Boston Red Sox buyer beware: Zack Greinke

Dave Dombrowski is on a mission to find a No. 1 starter to lead his rotation. The new Boston Red Sox president of baseball operations is determined to acquire a workhorse worthy of the “ace” label that this year’s crop of starters openly mocked with their suggestion that any of them could be that guy. We know how that turned out. Motivated to prevent history from repeating itself, Dombrowski will scour the market in search of a pitcher that actually is that guy.

The free agent market is teeming with front of the rotation options, but they aren’t all necessarily great fits for the Red Sox. Perhaps the most polarizing pitcher on that list is Zack Greinke.

The right-hander is expected to opt out of the final three years of his contract with the Los Angeles Dodgers, seeking one last enormous payday following a season in which he posted a major league best 1.77 ERA and struck out 200 batters for the fourth time in the past five years. His 9.3 WAR made him significantly more valuable than any other pitcher this season and trails only Bryce Harper among players at any position in the NL. Harper should run away with the MVP award, but Greinke will get his share of votes.

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The 32-year old will also likely be seeking a shorter contract than the other pitchers at the top of the market, which may be more appealing to a Red Sox team that would be hesitant to saddle themselves with a long-term commitment.

Greinke would appear to be an excellent target for the Red Sox on paper, but baseball isn’t played on paper and there are some significant red flags that accompany the veteran pitcher that don’t show up in the box scores.

There’s no doubting the talent of the former Cy Young award winner, who seems likely to add another trophy to his mantle. Unfortunately, talent isn’t always enough. There are legitimate concerns about whether or not Greinke, who nearly quit baseball in 2006 after being diagnosed with social anxiety disorder and clinical depression, could handle the pressure of playing in a city like Boston.

If Greinke’s comfort zone is when he’s out on the mound, the antithesis of that would be when he’s surrounded by reporters with television cameras staring him down. The prescription medication that he takes to control his condition can only do so much to temper the uneasy feeling he gets in that setting.

These concerns are more than merely speculation from the outside. A source close to the pitcher told the Boston Herald’s Scott Lauber that Greinke “definitely wouldn’t want any more stress or additional media attention.

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Los Angeles is one of the country’s largest media markets, but the pressure of playing for the Dodgers still pales in comparison to playing in Boston. Critics in this city can be harsh when things aren’t going well and there would be nowhere to hide when Greinke feels compelled to shy away. In Boston he would be tasked with carrying an under-performing rotation, while in Los Angeles that burden is shared with Clayton Kershaw, who has been the best pitcher on the planet over the last half decade.

Assuming that Greinke would crumble under the overwhelming pressure isn’t fair to him, but the Red Sox still have to factor it in as a risk. Investing heavily in a player that may very well decide quickly that he doesn’t want to be here after all would be bad for business.

We know from his time with the Kansas City Royals that Greinke can thrive in the American League. We know that he can perform in October, as he owns a career 3.55 ERA in the postseason. What we don’t know is how Greinke’s mentality would hold up in a pressure-packed city like Boston.

It’s certainly possible that at this stage of his career he’s ready for that challenge and prepared to handle the increased media scrutiny, but we don’t actually know that he can do it. In this case, what the Red Sox don’t know could come back to haunt them.