Justin Masterson isn't asking for much. While other soon-to-be free agent starters are signing massive extensions or declaring their intent to go to free agency if their team doesn't make an out-of-this-world offer, Masterson is talking about a positively sane three-year, $40 million extension. He'd also be open to a four-year, $60 million deal, but that's the biggest number we've seen from the right-hander's camp this winter.
Masterson certainly isn't anywhere near Clayton Kershaw's orbit, but as Dave Cameron pointed out earlier today, he and Homer Bailey are reasonably comparable in terms of overall value and future projection. Bailey got close to $100 million from a small-market club while Masterson is asking for about half. For now, Max Scherzer, James Shields and Jon Lester are leading the 2015 free agent class, and Masterson represents the next-best option.
He is entering his age-29 season after an uptick in strikeouts in 2013 to go along with his already impressive ground ball rate. He's been an average to above-average starter over each of his four full seasons in the Indians rotation and hasn't had any serious injuries during that time. He's durable and peaking, but he's not holding out for the big dollars. And it might actually turn out to be a very smart move.
It's hard to argue against the Indians agreeing to this deal. It represents something between a clear discount and market value and it guarantees they have a solid top half of the rotation starter for the next few years. Maybe it's not the Evan Longoria extension, but unless they know something about the health of his elbow that we don't, it makes sense for the Indians to sign this deal. It would be tough to explain rejecting the offer to their fans while also trying to convince them to start coming back to the park.
The interesting thing here is that Masterson isn't reaching for the $100 million contract that he might be worth given the Bailey deal. Instead, he's protecting himself against the doomsday scenario playing out at Ervin Santana's kitchen table.
Assuming Masterson has a solid season in 2014, the Indians will certainly extend a qualifying offer. Although Masterson is better than Ricky Nolasco, Ubaldo Jimenez and Matt Garza, the general trend is to give that level of pitcher something around four years and $50 million. Two of those players didn't cost a draft pick, and the one who did has a much higher ceiling, but you fold that into the problem Santana is having getting what he feels is a fair deal and you have a pretty clear picture. Masterson probably isn't good enough to drastically exceed the 4/$50MM model with a draft pick attached.
All of this comes before you consider those three big names looming on the free agent market. Ervin Santana and Ubaldo Jimenez were the best starters on the market after Masahiro Tanaka; Masterson would be the fourth-best option in 2015. The big-spending teams are going to target the available aces and Masterson will be left for the less wealthy, less desperate bunch.
In other words, unless Masterson has a standout, Cy Young kind of season, it's hard to imagine he gets more than $60 million on the free agent market next winter. He plays for a team with financial constraints, so he can't expect to sign a $100 million extension, but he also knows that the nature of the qualifying offer and the competition he'll have on the market is conspiring against him.
Four years and $60 million doesn't seem like a big request, but it's actually a very smart move. It's too reasonable for the Indians to reject and it's enough to be sure he's not leaving much on the table next offseason. Very rarely do you see a player open the negotiations with what appears to be a low-ball offer, but by doing so, and by doing so semi-publicly, he's essentially guaranteed himself a payday that might otherwise have vanished. Ervin Santana famously started the offseason talking about a $100 million deal and he might end up signing a one-year deal after Opening Day.
Masterson is learning from that mistake. If you don't think you're going to be the darling of the winter meetings, get ahead of the qualifying offer, take the deal you're worth and do so in a way that makes your offer look team-friendly. The Indians haven't responded to the offer, according to Chris Cotillo of MLB Daily Dish, but they're going to have to. Their ace just outmaneuvered them and likely earned himself an extension.