Evaluating 3 reliever options for the Yankees on the free agent market

MLB: New York Yankees at Miami Marlins
Sam Navarro-USA TODAY Sports

As the Yankees look to bolster their bullpen, they have various price points they can play at based on their levels of interest in different arms. In recent years, we’ve seen the Yankees rely less on their money to add impact relievers, instead opting for overlooked options to work their way into higher-leverage roles, with a multitude of examples in recent years. While their bullpen sported the best ERA in baseball this past season (3.34), the Yankees are looking to make a strength even stronger, especially after missing out on Yoshinobu Yamamoto.

Don’t expect the Yankees to shell out a nine-figure contract for Josh Hader, but these three arms could make significant upgrades for their bullpen in different ways next season.

A Reunion With the Yankees’ Sole Deadline Addition

New York Yankees relief pitcher Keynan Middleton (93) pitches in the sixth inning against the Detroit Tigers at Comerica Park
Aug 31, 2023; Detroit, Michigan, USA; New York Yankees relief pitcher Keynan Middleton (93) pitches in the sixth inning against the Detroit Tigers at Comerica Park. Mandatory Credit: Rick Osentoski-USA TODAY Sports

Technically speaking, Spencer Howard was acquired from the Texas Rangers as well, but he didn’t make a single MLB appearance for the Yankees, but Keynan Middleton certainly did. In his age 29 season, Middleton posted a 3.38 ERA with a 30/2% K%, and while walks and home runs were an issue last season, the Yankees seemed to make some alterations to his pitch usage that could be for the better. One issue that stemmed from Middleton’s pitch usage was that he struggled to get right-handed hitters out, but a lot of that had to do with a lack of sliders against right-handed hitters.

With the White Sox, he used his changeup 38.9% of the time against right-handed hitters, more than any other pitch in his arsenal in those matchups, and as a result, they had a .344 wOBA and .371 OBP against him. This changed with the Yankees, who had him throw 45.7% sliders against right-handed hitters, and they only had a .263 wOBA and .286 OBP against him after the trade as a result. Improved pitch sequencing made Middleton a lot better, and with New York, he posted a 1.88 ERA and 71% groundball rate with the Bronx Bombers.

He’s likely not to get a massive contract in free agency, and Keynan Middleton would fit the Yankees’ bullpen needs perfectly. The Yankees do have a very right-handed bullpen, and while Middleton would make them more right-handed, his ability to neutralize lefties would make them more formidable against left-handed hitters next season. In Middleton’s career, left-handed hitters have posted a .296 wOBA against him, and this could be a low-cost move with plenty of upside for the Yankees.

It’s unlikely that Middleton would require a large deal for 2024, and that would allow the Yankees to add a potentially high-leverage option without paying that price tag. It’s not unrealistic to expect the Yankees to acquire two solid starting pitchers and Keynan Middleton, especially given the fact that it would be a short-term deal. We know the Yankees aren’t opposed to reunions, as they’ve shown interest not only in retaining Wandy Peralta and Frankie Montas but it’s also been reported that the team has held internal conversations about signing Jordan Montgomery, conversations that become more prominent after missing out on Yoshinobu Yamamoto.

This would be a low-cost signing that keeps the Yankees in the mix for other pitchers on the market, and it could end up being a nice boost for their bullpen as well.

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Signing One of the Hardest-Throwing Relievers In Baseball

MLB: Toronto Blue Jays at New York Yankees
Sep 20, 2023; Bronx, New York, USA; Toronto Blue Jays relief pitcher Jordan Hicks (12) reacts during the eighth inning against the New York Yankees at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports

Jordan Hicks had a breakout season last year, establishing himself as one of the better relievers in the sport with his electric fastball. Averaging 100.1 MPH on his sinker, batters had a negative launch angle against the pitch, and it held a +12 Run Value on the season, his best pitch according to that metric. He leaned on his sinker heavily, using it 64.4% of the time with a 116 Stuff+. Across 65.2 innings pitched last season, Hicks had a 3.29 ERA and 58.3% groundball rate, as his stuff was too overpowering for batters to generate damage contact against, especially right-handed hitters.

Righties slugged just .348 against Hicks with a strikeout rate north of 30%, and he would be another hard-throwing weapon for the backend of the Yankees’ bullpen. One of the team’s biggest strengths over the past few seasons has been their ability to find bullpen support without making much of a financial investment, and while Hicks certainly wouldn’t make league-minimum salaries, he still has plenty of room to improve and get better as a reliever in the league. He’ll enter his age-27 season next year, and he could develop a few more skills with an organization like the Yankees who have excellent pitching coaches.

