Eyes on Cherington from Pittsburgh?

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Ben Cherington (right), with Red Sox owner John Henry and the proof that Cherington knows how to raise shipwrecks: the Red Sox’s 2013 World Series triumph, for openers.

Few baseball fans are as frustrated as Pirate fans. Few deserve even a small ray of hope more. Pirate fans got one such ray when longtime Clint Hurdle was purged at last after a season in which he lost a clubhouse that seemed hell bent on destroying itself when it wasn’t pursuing silly field feuds.

They got another such ray of hope when the Pirates decided Hurdle’s execution was merely the wick lighting the powder keg of a near-complete front office house cleaning, which only began when pitching coach Ray Searage was pinked after a season during which the Pirate staff became too-much-reputed headhunters.

They got a third such ray when the house cleaning continued when president Frank Conolly and general manager Neal Huntington were purged, after a couple of years in which reputedly blockbuster deals blew up right in the Pirates’ faces even despite a warning sign or two.

And now comes a fourth such ray, in the word that candidates to be the Pirates’ next president of baseball operations include former Red Sox GM Ben Cherington.

Currently second in command to Blue Jays president Tony Lacava, Cherington is one man in baseball if there’s any such man who knows what it means to actually be able to raise and reconstruct the Titanic. He did it in New England, maybe the second most arduous baseball market for turning shipwrecks into cruises to the Promised Land.

The Red Sox hired Cherington in the first place after the 2011 season ended with the iceberg hitting the ship. His job only began when he was overruled at the top and the Red Sox hired Bobby Valentine to skipper the ship after Terry Francona—and Cherington’s predecessor Theo Epstein—abandoned it before they could be made to walk the plank.

Hiring Valentine proved the equivalent of removing Captain Smith from the bridge when the iceberg hit and installing Captain Queeg in his stead. Valentine took a clubhouse already full of noxious gases from the 2011 sinking and threw one after another lighted match into it. He was probably lucky that all he got was canned just days after the regular season ended.

Somewhere during the worst of that nightmare Cherington figured out that just because someone else dumped Smith for Queeg was no reason for him to go J. Bruce Ismay. He began repairing the ship even underwater, masterminding the August 2012 deal with the Dodgers that sent Josh Beckett, Adrian Gonzalez, and Carl Crawford out of Boston.

Major payroll surgery, that, the kind bringing the rookie GM what he’d need to augment his still-very-much-serviceable veterans with what I observed after the Valentine firing: “pieces that weren’t exactly top of the line but weren’t exactly losers, either.”

Cherington also got to dump Valentine, which could only have been his due after the rookie GM found himself as much company psychiatrist as boss when one after another player went to him seeking to keep their marbles—singular—during the depths of the Valentine nightmare. And he was the epitome of grace in throwing the switch:

Our 2012 season was disappointing for many reasons. No single issue is the reason, and no single individual is to blame. We’ve been making personnel changes since August, and we will continue to do so as we build a contending club. With an historic number of injuries, Bobby was dealt a difficult hand. He did the best he could under seriously adverse circumstances, and I am thankful to him.

You’d be hard pressed to find any other baseball general manager who could have been that diplomatic about a man who was lucky to escape with his life. It’s true the 2012 Red Sox were bedeviled by 27 trips to the disabled list, but it’s also true that four other 2012 teams (the Athletics, the Braves, the Orioles, the Yankees) were battered by injuries and still either won divisions (the A’s, the Yankees) or went to their leagues’ wild card games. (The Braves, the Orioles.)

The season recently ended gave further object lessons in how to navigate troubled waters when crews hit sick call almost en masse. Managed intelligently, they were the Yankees, the Astros, and (doesn’t it just roll off the tongue, Washington?) the world champion Nationals. Managed like several flew over the cuckoo’s nest, they were the 2012 Red Sox.

Then Cherington swung the deal that brought former Red Sox pitching coach John Farrell back from Toronto to manage the team for 2013. He imported such inexpensive pieces as Stephen Drew, Jonny Gomes, Joel Hanrahan, Brock Holt, Mike Napoli, David Ross, Koji Uehara, and Shane Victorino.

He also picked up where Epstein left off in rebuilding the Red Sox farm. He watched Hall of Famer in waiting David Ortiz rally a team, a town, and a region after the Boston Marathon bombing. (This is our [fornicating] city!!) He re-fortified when injuries hit, and watched Uehara—whom he’d thought would be a perfect sixth- or seventh-inning relief option—step up as a lights-out closer.

And, he watched his freshly repaired team of savvy vets, comeback kids, and young sprouts refuse to lose more than three straight on the season and march all the way to the Promised Land for the third time since the new century began. It also made Cherington only the third Red Sox executive ever to be named The Sporting News‘s Executive of the Year.

