Ideal Trade Scenarios for New York Yankees to Focus on Pulling off This Winter

The MLB offseason has started busier than expected, as multiple organizations have already made moves large enough to change the landscape of their 2015 seasons.

The New York Yankees have been mostly inactive, though, as their lone move to acquire Justin Wilson for Francisco Cervelli helped shore up the bullpen. They've yet to make an impact move, but general manager Brian Cashman has money to spend and phone calls to make.

Chances are this won't be a quiet winter in the Bronx.

Two years have gone by since the Yankees have made an appearance in the playoffs, as a combination of injuries and ineffectiveness has hurt the team. Cashman will look to acquire enough talent to withstand any potential issues moving forward.

There are clear needs on the team, but the free-agent market isn't that deep. With so many bidders for so few stars, it might be best for the Yankees to look at making a few key trades.

Not all of the following trades will happen, but the proposed packages represent the ideal scenarios for the Yankees in the coming months.

A Diamondbacks Shortstop

Gregory Bull/Associated Press

Addressing the gaping hole at shortstop is something that will plague Brian Cashman until he finds the right man for the job. There aren't many free-agent options, making the Arizona Diamondbacks a candidate to make a trade or two this winter.

Nick Piecoro of The Arizona Republic wrote about how the D-backs have three valuable shortstops in their organization:

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When the season ended, the Diamondbacks had on their roster three young players, Chris Owings, Didi Gregorius and Nick Ahmed, whom rival scouts and executives believe have at least a chance to be everyday shortstops, and a fourth player, Cliff Pennington, who is at worst a serviceable utility infielder.

If the Diamondbacks wanted to add starting pitching and wanted to add it now, they could probably use one of their young shortstops, namely Gregorius or Ahmed, as currency.

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If young pitching is what Arizona wants, the Yankees can oblige.

Left-handed pitcher Ian Clarkin is a young starter who still needs a little work in the minors, but he projects as a reliable No. 3 in a rotation and would be a good fit for the National League West.

Jose Ramirez and Bryan Mitchell, two candidates to help the Yankees out in the bullpen next season, are valuable right-handers who throw hard and have potential as starters. The Yankees don't have the openings in the rotation to give them looks outside of spring training, so the D-backs would be an ideal fit for them.

Cashman could easily flip one of the aforementioned arms and another mid-level prospect for Gregorius, Owings or Ahmed.

Howie Kendrick

Ted S. Warren/Associated Press

Second base was a black hole for the Yankees in 2014, as Brian Roberts was mostly a failure in pinstripes and the inconsistencies of Kelly Johnson at the plate led to his departure midseason.

Martin Prado can play the position moving forward, but his versatility requires that the team has another option to play the position. Jose Pirela and Rob Refsnyder could be given a look as in-house candidates. There's no telling what the team will get from the youngsters, however.

The Yankees know plenty about Howie Kendrick, who has hit .342/.404/.480 in his career against them. Naturally, CBS Sports' Jon Heyman reports that the Yankees have already checked in with the Los Angeles Angels on his availability.

"The Yankees and Blue Jays are among teams that have called about Kendrick," he wrote.

Kendrick has only one more year on his deal, which is valued at just $9.5 million. His affordability would normally allow the Angels to ask for a nice return, but the fact that he's only under contract for one more year negates that advantage.

The Angels lack bullpen arms and big league-ready catching depth, so trading Jose Ramirez and Austin Romine for Kendrick would make sense for both sides.

Cole Hamels

H. Rumph Jr/Associated Press

Cole Hamels is available, which means Brian Cashman must at least give the Philadelphia Phillies a call.

Because Hamels is a no-doubt ace, the package required to pry him away will be huge. That means all of the team's top prospects will be in play. Gary Sanchez, Jacob Lindgren, Aaron Judge and Greg Bird must be dangled if Cashman is serious about Hamels.

Of course, he's owed a ton of money. He's owed $22.5 million in each of the next four years, and his team holds a $20 million option for 2019. He has been worth the money throughout his career, but the 30-year-old will surely decline by the end of the deal.

Calling Philly likely would represent due diligence for Cashman, but it's not out of the realm of possibility for the Yankees to steal Hamels away. If they do, a rotation of Hamels, Masahiro Tanaka, Michael Pineda, CC Sabathia and an innings-eating No. 5 starter has the potential to be the best in baseball.

Ian Kennedy

Ben Margot/Associated Press

A far cheaper alternative to Cole Hamels, Ian Kennedy is another pitcher likely available via trade this winter. He just finished a strong campaign with the San Diego Padres, going 13-13 with a 3.63 ERA and 207 strikeouts in 201 innings.

With the Padres likely continuing their never-ending search for offense, Kennedy could be dangled. Plus, he'll be a free agent following the season.

Kennedy's first go-around with the Yankees was brief. He was drafted by the organization in 2006, pitching parts of three years with the team. Those were met with varying levels of success.

He moved out west to the Diamondbacks, where he won 21 games in 2011, though, establishing himself as a quality starting pitcher. The Padres will try and sell him as a guy with the potential to win 20 games again.

Given Brian Cashman's familiarity with Kennedy, he'll know how to value the 29-year-old. A top prospect might be on the table, but not the full list like Hamels will necessitate.

A deal centered around Greg Bird or Miguel Andujar should entice the Friars.