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Article: The 5 Best Pitching Gambles In Free Agency

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#1 Nick Nelson

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Posted 05 November 2017 - 08:46 PM

At 9:00 am on Monday, MLB free agency will officially be open for business. At that point, the Twins front office can embark upon its quest to improve the starting rotation via external additions.

Let's take a look at some of the best potential bargains in this year's class.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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#2 mikelink45


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Posted 05 November 2017 - 09:00 PM

Easy question - none.Why would we do this?What is the upside?Someone else is always better than what you got.Nope.Save the money.Look at something better. 

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#3 spinowner


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Posted 05 November 2017 - 09:03 PM


Easy question - none.Why would we do this?What is the upside?Someone else is always better than what you got.Nope.Save the money.Look at something better. 

Save the money. Use it to extend some of our core position players.

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#4 Thrylos


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Posted 05 November 2017 - 09:06 PM

Hellickson has a really intriguing 2.36 ERA and0.960 WHIP the first time though an opponents' order (68-2/3 IP), which makes me think that despite his K% being low, he might be intriguing as a potential bullpen set up guy. However, a. would he do it? and b. would he do it at a rate ($2M plus incentives) which will make him a "bargain"?


I doubt both.


Tillman, Ross, and Cahill are about as healthy and effective as Phil Hughes.


Jimenez's last great season was in 2010, and even 2.5 seasons in Cleveland could not fix him much.His FB is 6 mph slower than its peak.Might take a flyer on a MiLB contract, but that's about it.  


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#5 Hollywood42



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Posted 05 November 2017 - 09:44 PM

Sigh. I understand being realistic and accepting we probably won't get Darvish or Arrieta. That's fine. But Trevor Cahill? Tyson Ross? Ubaldo freaking Jimenez? We should not even consider touching any of these guys with a 10 foot pole. Even if we could rely on any of them to be a decent #3-5 starter, which we can't, why in the world would we add another one of those to the mix? We already have Gibson, Mejia, Hughes, and May that will be competing for those slots. Plus Gonsalves, Romero, Jorge, and a few others in the minors that could slot in there. That's a minimum of 7 guys for 3 slots. Why in the world would we add another guy to that mix? None of the guys in this article are remotely good enough to consider adding to the team.


We need front end rotation help. We all know it. We just have to actually go out and do it. None of these guys are remotely helpful in the slightest. I think I actually gagged when I saw Jimenez on this list. Again, we probably won't get Darvish or Arrieta. That's cool. But to jump all the way down to this tier of pitching? Disgusting.


Two guys that could be good fits are Alex Cobb or Lance Lynn. They aren't #1 type pitchers, but they could work as #2-3 types. They'll both get decent contracts, but not big enough where the Twins are immediately out of contention for them. Plus, both of them would actually be helpful to us. Ideal situation, I think we should try to sign one of them. A rotation of Berrios, Santana, Cobb or Lynn, and then two of whoever's pitching best of the guys I listed about would be a competent rotation. Then in the ideal situation, we try to trade for a #1 at the deadline. We still have some assets in the minors that could get a deal done. For me, that's the ideal situation. Sign Cobb or Lynn now, and if we're looking like a contender at the deadline, go trade for an ace.


I'm all for being realistic in our expectations, and I really have enjoyed reading articles on this site, but I hated everything about this article, and it made me create an account just so I could voice my displeasure. Twins, please do not sign one of these bad pitchers. Be smart, make some good news, and improve the club

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#6 Mike Sixel

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Posted 05 November 2017 - 10:01 PM

Awful list
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There's always next year, or the next, or maybe by the time I'm Chief's age, I guess....

#7 Kirbek


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Posted 05 November 2017 - 10:42 PM

Lots of hope in this list.Too much hope for me.They just need one or two good bets.

I once knew a man from Nantucket.  He too was a fan of Kirby Puckett.

#8 The Wise One

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Posted 06 November 2017 - 12:06 AM

I think these people would make a fine opening season starting rotation for Rochester. Where is the story that the Twins dealt the entire Rochester rotation for an elite pitcher?

