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Sure, there are the big names: Jake Arrieta, Yu Darvish, Lance Lynn. All will have very competitive markets, and will likely end up with nine-figure deals.
One can argue that the smarter way to spend in free agency is targeting high-ceiling pitchers in buy-low opportunities. If you hit on one of these tickets, you can end up with a top-of-the-rotation starter; if you miss, you're not committed to anything beyond a one-year contract.
Brett Anderson's name has become something of a running joke among the Twins Daily writers, because I have reliably mentioned him almost every offseason as a player the Twins should look into. In some ways, he's the prototype for the free agent pitching gambles we're discussing here – talented enough to be a high-caliber starter if healthy, but with enough question marks that no team will give him more than a make-good deal. He's most often a good example of the downside.
As it happens, Anderson's out there again this offseason, but even I've lost hope for the oft-injured southpaw, who has thrown 60+ innings just once since 2011.
Luckily, there are plenty of others in the same category offering far more realistic upside. These five names – drawn from the Offseason Handbook – are my favorites among this group.
Chris Tillman, RHP (29): From 2013 through 2016, Tillman averaged 190 innings with a 3.91 ERA while pitching for Baltimore in the offense-packed AL East. His 2017 season was a total mess, yielding a 1-7 record and 7.84 ERA, so now Tillman will be looking to re-establish some value in search of a long-term deal next winter. He doesn't turn 30 until mid-April. As someone who allows a fair amount of contact, the right-hander could be swayed by the opportunity to pitch in front of an elite defensive unit that will help his numbers.
Trevor Cahill, RHP (29): The Royals traded for Cahill ahead of the deadline with hopes he'd help get them over the hump, but the move fizzled horribly as he battled shoulder issues throughout the second half, making only three starts for KC. Prior to the trade, Cahill had been highly impressive as a starter for San Diego, averaging 10.6 K/9 while posting a 3.69 ERA and 3.40 FIP. If they can recapture that form, the Twins would have a nice rotation weapon, or else they could try him as a reliever (he was excellent in that capacity for the Cubs in 2016).
Tyson Ross, RHP (30): Much like Matt Harvey and Phil Hughes, Ross's return this year from thoracic outlet syndrome surgery didn't go smoothly. He put up a 7.71 ERA in 12 appearances for Texas before being released in September. But between 2014 and 2015, he made 64 starts with a 3.03 ERA and 9.4 K/9 rate. He's definitely a talent worth betting on, and will likely need to settle for a minor-league contract.
Jeremy Hellickson, RHP (30): Coming off a strong 2016 campaign with Philadelphia, Hellickson had a chance to hit free agency for the first time and score a sizable multi-year deal. Instead, he accepted a qualifying offer from the Phillies, taking a $17 million salary and hoping to springboard back into the market this winter. That... didn't happen. The righty endured the worst season of his career (5.43 in 30 starts) and now he'll likely be seeking a one-year deal to rebuild his stock. The Twins can offer a contending environment and a great defense, so the right offer probably gets it done.
Ubaldo Jimenez, RHP (33): Gulp. What am I doing here? Jimenez was one of the prime culprits in a horrendous Orioles rotation this year. He led baseball in earned runs allowed. Turning 34 in January, he owns a 6.13 ERA and 1.58 WHIP over the past two seasons. It goes without saying there's major risk. But Jimenez still does have those occasional flashes of brilliance that make you wonder. He struck out 11 in an August start and 10 in a September start. Maybe a change of scenery and new pitching coach enables that dominant side to come out more often? It bears noting that Jimenez's last good year came in 2013 in Cleveland, when he posted a 3.30 ERA over 30 starts for Derek Falvey's Cleveland Indians.
Which free agent starter names in the Offseason Handbook stand out to you? If you haven't gotten yours yet, make sure to order and download now so you'll have a handy resource in hand as the free agency frenzy gets underway.
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