Jason Heyward is one of the youngest proven stars seen on the free agent market in a long time he is 26, and has a strong bat that got him a respectable .293/.359/.439 slash line last season. He is also an extremely good defensive outfielder who has a 4.8 dWAR over the past 2 seasons. The best part though about Hayward is that the odds of there being any decrease in his production over the next 5 or more years are very slim due to his young age. He certainly deserves to be earning $20-23 million per year for the next 8-10 years.
Justin Upton and Jason Heyward battled it out this year each trying to prove that they were the top choice for any team looking for a top tier outfielder. To me Upton has the edge in being a proven strong bat in a lineup, but Heyward has the defensive adge and is younger. It will be interesting to see who gets the bigger contract I think Upton will get a higher annual value, but Hayward will have an extra year or two on his contract that will get him the greater overall contract size.
It will definitely take some courage to dish out this much money for a guy who just two years ago batted .196 and has struck out more times than getting a hit in every season of his career. His power is worth more than any single aspect of the other players on this list. The only reason Davis isn't higher on this list is because power is all he has, but with power becoming more and more rare Davis is well worth his pay.
Cespedes is coming off of arguably the best season of his career. Yes his glove could use some work (7 errors last year), but his strong arm still keeps him a worthwhile outfielder. He is worth a lot for his bat which got him a .291/.328/.542 slash line and a 5.1 oWAR last season. He is 29 and will likely be the player for teams who miss out on Upton and Heyward. I would compare his position this year to that of James Shields a year ago. as Hayward and Upton are like Scherzer, and Lester.
Remember this is what I think Gordon should get not what I think he will get. I don't attempt to read GM's minds I look at the stats and use them to decide what I would do. Alex Gordon is simply not worth the money he will likely get, yes he was a leader in bringing the Royals to the world series 2 years in a row and winning it this year, but his offensive stats were well below that of the three outfielders I placed before him on this list, and his defense just doesn't make up for that. This combined with the fact that he is 3-6 years older than each of them makes him the clear fourth choice. On this contract the annual value is pretty low at 13-14 million/year. I think he could be worth 60-65/4 years making him worth a higher annual value but I think he would take the higher total value and security.
6. Colby Rasmus $80 million/5 years $16 mil/y
8. Gerardo Parra $80 million/6 years $13.3 mil/y
9. Howie Kendrick $60 million/4 years $15 mil/y
10. Ian Desmond $65 million/5 years $13 mil/y
11. Dexter Fowler $56 million/4 years $14 mil/y
12. Ben Zobrist $30 million/2 years $15 mil/y
13. Matt Wieters $60 million/5 years $12 mil/y
14. Denard Span $46 million/4 years $11.5 mil/y
15. Alexei Ramirez $36 million/3 years $12 mil/y