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There can be no hard line. It has to be case by case. Some pitchers might be worth it. Others will appear very risky from the onset of free agency...

I think you might have underestimated what Keuchel’s demands were. While probably lower now, he was reportedly looking for closer to a $22-25mill AAV. While he is better than Eovaldi, Eovaldi was the hot name at the time and getting better offers than the Lynn type deal already. While signing Pearce and ignoring the pen seemed silly, I think Dombrowski is counting on his ability to build cheaper bullpens and has a long history of using inexperienced closers. I would not be surprised if he planned to avoid spending heavily on a closer from Day One. Whether or not you agree with this strategy, it is something he has done multiple times with multiple teams with mixed results, that obviously include some successes. Not to mention, your thoughts at the time for Pearce was he would get multiple years at a much higher AAV. Maybe if the Sox had waited him out, he might have settled for a $2-3 mill deal. But even then, I don’t think DD was bringing in a new high salary closer. He seems to really like Brasier...

Ah but you came after the one guy who: 1) Thinks Cherington should own his mistake singular - Sandoval. (Hanley was a good player on a good d al. That he didn’t perform isn’t Cherington’s fault.) 2) Thinks Cherington deserves more credit for his success. I mean, we had to have the shortest rebuilding in MLB history, right? 3) Recognizes the insane and unparalleled success Larry Lucchino has had as a sports executive. The man has a Super Bowl ring, multiple World Series rings with multiple teams, and a Final Four watch. This is not all a coincidence or run of good luck, is it?

Hey!! Owners have collusion lawsuits to pay off here...

I think the movie cast signs sooner...

I misread that and thought is said "Dombrowski finally admitted they screwed up with Lester." That seemed like an odd thing for him to say, seeing as to hoe he was not even here at the time...

How big of him to point out other people’s mistakes. What’s his opinion of Miguel Cabrera’s contract?

There are plenty of players who should retire based on what they have left on the field. None of them will based on what they have left on the contract...

This off-season might also give JD Martinez pause in opting out. Not only has he already been victimized by a slow offseason once, but he will be 32 after the 2019. With 3 years and $62mill remaining, canhe really do better? AJ Pollock, who is only months younger than JD, did get 4 years, but for less money overall....

Even Slam Ball?

The 2018 NL East champion Atlanta Braves were 11th in MLB attendance and are typically in the 13-20th place in MLB. One could argue the Braves struggle to get fans to go to games in Atlanta, let alone Tampa, which is 6 1/2 hours away...

Apparently according to a few bloggers out there, it already has Bogaerts re-thinking extensions...

1) You really don’t want to see either Moreland or Pearce in the outfield if you value defense. 2) For as flexible as this bench is, the Sox really do lack anyone to backup SS or the OF with any degree of defensive skill...

The only rivalries anyone in Florida cares about involve college football teams...

Unless there is an injury, there isn’t room for either of them...

Juan Centeno, Oscar Hernandez and Austin Rei...

The best former-player-turned-analytical-expert I can think of is Steve Stone, who was MLB’s equivalent of Tony Romo before Romo even started playing football...

Burrell was a third baseman in college but moved from the position because the Phillies had Scott Rolen, who was the reigning NL ROY at the time. He was originally moved to 1b, but settled in the OF. His defensive abilities at third probably weren’t great, but were not the primary reason for moving him, especially since his bat was a fast track to MLB. Rolen was, after all, a defensive standout who was NOT going anywhere at the time...

Yes. He could be one of those Sandy Rosario types everyone wants in the organization but no one wants on the 40 man roster, meaning a long stream of DFAs and claims...

Well, there is a difference between Machado’s image being bad and not being as good as Harper’s. In fact, I re-looked at the marketability article and it was from 2016. Harper trailed only Kris Bryant, but that was also right after the Cubs won the World Series. He’s probably more marketable than Bryant right now. Machado does seem to be disliked by fans and Jesus Aguilar, but is he really so unpopular teams are avoiding him? It’s not like the other marquee free agents are falling into big deals left and right. Dallas Keuchel, for example, is still out there despite having a Cy Young award and no negative stigma whatsoever. Most likely the reason is simple Occam’s Razor - Machado wants more than anyone wants to pay and no one thinks he is as valuable as his agent does...

Possibly because his ability to play OF seems to be more durable than Machado’s ability to play SS? Also, Harper certainly was more marketable than any MLB player in MLB except Kris Bryant. Harper’s Q score was second highest in MLB recently, ahead of Trout and Betts. There is a reason this guy does more commercials...

Think it was his on-field antics and not just teams being reluctant to sign him through age 36 for a $30mill AAV? His career has been somewhat parallel to that of Evan Longoria, and Longoria has not been the same player since signing his 10 year contract...

Well if you’re talking about 2016 when Dombrowski started to evince his live for Swihart 1) The tax hit for Castillo was not a problem in 2016. 2) While I agree Brentz is not MLB talent, Dombrowski keeps bringing this guy back. Last off-season, it seems as though many did disagree with me when Brentz was slated to be the fourth outfielder and I said this was not a good idea. 3) Swihart was the starting LF for every game from May20 to June 4 when he injured himself colliding with a wall. This wasn’t him being the versatile 25th man....

But the Sox still had Bryce Brentz, Rusney Castillo, and even former MLB outfielders Brennan Boesch and Justin Maxwell that could have been called up instead. All of them were struggling with sub -.700 OPS’s in AAA, but the others all had outfield experience at the time...

If the Sox wait until late in spring training to DFA Swihart and he does get claimed, it’s actually likely the claiming team will DFA him and try to sneak him through waivers. If so, the Sox can claim him back