As mentioned earlier, Keynan Middleton took off with the Yankees after improving his pitch usage against right-handed hitters, we could see Jordan Hicks’ four-seam fastball become a greater weapon for him against left-handed hitters. His four-seam fastball had the worst Run-Value against left-handed batters (-2) but had a .307 wOBA and generated a solid chase rate as well. It was his first season relying on the pitch as a tertiary option, and it could be a matter of getting a better feel of the pitch in those counts in order for it to have better success.

He still held left-handed batters to a sub .700 OPS, and with his wicked sweeper, which generated a whiff rate of nearly 60%, Jordan Hicks is one of the filthiest pitchers in all of baseball. Among relievers with at least 50 IP this past season, Hicks ranked 11th in Stuff+ (126) and has incredible fastball velocity that makes the movement even more unhittable. Sometimes it’s just a matter of having a pitch that’s hard to track, and that’s certainly the case with Jordan Hicks and his incredible arsenal.

A Tommy John Surgery earlier in his career and a lack of consistent MLB success definitely lower the ceiling on how much Hicks will make in the open market, but FanGraphs projects him for a three-year deal at $27 million, and that’s not bad, given the production he could have in 2024. Steamer projects him for a 3.27 ERA over 66 innings next season, and given just how good his stuff is and just how much the Yankees love generating groundballs, Hicks could be a perfect fit for this bullpen and be a young option for their bullpen for years to come.

Poaching One of Baseball’s Breakout Pitchers From the Rays

MLB: New York Yankees at Tampa Bay Rays
Aug 27, 2023; St. Petersburg, Florida, USA; Tampa Bay Rays relief pitcher Robert Stephenson (26) throws a pitch against the New York Yankees in the eighth inning at Tropicana Field. Mandatory Credit: Nathan Ray Seebeck-USA TODAY Sports

One of the biggest breakouts from the 2023 season came from Robert Stephenson, whom the Tampa Bay Rays acquired in a deal with the Pittsburgh Pirates. Tell me if you’ve heard this story before — an AL East team with good pitching development takes a reliever from the Pirates and turns them into an All-Star caliber arm. Stephenson was electric for the Rays, as they tweaked his slider and turned it into a monster pitch that he used over 60% of the time while in Florida. While Statcast logs his slider as a cutter, the usage and shape of the pitch would suggest it’s more of a slider, but a name we can all agree on for it is “nasty.”

Stephenson’s cutter had a whiff and chase rate north of 40% with excellent contact management, as hitters had jus a .151 wOBA against it. As a result, he had a 42.9% strikeout rate and 28.7% swinging strike rate, meaning batters rarely put the ball in play when they swung against him. Robert Stephenson’s 2.35 ERA and 1.78 SIERA with Tampa Bay are mightily impressive, and the Yankees getting that sort of production in their bullpen would give them one of the most formidable units we’ve seen in recent memory.

Is he the sexiest name on the market? No, as he’s instantly outshined by the likes of Josh Hader, one of the best relievers in the 21st Century, but Stephenson can certainly produce like a top-10 reliever. Alongside Clay Holmes, this would be one of the most electric duos in the league out of the bullpen, and it would certainly give the Yankees the ‘super bullpen’ they reportedly want to put together for next season.

Projections are a bit lower on Stephenson since they have to adjust for the subpar career he had prior to joining the Rays, but they still view him as a good reliever. A 3.79 ERA across 61 innings would certainly boost the Yankees’ pitching staff, and there’s a very good chance he overperforms that mark. We could be looking at a sub-3 ERA arm with plenty of strikeout potential, and that’s exactly what the Yankees would want to add to their bullpen, especially in October. It would be a slam-dunk signing for New York, but his cost is in the air.

FanGraphs projects him for a two-year $10 million deal, but I’d consider that light for him, and teams would certainly have to bid a bit more for his services. A third year and slightly more money per season could sweeten the pot while also factoring in the risk of paying a pitcher based on 38.1 innings of work. A deal at around three years, $27 million, like Jordan Hicks, would make sense, and I think that at that price point, you’re getting one of the highest ceilings in the market while also getting a different look in your bullpen.

He isn’t just a carbon copy of the Yankees’ established high-leverage guys, and that means teams will have to adjust for an elite breaking pitch from Stephenson in one inning and a 98 MPH sinker from Clay Holmes in another inning. Stephenson could be a surplus on this market even at a nearly $10 million a season for three years, and the Yankees should look for the opportunity to snag one of baseball’s best-kept secrets for their bullpen.