto Chirinos, a Low-A shortstop prospect currently with the Tampa Tarpons.

Lastly, the Pirates' David Bedar, another lefty, would be one final reliever that would make sense for the Yankees to target. He’s tough on both left-handed and right-handed batters. The only drawback is that he’s extremely expensive. Baseballtradevalues.com lists his median trade-value in the neighborhood of $31.9 million. Acquiring him would likely require a package headlined by Oswald Peraza and also include a pitching prospect the likes of Ken Waldichuk. A trade for Bednar would be reminiscent of the Yankees trade of Aroldis Chapman to the Cubs. It would be a very similar deal in terms of prospect cost, but the dividends could be enormous as Bednar would be a huge part of a championship run. He’s a true high-leverage reliever, one of the best in the game.

Possible Yankee Trade Targets - Starters

I’ll start by saying that where there’s smoke, there’s often fire. Cashman knows he has an issue to deal with. Jameson Taillon is a free agent after the season. He needs to shape not only the postseason rotation, but also determine who the starters will be next season. Both Clarke Schmidt and J.P. Sears have shown they belong in the big leagues, but the Yankees may ultimately view both as better suited for the bullpen. If that’s the case, it wouldn’t surprise me one bit if Cashman made a serious run at a starter.

Joel Sherman of the NY Post floated the rumor that Cashman had spoken to the Reds about Luis Castillo and it's no secret that the Yankees have long coveted Castillo. Acquiring Castillo would be very costly in terms of prospects. Baseballtradevalues.com has Castillo valued at $35.7 million in median trade-value and quite frankly, I don’t think the Yankees match-up super well with the Reds. Any trade for Castillo would likely involve Oswald Peraza and would also likely include Jasson Dominguez or perhaps two mid-tier pitching prospects like Luis Gil, Beck Way or perhaps Randy Vasquez.

The other big-name starter on the trading block will be Frankie Montas of the A’s and he’ll fetch a trade package similar to that of what the Yankees would have to pay to acquire Castillo. Given the cost, I don’t think Brian Cashman will wind up adding a big-name starter. He may look to bring Taillon back after the season, or perhaps turn his eye to the free-agent market this offseason to shore up the rotation if Taillon’s market goes above where he’s comfortable.