And what if they don't? That's a possibility most in the Bronx would prefer not to think about, not with Jeter trying to close the book on what he called a "nightmare" season and Roberts preparing for the unenviable task of making Yankees fans forget about Robinson Cano.
"My job is to get ready to play," Jeter said earlier this offseason. "That's what my job has always been. I don't make out lineup cards. All I can do is get ready in the offseason, come there and be ready to play. My job is to play short.
"It's always been my job since I've come up. It's still going to be my job. I understand the concerns because of everything that went down last year. I understand that. But I'll be ready to go."
Jeter, of course, was limited to just 17 games last season. He served four stints on the disabled list with complications largely stemming from the left ankle fracture he suffered in Game 1 of the 2012 American League Championship Series against the Tigers.
The 39-year-old captain rushed to be ready for Opening Day and refractured the ankle during Spring Training. He missed the first 91 games of the season, then suffered a strained quadriceps in his first game back on July 11, returning to the disabled list.
A calf strain and lingering discomfort in the ankle followed over the next two months, prompting two more DL assignments and an end to Jeter's season in early September. At the time, Jeter said that a full winter of lower-half conditioning would get him in shape to return to playing shortstop on a regular basis.
So far, all reports have been positive. Jeter has been working out at the Yanks' facility in Tampa, Fla., taking ground balls and batting practice. It's a familiar setting for Jeter, who seemed to fill most of his summer with the same activities at the complex.
"It's good to have a normal offseason and get some work in," said Jeter, who agreed to a one-year, $12 million contract in November. "Everything is normal now."
The best tests will come in game situations. Now more than a year removed from surgery, plenty of observers will be watching Jeter's durability and defensive range. He's up against history: only one player in Jeter's lifetime, Omar Vizquel, has played in 100 games as a shortstop at age 39 or older.
"Given his age and given the severity of the injury, I think we all have concerns," Yankees managing general partner Hal Steinbrenner said. "But if anybody is going to succeed, it's going to be Derek. Nobody is tougher and nobody is going to work harder to get back."
Big changes are ahead at second base, where Cano was the Yankees' most productive hitter in 2013. Unwilling to match the 10-year, $240 million contract Cano landed with the Mariners, the Yanks capped their bid to keep Cano at seven years and $175 million, money they'd later put into the pockets of Carlos Beltran, Masahiro Tanaka and others.
To fill the void left by Cano's departure, they are rolling the dice that Roberts can have a solid comeback campaign. A two-time All-Star with the Orioles, Roberts signed an incentive-laden $2 million deal with the Yankees in December, representing a low-risk investment and a good challenge for Roberts to stay on the field after he missed 445 games over the last four seasons.
"It was something that appealed to me," Roberts told the YES Network. "I made it pretty clear that my objective, if somebody wanted me to and felt that I still could, was to play second base on a daily basis for the most part. So I think that's my goal, is to be the second baseman the majority of the games, hopefully."
Roberts made the final out at the old Yankee Stadium in 2008, and following a durable start to his career, has been sidelined by abdominal, concussion, hip and hamstring issues since the beginning of the 2010 campaign. The Yankees were encouraged that Roberts finished last year healthy with Baltimore, batting .249 with eight home runs and 39 RBIs in 77 games.
"I felt like I really should have played a lot more games than I did last year, but I'm excited for the opportunity," Roberts said. "My goal is to come in and try and play as many games as they want me to play, and obviously help us get to where we want as an organization."
The Yankees have cushioned the duo by re-signing defensive whiz Brendan Ryan to a two-year, $5 million contract. Ryan batted .220 in 17 games for the Yanks last year after being acquired from Seattle in a September trade. He'll offer versatility to manager Joe Girardi, having played shortstop, second base and third base during his career.
New York also signed utility player Kelly Johnson to a one-year, $3 million in December. Johnson is currently being looked at as a major part of a platoon at third base, but second base is Johnson's natural position and he plans to continue working there this spring.
The Yankees are trying to hammer down a role for Eduardo Nunez, who played 75 games at shortstop last season and could also get some work at second base. Others who figure to see time in the middle infield this spring include Scott Sizemore, Dean Anna and Corban Joseph.