Yankees reportedly discussing offseason strategy in Tampa ahead of 2024 season

MLB: General Manager's Meetings
Mark J. Rebilas-USA TODAY Sports

The Yankees’ need for starting pitching is one of their most obvious and pressing ones, as the team looks to make a splash for their rotation and make it one of the most formidable units in baseball. As the Bronx Bombers continue to navigate through the offseason, their pursuit of an elite starting pitcher has been halted by the price, as is the case for many teams in the league. According to Randy Miller of NJ.com, the Yankees’ brass are currently in Tampa discussing whether they should end up paying the price necessary over the coming weeks to land one of the top starters on the market.

Acquiring a top starter on this market won’t come without paying a price that makes the Yankees wince a bit, monetarily or from their prospect pool.

Pitching Market Begins to Take Shape For Yankees

MLB: New York Yankees at Chicago White Sox
Aug 7, 2023; Chicago, Illinois, USA; Chicago White Sox pitcher Dylan Cease (84) pitches in the first inning against the New York Yankees at Guaranteed Rate Field. Mandatory Credit: Jamie Sabau-USA TODAY Sports

Shopping at the top of this pitching market will prove to be pricey, and the Yankees will have to part ways with some of their best prospects to swing a big trade. The alternative is offering a deal that could end up above the six-year $162 million contract signed by current Yankee Carlos Rodon, which would provide financial complications for the team next winter when Juan Soto hits the free agent market.

One of the biggest issues with navigating the market is that there are short-term and long-term implications with every decision, but this meeting in Tampa seems to be centered around seeing if Brian Cashman will get the blessing to pay that kind of price tag.

Dylan Cease has had his name pop up over the last few weeks, with teams in the division like the Baltimore Orioles and Boston Red Sox involved in the sweepstakes, and reports surfacing of the New York Mets being involved as well. The Orioles and Red Sox both have excellent young talent across their farm system after years of rebuilding, but it’s Baltimore who stands out as a clear favorite here.

Their interest in the right-hander and their distinct advantage in these talks mirror the advantage the Yankees held in their pursuit of Juan Soto, and it’s possible the Orioles are just waiting for the White Sox to realize that nobody can top what they’re offering.

Chicago could keep the 28-year-old right-hander, who went 7-9 across 33 starts with a 4.58 ERA following some issues with his pitch repertoire that decreased the quality of his four-seamer and slider. The stuff is still truly excellent, and perhaps a team could find a way to get Dylan Cease to throw more strikes and regain the tick of velocity he lost on his fastball.

mlb: cincinnati reds at chicago cubs, yankees, marcus stroman
Jul 31, 2023; Chicago, Illinois, USA; Chicago Cubs starting pitcher Marcus Stroman (0) pitches during the first inning against the Cincinnati Reds at Wrigley Field. Mandatory Credit: Patrick Gorski-USA TODAY Sports

Marcus Stroman’s name has popped up, and Bob Nightengale followed his report that the Yankees declined to make an offer with another suggesting the interest was mutual. Randy Miller shot down the idea that the team wants anything to do with Stroman, who has had a track record of lashing out against former teams and teammates on social media. He is also garnering interest from the San Francisco Giants, who have emerged as the favorites for Japanese southpaw Shota Imanaga, who needs to decide by this Thursday.

Blake Snell could be the most likely option for the Yankees in free agency if they go that route, but he’ll likely get a nine-figure contract that extends over six or seven years, although reports have surfaced that he could take a shorter deal. The idea would be that Snell takes a short-term contract with high AAV and resets his market to make close to $40 million a year over the next year or two and then secure a nine-figure deal after, which would certainly boost his total career earnings.

It’s unclear whether the Yankees will have a clean shot at Jordan Montgomery, who seems to want a return to the Texas Rangers following their incredible World Series run. They’re another team in desperate need of pitching help, and Montgomery makes perfect sense given the mutual interest and the success he had in the Lone Star State. Their TV Deal issue could be resolved in the coming weeks, which could finally give them the money needed to sign a big free agent.

MLB: World Series-Texas Rangers at Arizona Diamondbacks, yankees
Nov 1, 2023; Phoenix, AZ, USA; Texas Rangers starting pitcher Jordan Montgomery (52) celebrates defeating the Arizona Diamondbacks to win the World Series in game five of the 2023 World Series at Chase Field. Mandatory Credit: Matt Kartozian-USA TODAY Sports

The Miami Marlins and Cleveland Guardians could be teams of interest as well for the Yankees, with Jesus Luzardo and Shane Bieber both presenting starting options under the age of 28 who could slot into their rotation. Luzardo brings a high-90s fastball with a solid changeup and wipeout slider, striking out 208 batters in 178.2 innings last season, but he would come at an incredible prospect cost. Shane Bieber took a step back last season in production but still posted a modest 3.80 ERA and is working at Driveline this winter to improve his pitch quality.

Whatever the Yankees decide to do, they’re going to need to pay a hefty price tag, but perhaps this meeting serves as a way for Hal Steinbrenner to pass down his blessing and green light a potential blockbuster trade or a big-time signing.