The New York Yankees are beginning to work through some major outfield question this offseason while their peers are still duking it out in the World Series.

New York Post | Joel Sherman ($): Sherman’s been breaking down all the major free agent decisions the Yankees will have to make this winter, and today the topic is centerfielder Trent Grisham.
How much is too much when it comes to the New York Yankees running it back with the same outfielders next season? That's what general manager Brian Cashman needs to figure out when free agency begins following the 2025 World Series.
How many of the MLB pitchers to get at least 10 strikeouts in one World Series appearance can you name in six minutes?
PITTSBURGH — The Pittsburgh Pirates must add offense to their lineup in 2026 and one New York Yankees free agent could provide them with that next season.
Among the countless Hall of Famers who never experienced the joy of winning a World Series, there are several notable legends who stand out. Here's our list of the 25 greatest.
New York Yankees center fielder Trent Grisham had a breakout first season in pinstripes, and as he enters free agency, he'll be a desirable outfielder with an impressive track record.
The Kansas City Royals have work to do this offseason. Their offense failed them in 2025 and resulted in them going 82-80 and missing the postseason, while also finishing in third place in the American League Central.
The New York Yankees are about to go on the clock. Once the 2025 World Series is over, the club will have five days to extend free-agent center fielder Trent Grisham a qualifying offer.
The qualifying offer sits at $22.025 million for one year. Trent Grisham finally paired patience with real damage at the plate. If he declines, the Yankees get a late comp pick and keep flexibility.
America's favorite pastime has more memorable performances than any sport. As such, figuring out which pitchers had the best seasons ever is no easy task.
The New York Yankees will likely have some level of turnover in their outfield next season with both Trent Grisham and Cody Bellinger set to reach free agency, which could open up opportunities for some of the organization's younger options at the position.
A number of teams (and their fanbases) have already turned their attention towards the offseason. Identifying free agent targets is a big part of that prep work, so it’s worth taking a look at the players who’ll be available at each position.
The New York Yankees have a lot of decisions to make this offseason. None of them will be easy, and really, they won't get to decide all of them - but they have to create a plan.
The Kansas City Royals could use some outfield help heading into 2026. According to FanGraphs, no team’s group of outfielders was worse in 2025 than Kansas City’s, with their 73 team wRC+ and collective -1.1 fWAR both ranking last in baseball.
The Detroit Tigers suffered a heartbreaking exit in Game 5 of the ALDS against the Seattle Mariners, falling one moment short of their first ALCS since 2013.
The Detroit Tigers suffered a heartbreaking exit in Game 5 of the ALDS against the Seattle Mariners, falling one moment short of their first ALCS since 2013.
The Milwaukee Brewers are down a game in the National League Championship Series against the Los Angeles Dodgers and need a win in Game 2 to avoid falling into a 0-2 series deficit before the series shifts to Dodger Stadium.
The Kansas City Royals' outfield is a very serious problem, and most seem to acknowledge it. After finishing dead-last in Major League Baseball with -1.1 outfield fWAR, the Royals will be on the prowl for an impact addition this offseason.
The Kansas City Royals' outfield is a very serious problem, and most seem to acknowledge it. After finishing dead-last in Major League Baseball with -1.1 outfield fWAR, the Royals will be on the prowl for an impact addition this offseason.
With the offseason ahead, it’s time again to make tough decisions.
With center field a question mark for the New York Mets heading into the offseason, would this outfielder be a possible option for the club? During Friday's episode of Baseball Night in New York on SNY, baseball analyst Hannah Keyser called Trent Grisham a fit for the Mets.
It didn’t take very long at all for the first umpiring controversy of the ALDS between the New York Yankees and the Toronto Blue Jays.
Trent Grisham went 2-for-5 with two home runs and four RBIs, and the New York Yankees pulled away for a 10-5 win over the Minnesota Twins on Wednesday night in Minneapolis.
It’s not uncommon for an MLB player to see their production rise as they hit the prime years of their late 20s. Similarly, every year there are players who break out in the year before free agency hoping to parlay things into a big, new contract.
A big reason why the New York Yankees find themselves comfortably in a wildcard spot is the play of veteran centerfielder Trent Grisham. In what could
Trent Grisham not only continues to perform but has won his way into the hearts of Yankees fans. Let's take a closer look at how he's done it.
Losing Juan Soto to their crosstown rivals in Queens was a tough blow for the New York Yankees heading into 2025. But little did they know that the next best thing was already waiting in the wings (well, on the bench).
Needing to find a way to put a positive end to a disappointing homestand, the New York Yankees made history on Wednesday afternoon against the Washington Nationals.
New York Yankees outfielder Trent Grisham is playing like a superstar. If he keeps it up all year, he’ll be a hot commodity on the open market. However, the Bombers should be very careful when the time comes to consider bringing him back to the Bronx.
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