Portland Sea Dogs employee Dan Acheson grabbed a drill Thursday and went to work.

Acheson removed a collection of wooden jerseys from the Hadlock Field façade, each jersey representing a Boston Red Sox player who played for the Sea Dogs.

Jon Lester, Felix Doubront, John Lackey, Stephen Drew – all gone.

For the second time in three years, Red Sox General Manager Ben Cherington looked at his underachieving roster and blew it up.

The Red Sox traded Lester, Lackey, Drew, Andrew Miller and Jonny Gomes on Thursday, the deadline for non-waiver major league trades. They already had dealt Doubront on Wednesday.

“Hopefully, we turned it into moves that make us better,” Cherington said Thursday evening during a televised news conference from Fenway Park.

Hey, who can argue with Cherington’s track record?

In 2012, after Boston traded Adrian Gonzalez, Josh Beckett, Carl Crawford and Nick Punto, Cherington went to work rebuilding the roster.

The result: a World Series title in 2013.

The funny thing about this 2014 team is that many of the players are the same ones who were celebrating a championship on the Fenway grass last October.

This team expected to contend again. The players’ slogan during spring training was to “turn the page,” and focus on winning another title.

Even after a disastrous start, the Red Sox had hope. Just over a week ago, Boston swept Kansas City in three games and then beat the Blue Jays 14-1 in Toronto.

“We got through the Royals series and got to Toronto and won the game Monday night – we were still thinking of winning,” Cherington said. “We were actually looking to add players.”

Boston then lost eight of its last nine games. Cherington found himself busy at the trade deadline, not to add players to a contending roster, but as a seller trying to rebuild.

“Nothing celebratory about this,” Cherington said. “These moves are made because we collectively as an organization haven’t performed well enough.

“We knew coming into this week we had a job to do … try to kick-start building the next team.”

Boston added three players who will jump into action this month, as well as next year: outfielders Yoenis Cespedes and Allen Craig and starting pitcher Joe Kelly.

There also will be chances for new players to prove themselves. Xander Bogaerts moves from third base back to the position he wants: shortstop. Will Middlebrooks receives another opportunity to stick in the big leagues, back at third base.

And all of Boston’s young pitchers, many of whom stood atop the Hadlock mound in previous years, will get an extended tryout – including Anthony Ranaudo, who will make his major league debut Friday night at Fenway against the Yankees.

“We have an important 54 games (remaining) because we have a lot to find out,” Cherington said. “And there’s more work to do in the offseason, too.”

Indeed. You do not deal veterans like Lester and Lackey and figure to contend.

“The expectation is (the Red Sox will be) active in the starting pitching market in the offseason,” Cherington said.

So the Red Sox will play out the schedule – sort of an extended tryout for 2015 – and then look to make more improvements during the winter.

Then next spring, who knows?

Did anyone predict a championship early in 2013?

Did anyone foresee this year’s collapse back in March?

The Red Sox will continue to mix in veterans with players groomed in their minor leagues, like those in Portland.

Soon, more jerseys will be hung up at Hadlock Field, representing more players from here reaching the majors – joining the veterans Cherington traded for on Thursday.

Will they be good enough to contend for another title at Fenway?

Or will Acheson be looking for his drill and heading for the Hadlock façade?