Yanks could pass on the top free agent pitchers now and look for better next winter

Is a Garza now worth a shot at a Kershaw later? (Getty)
Garza now or maybe a shot at Kershaw later? (Getty)

Six years ago, the Yankees took one of the biggest risks in franchise history. The Twins were shopping two-time Cy Young Award winner Johan Santana one year before free agency and he was a perfect fit for the Yankees, a team in need of a workhorse ace left-hander. There were offers and counteroffers, a bidding war between the Yankees and Red Sox, and weeks of rumors. It was exhausting, really.

Santana was a perfect fit for the Yankees … except that he wasn’t. Not only would they have had to trade away some of their top prospects to acquire him, but they’d also would have had to give him a nine-figure contract extension to keep him around. Johan was also showing some signs of decline, particularly in his spiking homerun rate and sudden decreased usage of his slider. There were definite red flags. It was a risky move but the type of move the Yankees usually make, except this time they didn’t. They passed on Santana and off he went to the Mets for a mostly forgettable four-player package.

The Yankees passed on Santana for two reasons. One, they wanted to keep their young pitching. Given the state of the franchise at the time, it was the right move. Two, there was a better option coming along the next offseason. CC Sabathia, another Cy Young winning workhorse left-hander, was due to become a free agent following the 2008 season, when New York could acquire him for nothing but money (and a draft pick). It was an incredibly risky move because there was no guarantee Sabathia would actually hit the open market, but the Yankees rolled the dice and a year later they got their man. They kept their young starters and got their ace lefty. Santana, meanwhile, gave the Mets one Cy Young caliber season before starting to break down. The plan couldn’t have worked out much better for the Yankees.

Fast forward to present day, and the Yankees are in a bit of a similar situation. No, they aren’t trying to trade for a Cy Young winning ace southpaw (that would be David Price), but they are in the market for pitching and there are some pricey options sitting out there for the taking, namely Ubaldo Jimenez, Matt Garza, and Ervin Santana. Those are the three best free agent starters available right now while Masahiro Tanaka sits in posting system limbo. And you know what? None of those three guys is a slam dunk, we gotta have him starter. Jimenez was awful as recently as the All-Star break, Garza has been hurt the last two years, and Santana was awful in 2012. The track records are as sketchy as they get for a high-priced starter.

Those are the top free agent pitchers available right now, with Hiroki Kuroda off the board and Tanaka not yet available. Now, courtesy of MLBTR, here is a sampling of the hurlers scheduled to hit the open market one year from now, during the 2014-2015 offseason (2015 season age in parenthesis):

Homer Bailey (29)
Clayton Kershaw (27)
Jon Lester (31)
Justin Masterson (30)
Max Scherzer (30)
James Shields (33)

Those are six pretty great pitchers, right? Just about all of them are reasonably young too. I’d rather have any of those six over Ubaldo or Garza or Santana, that’s for sure. Obviously those guys could sign extensions between now and next winter — Kershaw, Scherzer, and Lester seem most likely to ink an extension at this time — but there’s just so many of them that one or two figures to slip through the cracks and be available next offseason.

If Tanaka doesn’t get posted — I still think they should go all out to land him if he does indeed become available at some point — I think the Yankees would be better off repeating their Santana-Sabathia strategy. Rather than pay for an imperfect solution like Garza or Ubaldo or Santana right now, they could sign a stopgap starter (Bartolo?) for this year before going hard after one (or maybe even two) of those top guys next winter. They’ll want to have as much money available as possible if, say, Kershaw and Scherzer hit free agency next winter. Or Bailey and Masterson. Or Lester and Shields. You get the point. A stray Ubaldo could gum up the works.

Would this plan be risky? Absolutely. There’s a chance all of them will sign extensions before free agency and the Yankees will be left out in the pitching cold. Is it worth the risk? I think it is when there are six (not one or two) of these guys and the alternatives are Garza, Jimenez, and Santana. That’s easy for me to say when my neck isn’t on the line, obviously. It could be that the Santana-Sabathia situation was a one-time thing the Yankees are not willing to risk again, but because they took that risk once before and it worked out so wonderfully, we kinda have to assume it isn’t completely off the table in the future. If Tanaka is not posted, the Yankees’ best course of action maybe be signing a stopgap starter and focusing on those premium arms slated to hit the market next winter.

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Update: No traction in talks with Cano, Yankees have other offers out

3:56pm: According to Jon Heyman, the Yankees are “currently engaged” in talks with Beltran, Drew, Kuroda, Jacoby Ellsbury, Shin-Soo Choo, and various unnamed mid-rotation starters. Matt Garza and Ubaldo Jimenez are not in the mix at the moment.

