Last week, we detailed an argument why the Yankees should wait until next season to tap the free agent starting pitching class. Today, we’ll detail each of the potential free agent options and whether they’ll be a fit. Before we dig into the potential free agents, the Yankees currently have approximately $127 million committed to the 2015 roster. After arbitration hearings, this amount will likely rise to $140 million. To put this in perspective, four players (A-Rod, Mark Teixeira, CC Sabathia, and Jacoby Ellsbury) account for nearly $90 million. Derek Jeter, Brett Gardner, David Robertson, Alfonso Soriano, and Hiroki Kuroda will be free agents.

Needless to say, the Yankees will have plenty of holes to fill in the rotation. Here are some intriguing 2015 free agents that can be added to the rotation..

Option #1: Clayton Kershaw, LHP, LA Dodgers, 25-years-old

Background: The reigning Cy Young Award winner is ‘intrigued‘ by free agency which is music to every baseball fan’s ears. Still, the Los Angeles Dodgers have been baseball’s highest spenders over the last few seasons and just inked a lucrative television deal. The Dodgers allegedly floated a $300 million dollar contract offer to Kershaw, which is insane and idiotic even for someone of Kershaw’s pedigree.

Still, Kershaw is baseball’s best pitcher when elite pitchers are rare commodities. He has an ERA below 3.00 over the last five seasons, which includes three ERA titles. Kershaw also has two Cy Young award wins and two strikeout titles. Last season was arguably his best season to date. Kershaw posted a 1.83 ERA, 0.91 WHIP, and 232 strikeouts in 236 innings. 

Fit For The Yankees?: I doubt Kershaw makes it to free agency. The Dodgers have the deepest pockets in baseball and there’s little doubt they’ll let him slip away. The Yankees would obviously be interested in signing Kershaw, but I question future roster flexibility by making such a move. If the Yankees gave Kershaw $30 million per season, they’d have $120 million committed to five players before accounting for Brian McCann, Carlos Beltran, arbitration signings, and a middle infield. That’s a lot of dough even for the Yankees. Perhaps a backloaded contract would work because a player of Kershaw’s caliber rarely makes it to free agency. Plus, we have to wonder if we’ve seen Kershaw’s best seasons. His age makes him very attractive, but have we seen his best seasons and can he continue his dominance in the AL East?

Whether or not that $300 million contract rumor has any merit is a moot point. Contracts over seven years for any pitcher is a huge risk. We’ll check back on this situation if Kershaw does indeed make it to free agency.

Option #2: Max Scherzer, RHP, Detroit Tigers, 29-years-old

Background: On the surface, Scherzer appears to be an obvious target, but a closer look raises some obvious question marks. There’s no denying that Scherzer’s 2013 Cy Young campaign was downright dominant. Schzerzer went 21-3 with a 2.90 ERA and 240 strikeouts in 214 innings. Scherzer had more strikeouts than teammate, Justin Verlander and averaged 6 2/3 innings per start, third best in the AL. 

Despite an outstanding 2013 campaign, many wonder if Scherzer’s 2013 campaign was an aberration rather than a sign of things to come. Scherzer posted ERAs of 4.24 and 3.74 in 2011 and 2012 before putting it all together in 2013. Scherzer also benefitted from receiving the most run support in the AL and his flyball to home run ratio (7.3%) was way down from his career norm (11.0%). Given his high strikeout rate, Scherzer did not throw a complete game last season, which is very odd for a Cy Young Award winner. Couple his reputation for having inconsistent mechanics and I’m left believing we’ve seen his best season.

Fit For The Yankees?: The first question that comes to mind is–should Scherzer command more dollars than Justin Verlander?

Verlander essentially signed a seven-year, $180 million extension last season, making him the highest paid pitcher. Starting in 2015, Verlander will make $28 million per season (!!) Scherzer is represented by Scott Boras, so he won’t be shy by asking for Veralander money. I’m not comfortable paying a premium for Scherzer when we’ve probably seen his best season. Scherzer’s high strikeout rate is attractive, but that also leads to shorter starts and more stress on the bullpen. Couple the fact that Detroit is hesitant to give him an extension is very telling. Detroit just traded away Price Fielder’s $150 million contract in order to gain more payroll flexibility. Sinking that money into Scherzer does not appear to be in their plans this off-season. It doesn’t mean it won’t happen, but personally, I’d like to see the Yankees stay away from Scherzer. His track record isn’t consistent enough to warrant Verlander money. His fly ball rate also scares me off.  

