Theo Epstein to Cubs: 11 Biggest Mistakes He Made With the Boston Red Sox

With the Theo Epstein era in the rear view mirror, there will now be plenty of time to reflect. Some, no actually a lot of that reflection will and should be positive. After all, Epstein brought not just one, but two World Series Rings to the Boston Red Sox and their adoring fan base.

He had his lows though. While player development was unquestionably a major strength, his frequent trips into the high priced free-agent market did not always yield the results that were both assumed as well as paid for. In addition there were some trades that worked, and there were some that did not. Here's a look at 11 decisions that Theo would probably candidly admit were mistakes.  

Allowing Orlando Cabrera To Leave

When the Nomar Garciaparra trade went through, Red Sox fans immediately were concerned about who would play shortstop. After all Nomar had manned the middle for nearly eight full seasons. 

Enter Orlando Cabrera. The Montreal Expos shortstop who was known for his outgoing personality and flashy glove was immediately embraced by both the fans and his teammates in Boston. He played hard, he made great plays in the field and he came up with timely hits. In his two months with Boston he would hit .294 with six home runs and 19 doubles. In the playoffs he performed very well and of course as a member of that first World Series Team he became a part of Red Sox history. 

When he declared free agency in the winter of 2004 there were plenty of fans that wanted the Red Sox to retain his services. Instead Theo Epstein chose to sign Edgar Renteria to a four-year 40 million dollar contract. 

Five days later Cabrera would sign a four-year 32 million dollar contract with the Los Angeles Angels. Cabrera had a proven record of performing in Boston. Renteria would end up wilting under the pressure. The Red Sox shortstop position would remain in flux for years.  That plus the fact that Cabrera was cheaper by $8 million dollars makes this a critical error on the Epstein record.  

Edgar Renteria

Fresh off their epic World Series win October of 2004, the Boston Red Sox found themselves without a shortstop. Star Nomar Garciaparra had been dealt at the trade deadline in the summer of 2004 and his replacement Orlando Cabrera had been allowed to depart via free agency following the World Series. 

Enter Edgar Renteria. Renteria signed a four-year $40 million dollar deal on December 15th 2004 and at the time there really was very little reason to expect that the signing wouldn't be one that Theo could be proud of.

Renteria arrived as a two-time gold glove winner and four-time All Star. He won a World Series as a 22-year-old member of the Florida Marlins in 1997 and had played a key role in leading the St. Louis Cardinals back to the World Series in 2004 where they would be swept by his new team in Boston.

In Boston everything changed. Renteria would commit a career high and major league high 30 errors on the field. At the plate he never really gained traction and would strikeout 100 times, his most since 1997. While he wasn't a problem in the clubhouse he also never really meshed with all the different flamboyant personalities the Red Sox had in 2005. Guys like Manny Ramirez, David Ortiz, Johnny Damon and Kevin Millar.

In the end he lasted only one season. He was traded to the Braves for third base prospect Andy Marte less than one calendar year after he signed as a free agent. The Red Sox still had to shell out $8 million dollars for him after he left as part of the deal with the Braves. The Renteria failure began a revolving door at the shortstop position that has still yet to really be stabilized as of today.  

The Revolving Door of Alex Gonzalez.

The Red Sox never-ending quest to find a decent shortstop has already dominated this slideshow. It's not done yet. Once the Edgar Renteria era came to it's unceremonious ending in December of 2005, the Red Sox once again found themselves needing someone to play shortstop. 

Enter Alex Gonzalez. Gonzalez was similar to what the Red Sox had with Orlando Cabrera. He was an excellent fielder who in spite of never having won a gold glove, was known around the league as a very above average fielder.

Gonzalez was not known for his offensive prowess. He didn't hit for very high average, when he got to Boston his career high over seven seasons was a modest .277. He also had four seasons in which he would strikeout more than 100 times. He had some pop in his bat and hit 23 home runs in 2004 as well as a very, very famous walk-off home run in the 12th inning of Game 4 in the 2003 World Series against the New York Yankees.

