At least this time around, he gets to put that experience to good use.
Brantley, 30, has progressed to lateral agility drills as he works his way back from right ankle surgery in October with an eye toward playing as much as possible this season. If that means he isn't ready for Cleveland's opener at Seattle, so be it.
"I think I'm getting older, and I think I'm starting to understand it more, that I need to make sure that I'm 100 percent healthy when I come back," Brantley said Sunday. "It takes time. It's not going to happen overnight, but put in the hard work that you need to get done, and everything comes out good in the end."
Brantley hasn't always had that big-picture approach as he worked his way back from an injury. Manager Terry Francona has noticed a difference this spring.
"Because he's been through so much, I think we haven't had to put the reins around him as much as maybe in the past," Francona said. "I think he's trying to look at this thing logically, also. But if hard work means anything, which it does, he's going to be just fine."
If Brantley can stay on the field, he could provide a huge boost for Cleveland as it tries to recover from last year's disappointing loss to the New York Yankees in the AL Division Series. Before his recent run of injury woes, Brantley was one of the majors' best all-around players, capable of making a key play at the plate, on the bases or in the field.
He had a breakout season in 2014, batting .327 with 20 homers, 97 RBI and 23 steals in 156 games. He was working on another good year in 2015 when he hurt his right shoulder diving for a ball in Minnesota.
The two-time All-Star needed two surgeries to fix his shoulder and played in just 11 games in 2016, missing Cleveland's run to the World Series. He appeared to be back on track last year before he injured his ankle while chasing a fly ball to left field during a game on Aug. 8.
Brantley made a surprising return late last season and was selected for the playoff roster against New York, but went just 1 for 11 in the five-game series. Despite the string of injuries, Cleveland decided to pick up his $11.5 million option for 2018.
"Whether it's second week of April, whenever, we're going to be really happy to have him back," Francona said, "because that's a position then that you don't have to platoon, you just kind of wind him up and let him go play."
Brantley said everything has gone smoothly so far this spring. There is no public timetable for his first appearance in the Cactus League, and he said he has no number in mind in terms of how many exhibition games he needs to be ready for opening day.
"It's more how I personally feel and respond every day," he said. "I just want to get out there and get the reps when I'm needed, and if I'm ready to go, I'm ready to go. If I'm not, I'll be there when I'm 100 percent healthy and get back to helping this team win."
Brantley spent part of his Sunday morning peering over the shoulder of Mike Napoli while he played cribbage with pitchers Josh Tomlin and Adam Plutko. There was a hearty round of laughs as the game broke up and the players headed off to their rest of their day.
Brantley, who was acquired by Cleveland in the CC Sabathia deal with Milwaukee in 2008, also is drawing strength from his teammates as he looks to rejoin them on the field when he can.
"They help me. They keep me positive and keep me going," he said. "I can't thank them enough for what they do for me. Just picking me up every day if you're not healthy and telling how much they miss you and then at the same time, I'm doing anything I can to help them. It's a team effort all the way around."