The issues I have with Helton are as follows:
1. That contract is atrocious. It honestly might be the worst in baseball, and unless the Rockies are kicking back $45-$50 mil to get the deal done, we shouldn't even be talking about including MDC. MDC may not amount to anything but he's young and cost controlled middle relief, and his peripheral numbers are actually pretty decent. I'd hold on to him for now.
2. Helton sucked last year. Whether it be due to the humidor, the illness he suffered, or just natural decline, he was comparable to Youkilis last year and cost a ton of money. Like others have said, if he really is on the decline, signing him when you have Youkilis seems redundant.
3. He, for his entire career, has played in arguably the most hitter friendly ballpark in the MLB (with an exception to last year). How much have his numbers been inflated?
The advantages to Helton are:
1. Like a700 said, when healthy, he is head and shoulders above Youkilis. The man was easily one of the top 10 hitters in baseball from 2000-2004. OPS+ of 158, 160, 143, 168, and 159 respectively. Average of 37.2 HR a season. SLG of .698, .685, .577, .630, and .620.
2. Even when he's not healthy he's an OBP machine. He had a OBP of .404 last year, his "off" year. Youkilis, by comparison, had an OBP of .381. Imagine a 3-6 of Ortiz, Ramirez, Drew, and Helton? So many people would be on base, and this lineup would work the count so well, that less than 900 runs would be a disappointment.
3. Acquiring Helton for middle relief and prospects will allow us to spin Lowell of for some additional bullpen help.
Basically, I'd love to see Todd Helton on the Red Sox. The advantages he'd bring to the team are unbelievable. I just think he'll never come here with the way the contract he has is currently structured. It's too bad the thing that's putting him on the market is the thing that's holding him back from moving to a different team.