How Can the Yankees Improve Their Pitching Staff at the Trade Deadline?

Here we are in the dog days of summer and the Yankees find themselves at the bottom of the American League East. Their plan to just roll with a flawed roster that was exposed by the Houston Astros last October has backfired in 2023. They now sit a few games back of the last Wild Card spot in the AL and with the trade deadline upon us, the window of opportunity to improve this disappointing team is closing. Should Brian Cashman strike while he still can?

Recently, Hal Steinbrenner reiterated that his goal is still to win a championship every year. Well, if that's actually the case, then Cashman should be extremely busy over the next few days. Back in May, I offered some suggestions to help the struggling offense. All of those options are still available, so let's shift focus to the ice cold pitching staff. Are there any arms out there that can help the Yankees for the stretch run?

Starters

Despite the rash of injuries that ran through the Yankees' starting rotation to begin the season, they were an effective group over the first three months of the season. Gerrit Cole pitched like the ace that he's paid to be, and the trio of Clarke Schmidt, Jhony Brito, and Domingo German did just enough to keep the team afloat. Yankee starters posted a solid, if unspectacular, 4.20 ERA through the end of June.

Unfortunately, the bottom has fallen out in July. Thus far this month, starters have surrendered 23 home runs - the highest monthly total of the season for the group - and pitched to an unsightly 5.10 ERA. Since Carlos Rodón hasn't been the savior the Yankees were hoping for, they could use some reinforcements in the rotation.

The St. Louis Cardinals have surprisingly been a non-factor in the National League playoff race, so they'll be sellers at the deadline. Of their starting pitchers, 27-year old Jack Flaherty is the most tradeable commodity. The good news for the Yankees is that he'll be a free agent next year, which means he'll cost relatively little in terms of prospects. The bad news is that he hasn't been a healthy, front-end starter since 2019. Who knows, maybe the Yankees acquire him and convince him to ditch his fastball in favor of his much more effective slider and he gives them a strong couple of months. More likely, he would be just another back-end starter in New York, and they have plenty of those.

Cut from a similar cloth as Flaherty, White Sox starter Lucas Giolito could have also been a Yankee trade target. However, in a shocker he was dealt to the Angels earlier this week. Same goes for his aging former White Sox teammate Lance Lynn, who was just sent to the Dodgers. Yet there might be another option on the north side of Chicago.

The Cubs are losing ground on the Brewers and Reds and figure to be dealing at the deadline. That would make Marcus Stroman a potential match for the Yankees. His reliance on a sinker and a lot of breaking stuff fits right in with the Yankees general pitching strategy and he's been a solid middle of the rotation starter for years now. The only problem here is that Brian Cashman effectively alienated Stroman - a New York native - from ever wanting to join the Yankees a few years ago. That makes any potential swap for Stroman complicated, but not impossible.

As long as we're talking about complicated scenarios in New York, let's talk about the Mets. Rumor has it that they could look to move Justin Verlander in the coming days. This wouldn't be the first time the Yankees pursue Verlander via trade, and he's not exactly the ace he used to be. Yet it's hard to argue that he wouldn't instantly improve the rotation and give the Yankees one of the most formidable set of starters for a potential playoff run in the American League. Hal would have to part with some of his precious money to make the deal happen, but it would be well worth it.

Could we see Justin Verlander in Yankee pinstripes this season?

D. Benjamin Miller/Wikimedia Commons/Public Domain

Relievers

The fall from grace of the Yankee starting rotation is child's play compared to the bullpen. They were the strongest unit on the team through the end of June, with a sparkling 2.83 ERA and enough depth to withstand some early injury struggles. In July they've fallen flat on their faces, sputtering to a 4.68 ERA with walk rates that would make Nolan Ryan blush. Some fresh arms are needed, and fast.

If Brian Cashman is looking for some low-hanging fruit, he could do worse than White Sox righty Keynan Middleton. The free agent-to-be has shown significant improvement in 2023 by pitching primarily off his changeup instead of his fastball. He'll turn 30 this September, so it wouldn't take much to pry him out of Chicago.

Keynan Middleton would bolster a struggling Yankee bullpen down the stretch.

Keith Allison/Wikimedia Commons

Also on the relatively cheap end would be Scott Barlow of the Kansas City Royals. The 30-year old righty has experience as a closer, offers a four-pitch mix that includes a quality slider and curve, and has one year of team control left. He has pitched far better than his 5.15 ERA indicates this year, so the Yankees could cash in on his expected positive regression.

There are some arms available that will cost quite a bit more in terms of prospects, but would also bring significant improvement to the Yankee bullpen. Long Island's own Jason Foley is toiling in oblivion with the Tigers currently and could likely be had for the right price. The Yankees surely have noticed his nasty sinker that has frustrated batters to the tune of a .564 OPS against so far this season. The earliest he could become a free agent is 2028, so Foley could be a mainstay in the Yankee 'pen for years to come.

For a couple of years now, Clay Holmes has been doing a pretty good impression of a closer for the Yankees. However, if they want to upgrade to a true shut-down fireman, they should look no further than Pittsburgh's David Bednar. The two-time All-Star has converted 20 of 21 save opportunities this year with a miniscule 1.35 ERA that's backed up by the sea of red on his Savant page. With the Pirates sitting firmly in last place of a weak division, they could be looking to deal the 28-year old righty. He does have three years of team control left, so it would take a haul to get him. Since the Yankees have proven unable to develop prospects these days, trading them for established big leaguers might just be the best way to maximize their value. So go ahead Cashman, make like Monty Hall, and deal.