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#9 drjim


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Posted 06 November 2017 - 06:32 AM

I'd be on board if it was the second starter acquired and on a 1 year deal. Try to catch something on short money and build some depth.
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#10 Penthang


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Posted 06 November 2017 - 07:03 AM

The only way I’d want to see one of these guys signed is if it is after Cobb or Lance or a trade for someone in that tier, and only then on a minor league deal. Theoretically they each have some potential to bounce back and contribute but I’d really rather see one of the probable AAA guys succeed into the rotation that one of these guys. We should start the year with some good high potential arms just a step away with a lot more upside than any on this list. As I recall Molitor was quite high on Gonsalves during spring training last year. This has the feel of a Terry Ryan move to me leaving me with the feeling that until someone’s arm falls off the young guys won’t be given a shot.
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#11 mazeville


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Posted 06 November 2017 - 07:10 AM

After Phil Hughes and Glen Perkins I don't want to touch any pitcher with thoracic outlet syndrome. 


At best you could do a minor league deal. But what's happened to some of these guys has been scary. 

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#12 IaFan1



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Posted 06 November 2017 - 07:18 AM

Tyson Ross intrigues me. A second year out from thoracic surgery and still only 30. When healthy, he could be close to a #2 type pitcher. 

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#13 Doctor Wu

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Posted 06 November 2017 - 07:22 AM

Not sure what happened to Hellickson last year, but I still think he's young enough and has some attributes that would help the Twins' rotation. He might be worth taking a chance on.

#14 ashburyjohn


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Posted 06 November 2017 - 07:24 AM

I hated everything about this article, and it made me create an account just so I could voice my displeasure.

Welcome! Great first-post. Have a look at the TD Comment Policy (nothing of which you came remotely close to violating BTW), and then we look forward to seeing more from you. :)

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#15 tarheeltwinsfan


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Posted 06 November 2017 - 07:30 AM

1) I'm afraid the odds are against any of these 5 pitching well enough to be of any help to the Twins. What if even 1 of the five proved effective. The odds are still 80% that the Twins won't select the 1 of the 5 that will help. 2) Give our best young pitchers experience in the majors, which they all will eventually need in order to succeed, rather than signing any of these 5. Please.

#16 Tommygun921


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Posted 06 November 2017 - 07:38 AM

I could realistically see the Twins taking Tillman or Hellickson on a 1 year deal. Unless one of the others were to sign a minor league deal. I'd certainly rather see them take a chance with Tillman or Hellickson over them trying Santiago again.

#17 diehardtwinsfan



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Posted 06 November 2017 - 07:40 AM

Ross on a minor league deal makes a ton of sense. I have no issue with those types of signings.

Cahlil is the guy in this group that might be worth targeting, though I hope that Falvine's medical staff is a bit better than Ryan's. Shoulder injuries tend to be something a player recovers from more than say elbow injuries.

My problem is that I'm not sure a 1 year make good deal makes sense for this team unless they are really serious about going after a big pitching FA next season. Personally, I doubt that enough of our younger guys are going to be able to prove in 2018 that they are ready for what would now be 2 (or possibly 3 with Gibson) openings in the rotation.

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#18 MN_ExPat


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Posted 06 November 2017 - 07:47 AM


After Phil Hughes and Glen Perkins I don't want to touch any pitcher with thoracic outlet syndrome. 


At best you could do a minor league deal. But what's happened to some of these guys has been scary. 

True, I'd agree totally on the TOS... but Perkins tore his labrum. The fact that he could even come back pitch again at all was a victory for him (still scary though).

#19 laloesch



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Posted 06 November 2017 - 07:50 AM

Well if were doing this Vegas style I put some money on Lance Lynn.I think he'd be a decent addition to the rotation.Not an ace but he would be a solid #3 and push Gibson down to the bottom of the rotation. 

#20 dbminn


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Posted 06 November 2017 - 08:19 AM

Ross on a minor league deal would be okay but not necessary. None of the others.