Gonzalez enjoyed a respectable and solid 2006 season in Boston. His glove was exceptional and his bat was about what could have been reasonably expected. Theo and the Red Sox would of course let Gonzalez go and invest in an "upgrade" in Julio Lugo.

That would end up as a mistake and Gonzalez of all people was the man who came to town midway through the 2009 season when Lugo was traded in the midst of yet another miserable year. Gonzalez was never a great player in Boston, but his shortstop production was as good if not better than the shortstops he often found himself replacing, and Gonzalez was never granted an absurd contract that he had very little chance of living up to. 

Julio Lugo

Following Edgar Renteria's departure, the Red Sox filled in the gap at the shortstop with slick fielding but light hitting Alex Gonzalez. Theo still longed to have a higher profile and higher production player at the shortstop position, so in the offseason between 2006 and 2007 the Red Sox handed 31-year-old Julio Lugo a four-year $36 million dollar contract. 

If Sox fans thought the Renteria deal was bad, then this one would end up making it look fairly harmless. While the Red Sox were able to get out of the Renteria deal, they would end up never being able to rid themselves of this one. 

Lugo was just not a good fit in Boston. Before arriving in Boston he had never finished a season with an average below .250. In 2007 he hit .237 and would strike out 82 times, his most since the 2004 season. Lugo's lack of performance frustrated fans but with the Red Sox winning the AL East and eventually the World Series, he was somewhat immune to too much criticism. When a string of nagging injuries limited him to just a half season of mediocre production in 2008, Lugo began to really fall out of favor in Boston. 

2009 brought more injuries and an eventual midseason trade to St. Louis for minor leaguer Chris Duncan. The Red Sox would end up paying nearly all of the $36 million they signed Lugo for and got very little in return. 

Bronson Arroyo

There's an old adage in baseball. 

"You can never have too much pitching"

Perhaps there should be another one added to the baseball lexicon as well? 

It could read something like: " You can have too many overweight sluggers that can't hit breaking balls."

Had that saying been a prominent part of the baseball lexicon, then it's unlikely that the trade on March 20th 2006 would ever have been made. 

That day Theo Epstein traded Bronson Arroyo, a solid but unspectacular starter who had been through the postseason wars of 2003, 2004 and 2005 with the Red Sox to the Cincinnati Reds for a massive physical specimen by the name of Wily Mo Pena. 

Epstein clearly saw in Pena similar qualities to David Ortiz. Ortiz like Pena, was an imposing physical specimen who had worn out his welcome in Minnesota in spite of prodigious power numbers. In 2005 Pena had bashed 19 home runs in just over 300 at-bats. Expand those at-bats closer to 600 and you might have another 35-plus home run hitter on your hands. One problem though, Pena had also struck out 116 times in those limited at-bats. That's because Pena, like the legendary character " Pedro Cerrano" from the movie " Major League," could not hit breaking balls. 

That would prove to be Pena's undoing in Boston as he spent less than two full seasons there. Pena was shipped out of town in 2007 and Arroyo would go on to become a very respectable starter in Cincinnati, where over six seasons he compiled a record of 79-72 with an earned run average of 4.14. 

Those aren't amazing numbers, but at a cost of just a touch over $10 million dollars a year, they seem like bargains compared to what Theo and the Sox would end up spending on other less effective starters down the road. 

Daisuke Matsuzaka

Most Red Sox fans saw the title of this slideshow and probably immediately thought "Dice-K". After all very few players in Boston Red Sox history arrived in Boston with more hype and offered up a weaker return. 

On November 14th 2006, the Boston Red Sox were informed that they had the winning bid of just over $51 million dollars for the privilege of just negotiating with Daisuke Matsuzaka. 

"Dice-K" as he was known, was a legendary pitcher from Japan. Rumored to have a five-pitch arsenal that he had used with effectiveness against Major League hitters in the World Baseball Classic, he was hyped by many as a future "ace" or a No. 1 type of big league starter. 

