How far should the Yankees go to keep Masahiro Tanaka?

Masahiro Tanaka signed a seven-year $155 million contract with the Yankees prior to the 2014 season. The contract included an opt-out clause that the pitcher could exercise following the 2017 season.

The Yankees outbid at least six other MLB teams and paid an additional $20 million posting fee to Tanaka's Nippon Professional Baseball team in order to sign the right-hander. At the time, it was the fifth largest contract ever awarded to a pitcher.

Tanaka had gone 24-0 with a 1.27 ERA in 2013, leading the Rakuten Golden Eagles to victory in the Japan Series. He concluded his seven-year NPB career with a 99-35 record, 2.30 ERA, 1,315 innings, and 1,238 strikeouts in 175 games (172 starts).

After his agent announced that the pitcher would not tour the country to visit interested teams, but would instead travel to Los Angeles and make himself available for two days only to greet all suitors, the club flew an eight-person delegation out to woo him.

The group was led by team president Randy Levine, GM Brian Cashman, manager Joe Girardi, and pitching coach Larry Rothschild. They carried with them a recruiting video which the front office had begun working on the previous summer. It featured a narrated tour of Yankee Stadium and projections of how they thought the righty's stuff would work in the Bombers’ hitter-friendly ballpark. The video was capped off with a personal recruiting pitch from Tanaka's countryman, Yankees legend Hideki Matsui.

The Yankees dramatic efforts to sign Tanaka evoked memories from nearly forty years prior when George Steinbrenner was trying to convince Reggie Jackson to don the pinstripes prior to the 1977 season. The Boss took the MVP and three-time World Series Champion around New York City, wined and dined him at the 21 Club, and kept pursuing the slugger until a deal was finally struck in a hotel bar in Chicago. How was the deal closed? Steinbrenner agreed to give Jackson a Rolls Royce as a signing bonus, and the two signed a cocktail napkin.

The Yankees pulled out all stops to get their slugger in 1977. They did the same to get their ace in 2014. They got them both.

Now that Tanaka has entered his opt-out year, the question is, how far are the Yankees willing to go to keep him?

248 different pitchers made starts for AL teams from 2014-2016. Over that three-year period, Tanaka is #5 in ERA, #2 in WHIP, #4 in ERA+, #13 in FIP, and #8 in WAR.

Tanaka had a better ERA than 97% of the AL pitchers who started from 2014-2016, better WHIP than 99%, better ERA+ than 98%, better FIP than 94%, and better WAR than 96%.

Ace?

Yes.

By any measure, Tanaka is an ace.

The following table shows the stats of the top performing AL starting pitchers from 2014-2016. If you don’t know what some of the advanced stats are, give this a read.

Tanaka insisted on the opt-out clause. He wouldn't have demanded it if he wasn't planning to use it.

The only scenarios I could imagine where Tanaka fails to exercise his opt-out is if he either misses most of the season due to injury or performs at a level far below his established benchmark.

I don't envision either happening.

Tanaka declined to participate in the World Baseball Classic so he could focus his energy entirely on getting ready for the 2017 season with the Yankees.

Make no mistake about it, Tanaka is playing for a contract this year.

What should the Yankees do? Negotiate a contract extension with Tanaka.

Now.

They should have done this in the off-season.

The Yankees have a dismal track record when it comes to negotiating with and re-signing their own free agents after they've hit the open market. Witness:

• Derek Jeter's contract talks following the 2010 season were contentious, to say the least. Jeter publicly stated that he was "angry" about how things went, especially when he was told by the organization to go "shop around" if he didn't like the deal he was offered.
• After winning 21 games in 2003 and helping the Yankees reach the World Series for the sixth time in eight years, Andy Pettitte was allowed to leave via free agency. Cashman didn't bother presenting Pettitte with an offer, not even during the Yankees exclusive negotiating window. Pettitte went on to help the Astros reach their first World Series in franchise history, while the Yankees began a five-year drought without a pennant. Cashman later said he regretted his decision to allow Andy Pettitte to simply leave.
• Bernie Williams was set to depart the Yankees to join the Red Sox after his contract talks with Cashman became acrimonious following the 1998 season. The Yankees were courting Albert Belle to be Bernie's replacement. Bernie only agreed to stay in the Bronx after a personal intervention by the Boss. Who among you think the 1999 and 2000 World Series Championships would have occurred with Albert Belle in place of Bernie Williams?

Sadly, there are many other examples.

This season, Dellin Betances was late to begin spring training because his arbitration negotiations had stalled. Following the arbitration decision, the Yankees publicly humiliated Betances. Yankees president Randy Levine ridiculed him and his negotiating position. This wasn't even a long-term free agent contract. It was a one-year arbitration agreement where the two sides were only about $2 million apart. Betances wanted $5 million, while the Yankees only offered $3 million. Levine said, "that $5 million number? It might as well have been $50 million."

Well, it wasn't $50 million.

But Tanaka is going to get a lot more than $50 million. There is $67 million left on his contract now that he would be opting out of.

Even if you could take all of the personalities out of the equation, allowing your players to hit the open market introduces all kinds of variables that you have no control over.

What if the Red Sox go all out to sign Tanaka just as the Yankees had done? Right now, they can't. They aren't allowed to. But they will be once Tanaka opts out.

The Yankees have to act now.

Tanaka is only 28, and he doesn't turn 29 until November 1. A new seven-year contract would expire at the end of his age 35 season. It would surprise me if he signed for less than seven years. It wouldn't shock me if he asked for eight or nine years.

Tanaka is making $22 million per year right now, but is set to earn $23 million in the final year of his current contract if he doesn't opt-out.

A new contract worth $25 million per year for seven years may be a low estimate.

$30 million per year is not out of the question for Tanaka.

Here are the highest value pitcher contracts currently on the books:

1. David Price, $217,000,000 (2016-22)
2. Clayton Kershaw, $215,000,000 (2014-20)
3. Max Scherzer, $210,000,000 (2015-21)
4. Zack Greinke, $206,500,000 (2016-21)
5. Justin Verlander, $180,000,000 (2013-19)
6. Felix Hernandez, $175,000,000 (2013-19)
7. Stephen Strasburg, $175,000,000 (2017-23)

Forbes just announced that the Yankees are still the most valuable MLB franchise. This is the 20th consecutive year that the organization has held that honor. The Yankees are worth $3.7 billion, with $526 million in annual revenue.

The Yankees own their own television network.

As was reported here, the club appears to be doing its best to sell every square inch of Yankee Stadium for branding purposes. If the club wants to sell naming rights to the restaurant in centerfield to help pay for top talent, they have my blessing. I think most fans would agree. We haven't been told to refer to The House That Ruth Built as "Yankee Stadium, Sponsored by Hyundai" yet. And we aren't seeing ads cover the pinstripes on the home uniforms yet. We'll cross that bridge when we get to it.

The Yankees have the third highest payroll in MLB for 2017. Following the season, Sabathia's $25 million contract comes off the books, as does A-Rod's $21 million salary.

The Yankees have plenty of money to sign Tanaka. In fact, the club has enough money to sign both Tanaka and Mike Trout.

How far should the team be willing to go? Far. As far as it takes. All the way.

The Yankee front office has repeatedly promised us that they would do what it takes to put a championship caliber team on the field every year.

You can't win a championship without an ace. Tanaka is our ace. The Yankees need to go all out to keep Tanaka in pinstripes.

What do you think? How far should the Yankees go to keep Tanaka?