Just how deep are the pockets of the Cincinnati Reds?

Feb 15, 2014; Goodyear, AZ, USA; Cincinnati Reds pitcher

throws during team workouts on the practice fields of Goodyear Ballpark. Mandatory Credit: Mark J. Rebilas-USA TODAY Sports

The Cincinnati Reds took a big risk last month, agreeing to terms on a six-year, $105 million deal with right-hander Homer Bailey. As much as that move poses a risk for the organization, it could also prove to pay dividends – especially if Bailey continues to build each year while continually improving on the mound.

Since 2008, he has annually lowered his ERA, from a career-worst of 7.93 in eight starts with the Reds to a career-best mark of 3.49 last season, when he topped 200 innings pitched for the second consecutive season.

The 27-year-old Bailey has also tossed a no-hitter in each of the previous two seasons, while posting a 2.55 SO/BB ratio over the course of his career. His top two seasons in terms of that statistical measure came in the past two seasons (3.23, 3.69). Clearly, a trend has emerged.

The Cincinnati front office, led by former St. Louis Cardinals general manager Walt Jocketty, appears to be intent on locking up talent – especially big name players – prior to free agency. In April 2012, the organization signed both Joey Votto (10 years, $225 million) and Brandon Phillips (6 years, $72.5 million) to record extensions. After the Bailey extension, the question begs to be asked: how deep do the Reds’ pockets go?

At the time the extension was announced, many around the game pointed to the coming offseasons, when the Reds would have to come to a conclusion on 60 percent of their starting rotation – in the form of Mat Latos, Mike Leake and Johnny Cueto – all of whom are under contract through the 2015 campaign.

Starting with Latos, one would assume that he will fetch a payday greater than his Reds’ teammate, Bailey, given his numbers – both over the course of his career and in the past couple seasons – are better across-the-board.

Latos is heading into his age 26 season, while Bailey turns 28 in May. So when you factor in the fact that Latos’ career earned run average is nine-tenths of a run lower than Bailey’s over the course of his career, he allows over a hit less per nine innings of work and is coming off a two-year stretch in which he combined to go 28-11 with 372 strikeouts in 420 innings of work – it’s clear we’re talking about a pitcher entering his prime.

In a recent interview, Reds owner Bob Castellini told John Fay of the Cincinnati Enquirer that he was “going to try to sign all these guys,” but admitted that he wouldn’t “blow the franchise up by overextending.”

Latos will likely see a deal somewhere in the neighborhood of an AAV (average annual value) of $20 million. Leake is coming off a season in which he posted numbers similar to Bailey and Latos, winning 14 games, posting an ERA in the low-3.00s and notching just under 200 innings.

Cueto, one season removed from a masterful 19-9 campaign where he finished fourth in the National League Cy Young voting, will look to bounce back after injuries limited him to just 11 starts last year. However, in those 11 starts, he posted a 2.82 ERA – right on par with his 2012 performance.

What is all comes down to is the fact that the Reds are a small market team with a large market spending list. Votto’s contract isn’t off the books until 2024, at which point he’ll be 40 years old. So unless he’s moved in the next few years (which is highly unlikely), Votto will be a Red for life.

Phillips, on the other hand, was the topic of numerous trade rumors during the offseason – especially after Robinson Cano left the New York Yankees to sign a mega deal with the Seattle Mariners. That being said, he’s in Reds camp, so he’s the club’s second baseman moving forward. There is, however, a decent chance he’s traded in the next two years. He’s under contract with Cincinnati through the 2017 campaign.

The pitching talent the Reds have been able to both develop and acquire is one of the most overlooked pieces of front office work in the game today. But the real question facing the organization is this: can this club win before their trio of pitching studs hit the open market or will it be better served shopping them if the team stumbles out of the gates in 2014?