1:12pm: Via Buster Olney: The Yankees still have offers out to various free agents even after agreeing to sign Brian McCann last night. He says there is currently no traction in talks with Robinson Cano and the team doesn’t want to sit around and wait. I dig it. In addition to Cano, I’m guessing they have offers out to … Carlos Beltran, Stephen Drew, Grant Balfour, and Hiroki Kuroda. Whaddya think?

King: Yankees have Ubaldo Jimenez on their radar

Via George King: Among the players on the Yankees’ radar this offseason is free agent right-hander Ubaldo Jimenez. The Indians made him a qualifying offer earlier this week and he’ll presumably reject it before next Monday’s deadline, meaning it will cost a high draft pick to sign him. For New York, that means the 18th overall pick.

Jimenez, 29, had a 3.30 ERA and 3.43 FIP in 182.2 innings this season, but he was awful in the first half (4.56 ERA and 4.50 FIP) and great in the second half (1.82 ERA and 2.17 FIP). He’s been incredibly up and down in recent years and there’s an A.J. Burnett-esque quality to him in that you don’t really know what you’re getting from start to start. Jimenez is still relatively young and he misses bats (9.56 K/9 and 25.0 K%), but his fastball velocity has declined in each of the last four years. The Yankees need pitching and should be looking at everyone, but Ubaldo is so very unpredictable. I don’t really know what to think.

Mailbag: Drew, Infante, Ubaldo, Playoff Roster

Five questions and five answers this week. Use the Submit A Tip box in the sidebar to send up anything at any time, mailbag questions or otherwise.

(Leon Halip/Getty)
(Leon Halip/Getty)

John asks: Hypothetically speaking (how else would we speak when speculating about the offseason?), if Robinson Cano were to get say $29M per year for nine years from the Dodgers, could the Yankees sign Brian McCann, Stephen Drew and Omar Infante for $29M combined? And, if so, might that be a better strategy for 2014 and beyond?

I don’t see how they could get those three for only $29M total. McCann is looking at Yadier Molina money on the open market ($15M annually) while neither Drew ($9.5M) nor Infante ($4M) have a reason to take a pay cut following their strong seasons. I think the best case scenario is something like $35M total, broken down into $15M (McCann) plus $12M (Drew) plus $8M (Infante). I’m probably underselling Drew and Infante given the dearth of quality middle infielders. It might be closer to $40M total than $35M when it’s all said and done.

If the Yankees can’t re-sign Cano — I would be stunned if they didn’t at this point — then spreading the wealth around is pretty much the only thing they can do. There’s no other superstar available this winter who is worth a nine-figure commitment. (Maybe Shin-Soo Choo. Maybe.) McCann plus Drew plus Infante would be a real good start, bhe Yankees need more pitching and outfield help though. This team isn’t one or two players away from getting back into contention. This roster has an awful lot holes.

Chris asks: Would you be in favor of reducing the time between signing and free agency? Teams today are forced to decide between players hitting their free agency years around age 28-30. Small market teams won’t pay for players past 30 and subsequently lose their players while big market teams continuously pay and pay. It hurts everyone. Isn’t the answer to make players free agents earlier? Cano would be worth millions and millions more if he was two or three years younger.

Oh yeah, absolutely. I am decidedly pro player when it comes to this stuff. Let them become free agents as soon as possible. Teams would never agree to it and, frankly, small market clubs would have no chance to contend if they didn’t get to control their young players for what is usually the most productive years of their career. If they knocked it down to five or even four years of team control before free agency, clubs like the Rays and Athletics would have no chance to contend. It would be a franchise killer. Baseball’s salary system is screwed up in that players earn the most when they’re on the decline, but it is what it is. The six years of team control are a necessarily evil.

Karl asks: How much amateur money is at stake over the possible variation in the final standings? Any chance a post-qualifying offer Hiroki Kuroda signs with the Dodgers to chase a ring and gets the Yankees a comp pick?

I’ll answer the second part first: yes I could definitely see Kuroda signing elsewhere in hope of winning a ring. The Dodgers are an obvious destination but the Tigers, Rangers, Nationals, and Cardinals could also be fits. Despite his ugly finish to the season, I’d have no trouble making Kuroda a $14M qualifying offer. It’s a no-brainer in my book.

As for the standings, the Yankees could finish with anything from the 12th through 16th best record in baseball. The Blue Jays have a compensation pick early in the first round, so that would give them the 16th through 21st overall pick. Right now they have the 17th overall pick and the only way they can move up to 16th is if they get swept by the Astros while the Diamondbacks sweep the Nationals this weekend. That’s the only possible way to move up at this point.