Option #3: Justin Masterson, RHP, Cleveland Indians, 29-years-old

Background: Some will remember Masterson as a member of the 2008-2009 Boston Red Sox. Masterson struggled with during his brief stint with the Red Sox and was included in Boston’s package for Cleveland catcher, Victor Martinez. Masterson has two good seasons, 2011 and 2013, on his resume while his other four seasons leave a lot to be desired. Last season, Masterson went 14-10 with a 3.45 ERA and 195 strikeouts in 193 innings. Masterson made his first All-Star team and was Cleveland’s ace. Cleveland is gauging his trade interest, but nothing appears imminent. Masterson is set to earn $10-$12 million dollars in his last year of arbitration. Cleveland GM Chris Antonetti wants to extend his ace starter to prove to his fans that last year’s 92-win season was not a mirage. 

Fit For The Yankees?: There have been Masterson-for-Brett Gardner trade rumors floating out there. I doubt there’s any merit to it, but that’s a no-brainer for the Yankees. In terms of valuation, I think we need to see how he performs in 2014. Masterson has not strung together two straight All-Star worthy seasons. If he puts up a similar slash as he did during 2013, he’ll warrant $15-$17 million per season. He’s a cut or two below Kershaw and Scherzer, but he won’t be cheap. I want to see his 2014 before putting a recommendation on him. 

Option #4: Jon Lester, LHP, Boston Red Sox, 30-years-old

Background: This situation is very, very complicated. Lester was drafted by the Red Sox and has been a member of the organization since 2002. Lester has won three World Series titles with the Red Sox and has stepped up as the ace of the staff. The Red Sox are negotiating with Lester, but nothing is imminent. Lester has been very solid over last six seasons, winning at least 15 games and throwing 200 innings five times. Despite his consistent performances, Lester had a rough 2012 campaign (9-14, 4.82 ERA) before turning things around last season (15-8, 3.75 ERA). Alike most strikeout pitchers, Lester’s strikeout rate has steadily declined, posting a 9.7 K/9 in 2010 and just a 7.5 K/9 last season. Some wonder Lester’s best days are behind him. Others view him as a pitcher that worked through his 2012 and found himself last season.

In terms of a new contract, Zach Greinke signed a six-year, $148 million deal in his Age 29 season. Despite being two years older, Lester will likely be in this neighborhood. 

Fit For The Yankees?: I think the Red Sox will lock him up before he reaches free agency. Lester has been with the Red Sox for over a decade and embodies the team mantra. If he does reach free agency, I hope the Yankees aren’t interested. Lester isn’t an elite starter and will have over 1,500 career innings on his arm. His strikeout rate is declining and I don’t want to pay a premium for his years in Boston. Pass.

Option #5: James Shields, RHP, Kansas City Royals, 33-years-old

Background: I’m a big fan of ‘Big Game James’. Shields, who was a long time member of the Tampa Bay Rays, was traded last season to the Kansas City Royals. The Royals surrendered a boat load of prospects including #1 OF prospect, Wil Myers. Shields did not disappoint the Royals, posting a 13-9 record, 3.15 ERA, 228 innings, and a 7.7 K/9. Over the last seven seasons, Shields has been a workhorse, winning double digit games and exceeding 205 innings each season. Despite his string of solid seasons, Shields has only finished Top 3 in Cy Young voting one time. Still, Shields has thrown the most innings (1,683 innings entering 2014) and is the oldest (he will be 33-years-old in next December). 

Fit For the Yankees?: I like Shields if the Yankees can get him for four seasons and roughly $60-$70 million. He’s an older pitcher, but his track record and durability makes him a welcome addition for any staff. He’s proven he can handle the battles within the AL East. It will be interesting to see whether the Royals can lock him up now before he gets to free agency. They traded a lot of valuable, team-controlled youth for him. It wouldn’t make sense to trade all of it away for a two year rental.

Conclusion: Masahiro Tanaka has officially been posted, so the Yankees are expected to heavily be in the mix. If the Yankees don’t land him, they’ll likely look to next year’s free agent class. Of note, I’m not in favor of signing Max Scherzer or Jon Lester. I want to see one more season from Justin Masterson and Clayton Kershaw probably isn’t a realistic option. I’m big fan of James Shields and adding him to the rotation would be awesome.