The Boston Red Sox have begun to fill out their roster for the 2013 season and beyond. This has taken place amid pledges by GM Ben Cherington that the team will be spending freely this offseason, contrary to the commonly held belief that the Sox would be acting conservatively in the wake of last August’s payroll purge.

The team has quite a number of needs going into the offseason, with pitching chief among them. The Sox have a bad history with free agent signings in the pitching department, with many of the biggest busts in franchise history coming from acquiring these would-be aces.

This is not to sell them short on other areas where they have come up woefully short. Theo Epstein, in particular, made a habit of bringing in players who simply did not produce in a Sox uniform.

He certainly is not the only one guilty of handing out terrible contracts, though. Here’s a look at the 10 worst contracts the Sox have committed to:

Carl Crawford

The deal: Seven years, $142 million (Free Agent)

Key career numbers in Boston: .161 G, 260 BA, 23 SB, 126 SO

Crawford never really got a fair shot in Boston, getting off to a slow start in 2011 before battling injuries the rest of the season. His attempts at coming back in 2012 were admirable, but clearly he just needed to rest and be ready for next season.

He’s now doing that, and the Crawford of old will look to emerge when he hits the field in 2013. It will just be for the Los Angeles Dodgers.

Given the fact that he is another left-handed bat, Theo Epstein’s most expensive free agent signing seemed superfluous at the time, and even caused owner John Henry to say that he never wanted Crawford last offseason. Once he took over, new GM Ben Cherington could not get Crawford out of town fast enough, perhaps deciding that it was not shrewd to invest over $20 million per season on a player who thrives on athleticism but is on the wrong side of 30.

Adrian Gonzalez

The deal: Seven years, $154 million (Contract Extension)

Key career numbers in Boston: .895 OPS, 1114 AB, 42 HR, 105 BB

Gonzalez certainly was not a bad offensive player during his time in Boston, and especially in 2011 carried the team in stretches. He also played outstanding defense, winning a Gold Glove for his work at first base in his only full season playing for the Sox.

However, the weight of expectation seemed like it was too much for the low-key Gonzalez, who famously bristled at the number of national TV games the Sox had to play.

His trade to the Dodgers at last August’s waiver deadline proved just how weary the Sox had grown of Gonzalez failing to produce the middle-of-the-order power expected of someone making an average of $22 million per season. Averaging one home run per every 26.5 at bats is simply not going to cut it; 2012’s MLB leader, Giancarlo Stanton, averaged one per 12.1 ABs.

John Lackey

The deal: Five years, $82.5 million (Free Agent)

Key career numbers in Boston: 61 GS, 26-23, 5.21 ERA, 1.504 WHIP

The much-maligned Lackey still has two years remaining on his deal, so with strong performances in 2013 and 2014, he may be able to make his way off this list. He has certainly shown himself to be a capable pitcher at times during his career, amassing 102 wins over his eight seasons with the Angels.

The Sox have not seen that pitcher.

Since he came to Boston, Lackey has been a huge problem both on and off the mound. While his 2010 season was at least passable (a 4.40 ERA in 33 starts), 2011 was a complete train wreck.

Not only did Lackey post a 6.41 ERA, but he also was thrust into the spotlight as one of the key players in the “fried chicken and beer” saga that led to the ouster of manager Terry Francona after one of the greatest September collapses in the history of baseball.

Daisuke Matsuzaka

The deal: Six years, $52 million; $51.1 million posting fee (Free Agent)

Key career numbers in Boston: 116 GS, 50-37, 4.52 ERA, 1.418 WHIP

It’s impossible to talk about Matsuzaka’s contract without referring back to the criminally insane “posting” process that brought him to Boston in the first place. While the $51.1 million fee didn’t count against the average annual value of his deal, the $103 million the Sox spent in total on the right-hander was a horrific investment at best.

Things started off well enough in the first two years of the deal, with Matsuzaka playing a key role on the 2007 World Series championship team and finishing fourth in the AL Cy Young voting in 2008. However, he would never again be healthy for a full season.

Indeed, in the final four years of the deal, the numbers get really ugly: 34 starts (8.5 per season), 11-14 record, 5.53 ERA, 1.537 WHIP. That only tells part of the story, too; Matsuzaka’s throwing regimen between starts was a constant source of friction between the player and the team, and he ended up missing essentially a full season between 2011 and 2012 due to Tommy John surgery.

J.D. Drew

The deal: Five years, $70 million (Free Agent)

Key career numbers in Boston: 606 G, .264 BA, .455 SLG

Like Gonzalez, Drew’s problem was not that he was bad. Indeed, he made the All Star team in 2008 and hit a grand slam in the 2007 ALCS against the Cleveland Indians that may very well have saved the Sox’s season.

