It's not as if Chicago's coterie of young players -- Kris Bryant, Javier Baez and Anthony Rizzo -- need any added incentive. But to a man on Monday, they said they'd love to send out the 39-year-old veteran of 15 seasons with a World Series title.
"I wish that we could keep him around forever. It's sad that this is his last year," Bryant said. "He lets us call him grandpa, and he's not even a grandpa. We give each other a hard time all the time. That's what makes him my favorite teammate."
Ross is a father of three young children. His older daughter, Landry, is 9, his son, Cole, is 7, his younger daughter, Harper, is 1 year old. And for that reason, the veteran says it's time to let go of his active status as a player.
"If you pride yourself as a family man and you don't put your family first, then that's not right," Ross said.
In contrast, though, Ross said he feels healthy and could keep playing. Three years after his Red Sox beat the Cardinals in a six-game World Series, Ross has had such a good time this season he's constantly considering a change of heart.
"I think about that every day," he said. "I love playing the game. I love competing. I love being part of the guys. I love this and I've had some success this year. It makes you think, 'Oh, are you really done?'
"I just think that coming back after this amazing year, who knows what the next would hold? And I really want to be a part of my kids' lives. I want to do some things with them. My son is getting into baseball. My daughter is getting into some extracurricular things like volleyball and cheerleading. I want to be a part of all that."
Ross is torn between his own family and the family of players that surrounds him on the field and in the clubhouse. Unlike his 2013 Red Sox, Ross looks around and knows that the Cubs have a foundation of youngsters that's going to make them contenders for years.
"It's tough," Ross said. "When you want to be successful at baseball, you've got to commit your life to it. I mean, Spring Training started in mid-February this year. We've been doing this for a long time. I live in Florida. My Spring Training is Arizona. And we play in Chicago. So it's not easy on the family. They've traveled a lot. I've gotten to live my dream. It's time."
The Boston team that was vanquished by Cleveland this postseason in an American League Division Series had only six guys remaining from the group that played on that most recent World Series winner. And one of them, David Ortiz, also just retired.
It's the transient nature of Major League Baseball. Lester and pitcher John Lackey played with Ross on the 2013 Red Sox and are in the World Series with him again this year.
Three years ago, Ross missed a couple of months of the regular season after sustaining a concussion. Ultimately, Ross caught Lester in the ALCS and the World Series.
"He brings that intensity," Lester said on Monday, reflecting on what Ross contributes. "He expects so much of you, and so you want to do more sometimes. It's like getting that approval from your dad type of thing."
In 2013, Lester won Game 5 over the Tigers in the ALCS, and Games 1 and 5 against the Cardinals in the World Series. The Cubs have already won all three times Lester and Ross have been paired this postseason, and both men are hoping for the same result in the next week.
"It's special to be with him now in this World Series, in kind of this, his last hurrah," Lester said.
The Cubs' younger players, of course, look at it from a completely different perspective. Ross was a bit player in Boston, but he has become a folk hero in Chicago. The fans love him and the kids look up to him. They keep him young, Ross said.
"The whole year I've been asking my questions to him," Baez said. "He's one of the first people I go to."
"It's fun to have him around," Rizzo added. "We've got to send him out on the highest note you can ever go out on in this game. I can't praise him enough for his leadership, for everything he's done for me as a player and a person and for this organization."
Asked if he also calls him grandpa, Rizzo deadpanned: "I call him way worse names than that."
Barry M. Bloom is a national reporter for MLB.com and writes an MLBlog, Boomskie on Baseball. Follow @boomskie on Twitter. This story was not subject to the approval of Major League Baseball or its clubs.