Lester's next contract could have an annual average value of more than $20 million.
With starting pitcher Homer Bailey officially off the 2014-2015 free-agent board after agreeing to a long-term contract extension with the Cincinnati Reds, the pressure could be rising for the Boston Red Sox and Detroit Tigers to get deals done with their own free agent-to-be front-line starters.
Red Sox ace Jon Lester and Tigers co-ace Max Scherzer, the reigning AL Cy Young Award winner, were already on track to be the cream of the crop when it comes to free-agent starting pitchers next offseason. Bailey had a decent chance to join them if he could duplicate his numbers from the previous two seasons.
But after the Reds guaranteed the 27-year-old Bailey (pictured) $105 million over the next six seasons—a total he wouldn't likely have reached had he struggled on the mound or battled injuries during the upcoming season—his 2014 performance is now highly unlikely to have a negative effect on the market value of Lester or Scherzer.
If anything, the agents for each pitcher would have an even stronger argument should their client have a better season than Bailey, who hasn't been quite as dominant as Scherzer over the past couple of seasons...
...and can't come close to matching Lester's much longer track record of success.
So while Bailey is a year younger than Scherzer and two years younger than Lester, that may have been his agent's lone argument as to why his client's contract should be comparable to either.
Barring a drastic decline from Lester—who Scott Lauber of the Boston Herald figures could ask for at least $20 million per season on his next contract—or Scherzer in 2014, their respective agents should be able to point to Bailey's deal and negotiate an even better one.
This is bad news for their respective teams, who aren't likely to view the compensation draft pick gained in June 2015, should either pitcher sign elsewhere, as much of a consolation prize considering how big of a hole either departure would create.
Had Bailey and the Reds been unable to reach an agreement, things could've been more favorable for the Red Sox and Tigers in their quests to sign Lester and Scherzer.
A subpar performance from Bailey in 2014 and there would be no $105 million deal set as the starting point in negotiations. A third consecutive strong season from Bailey would mean Lester and Scherzer (pictured) would have another established front-line starting pitcher to compete with on the free-agent market and their bargaining power could decrease as a result.
With this in mind, they could've been more open to signing a contract extension with their current team prior to the start of free agency.
As things stand, however, the sense of urgency from the Lester/Scherzer camps to get a long-term contract done prior to next offseason has likely decreased. Next year's free-agent market, as Joel Sherman of the New York Post pointed out, keeps getting worse with Clayton Kershaw also removed from the list after he agreed to a contract extension with the Los Angeles Dodgers last month.
The Red Sox and Tigers must now be the aggressors if talks are going to heat up and they must be willing to go well beyond what Bailey just received from the Reds.
By allowing Lester and Scherzer to become free agents next November, the Red Sox and Tigers will risk the price rising even higher following a typical season from either pitcher and the bidding war likely to ensue with just two or three front-line starting pitchers available—Cleveland Indians right-hander Justin Masterson, another long-term extension candidate, would likely be third on the list.