Based on last season’s slot values, that’s the difference between the 16th ($2.3M) and 21st ($1.97M) picks is kinda small. Nice chunk of change but not a game-changing amount. The 17th overall pick was slotted for $2.16M, but the values are expected to increase next summer. Based on historical data and all that, the difference in expected future value of the 16th pick and the 21st (or 25th or 30th, for that matter) pick is negligible. That’s all theoretical though, anything can happen in one given year. Obviously you’d like the higher pick.

(Jason Miller/Getty)
(Jason Miller/Getty)

Christopher asks: Would you be interested in the newly back on track Ubaldo Jimenez at around $13M? I think there’s great value there and he could be the steal that helps the Yankees get back on track.

Once upon a time I was in favor of trading Jesus Montero for Jimenez, and for a while there it looked like the Yankees dodged a serious bullet. Obviously that seems silly now because Michael Pineda still hasn’t thrown a single pitch for the team in the 20 months (!) since the trade. Seriously, he’s missed two years (and counting) with that shoulder injury. What a disaster.

Anyway, this is purely hypothetical because there is an $8M club option in Ubaldo’s contract for next season and the Indians will surely pick that up. The 29-year-old has a 3.38 ERA and 3.57 FIP in 176 innings this season but he’s been even better in the second half: 1.86 ERA and 2.39 FIP in 77.1 innings. Jimenez has been a big reason why the Tribe jumped over the Rangers in the wildcard race.

Update!: Turns out Jimenez’s club option became a mutual option after the trade. He’ll surely decline his half and become a free agent.

Now, as good as the second half has been, we have to remember Ubaldo was really bad just last season. Heck, he had a 4.56 ERA and 4.49 FIP in 98.2 innings of the first half this year. Last year it was a 5.40 ERA and 5.06 FIP in 176.2 innings. Jimenez would be worth a much deeper look if he was indeed going to be free agent — did he actually change anything? — but I’d be very skeptical about giving him $13M a year based on a good half-season. High reward but super duper high risk.

Donny asks: Since we might not actually get to see this come to fruition, I figured I would ask: What do you think the playoff roster might/should look like?

I’ve been saving this question for like, three weeks now. I didn’t want to answer it while the team still had a shot at the postseason because I figured there might be serious playoff roster talk at some point. Now that they’ve been eliminated, let’s have at it. Based on who is actually healthy and available right now, here’s the 25-man roster I would take into the wildcard play-in game/ALDS:

Catchers Infielders Outfielders Rotation Bullpen
Chris Stewart Robinson Cano Curtis Granderson CC Sabathia Mariano Rivera
J.R. Murphy Lyle Overbay Ichiro Suzuki Hiroki Kuroda David Robertson
Eduardo Nunez Alfonso Soriano Andy Pettitte Boone Logan
Mark Reynolds Zoilo Almonte Ivan Nova Shawn Kelley
Designated Hitter David Adams Vernon Wells Phil Hughes David Phelps
Alex Rodriguez Adam Warren
Travis Hafner
David Huff

The opponent would dictate the bullpen to a certain degree. If the Yankees drew an opponent with a right-handed heavy lineup, I would probably take Phil Hughes Preston Claiborne over Huff. In this general case I’d take the second lefty.

The Yankees have an alarming shortage of useful position players. Brendan Ryan is not eligible for the postseason roster because he wasn’t in the organization on August 31st, so Nunez is the starting shortstop by default. That leaves Adams or Reynolds as the everyday third baseman if A-Rod‘s various leg injuries don’t heal up in time. Hafner is pretty useless, but I’d rather have the extra bench bat than the 12th pitcher. I’d trim the staff down to ten pitchers if there was another position player worth taking. That … is not an inspiring roster. Geez.

Sunday’s Trade Deadline Open Thread

The non-waiver trade deadline is 4pm ET today, though we’ll occasionally see news of a deal leak out a little later than that. I remember word of the Kerry Wood trade broke at like, 4:15pm ET last year. Do the Yankees have a starting pitcher up their sleeve? We’ll find out soon enough. Let’s keep track of the latest here throughout the day, with the most recent news up top…

  • The Yankees aren’t going after any big-name arms at the moment, if anything they’ll make small, incremental upgrades. (Morosi)
  • Nevermind, Wandy’s not going to Cleveland. The Yankees wanted the Astros to pick up half the money on the lefties deal, but Houston said no and talks about the left-hander are dead. (Justice, Heyman & Jayson Stark)
  • The Yankees are not deep in any talks, and get this, it sounds like Wandy is heading to the Indians for two minor leaguers. How about that. (Olney & Richard Justice)
  • Bell Mike Adams is apparently headed to the Rangers. It was unlikely the Yankees would get him anyway, but at least now we don’t have to worry about it. (Ken Rosenthal)

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