Red Sox emerged from a crossroads the Blue Jays may soon face

Toronto Blue Jays starter Marco Estrada and Boston Red Sox ace Chris Sale had a memorable pitching duel that saw the Jays fall in extra inning. Watch the highlights with Blue Jays in 60 presented by Sonnet.

TORONTO — Coming off a crash-and-burn campaign, the Boston Red Sox expected big things in 2015 after they added high profile free agents Hanley Ramirez and Pablo Sandoval and acquired starters Rick Porcello and Wade Miley to augment a veteran core. Instead, they collapsed again, but out of the ashes of that season a young core that is the envy of the American League East really began to take form.

Mookie Betts, Xander Bogaerts, Jackie Bradley Jr., Eduardo Rodriguez and Steven Wright each made significant strides over the final two months of that season as the Red Sox went 32-26. During that stretch, one Toronto Blue Jays player described them as their toughest opponent in the AL.

Now, with their mix of high-priced veterans like Chris Sale, the injured David Price, Craig Kimbrel and Dustin Pedroia, a young core integrating the talented Andrew Benintendi, and a still middle-of-the-pack farm system, the defending AL East champs are among the game’s best-positioned organizations top to bottom.

“To me, the best way to break a young player in is with a club that has other players that are really the main forces,” says Red Sox president of baseball operations Dave Dombrowski. “If you can break in a player or two per year under that circumstance, to keep that youthful enthusiasm and keep that group growing and to keep some type of stability from a cost perspective, that’s the ideal. It’s not always possible.”

That’s the existential reality the Blue Jays are wrestling with at the moment, as their very talented roster is largely made up of veteran players with limited youthful upside beyond Aaron Sanchez, Marcus Stroman, Roberto Osuna, Devon Travis and Kevin Pillar. Complicating things is the gap between their top prospects and the big-leagues, with only triple-A first baseman Rowdy Tellez even remotely close to knocking on the door, and he hasn’t reached the porch yet.

As a result, the Blue Jays may at some point find themselves facing the kind of trade deadline decisions the Red Sox made in 2014 under Ben Cherington, Dombrowski made as president and GM of the Detroit Tigers in 2015 and New York Yankees general manager Brian Cashman made last year after win-now seasons went awry.

Cherington, now vice-president of baseball operations for the Blue Jays, traded John Lackey, Jon Lester and Andrew Miller in deals that landed Rodriguez, Joe Kelly and Yoenis Cespedes, who was later used to acquire Porcello. Dombrowski sent Price to the Blue Jays for Daniel Norris and Matt Boyd, while using Cespedes and Joaquim Soria to get Michael Fulmer and Jacoby Jones. Cashman flipped Aroldis Chapman and Andrew Miller for a bevy of prospects that include the gilt-edged Gleyber Torres and Clint Frazier.

“The ideal scenario is that you never get to that point,” says Dombrowski. “But if you get to that point, then I think what you try to do is be realistic with your expectations to win now and if you have a chance to win now, you normally try to do that if you feel legitimately you have that chance. But if you can ideally make some moves to keep that flow going, that’s the ideal.”

The Red Sox had a far deeper prospect base than the Tigers and Yankees at the time, but all three teams injected needed youth into their systems with those trades. Each has already reaped some rewards, as well.

“The part of which is not always easy is actually being realistic on where you are. If you inflate your abilities to win, that makes it very difficult,” says Dombrowski. “The Yankees last year, Brian Cashman, he made some really good decisions and good trades. He didn’t feel in his own heart that they were good enough to win it. I’m not saying other people in the organization would have agreed with him or disagreed with him, but that was in his own heart. He went out there and made some really good trades, good some good young talent in the organization and it started a rebuilding for him much more quickly than if he would have waited. That’s your job as general manager, and hopefully you have that ability to make that ultimate decision.”

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The Blue Jays are a long way from that point, and are working hard to push back its arrival for at least another year. Their 3-12 start to the season after Thursday’s 4-1 loss in 10 innings to the Red Sox represents a major obstacle to that goal and it will take a significant run to avert some level of retool.

The Red Sox, meanwhile, are off to a 10-6 start despite missing Price and set-up man Tyler Thornburg to injury.

“Our guys have done a good job,” says Dombrowski. “We’ve been able to weather the storm and keep our heads above water early in the season. It’s usually not that easy to get started off anyway because of the flow of play in games, cold weather, days off, facing the top pitchers and then we had some injuries, had some illnesses, had some bereavements, paternities and we’ve been able to keep our heads above water. We have a good solid club, so hopefully we can build upon this time.”

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