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The New York Yankees have had an eventful end to the work week. Less than 24 hours after agreeing to terms with left-handed starter Carlos Rodón on a long-term deal, the Yankees watched as outfielder Andrew Benintendi signed a five-year pact worth $75 million with the Chicago White Sox. Benintendi's contract is the most lucrative the White Sox have ever handed to a free agent.

Benintendi's departure means that Yankees general manager Brian Cashman will have to reconsider his plans for left field. The good news for Cashman is that he has a good outfield foundation from which to build. Right fielder Aaron Judge returned earlier this winter after last season's historic home-run barrage, while center fielder Harrison Bader will be in tow for an entire season after coming over at the trade deadline from the St. Louis Cardinals.

The Yankees do have some internal options they could consider for the left-field vacancy, including veteran Aaron Hicks and youngster Oswaldo Cabrera. Given New York's reported interest in retaining Benintendi, it's probably fair to assume that their preference would be to open camp with another option slotted ahead of Hicks and Cabrera on the depth chart.

Just who might that person be? Let's take a look at some of the possibilities available to the Yankees on both the free-agent and trade fronts.

Free agents

Michael Brantley
HOU • DH • #23
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The top free-agent outfielder remaining on the market is Michael Brantley. CBS Sports ranked him 15th entering the winter, but his stock was difficult to peg because of his age (he'll turn 36 next May) and the fact that he did not play after June 26 because of season-ending shoulder surgery. The Yankees would seem like a sensible suitor for Brantley on the surface. They're a contender, and they can afford to give him a lucrative one-year deal with the hope that the extended layoff won't hurt him. Even so, it's unclear if the Yankees have interest in Brantley, whose name has largely been absent from the rumor mill.

There are a number of other top-50 free-agent outfielders yet to find homes, beginning with the 28th-ranked Jurickson Profar and extending to Michael Conforto (No. 34), Wil Myers (No. 46), and David Peralta (No. 47). Throw in the unranked AJ Pollock, and the Yankees have some digging to do.

Profar is the closest thing the market offers to a Benintendi proxy -- at least in the sense that they're both slugging deficient. Otherwise, it's an imperfect comparison. Whereas Profar has hit .244/.333/.375 (103 OPS+) over the last three seasons, Benintendi has batted .282/.347/.410 (109 OPS+). Profar's raw numbers are damaged by him playing his home games in Petco, but there's still a gap there. It doesn't help that Benintendi is the superior fielder. 

Michael Conforto
SF • RF • #8
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Conforto, for his part, is perhaps the most intriguing upside play. He did not suit up for anyone last season after suffering a shoulder injury during a spring workout. In the seven prior years, all spent with the New York Mets, he hit .255/.356/.468 (124 OPS+) and launched 132 home runs. Conforto's left-handed power would seem to pair well with Yankee Stadium's dimensions.

Let's play the lightning round for the other three names mentioned above. Myers and Pollock are both short-side platoon types. Myers has outproduced Mookie Betts versus lefties during the Pandemic Era, while Pollock posted a .935 OPS against southpaws in 2022. Peralta is sturdy against righties, meaning he would be a fine dance partner for either, should it come to that.

Say the Yankees find none of the options above to be satisfactory. Might they be able to do better through trade? With the caveat that it's hard to know exactly who is and who isn't available, we happen to think so.

Trade targets

Bryan Reynolds
PIT • CF • #10
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The obvious top candidate on this front is Bryan Reynolds of the Pittsburgh Pirates. He's a switch-hitter with three years of team control remaining, a career .281/.361/.481 (127 OPS+) slashline and a public request to be traded. The one teensy tiny problem is that the Pirates don't have to deal him, and are reportedly seeking a Juan Soto-like package in return. Good luck.

Shy of Reynolds, the Yankees could dream on securing a long-term fit in the form of someone acquired from either the Arizona Diamondbacks or the St. Louis Cardinals' bloated outfield situations. 

Tyler O'Neill
STL • LF • #27
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The Diamondbacks aren't likely to part with Corbin Carroll or Daulton Varsho, but they also employ youngsters Alek Thomas and Jake McCarthy, as well as former Rookie of the Year Award winner Kyle Lewis. As for the Cardinals, they have Tyler O'Neill, Lars Nootbaar, Dylan Carlson, and Alec Burleson on their projected roster. That doesn't include Moisés Gómez or top prospect Jordan Walker, either of whom could step onto the big-league roster at a whim.

Now, we feel obligated to note that the Yankees have to give up someone to get someone. The Yankees exhausted some of their organizational depth (particularly pitchers) last summer, trading away prospects to obtain Benintendi, Frankie MontasLou Trivino, and Scott Effross. They do still have some intriguing prospects to shop around, but their comfort in parting with quality prospects will inform their price bracket.

With that in mind, we'll conclude by touching on two American League Central outfielders who rest a further downstream than the aforementioned players.

Max Kepler
MIN • RF • #26
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The Minnesota Twins have discussed Max Kepler with other teams and seem well-positioned to trade him given their recent signing of Joey Gallo. He offers good defense and he's a reliable source for a 90 OPS+ or better, plus he has two years left on his contract. The Detroit Tigers, meanwhile, might prefer to hang onto Austin Meadows so that he can regain trade value. Meadows, who has two years of team control left, appeared in just 36 contests last season because of injury and an absence to work on his mental health.

The reality of the trade market is that the Yankees will be inquiring about players well beyond the reaches of this article. No one can say for certain who the Yankees will add, but it seems like a safe bet that they'll find someone to their liking between now and the opening of camp.