![\"Oct](\"https:\/\/www.rawchili.com\/mlb\/wp-content\/uploads\/2025\/12\/cbffbf6fc151ccf6674627fa448bb817.jpeg\"\/)
<\/p>\nNEW YORK \u2013 As the Yankees move toward MLB\u2019s Winter Meetings, there\u2019s a familiar ring to their approach.<\/p>\n
Hal Steinbrenner would prefer to keep his payroll around $300 million, avoiding the last luxury tax threshold \u2013 an admission that inflamed a large swath of Yankees Universe.<\/p>\n
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But the Yankees managing general partner is open to expensive ideas by GM Brian Cashman, in pursuit of their first world championship since 2009.<\/p>\n
Based on those recommendations, \u201cI\u2019ll decide whether I\u2019m able or willing to pull the trigger,\u2019\u2019 Steinbrenner said recently.<\/p>\n
Already looking at an approximate $280 million payroll, an on-budget 2026 roster would seem to be a near-impossibility given the Yankees\u2019 unfinished business.<\/p>\n
How much more are the Yanks willing to spend toward their aim? We\u2019re about to find out.<\/p>\n
Here\u2019s a look at the Yankees\u2019 to-do list as baseball\u2019s annual bazaar begins Sunday night:<\/p>\n
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Impact outfield bat<\/p>\n
Oct 5, 2025; Toronto, Ontario, CAN; New York Yankees left fielder Cody Bellinger (35) rounds the bases after hitting a home run in the sixth inning against the Toronto Blue Jays during game two of the ALDS round for the 2025 MLB playoffs at Rogers Centre. Mandatory Credit: Kevin Sousa-Imagn Images<\/p>\n
Ideally, that would be Cody Bellinger.<\/p>\n
If not, the Yankees must have a spectacular pivot, which would be tough considering the \u201cthin market\u2019\u2019 for center fielders, in Cashman\u2019s words.<\/p>\n
By accepting the $22.025 million free-agent qualifying offer, lefty-hitting Trent Grisham provides the Yanks with a center fielder, and slugging outfield prospect Spencer Jones might be big-league ready.<\/p>\n
Jasson Dominguez\u2019s status as a Bronx big-league regular is in question, adding further incentive to strike a free-agent deal with Bellinger, 30.<\/p>\n
\u201cWe still need another outfielder,\u2019\u2019 Steinbrenner said, though he wouldn\u2019t categorize Bellinger\u2019s priority level.<\/p>\n
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But the lefty hitter\u2019s value is pretty apparent to the Yanks and his agent, Scott Boras, who has plenty of reasons \u2013 like Bellinger\u2019s versatile plus-defense, his Yankee Stadium stats, his lineup protection for Aaron Judge and his comfort level in New York \u2013 to demand a lengthy deal.<\/p>\n
Not to mention the supply-and-demand in Bellinger\u2019s favor.<\/p>\n
A pivot to Kyle Tucker, the top free-agent position player in free agency, might cost double that of Bellinger, reluctantly sending the Yanks into the trade market. <\/p>\n
Bullpen upgrades![\"Oct](\"https:\/\/www.rawchili.com\/mlb\/wp-content\/uploads\/2025\/12\/ef38155b911c3d3ad8ea78b42c1aa6d7.jpeg\"\/)
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Oct 1, 2025; Bronx, New York, USA; New York Yankees relief pitcher David Bednar (53) celebrates with New York Yankees catcher Austin Wells (28) after the game against the Boston Red Sox during game two of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images<\/p>\n
Along with a need for an outfielder, \u201cWe need to improve the bullpen for sure,\u2019\u2019 Steinbrenner said recently.<\/p>\n
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Steinbrenner expressed satisfaction with his rotation, but injury rehab will at least delay Gerrit Cole, Carlos Rodon and Clarke Schmidt to start the season.<\/p>\n
That could put the Yankees in the market for a short-term, veteran starter as depth, though the Yanks did re-sign lefty Ryan Yarbrough.<\/p>\n
They also brought back a potential free agent in lefty Tim Hill, plus they\u2019ve got a closer in David Bednar and right-handed setup men in Camilo Doval and Fernando Cruz.<\/p>\n
But there\u2019s a need for two more reliable relievers (preferably one lefty) to offset the losses of free agents Luke Weaver, Devin Williams (just signed by the Mets) and Jonathan Loaisiga.<\/p>\n
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Cashman swung trades to obtain Cruz (last winter), Doval and Bednar (both at the trade deadline) last season, and that might be the preferred route again.<\/p>\n
Right-handed hitting presence![\"Oct](\"https:\/\/www.rawchili.com\/mlb\/wp-content\/uploads\/2025\/12\/f462a27c831869e879a592b82f384243.jpeg\"\/)
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Oct 8, 2025; Bronx, New York, USA; New York Yankees third baseman Ryan McMahon (19) hits a solo home run during the third inning against the Toronto Blue Jays during game four of the ALDS round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Vincent Carchietta-Imagn Images<\/p>\n
Grisham\u2019s return, the pursuit of Bellinger, and the switch-hitting Dominguez\u2019s lack of production from the right side contributes to this need.<\/p>\n
In the infield, the Yankees have three lefty hitters in Ben Rice, Jazz Chisholm Jr. and Ryan McMahon, along with catcher Austin Wells, who had lefty-hitting backups in 2025.<\/p>\n
There\u2019s a need for complementary right-handed hitting depth at the corner infield spots, backup catcher and the outfield.<\/p>\n
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Rice figures to be the regular first baseman, but McMahon batted .184 versus lefties last season between Colorado and the Bronx, with a .534 OPS.<\/p>\n
McMahon might be in a third base platoon with Jose Caballero, who projects as the starting shortstop until Anthony Volpe (shoulder surgery) returns around May 1.<\/p>\n
A reunion with free agent veteran infielder Amed Rosario is a possibility, and Cashman has reached out to Paul Goldschmidt’s rep, after the free agent first baseman posted a .981 OPS against lefty pitching in 2025.<\/p>\n
But the overall lack of right-handed presence beyond Judge and Giancarlo Stanton is a concern that needs to be addressed.<\/p>\n