Following the exorbitant posting fee, the Red Sox issued Dice-K a six-year 52 million dollar contract. His arrival in Boston and in the United States created a massive amount of buzz and he appeared on the cover of Sports Illustrated's 2007 Baseball Preview. 

Well the performance never matched the hype. In fact with the exception of a not-as-good-as-the-numbers-would-lead-you-to-believe 2008 season, Dice-K was either mediocre, bad or injured for his entire Red Sox career. 

He fell behind in the count, he walked batters, he hit batters, he was overworked, he was under-worked, he didn't like Boston, he did like Boston. No one ever really figured Dice-K out with the notable exception of Major League Hitters who at times appeared to either be taking batting practice or just waiting to be walked when they set foot in the batter's box against him. 

By the time the 2011 season started, the expectations for Dice-K had morphed from No. 1 starter to more like No. 4 or No. 5. He started 2011 in the same manner of many of his seasons in Boston, inconsistently. He had a shutout in which he was nearly unhittable against the Angels, but that was followed by more poor outings.

Eventually Daisuke Matsuzaka would be placed on the disabled list needing Tommy John elbow surgery. By the time his recovery is complete it's expected that his contract with the Red Sox may be over. Whether or not he remains in the Major Leagues is anyone's guess but one thing is for sure, for $100 million dollars Theo and the Red Sox got very little return for their investment.  

The Eric Gagne Trade

The 2007 Red Sox were Theo Epstein's most dominant team. Wire-to-wire the team was at or near the top of the American League East. As the trade deadline approached, Theo sought to strengthen an already solid bullpen in an effort to close out an American League East title. 

Eric Gagne was at one time the most dominant closer in all of baseball. A three-year run from 2002-2004 peaked in 2003 when Gagne posted some of the most outrageous numbers in recent memory. 55 saves, an earned run average of 1.20 and 137 strikeouts in only 82.1 innings pitched. Injuries would seriously change his career trajectory and after missing all of the 2006 season, Gagne found himself in Texas battling for the closer job.

That was a battle he would win and as the closer in Texas, Gagne was solid enough to attract Theo Epstein's attention. On July 31st 2007, Epstein would pull the trigger on a trade to bring Gagne to Boston to bolster the bullpen for the stretch run. Gagne arrived in Boston but must have left any remaining pitching ability in Texas because he was downright awful for the remaining two months of the season. 

Gagne would go 2-2 with a 6.75 earned run average for the reminder of the regular season. He followed that up with an even worse postseason in which his earned run average was over 8.00. Gagne appeared on the Red Sox World Series roster but would never enter a game and when the 2008 season began, he was no longer a member of the team. 

It's important to remember that the Red Sox acquired Gagne via a trade, not a free-agent signing. That means that they parted with some players to acquire him. In this case it was three players: starting pitcher Kason Gabbard, AAA outfielder David Murphy and the young but talented Engel Beltre. Gabbard would get some starts but never really become a major leaguer. Beltre is currently only 21 years old but his career seems to have stalled a bit and he's still in double-A ball. 

It's David Murphy that makes this deal look even worse. Arguably one of baseball's most valuable fourth outfielders, Murphy is playing in his second consecutive ALCS for the Texas Rangers. He has played a key role on the Rangers as both a starter and a bench player and his solid hitting, mixed with timely power and decent speed have made him one of baseball's better role players. 

Gagne may no longer be playing baseball but Red Sox fans can't help but think of him every time they tune into a Texas Rangers game and watch Murphy make a play. 

Mike Cameron

Maybe if David Murphy had never left the Boston Red Sox organization then they wouldn't have felt like they needed a fourth outfielder between the 2009 and 2010 seasons. 

Had that been the case, then Mike Cameron would never have signed a contract to play in Boston. That would have been fine with Red Sox fans. 

