Kim Klement-USA TODAY Sports

Sylver: Facing Max Scherzer, Red Sox Get to See What Could Have Been

By Sean Sylver, 98.5 The Sports Hub

After giving up five home runs Sunday night in the Bronx, David Price seems far more likely to wind up on the DL with a case of John Wasdin-like whiplash than win a Cy Young.

And that’s if Fortnite doesn’t get to him first.

It’s July. Almost four years since the Red Sox traded Jon Lester to the Oakland A’s. Two gut-job renovations of their starting rotation followed, and we still don’t know if it’s good enough.

Oh, it’s good on paper. But then games like Sunday's 11-0 loss to the Yankees happen, and we’re reminded, despite all of the regular season success over the past two and a half years, just how far they have to go.

After a three-game set where the Sox lost ground to the Yankees in the division (they’re tied, but the Bombers have four games in hand), the hometown nine don’t have to stare across the diamond at pinstripes again until the beginning of August. They can beat up on the Royals, Rangers, Blue Jays, Tigers, Orioles and Twins in the coming weeks.

But there’s nowhere to hide Monday night, when they face the prohibitive favorite to go back-to-back-to-back for the National League Cy Young Award, Max Scherzer.

Which is just deliciously ironic, because the Sox could’ve had Scherzer four years ago.

Instead, John Henry and company spent much of 2014 hyping the cutting-edge organizational philosophy of avoiding long-term deals for pitchers over the age of 30. But they still reportedly made a lowball six-year offer to Lester before the lefty collected $155 million from the Cubs.

They never would have gone seven years and $210 million for Scherzer.

Jun 26, 2018; St. Petersburg, FL: Washington Nationals starting pitcher Max Scherzer throws a pitch at Tropicana Field. (Photo Credit: Kim Klement-USA TODAY Sports)
Jun 26, 2018; St. Petersburg, FL: Washington Nationals starting pitcher Max Scherzer throws a pitch at Tropicana Field. (Photo Credit: Kim Klement-USA TODAY Sports)

Instead, then-GM Ben Cherington pulled the old Dan Duquette scrap heap move and signed up Justin Masterson, traded for Wade freaking Miley, and gave Joe Kelly a try at the back end of the rotation.

Add that trio to freshly acquired Rick Porcello and good ol’ Iron Clay Buchholz, and you had a group that went 41-41 with a 4.55 ERA for a last place team.

It was Masterson’s final season in the major leagues. Kelly has started just six games since and now toils in the bullpen. Buchholz, true to form, made only 18 starts that season, was banished to the ‘pen in 2016 and missed nearly all of last season with an injury. Miley was traded for Carson Smith and somehow the Sox didn’t lose the deal, as the lefty has gone 18-28 with a 5.41 ERA since.

I recently went back and read a handful of columns on Scherzer’s free agency and I saw this line: “If Porcello, Masterson and Clay Buchholz are healthy, there may not be a need” for Scherzer.

That’s like saying the Tea Totallers stood a chance against the Gas-House Gorillas in that classic Bugs Bunny cartoon.

Less than a year later, Dave Dombrowski grabbed Henry’s wallet and lavished $217 million on Price. He moved Yoan Moncada, at the time the top prospect in the game, and three of the team’s other top minor leaguers to get Chris Sale and Drew Pomeranz. This after Cherington had already jettisoned Andrew Miller and Yoenis Cespedes in the Eduardo Rodriguez and Porcello deals, respectively.

That’s what happens when you panic. That’s what happens when you’ve been unable to draft and develop a quality major league starting pitcher in well over a decade. That’s what happens when your organizational philosophy twists in the wind and you miss out on Lester and Scherzer.

Of course, hindsight is 20/20. We didn’t know Scherzer would cement a Hall of Fame candidacy in the years following the deal. But he’d won a Cy Young in 2013 and led all starters in wins and strikeouts over the previous three seasons. He’d made 30-plus starts each of the previous six. He was the guy in 2014, and the Red Sox passed on him, Lester, even consolation prize James Shields in favor of an approach they punted on less than a year later.

Four years later, they have the highest payroll in the majors, their minor league system is bare, and they have zero starting pitcher wins in seven postseason turns the last two Octobers. Losers of four of their last six to the Yankees and tied atop the AL East, they may need a lights-out performance from Sale in the AL Wild Card Game just for the privilege of going on the road against the defending champion Astros in the ALDS.

But first, they get to deal with Max Scherzer, sporting familiar hues of red and blue, while David Price gets the green.

Sean Sylver can be heard on 98.5 The Sports Hub. You can follow him on Twitter @TheSylverFox.