Bailey himself has also confirmed that the talks are nearing their conclusion, telling John Fay of the Cincinnati Enquirer that discussions are "going in the right direction" and that "the majority of it is worked out." The right-hander wouldn't get into details about the years or money involved, but it seems that we'll have that information soon enough.
Bailey was one of six Reds players to file for arbitration this winter, but is the only one left without a contract for the coming season. (Just two arb-eligible players remain unsigned in all.) Just one year removed from free agency, the big Texan filed at $11.6 million, while Cincinnati countered at $8.6 million; no matter the length of the extension, his 2014 salary must be between those two numbers. Given the typical progressive structure of multi-year extensions, it seems likely that Bailey's 2014 salary will end up being closer to the latter number, but it's anyone's guess at this point. It should be noted that he earned $5.35 million in 2013.
The 27-year-old was widely regarded as a disappointment through his first five seasons with the Reds: he posted a middling 4.89 ERA in 436 innings between 2007 and 2011, never once breaking even 140 innings in a season. But the former first rounder has really come into his own and lived up to his top-prospect promise the last two years, putting up a much-improved 3.58 ERA and eclipsing the 200-inning mark in both seasons. Oh yeah, and he's also thrown two no-hitters in that span.
Nevertheless, it might seem to some that $100 million is an overpay. Adam Wainwright got just five years and $97.5 million from the Cardinals last spring after all, and Bailey's success is both more recent and limited. But that just may be where the market is at this point with the influx of TV money and record-shattering revenues. If he does indeed get $100 million over six years, that'd put his average annual value at $16.67 million, which is right around what the Angels are paying C.J. Wilson and Jered Weaver. Bailey may never hit that "ace" ceiling many had him pegged for when he was drafted, but if he can continue to emulate this most recent version of himself the Reds are probably going to be happy about keeping him around into his 30s, even with the relatively high price tag.
If/when Bailey does agree to his extension, he'll become the second big-name starting pitcher set for 2015 free agency pulled off the market in the last month, joining Clayton Kershaw. Bailey's early removal from the list of available arms would leave Max Scherzer, Jon Lester, and James Shields as the top threes starters available next winter, though it's not a sure thing that they'll survive to free agency either -- both Scherzer and Lester have popped up in extension rumors recently.