What to do with Edwin Jackson? Exploring the Cubs options for their most expensive player

What to do with Edwin Jackson? Exploring the Cubs options for their most expensive player

Edwin Jackson has been bad. There is no denying this. There have been games where he's been decent; he's thrown seven quality starts this season, even though it feels like he gets beat up every time out. It's sad to have to finally admit that it looks like the first big Theo Regime free agent just isn't working out.

He had a down season last year, but his peripheral numbers suggested that the poor ERA was an aberration. Most right-thinking people believed that, based on his history, velocity, and consistent exterior numbers, that he would return to being the pitcher that he was for the White Sox, Cardinals, and Nationals.

And through mid-May, this was true. But since, he's been terrible. His ERA (not the best pitching indicator, but still) is up to 5.76. In his last 8 starts, his ERA is 7.52. Batters are hitting .319/.377/.554 off of him during that stretch. That's not just bad, that's not good enough to be in the Major Leagues.

Evan Altman gave a solid suggestion as to why Jackson has been so bad, but I'm not here to make any such hypotheses on that topic. All that matters to me is that he's bad, he's had long enough to figure it out to suggest he won't be getting better, and something needs to be done. So let's look at a few options.

Put him in the bullpen!

I go back and forth on this option. On the surface it makes sense, for at least a few reasons. First, as Evan also suggested, the uptick in his velocity may be more conducive for getting guys out as a reliever. Second, it allows the Cubs to look at another starter. Dan Straily is starting for the Cubs today, and would fit into a rotation alongside Travis Wood, Jake Arrieta, Kyle Hendricks, and Tsuyoshi Wada, should he pitch well.

Dallas Beeler is another guy that pitched well at AAA this year, and also did well in his spot start earlier this season. No matter how bad any guys replacing Jackson are, it's still likely worth the tradeoff of finding out just how good or bad they are. The bullpen scenario gives the Cubs an idea of what pitchers may be useful going forward, even if it is only as 6th, 7th, or 8th starters.

The downside is that, by bullpening Jackson, you essentially admit that he's a lost cause. Stick with me on this one. If you leave him in the rotation, you leave open the option that he may have a string of decent starts that improves his numbers. Going into the off-season, at least that gives you some ability to sell a pitching-desperate team on taking him off your hands.

And in general, teams don't usually like to openly give up on 30-year-old starting pitchers with decent velocity and 2 years, $22 million left. It's a bad move for business, unless you're chasing a pennant and desperately need wins. Leaving him in the rotation serves two purposes: if he sucks, you lose more games and get a higher pick; if he rights the ship and pitches well, it makes dealing him a bit easier.

Keep him, pray he figures it out.

Maybe the Cubs look into dealing him in the winter but decide that, for whatever reason, two seasons of bad are an anomaly. Even with the Jackson contract, the Cubs still only have around $50-$60 million in contracts on the books for 2015 (with estimated arbitration raises). It's not like Jackson is preventing them from going and signing a difference-maker.

Let's say they land Jon Lester and plan to pair him with Jake Arrieta, Travis Wood, Kyle Hendricks, and Jackson. You could certainly do worse than that rotation. Of course, you could do better as well. But in the mind of the Cubs front office, if you still don't think your team will be ready to compete until 2016, you might be able to deal Jackson next July if he surprises you and has a decent first half. It's an option that fills our hearts with ache, but we must prepare ourselves for nonetheless.

Bad contract swap!

As Cubs fans, we're familiar with the bad-contract-dump. From Todd Hundley to the Dodgers, Sammy Sosa to the Orioles, Milton Bradley to the Mariners, and Carlos Zambrano to the Marlins, we've learned the hard way that big contracts carry a huge downside. However, sometimes those swaps can work out (look up what the Cubs got for Hundley, for example).

The bad contract swap requires two things: a team that has another bad contract they want to unload (duh), and the general ability for the Cubs to accept that player. For example, trading E-Jax to the Phillies for Ryan Howard would not work, as he's blocked by Anthony Rizzo. Otherwise, that trade would actually be reasonable (depending on the Phillies eating some of the money on their end).

There are a few bad contracts in Major League Baseball that are worth exploring.

