Zack Greinke was, in my opinion, the best free-agent starter on the market this winter, so it's fitting he signed the winter's biggest contract so far and the biggest annual salary in baseball history (so far, at least) for any player. Despite its sheer size and the risk any team faces in signing a free-agent pitcher, the deal has a pretty good chance to work out for the Diamondbacks on paper -- but they're going to have to add a couple of additional pieces to turn this team into a playoff contender.
Greinke is awesome -- in production and in the aesthetic sense, as he's an artist at work on the mound, the closest starting pitcher in the majors today to Greg Maddux in his command and feel for setting up hitters. I wrote in my free-agent profile of Greinke that I thought he provided the best probability of maintaining most of his value over a long-term deal of all of the free-agent starters, because the command, off-speed weapons and ability to change speeds speak to someone who'll still be effective even at 88-89 mph. He gave the Dodgers 600 innings of a 2.30 ERA, and averaged around five added wins of value a year with his pitching alone. He's an elite defensive pitcher who can do a few things with the bat, too. If you set the over/under on his WAR over the next six years at 24, I'd probably still take the over, even though those are his age 32-37 seasons. As long as he stays healthy, which he has done throughout his career thanks in large part to a low-effort delivery, he should provide solid value even at this price tag.
The Diamondbacks were 79-83 last season, about a .500 team by run differential, plagued by a number of dead spots in their lineup, a weak rotation with no one better than league average and a bullpen that performed poorly in high-leverage situations. Their wOBA -- weighted on-base average -- allowed in such situations, according to Fangraphs, was third-worst in the National League, ahead only of the Rockies and Phillies. Their overall performance banked on some individual seasons that don't seem very likely to recur, such as those of A.J. Pollock or David Peralta, but there's also some cause for optimism, from Robbie Ray's rookie campaign to the prospect of seeing a full, healthy year from Jake Lamb at third. The net result of a quiet offseason for Arizona was probably a team slated for a slightly better campaign in 2016. Adding Greinke pushes them into the mid-80s in wins, maybe the high 80s, but very likely isn't enough to make them playoff contenders in a division with the Giants and the Dodgers, as both clubs figure to acquire more starting pitching of their own this winter. The Diamondbacks need to see some offense from their middle infield and they need to add at least one more starter; the latter move would push either Rubby De La Rosa or Patrick Corbin to the bullpen, where they might provide the late-game relief option the team needs. The move will cost Arizona its first-round pick in the 2016 draft, which would have been 13th overall. This is a significant and arguably excessive hit given how high the annual salary is relative to any other deal we've seen so far.
The Dodgers are left in a bit of a hole now, having apparently made an aggressive offer but coming up short of the Diamondbacks in years and in annual salary. There are plenty of remaining free agents who'll provide the Dodgers with some of the value they lost -- adding a Scott Kazmir or a Mike Leake could recapture three wins to Greinke's expected five or six -- but if they want a second ace to go with Clayton Kershaw, it probably would have to come through trade. Would Corey Seager and Julio Urias fetch them a Felix Hernandez or a Chris Sale? Would the Dodgers' front office be willing to part with two prospects who rank among the top half-dozen in all of baseball? Trading Seager would leave them with potential holes at both middle infield spots on top of the void they already have in left field, and while Joc Pederson has a ton of potential, his poor contact rate is a major impediment to him being an everyday player. Their non-Kenley Jansen relief corps was awful last season as well. They have a lot of needs to address, and money can't solve them all, especially now that the ideal option for their rotation has gone to a division rival.

Earlier on Friday, the Cubs agreed to a two-year, $32 millions deal with John Lackey. It seems reasonable given his production post-surgery and the length of the other starting pitching contracts we've seen this winter. Lackey's main attribute now is his durability, with 605 innings in 93 starts over the past three seasons, with a 3.35 ERA and excellent control. I do have some concerns about his vulnerability to left-handed hitters, and his performance in 2015 was probably a bit of an outlier, but he could be a 2.5-3 win option for the Cubs in the third spot after Jake Arrieta and Jon Lester, benefiting from what should be a strong infield defense. The move cost the Cubs their first-round pick, 28th overall, which is less valuable than the one Arizona gave up, but is still a significant loss for a team that has had tremendous success with its first-round picks the last several years.