Cunningham's recent past includes a forgettable showing in the big leagues last season with the Padres, who traded him to the Indians for Minor League pitcher Cory Burns in December. Cleveland believes Cunningham is a candidate to turn things around, which could make him a solid option as a reserve outfielder.
That will all be sorted out during Spring Training. For now, Cunningham is content with using this annual event to get acquainted with his new organization. The Winter Development Program is typically reserved for the upper-level prospects with the best shot at making an impact on the big league club in the coming season.
Of the 11 players invited to this year's program, Cunningham is the only one who has tasted the Major Leagues. Given that fact, the Indians were impressed that the outfielder was so willing to spend part of his offseason braving the Cleveland winter.
"We're just blown away by the person," said Ross Atkins, the Indians' vice president of player development. "He's been in the Major Leagues for parts of four seasons. We called him and invited him to be here, just to get him acclimated to Cleveland and to us and he didn't hesitate.
"He's here with 10 other guys that have never touched the Major Leagues."
Cunningham said it was an easy decision.
"When a team calls you and gives you an option to do something," Cunningham said, "you really don't want to turn that down. Also, I've learned a lot here. It's been nice to be able to come over here. I've met a lot of front-office guys, and I've met some former players. It's been a really good experience."
Team president Mark Shapiro, general manager Chris Antonetti and manager Manny Acta were all slated to speak to the players. Other guest speakers include Cleveland Cavaliers general manager Chris Grant, Browns head coach Pat Shurmur, former Red Sox manager Terry Francona and longtime baseball writer Peter Gammons of MLB Network, among others.
The players will spend this week in Cleveland before finishing the program with a second week at the club's Spring Training base in Goodyear, Ariz.
Beyond Cunningham, the list of participants this year includes right-handers Austin Adams, Rob Bryson and Tyler Sturdevant; lefty T.J. McFarland; catchers Chun Chen and Roberto Perez; outfielders Tim Fedroff, Jordan Henry and Thomas Neal; and infielder Juan Diaz.
Some of those players could reach the Majors at some point this season, but Cunningham has the best shot at making the team out of camp this spring.
"Tons of ability. Tons of potential," Atkins said. "He's already someone that our scouts feel can complement our team really well."
Last year with San Diego, the 25-year-old Cunningham hit just .178 with three home runs and nine RBIs in 52 games. That was a significant drop-off from his 2010 showing, when he managed a .288 average over 53 games. Overall, Cunningham has hit .231 over 150 games spent between stints with the A's and Padres.
Cunningham's potential can be spotted in his 2011 showing at Triple-A, where he hit .329 with nine homers, 34 doubles, 63 RBIs and a .398 on-base percentage in 87 games with Tucson. Against left-handed pitchers, the right-handed outfielder posted an impressive .395 average in the Minors last year.
Cunningham believes he knows what happened when he made the jump from the Minors to Majors, and he is quick to say it should not be an excuse.
"There's always things to improve on. I'm always learning," Cunningham said. "What I had to really deal with was the matter of pinch-hitting and not playing every day, but playing every third day. A lot of people want to say that's not an opportunity, but that is an opportunity.
"If I would've succeeded, I might not be in this position right now. I'm just thankful for another opportunity."
This spring, Cunningham will compete for the fourth outfielder's role behind the starting trio of left fielder Michael Brantley, center fielder Grady Sizemore and right fielder Shin-Soo Choo. All three of those players hit from the left side, so having a right-handed hitter such as Cunningham on the bench is ideal.
Depending on what happens at first base, Shelley Duncan could serve as competition. This winter, the Indians also signed outfielder Felix Pie to a Minor League contract that included a Spring Training invite. Chad Huffman, Ezequiel Carrera and Trevor Crowe might also be considered.
Potentially working in Cunningham's favor is the fact that he is out of Minor League options, meaning he would have to first be cleared through waivers before being sent down. Given that fact, Cunningham will likely be given every chance to earn a spot on the Opening Day roster.
That is all Cunningham can ask for at this point.
"They said I do have a good opportunity," he said. "That's all I need to know. I'll come in and just do my job and play hard and, hopefully, everything works out well."