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Red Sox Reset Just First Step Stuck
Posted on August 28, 2012 at 10:12 AM.

Second chances are quite rare, especially in professional sports.

It was a startling fall for the Boston Red Sox that began last September. Actually, it started a couple of seasons before as the organization morphed from making those under the radar transactions to simply playing the free agent market. It is one of the curses that comes with winning in the big market.

Once a big market team wins a World Series, the expectations become nearly impossible to meet as fans, owners, and even sponsors expect that title every season. But, Major League Baseball isn’t the NBA where a couple of star players can run right through the league in most years. It simply doesn’t work that way.

The Red Sox got caught in that win at all costs game, just like the Yankees did during the mid-2000’s. Money can help gather some great talent, but it cannot mask inefficiencies that the free agent market simply can’t help. The Red Sox lost their way and were in need of hitting the reset button after committing over $250 million to just three players while also having players like Dustin Pedroia, Jon Lester, and David Ortiz under big money deals.

All of that money couldn’t mask a lackluster rotation that received terrible performances from every single rotation member. It couldn’t mask a first half of the season that saw two-thirds of its starting outfield on the disabled list. It couldn’t mask the lack of an everyday shortstop. And, it couldn’t mask the controversy that began to permeate the organization.

Although the names signed to the big money deals were quality names, the results just haven’t been there for the organization. With the failed attempt to move Daniel Bard to the rotation, it has become clear that the Red Sox are quite thin on starting pitchers. The organization that once boasted a rotation led by Pedro Martinez and Curt Schilling was failing at it’s very core reason for success and two World Series titles.

Most big market teams have to wait. Usually, their big contracts are simple untradeable. The Yankees had to endure the last couple of seasons of Jason Giambi’s contract and had to endure the entire contract of Carl Pavano. They had quite a bit of money tied up into dead contracts before all of those deals expired. During that time, the Yankees starting pay attention to their farm system again, bringing up players like Robinson Cano and Brett Gardner. They made and continue to make some of those under the radar deals like when the acquired Nick Swisher before the 2009 season or their recent signings of Eric Chavez, Andruw Jones, and Raul Ibanez. They still spend money on big contracts, but they changed their model a bit.

The Yankees had to wait. The Red Sox would be in for a long wait as their contract commitments looked as if they would leave General Manager Ben Cherington and the Red Sox front office without much payroll flexibility for at least the next two seasons. That lack of flexibility was compounded by their poor decisions over the past few years. Josh Reddick is now with the A’s. Jed Lowrie is in Houston. Kevin Youkilis was given away for nothing. It looked as if they would have to spend more money or simply wait. With little help available in the minors, it looked like it would be a long wait.

But, then the Dodgers happened.

The Guggenheim Group has transformed the Dodgers from bankruptcy to the epitome of a large market team. They want to win now. They wanted an elite first baseman. They wanted Adrian Gonzalez.

They wanted him so badly that they were willing to take Carl Crawford’s $102 million owed to him over the next five seasons. They wanted him so badly that they were willing to take Josh Beckett and his $32 million owed to him over the next two seasons. They wanted Gonzalez so badly that they will hope that Carl Crawford can come back from Tommy John Surgery and be an effective outfielder once again. Gonzalez was so coveted that they took Boston’s biggest problem in terms of negative attention and least performing pitcher and hope he can be a decent pitcher in the National League.

The coveted Gonzalez so much that they even threw in some intriguing prospects into the deal.

Rubby De La Rosa is a 23 year old right handed pitching prospect with some Major League experience. In 13 appearances (10 starts) as a rookie last season, he was 4-5 with a 3.71 ERA in 60.2 innings while averaging 8.0 H/9, 0.9 HR/9, 4.6 BB/9, and 8.9 K/9. He was shut down last season and required elbow surgery, but he works in the mid-90’s.. He’s an injury risk, but does have a moderately high ceiling.

Allen Webster is a 22 year old right handed pitching prospect who also throws in the mid-90’s. Ranked as Baseball America’s 95th best prospect before the season, Webster profiles to be a mid rotation starter in the Major Leagues. Pitching at double-A this season, Webster has made 22 starts (27 appearances) and has compiled a 3.55 ERA along with averages of 8.9 H/9, 0.1 HR/9, 4.2 BB/9, and 8.7 K/9. He is still a year or two away from being Major League ready, but he is a legitimate pitching prospect.

Ivan De Jesus was once a shortstop prospect. Injuries have now taken a toll, but his 8 seasons in the Minors have produced a .298/.370/.398 batting line. He could be a useful utility man.

James Loney will play for the remainder of the season and then likely see if the free agent market has anything for him.

The Red Sox can be questioned for getting rid of Adrian Gonzalez. After all, he was the player that they chose to build around. They could’ve simply signed Albert Pujols or Prince Fielder this season rather than trade for Gonzalez last winter. Gonzalez was supposed to be the new backbone of the Red Sox lineup for years to come.

But, this mix just wasn’t working. On the field results were bad. Off the field attention was getting out of hand. And, the Red Sox got a gift of a way out of it. This deal isn’t a salary dump as they actually acquired two pretty good pitching prospects. But, most importantly, they do get back their payroll flexibility.

It was a good first step in recognizing that the organization was adrift. Now the hard part begins.

Ben Cherington’s club is still incredibly thin on the pitching side. Webster and De La Rosa help restock the barren system, but the club is still lacking organizational depth. The lineup is now without a legitimate, elite hitter. Dustin Pedroia and Jacoby Ellsbury remain, but Ellsbury may just want to test the free agent market. Cherington has many holes to fill.

He now has money to do that work. The real impact of this deal won’t be known until Cherington and the organization put a plan into action. Are they going to go out and hand out more big money contracts to different players and hope that their issues were a chemistry problem? Or, will they identify one player, perhaps Zack Greinke, bring him in and then look for value signings?

These are the questions that Ben Cherington has to answer. General Managers don’t normally get this kind of a reboot. The Red Sox are clearly his team now. He now has the money to spend to remodel the team back into a pennant winner. His ability to do so will be the true evaluation of this trade.

If De La Rosa and Webster can be serviceable Major League pitchers and Cherington can make a few wise signings while returning the Red Sox to being a developmental organization, trading his best hitter was a wise idea. Only the winter will tell whether or not the Red Sox will make good on this second chance.

Second chances are rare, especially for baseball teams. The Red Sox now have one.
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