Carl Crawford was a disappointment in Boston, while Vernon Wells hasn't lived up to expectations in LA. (US Presswire)

With the winter meetings coming next week and Rays third baseman Evan Longoria signing another club-friendly (albeit much less friendly than last time) contract on Monday, what better time than to examine some of baseball's worst deals? We looked at catchers and infielders on Monday, so now it's time to check out the outfield along with designated hitters.

As noted in the infield/catcher article, we're only looking at what's left on a contract, not the entirety of the original deal.

One last thing to mention before we dive in: As I scroll through all the monetary obligations of each of the 30 MLB clubs, I find that it's slim pickings in terms of what I believe are egregious contracts. Baseball is absolutely flush with money right now, and it's starting to legitimately trickle down to smaller-market teams. Take note, in particular, of the Reds' giant deal with Joey Votto (13 years, $263 million). With many teams just about to sign huge regional TV deals, we'll see more and more of this. So, in some cases, I felt like I was nitpicking.

Anyway, no need to go on any further.

Eye on Baseball
Offseason content

Left field

Winner: Carl Crawford
Remaining salary: Five years, $102.5M

In essentially a full season (161 games in the past two years) with Boston, Crawford hit .260/.292/.419 with 14 homers, 75 RBI, 88 runs and 23 steals. While I believe that he's plenty capable of bouncing back to previous form, I just don't see how he's going to be able to prove himself worthy of more than $20 million per season for the next five as a corner outfielder. I think he'd need to do something like hit .310/.375/.500 with 40-plus stolen bases, 20-plus homers, more than 100 runs and excellent defense in every season in order for us to even consider him coming close to that contract. He turns 32 next season. Also, he only walked three times while striking out 22 last season. As a tablesetter -- as opposed to a power hitter where it might be OK with a high homer total -- that's atrocious.

Runner-up: Jason Bay. He doesn't have a team just yet, but he's going to make $16 million from the Mets in 2013 (and $5M more due to oustanding signing bonus and the buyout of a 2014 option) after hitting .165/.237/.299 last season in just 70 games. For 2013, I'd easily rather have Crawford, but Bay "loses" here because Crawford has an extra four years on his deal.

Also considered: This is pretty funny. How long have we all lamented the Alfonso Soriano deal? Well, he "only" has two years and $38 million left. Plus, he hit .262/.322/.499 with 32 homers, 108 RBI and 33 doubles last year -- along with greatly improved defense. Don't get me wrong, he's still overpaid, but this isn't sticking out like nearly as bad a sore thumb as three years ago.

Center field

Winner: Vernon Wells
Remaining salary: Two years, $42M

The only explanation needed on this albatross of a contract is why I moved Wells to center. It's pretty simple, actually, Wells used to be an everyday center fielder and played there six times last season. Left field is "loaded" with bad contracts, and center is not. So, I made the move.

Runner-up: Curtis Granderson (one year, $15M left). It's a major stretch due to his home-run power to include him here. But he has actually become one-dimensional (lacking steals/doubles/triples, diminishing defensive range and poor batting average/on-base percentage), and there aren't any real huge contracts for center fielders.

Also considered: Alex Rios (two years, $25M left). He's definitely fine right now after a great 2012 season. And if that continues, he never sniffs this list. But there's always the fear he regresses to 2011 levels.

Right field

Winner: Jayson Werth
Remaining salary: Five years, $99M

Werth is coming off a good season, especially in the second half after a quick recovery from a broken wrist. He hit .300/.387/.440 and has served as a good mentor to several younger Nationals players, including prodigy Bryce Harper. Still, even the biggest of Werth/Nationals fans have to admit that the Nats are majorly overpaying for Werth's services. There are five years and roughly $20 million per season left on the deal, and he turns 34 this coming May. The good news is the Lerner family (the richest ownership group in MLB) can afford it.

Runner-up: Nick Markakis (Two years, $30M left). Much like Werth, I don't have a huge issue with this one. It's just that pretty much all the overpaid outfielders reside in left. The reason that Markakis is here is because he's a corner outfielder paid $15 million a year and carries 162-game averages of 18 homers, 85 RBI, 89 runs and a .453 career slugging percentage. Right fielders who make $15 million or more a year need to be top-level run producers.

Also considered: Until Nick Swisher signs somewhere for probably far too much (prediction alert!), we don't really have any other viable options. No, I have no problem whatsoever with Torii Hunter's recently-signed deal in Detroit.

Designated hitter

Winner: Michael Young
Remaining salary: One year, $16M

A seven-time All-Star and well-documented great guy, Young hit .277/.312/.370 last season with eight homers, 67 RBI and 79 runs. When he does play defense, he's pretty bad due to having lost all his range over the years. He's 36 now, so the smart money was on last season being more decline and less off-year.

Runner-up: Adam Dunn (two years, $30M left), for a similar reason to Rios. If Dunn's gonna hit 41 bombs with a .333 OBP and not hurt the White Sox on defense, though, this isn't so bad. In fact, I'd be OK with it.

Coming Wednesday: Starting pitchers

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