Joel Sherman

Joel Sherman

MLB

Why Yankees’ pursuit of Tanaka may not pay off like it did with CC

A similarity exists between the Yankees’ current pursuit of Masahiro Tanaka and their successful recruitment of CC Sabathia.

The Yankees failed to make the playoffs in 2008, in part because they had practiced some financial restraint, notably not making a big trade for and signing of Johan Santana after the 2007 campaign.

They had a bunch of big contracts come off the books (Bobby Abreu, Jason Giambi, Carl Pavano). So, they had plenty to spend, but clearly made landing Sabathia priority No. 1, feeling they could not win without putting a stalwart atop the rotation. They had been plotting a season ahead to land him, going as far as to have at least one scout at pretty much every one of his walk-year starts.

Sabathia further enhanced his reputation by not only having his best season in his 2008 walk year, but by ignoring the risk to his health and coming payday by accepting a greater workload to help his team down the stretch and in the playoffs.

However, the Sabathia chase was complicated by consistent rumors he preferred to return to his home state of California, which ultimately pushed the Yankees to raise their offer from six years to seven to finalize a contract with Sabathia.

Now, here are the Yankees having missed the playoffs for just the second time since 1994, in part because they have been restrained financially with an eye on trying to get under the $189 million luxury-tax threshold in 2014.

They had a bunch of big contracts come off the books (Andy Pettitte, Mariano Rivera, Robinson Cano, Curtis Granderson, Kevin Youkilis, most of A-Rod’s dollars). So, they have had plenty to spend, but clearly have made landing Tanaka priority No. 1, feeling they cannot win without putting a stalwart atop the rotation. They had been plotting a season ahead to land Tanaka, going as far as to have at least one scout at pretty much every one of his walk-year starts.

Tanaka further enhanced his reputation by not only having his best season in his 2013 walk year, but by ignoring the risk to his health and coming payday by accepting a greater workload to help his team down the stretch and in the playoffs.

However, the Tanaka chase has been complicated by consistent rumors his wife prefers the West Coast and that could sway the decision. Will this ultimately move the Yankees to a new level in the negotiation – from five to six years or six years to seven or from $18 million annually to $20 million or more?

Nevertheless, one huge difference resonates from five years ago to now that could be the difference between the Yankees landing Sabathia and failing to land Tanaka. Even five years ago, what the Yanks wanted they pretty much got, especially if it became a game of finances. Competitors did not believe they could run dollar for dollar with the Yanks and basically didn’t even try.

But in 2014, at least the Dodgers do. In the 2008-09 offseason, the Dodgers were owned by Frank McCourt. Now, you wonder whether the Yankees have the stomach for a financial back-and-forth with this version of the Dodgers. And is it possible there are organizations beyond the Dodgers ready to do the monetary staredown with the Yanks?

To answer that, let me start here: I am a strong believer in the law of unintended consequences. In the last labor agreement, MLB was determined to get restrictive/punitive spending caps put on the draft and young international amateur free agents. But in a case of be careful what you wish for, the unintended consequence has been to leave big-market teams with more of their money and a desperation to figure out where to spend it to secure high-end talent. You can create laws to keep the rich from purchasing yachts and luxury cars. Fine, they will just buy more mansions. They are going to find ways to spend their money.

Which is why the free-agent market has soared ever higher. And it is why the international free agents not tied to financial limitations are scoring so big. The Dodgers really have exploited this market, signing Yasiel Puig, Hyun-jin Ryu and Alexander Guerrero. For a combined $106 million, L.A. landed three potential impact players in their 20s. And there are certainly executives who believe they will bid what is necessary – even after giving Clayton Kershaw $215 million and Zack Greinke $147 million – to get Tanaka, who is just 25.

As one executive from a team that has inquired on Tanaka said, “The Dodgers could justify it. They have expensive starters in [Josh] Beckett, [Clay] Billingsley and [Dan] Haren coming off the payroll after this season and [team president] Stan Kasten spent all those years in Atlanta with [Tom] Glavine, [Greg] Maddux and [John] Smoltz and knows how powerful it is to have a core of starters to build around. He could have Kershaw, Greinke, Tanaka and Ryu all in their prime. That would be pretty hard to beat.”

But the same elements – Tanaka’s age and multiple teams basking in local cable riches – could deepen the competition beyond L.A. and NYC. The Cubs, in particular, are believed to be serious bidders by many outside executives. Cubs president Theo Epstein has bemoaned the inability in free agency to buy stars in their prime. Tanaka is different, an ideal age and skill set for a Cubs organization that believes it has the best set of position prospects in the game ready to reach the majors in the next 24 months.

The White Sox, Angels, Diamondbacks and Mariners also are viewed as legitimate suitors, and the Rangers, Blue Jays and perhaps others are believed to be staying in touch with Tanaka’s rep, Casey Close, who by the way also reps Kershaw and Greinke.

For those pitchers, Close got the contractual right for Greinke to opt out of his six-year contract after three seasons and Kershaw to opt out of his seven-year deal after three seasons. You can expect, therefore, he will demand such a clause for Tanaka. And, hey, by the way, Sabathia got an opt-out from the Yanks after three years of his initial seven-year deal.

By 5 p.m. Friday — the deadline for signing Tanaka — we will know if the similarities to Sabathia included a Yankee celebration, too.