That approach has resulted in some bold-face additions to the Yanks' 2014 roster. Thanks to a spending spree of more than $300 million, manager Joe Girardi is pondering a lineup that will include Brian McCann, Jacoby Ellsbury and Carlos Beltran, as well as a few items still in the works.
"Our need to be aggressive is because of how our season went," Cashman said. "The obvious answers aren't coming from within, so we have no choice but to be aggressive."
There were also pieces that the Yankees expressed interest in retaining, but ultimately did not. Robinson Cano was a top target and the Yanks offered seven years at $175 million, but that could not match the Mariners' larger offer. Curtis Granderson also switched boroughs, inking a four-year deal with the Mets.
"It's probably not what I would have imagined was going to happen," Girardi said, "because I think you always hold out that the players you have are going to [stay] and that you're going to add to it.
"But that's the nature of this business, players leave. We've added three guys that were with different teams last year, so it's happened to other teams as well. But what we've added to our lineup is as much as I've seen since I've been here. We've added a lot."
And with all of that activity, Cashman said that the Yankees still must fill holes going into the new year. The new-look lineup promises to ring up runs on the scoreboard, but people in the organization still have doubts about the pitching staff, an issue that the Yanks continue to look to address.
Given that, the Yankees head into 2014 with a healthy list of questions that soon will be answered. Here is a look at 10 of the most pressing, in no particular order:
1. How realistic is the goal of a $189 million payroll?
Managing general partner Hal Steinbrenner has spoken publicly numerous times about his desire to reduce payroll below $189 million in 2014, so that the Yankees can take advantage of a reset in their luxury tax bill, thus allowing them to pump dollars into their club, rather than the rest of the league.
Steinbrenner has also been clear that it is a goal and not an absolute mandate, and that a lower payroll will not come at the expense of a championship-caliber club. Those words are about to be put to the test, as it would take some fancy footwork for the Yanks to fill all of their needs and still remain under $189 million.
Generally speaking, their only chance at this point is if Alex Rodriguez's suspension is upheld for the 2014 season, reducing their luxury tax hit on his contract from $27.5 million to $2.5 million. Even then, a run at elite Japanese pitcher Masahiro Tanaka could blow $189 million away. In that event, they could always try to reduce payroll again in 2015.
2. How will CC Sabathia and the starting five look?
The Yankees still point to Sabathia as their ace, and one positive is that the big lefty can still be counted on as an innings-eating workhorse. There were concerns this past year as Sabathia's velocity stalled and his home run rate rose. They are trends that the Yanks hope will reverse in his second year back from elbow surgery, but Sabathia himself has acknowledged that he has a lot of innings on his arm and some slowdown was inevitable.
Behind Sabathia, there are more questions. Cashman said that he wanted to import 400 innings to slot alongside Sabathia and Ivan Nova, and he found approximately 180 to 200 of those in Hiroki Kuroda, who was the Yankees' best starter for a long stretch last year before running out of gas in mid-August. The Yanks pushed Kuroda hard because they had to, and Girardi will likely take greater care with him in the second half in 2014.
Tanaka obviously would be a terrific fit on paper, and you can expect the Yankees to bid heavily for the Rakuten Golden Eagles standout. His arrival is no sure thing, as the Yanks will have competition and should probably anticipate being drawn into a bidding war.
As a backup plan, they've touched base with the other free-agent starters on the market, a group paced by Bronson Arroyo, Matt Garza and Ubaldo Jimenez.
The Yankees also have a group of candidates like David Phelps, Michael Pineda, Adam Warren and Vidal Nuno to compete for a rotation spot in camp.
3. When (and how) will A-Rod's situation be resolved?
The Yankees, Rodriguez and Major League Baseball should have a final resolution on the appeal of Rodriguez's 211-game suspension shortly after the new year, which is good news for all parties involved. Independent arbitrator Fredric Horowitz has the ability to uphold, reduce or altogether lift Rodriguez's record-setting ban.
Club officials have said that they continue to proceed as though Rodriguez will be an active player in 2014, for budgetary reasons as well as in talent evaluation. If Rodriguez will be unavailable for most or all of the season, the Yanks would have some additional money to spend, but also will need help at third base. Currently, infielder Kelly Johnson would be the likeliest candidate on the roster to fill the position.
4. What should the Yankees expect from Derek Jeter?
Jeter played just 17 games in what he referred to as a "nightmare" season, and the organization re-signed him to a one-year, $12 million deal in early November. That contract is a challenge for Jeter to prove that last season was a fluke, and that a full offseason of lower-half training will allow his legs to recover and give the captain a strong base to play out a demanding season.
