Who Should Be Extension Priority #1?

[RZNJ]

1 hour ago, CaptainRedbeard said:

The second question is - what extensions can the Orioles do with guys other than these 4, who are not Boras clients? Don’t want to rehash the “Boras clients don’t extend” debate, but let’s assume whatever they can do with these 4 doesn’t impact the ability to do other extensions. 

Grayson: With 5 years of control after this one, it would have to be something like 6 years + a couple option years. Possible, but not super high priority. 

Bradish: Entirely TBD on how he returns from injury, and even then a bit of the same question as Grayson with so much control remaining. 

Westburg, Cowser and Kjerstad: Lumping them all together because I think it’s similar considerations. At their ages when their years of control expire, I don’t think it really makes sense. All 3 have been phenomenal to start the year but still have significant question marks about their games (really high whiff rates and not great K/BB for Westburg and Cowser, Kjerstad’s defense, chase rate and of course not yet facing MLB yet).

Mayo and Basallo: Given their ages they are going to be the best candidates, IMO. However, it’s premature now for obvious reasons, particularly with the major questions about how much defensive value they are going to provide at the MLB level. 

Unfortunately I have a hard time seeing any extensions happening in the near future, even if Elias and Rubenstein have all the best intentions of wanting to do them. 

I actually think you hit on it.   The more realistic extension candidates are Cowser, Westburg, Kjerstad, Mayo, and Basallo.

[Moose Milligan]

Gunnar, Adley, Holliday.  50/50 on Burnes.

Gunnar because he's the best player, probably the most valuable.  Adley #2 because things turned around here when he came up, he's probably the face of the franchise, and is growing into the undisputed leader of the team.  I don't know if he has another level to unlock yet, but I also believe his importance to the team over the past two years can't be simply calculated in WAR and it won't be measurable moving forward by advanced stats.

Holliday 3rd, and that's just because he's the newest.  Arguably the most talented of the group.

Burnes, like I said in the other thread, it just depends.  

[Too Tall]

23 minutes ago, interloper said:

I'm gonna tell your wife you're spelling her favorite player's name wrong. Look out!!

Oh my! I sure did! I'm a math major, she'll not be at all surprised and in fact get a laugh out of it. Thanks for the heads up. 

[DirtyBird]

Gunnar

Mountcastle

Holliday

[JimGinSP]

With Elias and Rubenstein across the negotiating table Boras will know he is up against experts in talent evaluation and financial risk evaluation respectively.  This won’t be Buck circumventing Dan to convince Peter to pay his “big hairy guy” Chris Davis.  Parameters will be established and plan B’s will be in place to implement should Elias and Rubenstein choose to walk away from the table.  That being said discussions with Henderson should be the priority play with the Rutschman discussions happening concurrently but at a slower roll.   I don’t think you want Rutschman finding out that Henderson has been approached by the O’s first.  

[Malike]

I think Burnes will likely end up with a huge deal. I don't lump him with Snell and Montgomery and what happened with them in the off-season. I think some team will actually give Burnes 7 or 8 years north of 250M dollars.

[yark14]

All of the above. Plus Westburg and Cowser.

[DirtyBird]

1 minute ago, yark14 said:

Plus Westburg and Cowser.

Need to lock them in until they are at least 40 years old

[G54377]

I said Gunnar, but I also think a Burnes extension is basically a dead end road. 

[Philip]

Anthony Franco at MLB TR just said a Gunnar extension would be ~300 million.

wow…

[forphase1]

Of those 4, it's Gunnar #1 by a large margin imo.  Then Holliday, forward closely by Adley with Burnes a very distant 4th, unless he's willing to do a 3 or 4 year contract.  I really don't want to sign Adley for more than a couple of his FA years,  and I'm not sure he goes for that. 

[Orioles West]

Gunnar, Adley, and Jackson - based on the limits of the OP choices, but I understand wanting to keep Burnes around.

On the G-Rod mentions, not a bad idea. O's have control, but if he continues to be a frontline starter, an extension could be cheaper than the last 2-3 arbitration years.

[Rbiggs2525]

3 hours ago, RZNJ said:

I actually think you hit on it.   The more realistic extension candidates are Cowser, Westburg, Kjerstad, Mayo, and Basallo.

Crazy thing is I think you could offer all these players the same contract. Something along the lines of 8 years 60-80 million.

[Billy F-Face3]

I had to think about it because Adley has always been a high priority for me. He's the franchise Catcher we never had. And in my opinion, the Catcher position is the Quarterback of a Baseball team. It's that impactful of a position and you need a good one to compete for championships.

But with that said, Burnes is the Ace we've been waiting for since Mussina turned coat, and his contract is up at the end of the season. He's also one of the most reliable and durable pitchers in baseball. I think we should do what we can to keep him happy and make a business deal with him to keep him an Orioles pitcher.  

If you're assuming that Rodriguez or Bradish will take over the Ace role, I think you've seen enough pitching injuries this year to tell you that you can't assume that will happen. You need to make sure any one of your top 3 starters can assume the #1 spot if pressed.

Timing dictates Burnes as our biggest priority to work on.

With Gunnar, he might be a future MVP and I've been one of his biggest fans since the moment he was called up. But his agent is Scott Boras, so good luck getting him to agree to an extension before free agency. And on that note, you'll have Scott Boras with a conflict of interest when you're trying to sign both Gunnar Henderson and Jackson Holiday long term and they both want to play shortstop.

[sevastras]

18 hours ago, Bemorewins said:

Gunnar is obviously a superstar talent who is ascending at age 22. He already owns a sliver slugger and a ROY award. 

I thought you were mistaken on the silver slugger award. I had to look it up. That was a very low bar and he benefited greatly by being in the utility category. 
Gunnar is a special player and I would sign him to an extension as the primary goal. Obviously I would have all three on the team as long as they could, though.