*Matt Kemp (OF, Dodgers)

The Dodger's have made no secret of the fact that they've tried to deal Kemp. Since falling off from his MVP-type-season of a few years ago, Kemp is basically a replacement level player (he has a 0.2 WAR in 2014). His batting stats are decent, as his .804 OPS suggests. However, his defense is below-average in center field and it's basically stuck him in left field. But guess what? The Cubs could use an outfielder.

There is potential upside for both, here. Jackson has pitched for the Dodgers before, and perhaps a change of scenery could help him hit the reset button (at least that's what the Dodgers will tell themselves). The Dodgers are very serious about “going for it” right now, and starting pitching depth is necessary for any team with serious aspirations.

The Dodgers have plenty of outfielders and it's been rumored that they don't really want a ton in return for Kemp, just salary relief. If the Cubs were willing to take on the rest of his deal, a straight swap of Jackson and Kemp would make a lot of sense for both teams.

*B.J. Upton (OF, Braves)

I cringed just writing this. Upton is under contract through 2017, and has been flat awful. He slashed .184/.268/.289 in 446 PA in 2013 and .210/.281/.333 so far in 487 PA in 2014. Ouch. The Braves have to be completely desperate to unload him. However, I think the Cubs would really need to be enticed into this deal.

Even forgetting that his contract runs a year longer with $20 million more than Jackson, the swap is flat unfair. The Braves would have to eat a large portion of Upton's money, send another really good player with Upton, send a top prospect, or some combination of the three. If the Braves offered to pay for the entire 2017 season of Upton's deal and, oh let's say, offered a solid starting pitching prospect as well? It might be worth the deal.

*John Danks (LHP, White Sox)

This one is a little out there, as I haven't really heard the White Sox to be needing to unload Danks. However, GM Rick Hahn is an outside-the-box type guy. With a rotation with four potential left-handed starting pitchers in 2015, it would make sense that they could stand to swap one for a righty.

The money and years on the deals are almost identical, the players wouldn't even need to change residences, and it actually makes sense. Danks has been a tad better than Jackson the last two years, and when factoring in that he has pitched in the AL, maybe the Cubs need to throw in a low level prospect to get it done. Jackson plus Stephen Bruno for Danks? DO IT!

*Ricky Romero (LHP, Blue Jays)

This one is worth exploring. Romero has been bad and hurt the last few years. He's had elbow injuries, problems with both knees, and effectiveness issues tied in. If you think Jackson has been bad, check out Romero's stats from 2012 on. The difference is the money, though. Romero is owed $7.5 million in 2015 and $13.1 million in 2016, but with a $600K team buyout option.

So we come to another instance of “realistically good for both.” The Blue Jays could use more pitching depth, as they fancy themselves contenders in the AL East. They were fairly upset to have missed the boat on both Jeff Samardzija and Jason Hammel.

If they could get a return to previous mediocrity from Jackson, it's a great gamble to take. They essentially get a starter for the next two years for only $14 million investment. Even if he's relatively bad, at least he eats the innings and adds depth.

From the Cubs end, they get salary relief to allocate towards other players. They only end up owing Romero slightly more than $8 million after the buyout, so they save around $14 million over the next two years. That money could turn into signing a different starter like Justin Masterson to take Jackson's spot.

For the fact that the Blue Jays take the lion's share of the risk, the Cubs again likely throw in a low level prospect (maybe Dan Vogelbach?) to get this deal done. If they do, it's a win-win for both.

The Edwin Jackson situation is a tough one for the Cubs right now. They have young kids that need a look and Jackson struggling every fifth day. They also have no need to push for more wins right now and a lot of money and time left on his contract. It's delicate to say the least.

Jackson may end up in the bullpen at some point this year, or he may not. But I think the Cubs will have plenty to talk about going into the off-season, whether it be about his standing on the team going into 2015 or what kind of bad contract they could accept in a trade. Either way, Jackson just hasn't worked out for the Cubs and it's time to move forward.

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  • Am I wrong in believing that Jackson's remaining contract is 2 years and $22M, not $26M? There was an $8M signing bonus. The average salary per year is $13M, but that isn't his actual salary. That is "only" $11M.

    I appreciate the attempt of this post. It is interesting and a conversation starter. Given that 2 of the 4 teams listed are teams that Jackson has already pitched for, I find an already unlikely scenario even more unlikely. I'm sure they've already developed a negative taste in their mouths in reference to EJax. Can't believe the Dodgers or White Sox would get desperate enough to give him a second go.