The Yankees aren't in the business of betting against Jeter, and for good reason, but there are still plenty of reasons for concern. He will turn 40 in June, and the number of everyday shortstops at that age is short and sweet. They re-signed defensive whiz Brendan Ryan as insurance and really won't know what they have until Jeter resumes playing in the spring.
5. How will Ellsbury, Beltran and McCann adapt to life with the Yankees?
Girardi said shortly before the holidays that he has already started to formulate lineups in his mind, and it's easy to see why he would be excited. The Yankees are betting big on three established stars, but as we've learned many times, there are no guarantees in free agency.
Ellsbury is a dynamic game-changer at the top of the order when healthy, which is why the Yankees made a massive $153 million commitment to him. The disabled list obviously has been an issue in his recent history, but Ellsbury said that he is completely healed after Boston's championship run, and the Yanks didn't see anything in his physical to warrant a red flag.
McCann offers a brand of power that the Yankees so sorely lacked from their catchers in 2013, and they also fell in love with his reputation for leadership in the clubhouse and on the field. Yankee Stadium promises to be an excellent fit for his left-handed stroke, but he also has had a few injury flags pop up. Catchers in their mid-30s tend to slow down, but for the first few years of the deal, the Yanks hope there is nothing to worry about.
They're also pleased by the addition of Beltran, adding another switch-hitter to the lineup, albeit one with some miles on the tires. Beltran has a reputation for being a solid clubhouse presence -- despite some hard feelings about his time with the Mets -- and his postseason track record is appealing. It all looks promising on paper, but of course a lot can change during a 162-game schedule.
6. How will the Yankees reduce their crowded outfield?
Cashman said that it would not be a "preferable situation" for the Yankees to carry six outfielders, which is a strong hint that something should happen there very shortly. The names most prominently on the bubble are Ichiro Suzuki and Vernon Wells. The Yanks would entertain a trade involving Ichiro, who has one year remaining at $6.5 million, but thus far haven't been able to drum up much interest. Thanks to some creative accounting, Wells actually doesn't cost against the Yankees' luxury tax bill in 2014, with his contract being paid by the Angels. Thus, he's a strong candidate for release if the Yanks determine that's necessary.
7. Who is Mariano Rivera's replacement?
Rivera strolled into the sunset back in late September saying that he believed David Robertson has earned a chance to serve as the next Yankees closer. That very well may turn out to be the case, but Cashman said recently that Robertson is unproven as a closer, and thus the organization is continuing to see what else is out there.
Grant Balfour's name popped back up on the radar after his deal with the Orioles fell apart. That would be one avenue the Yanks could pursue, but it would not be surprising if they ultimately choose to go with Robertson, whose sneaky fastball and high strikeout rates have tempted evaluators to picture him having a solid closing career.
8. What does the future hold for Brett Gardner?
The Yankees quickly turned down a trade offer from the Reds at the Winter Meetings that would have shipped Gardner to the Reds for second baseman Brandon Phillips. It is not difficult to see why teams view Gardner as an attractive and affordable piece, especially coming off a season in which he was healthy into September and seemed to come into his own.
But the Yanks also like Gardner for those same reasons, and do not intend to trade him unless they can score an upper-echelon starting pitcher in return. They do like the idea of Gardner as an Ellsbury-lite type of player, and whether it's first and second or ninth and first in Girardi's lineup, batting them back-to-back could have some fun consequences during the year.
9. How will the reconstructed bullpen perform?
Beyond replacing a Monument Park legend in Rivera, the Yankees also had some other business to tackle with their relief corps. They signed veteran lefty Matt Thornton to a two-year contract in December as a replacement for Boone Logan, who found a three-year deal with the Rockies.
That tackled one problem, but the Yanks still are patching together the alignment. Assuming Robertson gets the closing gig, he can count on Shawn Kelley and Preston Claiborne helping to set up. Behind them is a jumble of names that the Yankees don't seem ready to commit to yet. In fact, Cashman suggested that the Yanks might need to fill their pitching needs -- both rotation and bullpen -- via non-roster invitations in the spring, and maybe even later than that.
10. Can Mark Teixeira reach his baseball card numbers?
Teixeira often said, memorably, that you should be able to look at the back of his baseball card and count on seeing 30 home runs and 100 RBIs each year. For the better part of a decade, he was right, though those numbers dipped to 24 homers and 84 RBIs in 2012 and fell off completely in 2013 when he was able to play in just 15 games.
The right wrist surgery Teixeira had performed this past year can be tricky to return from, but there are success stories that suggest it can be done -- Jose Bautista is a prime example; David Ortiz is another. Teixeira said he feels close to 100 percent and that he will try to focus on hitting homers, driving in runs and playing top-notch defense. If he does, as far as the Yankees are concerned, that'll be enough.