The rebuild, which Cherington picked up and ramped up without even thinking about tanking? (Tanking’s never an option for a team whose owner learned what not to do and how not to do it watching the win-or-be-gone George Steinbrenner style, anyway.) Mookie Betts, Xander Bogaerts, Rafael Devers, Andrew Benintendi, Jackie Bradley, Jr., all of whom loomed large in the 2018 World Series triumph, were Cherington recruits.

It was just a shame Cherington wasn’t around to savour it.

His only missteps were some free agency signings that blew up in the Red Sox’s faces: Pablo Sandoval, Hanley Ramirez, A.J. Pierzynski, Grady Sizemore. When Dave Dombrowski accepted his Detroit walking papers and the Red Sox walked Cherington out to walk Dombrowski in, Cherington still left the Red Sox a solid nucleus that didn’t exactly escape Dombrowski’s sights in 2015.

Dombrowski signed and dealt for several nuggets of his own. He watched the Red Sox go last-to-first in 2016 and repeat in the East in 2017, both of which ended in early postseason exits. Then, after hiring Astros bench coach Alex Cora to manage the crew following Farrell losing the clubhouse at last, Dombrowski watched Cherington’s seeds flower fully as the Red Sox won last year’s World Series.

But Dombrowski reverted to form and drained McCherington’s Navy while ignoring the under-constructed, over-taxed bullpen as one after another 2019 Red Sox starter was hit by either injury or inconsistency bugs. Thus did the Red Sox execute Dombrowski in early September, when their season was too long lost.

And since the Red Sox didn’t reach out and bring Cherington back (they hired former Rays vice president Chaim Bloom), though it wouldn’t necessarily be either untenable or unheard-of (reference the 1967 Cardinals, who brought Bing Devine back successfully after canning him in mid-1964) the Pirates might want to give a long, serious, thoughtful look at him.

The Pirates’ sunken ship makes the Red Sox upon Cherington’s advent resemble a sturdy aircraft carrier by comparison. And if ever a team needed a man who can prove he knows how to raise a wreck from the bottom of the sea, the Pirates do.

Anatomy of an execution

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Just shy of eleven months ago, Dave Dombrowski wore a Red Sox helmet and let former Red Sox superstar David Ortiz interview him right after the Red Sox nailed a World Series. After midnight last night, Dombrowski went to the Red Sox guillotine.

Watch and ponder a 10-5, home run heavy Red Sox loss to the Yankees on national television Sunday night. Awaken Monday morning to discover the Red Sox threw out the first president of the season just after midnight. Down the stretch. With the Red Sox down to little if any hope of really defending their 2018 World Series championship.

Every once in awhile not even a World Series appearance or conquest is enough to save someone’s baseball job. It wasn’t for Dave Dombrowski. The GM-made-president of baseball operations, who finished what his predecessor Ben Cherington started and steered the Red Sox back to the Promised Land for the fourth time since the 21st Century began, is finished.

And the questions include the price the Olde Towne Team will pay for last year’s conquest. Dombrowski spent big with dollars and with prospects to make last year’s triumph happen. Now the Red Sox farm system is parched, and a lot of the dollars that finished constructing last year’s conquerors could prove a prison as much as a parade.

Forgotten at times during last year’s triumph was that Cherington built the core of the team. Dombrowski took the bows with everyone else after the Red Sox finished stunning the Dodgers last fall but all he did was finish what Cherington started. And everyone who remembered Dombrowski’s years of trying but failing to get the Tigers to the Promised Land and mortgaging the farm several times couldn’t resist asking how long before Dombrowski’s accomplishment with the Red Sox would endure before he’d be nudged out of Boston, too.

It’s unfair to Dombrowski in a few ways, of course. But running a team whose in-house culture is win/win-now/keep-us-winning isn’t simple business. And men who mortgage the farm on its behalf often have lower survival rates than men who know how to remake/remodel without tanking or without letting the farm become a dust bowl.

Cherington got four years. Dombrowski didn’t survive a fourth. Both were hired seemingly out of nowhere. Except that for one of them, “nowhere” was right under the Red Sox’s noses. Cherington was part of the Red Sox baseball operations offices since 1999 and built himself a solid player development background when he was hired to succeed Theo Epstein in 2011.

Cherington’s first order of serious business, alas, was to take it like a manperson when the powers above made him look like a fool after the infamous 2011 Red Sox collapse. He’d promised numerous players that whomever would take the bridge, after Terry Francona quit before he could be fired, it wouldn’t be the rumoured Bobby Valentine. The powers above hired Valentine (specifically, it may have been Larry Lucchino’s call); Cherington’s choice was almost anyone but. (Actually, at the time, it was Dale Sveum.)