    Still, the strategy is interesting. I'd personally be in favor of eating the whole contract to get better quality (any kind of prospect?). But what about another outside-of-the-box idea, like eating salary and trading him to a team for some quality vet bench players? There may be teams "out of it" or who will be soon who may be dumb enough to undervalue their bench. Strengthening the bench more for next year may be a solid investment of an EJax trade. Just a thought.

  • In reply to cubbie steve:

    Yes it is 2 years $22M.

  • In reply to Theo Epstein:

    Hopefully I gave you some good ideas, eh?

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    In reply to Theo Epstein:

    Cubs fans really appreciate that you pay attention. Props to you, Theo...keep up the great work!

  • In reply to cubbie steve:

    The typo is fixed now, thanks for pointing it out. In the part about Romero the math adds up to $22m, so I don't know what I was thinking in the first part! Thanks for reading.

  • So many teams want Javier Baez, why not tell teams you want Baez, you would need to take EJax and his contract also.........

    Dennis Eckersley was at the ends of his rope as a starting pitcher.....and he became a reliever and a HOF.

  • Jackson for Danks...the only reason the Sox had Jackson the first time was because Peavy was injured, including having to have Jake Peavy surgery. It is quite clear that the Sox would want value for Danks, and Jackson isn't it. Now, if you are talking Jordan Danks, the Cubs picking up $19 million, and Coop somehow getting Jackson back to where he was in 2010 and 2011, there might be a deal, but Rick Hahn doesn't need Theo's mistakes, and it looks like Coop has lost his magic (if the bullpen is any indication).

  • In reply to jack:

    "Rick Hahn doesn't need Theo's mistakes"

    You're right. He needs Theo's successes.

  • In reply to cubbie steve:

    Name one. Did Theo sign Abreu? If Avi Garcia is now healthy, did Theo sign him? Theo did sign EJax,

  • I think Rizzo, Arrieta, Rondon, and others might be insulted by your implication that Theo hasn't had successes. Throwing the most money at a free agent like Abreu doesn't make you a genius, and Theo had no need at 1B.
    Rick Hahn also did not sign Garcia, he acquired him in a trade. And based on what little Garcia has accomplished in the majors (his .740 OPS and 9 homers in 104 career games) and his stats in the minors, we can only count him as a success if we count Kris Bryant, Jorge Soler, and others for the Cubs.
    I like Rick Hahn as a GM and think he will be relatively successful in his career, but I don't really care for the philosophy that the White Sox operate under. It takes the "win now" approach, but under the understanding that winning now isn't realistic. So rather than try to build some top draft picks and trade players for prospects, they put together a slightly under .500 team and hang onto older veterans like they truly believe they may be able to contend next year.
    I'd be very sad, as a White Sox fan, about the potential of the future. Sale and Abreu are currently about as good as they could possibly be. There isn't much around them, and there isn't much on the horizon (other than Rodon). They can't even trade prospects for good players because they don't believe in developing the farm system. In the long run, I'd rather suffer through 3-4 awful Cubs seasons to work towards building a potentially great team than deal with 5-6 extremely mediocre seasons.

  • In reply to Ryan Davis:

    1. Other than Rizzo, you haven't listed anyone with much of any major league experience. Sort of counting your chickens before they have hatched.

    2, The point was that you said in the main piece that, in effect, the Sox should take Theo's mistake of Jackson off Theo's hands. Justify that, which your long discourse does not.

    3. What your discourse does seem to argue is that "tank now" works, except it certainly can't work for everyone. And we don't know if has worked for the Cubs yet.

  • In reply to jack:

    What success has Hahn had that has major league success? Abreu hasn't played a full season yet and while he has looked impressive, I'd say you're also counting your chickens, and then telling them all about Edwin Jackson and his bad contract until those chickens decide they'd prefer death to your blathering and hurl themselves alive into a vat of hot oil.