Cameron, a journeyman outfielder known for a spectacular glove and occasional ( as in one of 15 four-home run single-game outbursts in major league history) power hitting, was signed by Epstein and the Sox on December 16th 2009. It was a two-year $15.5 million dollar deal. Cameron was a non-factor for most of his Boston tenure. He would appear in just 48 games for the Sox in 2010 and only 33 in 2011 before being shipped to the Florida Marlins to finish up the 2011 season. 

It wasn't just that Cameron barely played. It was that when he did play he was generally ineffective. Cameron looked like a past-his-prime player doing everything he could to remain under contract and having very little of it work.

Cameron like Lugo would be dealt before the length of his contract was up, and like Lugo, much of his contract would still end up being paid by the Red Sox.  

John Lackey

Hindsight as the saying goes is 20/20. 

So perhaps with that in mind, the signing of one John Derran Lackey on December 16th 2009 was not a bad ideal (at the time)? 

Hard to believe for many Red Sox fans but looking back it just didn't look that bad. 

It sure turned out to be though. 

At the age of 31, John Lackey signed a five-year $82.5 million dollar contract with the Boston Red Sox. He may as well have signed a preliminary agreement to send Theo Epstein to Chicago. That's how much of a disaster the Lackey signing has turned out to be. 

Only two years into his contract there are many very serious voices around Boston that believe the Red Sox no matter how much the cost or how terribly uneven the trade is, must find a way to insure that John Lackey is not on the 2012 Opening Day Roster. 

What Happened? It's really somewhat of a mystery. Lackey entered Boston with a very good reputation around baseball. He was a classic "gamer." A guy that had arrived in the majors at the young age of 22 and immediately displayed both poise and ability. As a rookie in 2002, he threw seven shutout innings against the Minnesota Twins in the ALCS. The Angels won the World Series that season and Lackey had a ring and World Series memories before his career was even a year old. 

He would improve as the years passed, peaking in 2007 when in the midst of one of the last offensively dominated seasons in major league baseball, Lackey would lead the American League in earned run average ( 3.01), shutouts ( two) and finish third in the Cy Young voting. 

Lackey arrived in Boston with his age and experience factored into the equation. In spite of his large contract it wasn't No. 1 type of starter money. Lackey would be expected to go out every five days, allow three or maybe four runs, keep the Red Sox in games and let the Sox bats do the heavy lifting. His big-game experience would allow the Sox to start him in the postseason and provide clubhouse leadership around younger pitchers such as Jon Lester and Clay Buchholz .

Nothing even remotely similar to the scenarios laid out above ever came close to happening. There was and has been no postseason baseball in Boston since the Lackey signing. This is not a coincidence because when one of your starting pitchers has an earned run average over two seasons of 5.26, a record of 26-23 ( talk about run support!) and a WHIP ratio of 1.504, then the chances of the postseason aren't that good. 

After two seasons though, the Lackey signing is bad in ways beyond the numbers. His clubhouse influence as it turns out, has been either negligible or negative. In his defense, Lackey has experienced some personal off-the-field issues that don't need to be discussed in a baseball column. To his and his team's detriment, he allowed those issues to impact not just his performance, but also his demeanor.

Lackey in spite of some very poor performances often looked noticeably upset when removed from games or when his team didn't field a batted ball perfectly. Lackey also is rumored to have been one of several starting pitchers that didn't take his physical fitness routine seriously and thus faded even more severely for the September stretch run in 2011. 

The Lackey signing has been a true disaster and I'm sure Theo would admit as much candidly. 

Bobby Jenks

To Red Sox fans clamoring to allow Jonathan Papelbon to leave Boston in free agency, I would urge you to look at Bobby Jenks. 

That's because there are a lot more "Bobby Jenks" types of closer careers through major league history than Jonathan Papelbons. 

Jenks burst onto the big league scene in 2005 at the age of just 24 with all the subtlety of a freight train. He was big, brash and routinely threw his fastball well into the upper 90's. He became the White Sox closer in Chicago and led them into the postseason where he would record four saves along the way to the 2005 World Series Title . 