Poor Cherington. He found himself having to keep his back door open to help one after another Red Sox player keep his marble (singular) during the Valentine nightmare. Then, he executed the daring August 2012 trade that sent the Dodgers Josh Beckett, Adrian Gonzalez, and Carl Crawford and concurrently blew open a small tonnage of financial headroom while giving himself the space to hatch and execute a post-Valentine plan.

Cherington spent the 2012-13 offseason buying or dealing for a group of more than useful availables and spare parts—Mike Napoli, Jonny Gomes, Shane Victorino, David Ross, Stephen Drew, Brock Holt, and (especially) sleeper reliever Koji Uehara—and bringing home former Sox pitching coach John Farrell to take the bridge and dissipate the Valentine toxins.

That effort, plus the returns to health of such key men as John Lackey, often-injured (and oft-unfairly alienated) Jacoby Ellsbury, and especially future Hall of Famer David Ortiz, got the Red Sox 2013 World Series rings for Cherington’s efforts. It also got Cherington named as the third Red Sox executive ever named by The Sporting News as Executive of the Year.

Concurrently, he devised and executed a longer-range plan that rebuilt the Red Sox farm without even thinking about tanking, which is never an option for a team whose owner John Henry learned what not to do and how not to do it watching the similarly win-now-or-be-gone thinking of the late Yankee owner George Steinbrenner.

Mookie Betts, Xander Bogaerts, Rafael Devers, Andrew Benintendi, Eduardo Rodriguez, and apparently defense-first Jackie Bradley, Jr.—all of whom factored large enough in last year’s conquest—were Cherington’s handiwork, either by in-house development or trade such as the deal that brought Rodriguez to the Red Sox in late 2014.

Where the earnest Cherington mis-stepped was with some of his subsequent free agency signings, including Pablo Sandoval, Hanley Ramirez, A.J. Pierzynski, and Grady Sizemore. When the Red Sox executed him in favour of Dombrowski, Cherington still left them a solid nucleus that didn’t go unnoticed by the incoming Dombrowski.

It didn’t take Dombrowski long to sign such nuggets as David Price and Craig Kimbrel, and watch as the Red Sox went from last to first in the 2016 American League East, though they were shoved out of the postseason by the eventual pennant-winning Indians. Dombrowski traded for Chris Sale, signed Mitch Moreland, and basked in the 2017 AL East title despite another postseason exit short of the Promised Land.

Then he answered Farrell’s apparently losing his clubhouse at last by canning Farrell and hiring Astros bench coach Alex Cora—while the Astros were still advancing toward their 2017 World Series conquest. And Cora let his new players know immediately how they fell short enough: “You guys were easy to game plan against. Too many bad takes [at the plate].”

Dombrowski also landed J.D. Martinez at almost the eleventh hour of last year’s spring training, then watched Benintendi, Bogaerts, Devers, and Betts especially come into their own, Betts almost running away with last year’s American League Most Valuable Player award. Marry that to Price and Sale shaking away whatever problems they might have had otherwise, and the Red Sox turned the 2018 postseason into a thrill that climaxed when Sale struck out the side to end the World Series hoisting the trophy in Dodger Stadium.

Except that there were a few serious cracks in the structure Dombrowski finished atop Cherington’s foundation:

* Almost typical of a Dombrowski administration, the Red Sox didn’t just empty the farm, they took a torch to it. Assorted observers say the farm’s being rebuilt little by little, though.

* Dombrowski ignored the Red Sox bullpen almost entirely both last offseason and approaching this year’s new single mid-season trade deadline. Some say it’s outperformed its expectations this year; others say it became taxed too heavily as one after another Red Sox starter faltered for assorted reasons—especially after they were barely worked in spring training and looked like spring-training pitchers in April.

* Betts has one more season coming under Red Sox control and, unless something happens between now and October 2020 to constitute an offer he can’t refuse, it looks as though he’s going to play the market for the first time then. The Red Sox may have ideas about trading him this winter, but if they go there they won’t get that solid a return for a one-year rental.

* Martinez is posting another magnificent season at the plate, but he has an opt-out clause he can exercise at season’s end and enough observing the Red Sox fear he’s liable to try playing hardball. For more money? For a longer commitment? Nobody knows just yet, but the Red Sox have to brace themselves for either.

* With Nathan Eovaldi, a postseason hero out of the bullpen last fall, missing too much time to injury this year and then having to shake away rust in a return to the rotation, it leaves the Red Sox with him, Sale, and Price as underperformers among the walking wounded and on long-term contracts while they’re at it.

