"You take them one at a time," Jocketty said on Thursday after Bailey's deal was announced. "We had to make a decision on Homer now. We were actually working on it some over the offseason. It really came to a head the last few weeks as we came to the arbitration process. We'll take each one as they come and it gets to a critical point to make a decision."
After the 2014 season, No. 2 starter Mat Latos will have completed his two-year, $11.5 million contract and will be third-year arbitration-eligible like Bailey was this winter. That will put Latos a year away from free agency, and there's already speculation that Latos could command a contract that is well north of Bailey's. No. 4 starter Mike Leake, who signed a one-year, $5.925 million contract last month, will also be third-year arbitration-eligible after this season.
Ace Johnny Cueto is headed into the final guaranteed season of his four-year, $27 million contract. Cueto, 28, has a $10 million club option for 2015 that carries an $800,000 buyout.
With the expense of Bailey's signing, Jocketty acknowledged the difficulty in retaining all of his starting pitchers.
"It's going to be tough," Jocketty said. "We thought looking at how Homer has improved, how he's grown the last few years, you look at him trending upwards. He's still very young and durable. He has the type of temperament and mentality to anchor this staff."
Reds president and CEO Bob Castellini noted that there are challenges to remain contenders each season.
"Nobody has a crystal ball. Anything can change in anybody's business," Castellini said. "In this sector especially, we're prone to changes. People don't have crystal balls in any business, but what we have is the optimism. We have sponsors that have been terrific, we've tripled our sponsorship as far as number of sponsors in just nine years. We've taken our radio affiliation and increased that by almost 2 1/2 times in nine years. These are people that really care about our franchise."
There will be another wave of pitchers coming up through the organization to potentially keep the window of contending open. Lefty Tony Cingrani, who was a rookie last season, is under club control for another five seasons. The organization's top prospect, right-hander Robert Stephenson, reached Double-A last season, as did Michael Lorenzen, who was the 38th overall selection in the 2013 First-Year Player Draft. Nick Travieso, the 2012 first-round pick, was in Class A Dayton last season.
There are few Reds players now locked up in long-term contracts, the biggest being Joey Votto's 10-year, $225 million contract through 2023. Brandon Phillips (six years, $72.5 million) is signed through 2017, and Jay Bruce (six years, $51 million) is signed through 2016.
The Reds had to be creative with Bailey's contract by deferring large amounts each season until November. It's also heavily backloaded and includes a $25 million mutual option for the 2020 season that carries a $5 million buyout.
In the past, the club has deferred salary to future years in deals with the likes of pitcher Bronson Arroyo.
"We've got some other young pitchers who are quality guys," Jocketty said. "When their time comes, we'll evaluate where we are financially and see what we can do with them."