Jenks would assume closing duties in Chicago and for five seasons he held the position. As the 2010 season drew to a close, Jenks' contract was up and so was White Sox manager Ozzie Guillen's patience. Jenks had packed on some pounds and also lost a fair amount of his effectiveness. 

In 2007 Jenks had 40 saves with an earned run average of 2.77. By the end of 2010, the saves had declined to 27 and the ERA had increased to 4.44. He was not offered a contract and hit the open market. 

Theo had an interesting bullpen situation as the 2011 season loomed on the horizon. He had closer Jonathan Papelbon under contract for one more season. He had young flamethrower Daniel Bard being groomed for a future as a closer. Jenks seemed like an logical candidate to provide a potential bridge to the future should Bard prove not quite ready for prime time and should Papelbon choose to depart Boston via either trade ( which didn't happen) or free agency ( which very well might happen).

The Red Sox would sign Jenks to a two-year $12 million dollar contract and from the looks of it are likely to get next to nothing back in return. Actually that's not totally true. Jenks did appear in 19 games this past season and each time he probably made the Red Sox and Theo regret signing him.

Jenks on the disabled list was probably a good thing for the Red Sox because when he was actually in games he was terrible. Compiling a 2-2 record with an earned run average of 6.32, Jenks gave up hits, issued walks and became one of those pitchers that would only appear if the game's outcome was already a foregone conclusion.

Jenks tenure in Boston may be a foregone conclusion as well. With only one season and $6 million dollars remaining on his deal, he may become yet another in a long line of bad deals that the Red Sox will eat this offseason.  

Carl Crawford

There are times when regardless of how a player performs there is very little chance of him ever truly earning the amount he will be paid. The New York Yankees are already well into a contract they signed with Alex Rodriguez that will pay him at or around 30 million dollars a year through the year 2016. There is almost no chance he will perform at a level to validate that money. 

The Yankees have Alex Rodriguez and the Red Sox have Carl Crawford. 

Crawford, who was one of the highest profile and highest contract signing free agents of the 2010-2011 offseason, inked a seven year deal worth 142 million dollars. He responded with a 2011 season in which he underperformed in nearly every way possible. He was not nearly the gold glove caliber fielder he had been in Tampa. All of his numbers from batting average, to stolen bases, to extra base hits were down by fairly large margins. Crawford was also injured on several occasions. 

It's highly possible that Crawford reverses this trend over the next few years. Crawford by most indications is a fairly hardworking stand up guy. He was quite publicly candid in owning up to his subpar season with the very tough Boston fans and media. 

The problem is that even if Crawford performs at the level he did in Tampa, even if he hits around .300, hits around 20 home runs, steals 30 or more bases and plays above-average left field, that still won't be production in accordance with being the highest paid outfielder in Major League Baseball. That's a problem that won't go away and it's one he's somewhat powerless to overcome. 

Carl Crawford will take the field on opening day 2012 as a 30-year-old outfielder with a very good track record. I won't be at all shocked if his 2012 numbers are vaguely similar to his 2010 numbers that he produced in Tampa: a .307 average, 19 home runs, 47 stolen bases. Those all seem very possible although the steals could easily drop off. Those are great numbers to be sure. They don't in any way make him worth more than men like Ryan Braun, Matt Kemp or his own teammate Jacoby Ellsbury. 

At the age of 30, Crawford will likely begin to notice some more realistic declines over the next few seasons. His speed in particular could fall off. That's not unusual for someone his age and it doesn't matter how much someone is paid —he can't pay off the aging process and ask it to be put off for a few years.

The Crawford deal is bad not because Crawford is a bad guy or a bad player. I really don't see him repeating the disastrous 2011 season. I just can't see him ever producing numbers that would validate his seven-year, $142 million dollar contract. He wasn't worth it on the day he signed it and he won't be worth it in two, three, four or seven years either.