They have taken some gambles with giving mid tier money out to average players that they think they can get to perform. Grichuk, Kendrys Morales, Tanner Roark, Jaime Garcia, etc. Kikuchi might be another name to add to add to that list in time but we shall see.
But on the other hand they have hit on some of these signings big time. Semien and Ray being the prime examples.
The book is still out on the bigger deals they've done. Ryu looks real iffy right now but he was good enough in his first two years that the deal won't be a total disaster. Then there is Springer who looks great but had a frustrating year last year. If he can stay healthy the next 2 or 3 seasons that one should be fine as well.