"One of the things I asked was. 'Where are we going? What are we trying to do here?'" Bailey said. "If it's a thing where we're sneaking in at third place with a very talented team, I don't want to be a part of that. I want to be part of something that's winning divisions and going deep in the playoffs and competitive every year. Just talking with him, it seems like that's the goal of this organization. That says a lot."
That was enough reassurance for Bailey and his agents to move forward on staying in Cincinnati long term. It all came to fruition on Wednesday when Bailey signed a six-year, $105 million contract through the 2019 season. The deal comes with a $25 million mutual option for 2020 and carries a $5 million buyout.
Reds general manager Walt Jocketty announced the signing on Thursday, the same day an arbitration hearing had been scheduled in Tampa, Fla. The deal also prevents Bailey from potentially leaving as a free agent following the 2014 season, and also covers five possible free-agent years.
"Obviously, we're very excited about it and very pleased," Jocketty said. "Homer is homegrown. He was drafted, signed and developed in our organization. It's important as an organization to reward our players that have earned this type of respect with contracts to keep them part of the organization for a long time, and hopefully finish his career here."
According to figures obtained by The Associated Press, Bailey will receive $9 million this season, $10 million in '15, $18 million in '16, $19 million in '17, $21 million in '18 and $23 million in '19. In a unique structuring, a large portion of the salary is being deferred each year until November. If Bailey is traded, he would receive each year's salary on time without the deferral.
"I don't care how much you're making -- some might disagree -- winning and being competitive on the field says a lot about happiness and where you're at," Bailey said. "Just the way this organization is run day in and day out says a lot and gives a lot of comfort to me."
Bailey, 27, made $5.35 million in 2013, and posted an 11-12 record. But he also achieved career bests with a 3.49 ERA, 209 innings and 199 strikeouts.
The seventh overall pick in the 2004 First-Year Player Draft, Bailey made his anticipated big league debut in 2007. Since then, he has a 49-45 record with a 4.25 ERA in 143 starts. The early days of his career featured some struggles and injuries that delayed his development. He spent parts of 2010 and '11 on the disabled list with shoulder injuries.
Over his last three seasons, the right-handed Bailey has shown marked improvement, going 33-29 with a 3.79 ERA. Over 549 innings in that span, he has a 3.40 strikeout-to-walk ratio, a 1.21 WHIP and a 105 ERA+. He's also thrown a pair of no-hitters -- vs. the Pirates on Sept. 28, 2012, and against the Giants on July 2, 2013.
In the 2012 National League Division Series against the Giants, Bailey also had one of his best starts. He gave up one earned run and one hit with 10 strikeouts but got a no-decision in defeat.
"He's worked hard. He's really overcome a lot of obstacles," Jocketty said. "He's grown a lot in the few years I've been here, and I've seen how he's matured into one of the top pitchers of the game today."
Bailey is the latest Reds player to be retained from within the organization. After the 2010 season, right fielder Jay Bruce was signed to a six-year, $51 million contract, and ace Johnny Cueto received a four-year, $27 million deal. In 2012, first baseman Joey Votto signed a blockbuster 10-year, $225 million contract extension.
"We couldn't find a better guy to sign and keep in the organization for a long time," Jocketty said of Bailey. "Pitching is very important to this organization and our philosophy of winning with pitching and defense. Now, Homer will be with us for a number of years to kind of anchor that rotation and take us hopefully to championships."
Reds president/CEO Bob Castellini was asked if the Bailey signing sent a message to the fans about the team's commitment.
"I think the fans have sent a pretty good message to us over the last eight or nine years," Castellini said. "Coming to the ballpark and they show a lot of enthusiasm, which means so much to not only the franchise, but the players on the field, too. Everybody talks about a small-market team, we're a small-market team with a big-market baseball heart."
Despite the size of the heart, it's still not an easy feat for smaller-market clubs to retain their own players. The decisions are made deliberately and soberly. The Reds have made the playoffs three of the past four years and are looking to take the next step.
"We're all human, but we have made a pact with our fans and our market that we will be contenders year in and year out," Castellini said. "That is a very difficult thing to accomplish, but we're sure trying."
During the early years of his career, Bailey was often part of trade rumors. There had been speculation that if he didn't want to stay with the Reds long term, he should be traded this offseason before he could become a free agent.
"I never saw where I was quoted saying [I didn't want to stay]," Bailey said. "I've been traded four times and I still wear a Reds uniform, right?"
Bailey is part of a Reds rotation that features some of the better young arms in baseball -- including Cueto, Mat Latos, Mike Leake and Tony Cingrani. There are also young arms just around the corner developing like Robert Stephenson, Nick Travieso and Michael Lorenzen.
Not only does he like the present Reds team, Bailey likes what it could be in the years ahead.
"When you take a look across our organization, you see a lot of good things," Bailey said. "That says a lot to me. The core group of players that we have currently in Cincinnati and the ones coming up show signs of things that continue to be good in Cincinnati as far as baseball is concerned."