On the other hand, many of the myriad knocks on Drew’s game ended up coming to fruition during his time in Boston. Chiefly, his penchant for getting hurt (he averaged missing 40-plus games per season) and dispassionate demeanor made him a frequent punching bag for Sox fans who expected more out of a player making $14.5 million per season.

His WAR during his Boston career generally hovered around the 2.0 mark, the bare minimum to qualify as a “starter.” In his final season, Drew had a WAR of −1.0, well below the value of a replacement player.

Drew had talent and did produce at times; however, $70 million should be able to buy five years of a player better than just a “starter.” 

Edgar Renteria

The deal: Four years, $40 million (Free Agent)

Key career numbers in Boston: .276 BA, 9 SB, .385 SLG, 30 Errors

Theo Epstein was not a good judge of shortstop talent. He allowed Orlando Cabrera to leave as a free agent following the 2004 World Series, instead electing to replace him with Renteria. That experiment did not go well, and the shortstop was jettisoned after just one season.

The Sox thought they were getting the same player who had won Gold Gloves in 2002 and 2003; Renteria responded by committing 30 errors. They thought they were getting a player who would give their lineup some much-needed speed; he stole nine bases all season.

What stood out more than the numbers, though, was how visibly miserable Renteria was in a Sox uniform. He had, to quote one Sox front office member, “an adjustment period that may have lasted longer than…hoped,” and he clearly never fit in with the team.

Julio Lugo

The deal: Four years, $36 million (Free Agent)

Key career numbers in Boston: 266 G, .251 BA, .664 OPS, 42 Errors

Another disastrous shortstop signing, Lugo had almost never been a full-time MLB starter before Epstein handed him $36 million in the wake of the Renteria calamity. Lugo replaced defensive wizard Alex Gonzalez, who had played fantastic defense the season before but was less of an offensive talent (allegedly).

The next two years and change were not pretty.

Lugo never lived up to expectations, hitting just .251 while playing mediocre defense at shortstop. He posted negative (i.e., below replacement value) WARs in two of his three seasons in Boston and just barely avoided a trifecta, putting up a high of 0.3 in 2007.

He was so bad that the team finally designated him for assignment in July of 2009, with Epstein succinctly saying that management all realized “a sunk cost is a sunk cost.”

Jose Offerman

The deal: Four years, $26 million (Free Agent)

Key career numbers in Boston: .268 BA, 30 HR, 31 SB

After nickel and diming Mo Vaughn to the point that he left for the Angels, Sox GM Dan Duquette decided to replace his superstar first baseman with Offerman, a player who had never hit more than seven home runs in a season.

His first two years on the Sox, Offerman was the second-highest-paid position player on the entire roster. Unfortunately, he produced like someone who should probably have been a backup.

His WAR reached its apex in 1999, Offerman’s first season with the team. What was that gargantuan total? 2.7, just above the designation of “starter.”

Offerman was a fine complementary player, but certainly not one expected to be the centerpiece of a lineup. While the Sox may have dodged a bullet in allowing the Angels to hand Vaughn an $80 million deal, they surely could have replaced him with someone substantially better than Offerman. 

Matt Young

The deal: Three years, $6.5 million (Free Agent)

Key career numbers in Boston: 24 GS, 4.91 ERA, 1.607 WHIP

Who is Matt Young?

A great question, as his tenure in Boston was so atrocious that many who were fans at the time have purged it from their collective memory.

Young was brought in by then-GM Lou Gorman to shore up a 1991 Sox rotation anchored by Roger Clemens, but things did not go quite as planned. Despite being the third-highest paid starter on the team, Young only managed to make 16 starts and post a 5.18 ERA, concluding the year with a 3-7 record.

Perhaps the Sox could have anticipated this drop-off, given that the year before Young had lost 18 games.

He will be best remembered for the “no-hitter” he threw in Cleveland against the Indians which he managed to lose (he walked in two runs) and had MLB strip from him since he only actually threw eight innings (since they were the losing team and on the road).

Steve Avery

The deal: Two years, $8.75 million (Free Agent)

Key career numbers in Boston: 220.1 IP, 5.61 ERA, 1.670 WHIP

Avery had a couple great years in Atlanta, winning 47 games between 1991 and 1993 and amassing a 3.17 ERA and one All Star appearance over that timeframe. However, Avery was injured in a September start in 1993 against the Padres and showed noticeable signs of decline after that point.

When he came up for free agency in 1997, Sox GM Dan Duquette used Avery’s early years as justification for making him the Sox’s highest paid pitcher and second-highest paid player overall behind only Mo Vaughn.

Not surprisingly, Avery was a nightmare. He won just 16 games and had a cumulative ERA of 5.61, including a 6.42 mark in 1997.