  • False. I also listed Arrieta and Rondon. The guys with no major league experience that I listed were in response to your mention of Avisail Garcia, who has had no real major league success.
    I mentioned Danks in the main piece as a potential bad contract that could be on the move. The White Sox likely will try to unload him, and I even mention that a straight swap isn't likely. It's an outside the box move, but Jackson wasn't awful with the Sox and it's possible they believe that they could get him back where he was.
    From the Sox perspective, if you can ditch Danks (and the extra $6m on his contract), get a starting pitcher that you think can be at least as good as Danks was (and he's been bad since 2012), and a moderate prospect like Bruno, it's totally worth exploring.
    And as for dissing the Sox rebuild style, it's cool if you don't want to go full rebuild. I like the way the Cubs have gone about their rebuild, but there are other ways to do it too. The problem is that the White Sox have limited ability to aquire good, young, talent to help them compete long term.

  • In reply to Ryan Davis:

    Lets get back to the Jackson point. I assume he has cleared waivers; do you think there is a reason why nobody claimed him? Like he isn't worth anything, certainly not $11 million a year?

    How does ditching Danks money help if you have to pick up Jackson money? Danks is still recovering from an injury; what is Jackson's excuse? An excuse that neither Bosio nor Coop could fix?

    Apparently, the Sox didn't have any problem acquiring Carlos Rondon. But, instead of going for a twopeat on the tank (to be distinguished from the Cub at least threepeat) they have someone who is already in AAA and probably will be up this season. Cubs are now only talking about players drafted under Hendry.

    As I said before, let's see if the Cubs Way actually results in a ML contender, which it hasn't yet, and nobody seems to say will before 2017. The goal is NOT improving the minor league roster, but what happens on the ML level. The minor league roster may be a means to that goal, but your analysis seems to be that the only goal is to acquire lower level minor league talent. Plenty of other teams are also doing that, and not all of them are going to win the 2017 World Series. Ask Tampa. At least they have the excuse of a tougher division.

  • In reply to jack:

    How does ditching Danks money help if you have to pick up Jackson money?
    They could save some money.

    Danks is still recovering from an injury; what is Jackson's excuse?
    Danks was recovering from an injury in 2013 that he sustained in 2012. If he's still recovering, then they should want to unload him even more.

    The goal is NOT improving the minor league roster, but what happens on the ML level.
    True, but improving the minor leagues is the best way to get better talent to the major leagues. It's very hard to continually improve the major league roster without improving the minor leagues first.

    As I said before, let's see if the Cubs Way actually results in a ML contender, which it hasn't yet, and nobody seems to say will before 2017.
    Many believe the Cubs could be competitive as soon as next year, and compete for playoff spots in 2016.

    but your analysis seems to be that the only goal is to acquire lower level minor league talent.
    I simply think that the White Sox plan of not acquiring a decent amount of young, quality talent, doesn't really jive with what they have going on with the major league roster. With ridiculous seasons out of Abreu and Sale, they're still several games under .500. Outside of Rodon, where is the help coming from next season? Trade for a good player? Would help to have some prospects. Good luck with that plan.

  • In reply to Ryan Davis:

    You are still evading the question, which I'll state in bold Why would anyone want to pick up Jackson? Especially the Sox?

    Rick Hahn says that he is interested in trades that will help now or improve the team in the future. How does Jackson help that?

    Steve Stone says the Sox need left handed hitters and a bullpen. How does Jackson help that?

    How does incurring $22 million in dead money obligations help in any event?

    And if Daniks is so crippled, why would the Cubs want him?

    Let's face it---Jackson is doing exactly what Theo paid him $53 million to do--help them lose. See my comment to the benching Arrieta topic.

    Can your beating around the bush refute any of that? You still haven't explained why Jackson has not been picked up on a waiver claim. I told you why.

    When people used to play hot stove league on the radio, the response was always "why would the other team make that trade?" Apparently while that doesn't go on on the radio any more, bloggers seem stuck in the rut of not answering that.

  • In reply to jack:

    You've still answered my question, why does a White Sox fan spend so much f'ing time commenting on a ton of ChicagoNow Cubs blogs?

    We get it, you're obsessed with Edwin Jackson and you view it as the ultimate failure and a sign that the Cubs can never succeed because Theo screwed up so royally by signing him. Do you have an Edwin Jackson Google Alert or something?

    I've seen a lot of your comments over the season and they're all fairly obnoxious. You poke holes in every f'ing thing that anyone writes. You take everything literally, you seem to have no sense of humor. You must be a real pleasure to be around in real life.

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