I get that but your premise is flawed. There's no sure thing just because a contract is bigger. Lots of bigger contracts were disasters because pitching is very damaging to arms and there also isn't always that much pitching out there. Here are the pitchers who got more than Nolasco, Santana and Hughes the last few years. In 2013 the big three deals were for Grienke, Edwin Jackson and Anibal Sanchez. Grienke's been great although his contract had an opt out that he used to sign with the Dbacks. Sanchez and Jackson were bad deals. n 2014- Tanaka, Garza and Ubaldo Jimenz. Tanaka was a bit special as a FA from Japan and younger than most. The Yankees gave him a 7/155 deal which hasn't been bad so far although this was a bit of down year. Garza, Jiminez and Nolasco all got about the same deal and Nolasco was probably the best of them. In 2015 Scherzer, Lester and Shields got signed for more than Santana. Lester had two good years but was not good this year and is trending down. He'll be 34 next year and owed 85m over the next three seasons (counting the buy out). Scherzer got a 7/210 deal and has been awesome so far. Shields, 25/year, has been a disaster. And before the 2016 season the big deals were David Price, Grienke, Johnny Cueto, Jordan Zimmerman, Jeff Samardzija, Wei-Yin Chen, Mike Leake, Ian Kennedy and Scott Kazmir. All nine of those guys got bigger deals than Ervin. Price had a great first year but was injured and feuding with the media and is still owed nearly 160m. Greinke is good. Cueto put up a 93 ERA+ and is injured. Zimmerman was worse than Kyle Gibson this year. He'll be 32 next year and still owed 75m. Shark's been serviceable but he's never been as good as his rep. Chen's been a disaster. Leake was already traded for nothing and two teams are dividing his salary. Kazmir missed the entire season and Kennedy sucks. So that's the whole list of pitchers who signed for more than our guys over the last few years. It's not a great list. Grienke and Scherzer are about the only two who have been worth it (so far) and they signed for a lot more than 150m. Tanaka, maybe. Too early to give up on Price but it looks bad. I'd probably rather have Santana's contract straight up over any of the rest of those guys. So it's not really realistic to say the the Twins should just sign one big contract. First, they'd have to compete with the Yankees, Dodgers and Nats for it which they simply won't do. And second, there's no promise that the player would perform.