Tony Pena, Brian Cashman

By Chad Jennings

After missing the playoffs two years in a row, Brian Cashman was given a vote of confidence last week in the form of a new three-year contract. He’ll be given an opportunity to get the Yankees back on track, and there’s a lot of work to be done. In no particular order, here are 10 things Cashman has to do between now and the start of spring training:

David RobertsonMake a decision on Dave Robertson –Qualifying offer? Multi-year contract? Transition to Dellin Betances in the ninth? One way or another, the Yankees have to make a Robertson decision fairly quickly. Qualifying offers have to be in place by the fifth day after the World Series. There’s really no one else who stands out as a qualifying offer candidate, but the Robertson decision is a big one.

Sort through the mid-season additions –The Yankees get the first crack at their own free agents. This winter, that means having the right to early discussions with a bunch of guys who weren’t around for very long last season but could be worthwhile targets this offseason. Brandon McCarthy was terrific after the mid-season trade from Arizona. Is he the kind of guy to stabilize a rotation full of uncertainty? What about bringing Chase Headley back to play third base, pushing Alex Rodriguez to designated hitter? Is Stephen Drew a buy-low option at shortstop? Could Chris Young be a right-handed fourth outfielder after his surprising month of September? He wasn’t a mid-season addition, but it’s also worth reaching out to Hiroki Kuroda to get a feel for his plans going forward. The Yankees get the first chance to talk to these guys. Might as well take advantage of it.

Trim the excess from the roster – Mostly this means finding a home for the Yankees catching depth. Essentially the Yankees are carrying three players — Francisco Cervelli, John Ryan Murphy and Austin Romine — for one big league job and possibly a role as Triple-A depth. Would be better to flip that abundance for something more useful. Could do the same with some of the team’s solid young pitching. Might even be worth shopping around some of the team’s young left-handed outfielders.

Choose the next shortstop – Maybe this is an oversimplification, but to some extent this is what it comes down to: pick a guy and go get him. Maybe that’s a buy-low option on Drew. Maybe it’s a risk signing of Hanley Ramirez. Maybe it’s some free agent in between or a trade possibility that makes sense. Ultimately, weigh the cost and the production and make a choice. Someone gets to be the next shortstop of the New York Yankees. Go find him.

Pick your battles with roster openings – The everyday lineup really has only two holes: shortstop and designated hitter. If Rodriguez is going to be the designated hitter, then third base is open. Bottom line is, though, the Yankees aren’t going to go out and spend big money on a third baseman, and a right fielder and a designated hitter. They’re not going to put $10 million a year into a bench player. So they have to pick their battles when it comes to finding the right pieces. Same with the pitching staff. Is it worth going all in on a guy like Max Scherzer or is it more practical to sign rotation depth and trust that Masahiro Tanaka and Michael Pineda can be the Nos. 1-2 starters next season?

Mark TeixeiraCheck on veteran players (then check again) – As a matter of course the Yankees will check in with guys like Mark Teixeira and Carlos Beltran to find out how they’re doing, but given the nagging injury problems that impacted the lineup last season, those routine status checks seem to carry significant meaning this offseason. Is Teixeira feeling stronger? Is Beltran back to his old self after surgery? How’s CC Sabathia’s knee (and how are his early bullpens going)? Is Tanaka feeling anything in that elbow? Is Ivan Nova still progressing as planned? What in the world is going on with A-Rod? The motto has to be: no surprises on the day spring training opens.

Fill out the coaching staff – The Yankees decided that Kevin Long was no longer the man for the job, and they decided to get rid of all-time nice guy Mick Kelleher to further change the dynamics of the staff. Clearly the Yankees did this with some alternatives in mind. Bring Mike Harkey back and adjust the staff accordingly? Reunite Joe Girardi with his old friend Dante Bichette (another hitting coach with a son in the minor league system)? Maybe get Frank Menechino back in the system? Push popular Triple-A manager Dave Miley into the mix? The Yankees decided to make a change. Firing guys was step one. Time for step two.

Build depth from the outside — There are key prospects who could break through into Triple-A either late next season or in early 2016, but for the time being, the Yankees might have to supplement their depth with smart low-risk signings. Cashman’s usually be very good at this — just this year he found some help from minor league free agents Yangervis Solarte and Zelous Wheeler — and he might have to do it again. Maybe a reunion with a Scott Sizemore-type who could add some experienced third base depth? Almost certainly going to need a Triple-A shortstop who could step into a big league bench role if need be.

Protect the Rule 5 eligible prospects – Quite often, the significant Rule 5 decisions are fairly easy. Top prospects are definitely protected, then the team picks and chooses among the more fringy players. This winter, though, the Yankees face a particularly curious choice about gifted but under-performing prospect Mason Williams. The team also has to choose among a fairly large group of upper level relievers that could follow Tommy Kahnle’s path out of the organization and into another team’s bullpen.

Put someone in charge of the minor leagues – Mark Newman, the Yankees longtime vice president of player development, is retiring this fall. That leaves the Yankees with a significant void in their front office, and Cashman will surely be involved in the search for the next executive to oversee the farm system. Things will roll along pretty smoothly for a while, but someone needs to step into that role pretty soon. It’s a big job for an organization that desperately needs to get more production out of its minor leaguers.

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