In fact, Sale—who’s now done for the season thanks to pitching elbow inflammation—won’t even see his contract extension begin until 2020, but some argue Dombrowski signing him to that extension might have seeded Dombrowski’s end. Sale swore when signing that his shoulder troubles were behind him. Everyone wanted to believe it. Then his inconsistent 2019—brilliance here, battery there—ended prematurely when his elbow immolated. Uh-oh.

But there’ve been enough bright lights in Red Sox fatigues to make you confident they can win next year. Betts, Bogaerts, and Devers still make for a powerful threesome at the plate, though the Red Sox may want to think hard and start thinking now about keeping Betts in the family. Even if Henry wants to trim payroll up the street, he can’t afford to let his franchise player leave the family.

Benintendi shook away his first half inconsistencies and is having a magnificent second half, and he should be ready for a full season’s high-level production in 2020. Rodriguez is having a breakout season. Matt Barnes and Brandon Workman have become late-inning godsends out of the bullpen.

And rookie reliever Darwinzon Hernandez’s bullpen performance in his first 25 gigs (2.83 ERA; 2.17 fielding-independent pitching [FIP]; 17.0 K/9) in addition to his widely enough reported early maturity may mean the Red Sox’s late-game/ending-game wipeout option of the future is preparing for that future already, even if Cora isn’t anxious to smother the kid with hype.

But Jhoulys Chacin, whom the Red Sox signed after the Brewers parted ways with him late last month, has no such fear. In a perfect position to know, Chacin isn’t afraid to compare Hernandez to Josh Hader, the Brewers’ bullpen assassin. “He reminds me of Hader,” Chacin tells MassLive.com’s Christopher Smith. “He throws that raised fastball that some guys just can’t catch up.

“I’ve talked to him a lot since I’ve been here,” Chacin continued. “I want him to stay healthy and keep doing what he’s been doing. I played with Hader and to see his fastball just raise up, (Hernandez’s) fastball does pretty much the same, too. Like I said, he just needs to stay healthy and take his approach every day to the field and I think he can be a pretty good pitcher.”

It isn’t just Hernandez’s fastball. He’s developed a solid slider and has a curve ball with wipeout potential. Any way you look at him, Hernandez at 22 may hold the Red Sox bullpen’s future in his left hand.

The Red Sox won’t talk publicly about Dombrowski’s execution just yet. Give them credit, sort of, for doing it almost stealthily. The NFL’s New England Patriots hogged the weekend headlines, first signing controversial wide receiver Antoine Brown, after he wriggled his way out of Oakland, then blowing the Pittsburgh Steelers out 33-3 Sunday night to open their season. The Red Sox dropped the guillotine on Dombrowski almost noiselessly.

They left Cora to be the public face of the putsch. It’s not exactly Cora’s most comfortable position, as he made clear after Sunday night’s loss when he was told the blade sliced  through Dombrowski’s neck. “I’m surprised and shocked, obviously,” the manager said. “Right now, I don’t have too much to say. This is the guy that gave me a chance to come here and be a big-league manager. They just told me so I’m not ready to talk about it.”

Martinez and Rick Porcello have said they were all but blindsided over executing Dombrowski, to whom both players were close going back to their Detroit days. Porcello had enough on his plate apologising publicly to Red Sox fans for his, shall we say, modest performance this season, without losing a man he considered a friend.

“At the end of the day” the righthanded former Cy Young Award winner said, “we’re the players who are on the field and we’re the ones who can make or break a lot of things. Ultimately, the onus comes on us. I’m still processing everything. Processing myself, too. It’s really hard to reflect on it, too. I’ll have potentially a better answer for you in a couple days. You never like to see anybody lose their job over what we’re doing on the field.”

As peculiar as it might sound to read in print, the Yankees have had little but front office stability with Brian Cashman as their general manager since 1998—and only one World Series title to show since the turn of the century. The Red Sox have had five full-time general managers since 1998 (Dan Duquette, Mike Port, Epstein, Cherington, and Dombrowski)—and four World Series titles to show since the turn of the century.

A lot of teams would kill for the Red Sox’s 21st Century track record—four World Series rings in fifteen years—even with the extremes of maximum success and (thanks to three dead-last division finishes) maximum recess. And a lot of GMs or baseball ops presidents would kill for Dombrowski’s overall resume: two World Series rings (his other ring: the 1997 Marlins), two American League pennants (the Tigers), in a little over two decades.

But a lot of them wouldn’t turn the farm into the dust bowl to get there, either.

The Red Sox for now will be run by a trio of assistant GMs, Brian O’Halloran, Eddie Romero (the son of 1986 pennant-winning Red Sox spare part Ed Romero), and Zack Scott. Several reports say Romero among the three is most considered to be a full GM/baseball ops president in waiting. Maybe the Red Sox won’t wait too long to make it happen.