The first of them cracked. Justin Upton and Yoenis Cespedes remained on the free-agent market, and all around the league, teams indicated they didn’t want to make the necessary commitments. The players wanted five or six or seven years. The teams wanted to give one or two or three. It was enough to make you think there could maybe be a potential bargain, but the market just doesn’t turn out like that. More often than not, a team gives in, and few should be surprised the team that gave in Monday was the Tigers. As always, all Mike Ilitch wants is to win. He’ll now get to watch his team try to win with Upton every day in left field.

The agreement is for six years and a little over $130 million, with Upton also having the opportunity to opt out two years in. That’ll give Upton the chance to hit the market again at the same age that Cespedes is now, and as we’ve written so many times, the opt-out clause has good value to the player. But at the same time, this is the Tigers — Ilitch’s Tigers. On one hand, Ilitch makes these analyses complicated. On the other hand, you could argue they couldn’t be simpler. Upton’s a good player. Ilitch was willing to pay for a good player.

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You have a choice. I’ll give you $100 right now, or you can let me flip a coin. If it lands on heads, I’ll give you $250. But if it lands on tails, I’ll give you $20. I’m using a fair coin, so the expected value of flipping the coin is $135 based on the 50/50 odds it lands on heads or tails. If you like risk or are a risk-neutral person, it’s an easy decision to take your chances with the coin because the odds are strongly in your favor. If you’re a risk-averse person, however, you’re more likely to take the sure thing because $135 isn’t a whole lot more than $100, and $100 is a whole lot more than $20.

Let’s add another wrinkle. It’s the same choice, but if you choose the coin flip, you have to wait a month. The dollar amounts are the same, but now there’s a time component. To get the value of the coin flip, you need to apply a discount factor to the $135. For some people, that discount factor is pretty close to one, but it might be much lower if you’re strapped for cash and the $100 would dramatically improve your life in the present.

Major league players face a much higher stakes version of this decision when their club comes to them with a contract extension. Do they take a sure thing now, or do they wait and gamble on themselves? While we’re focusing a lot on the 2015-2016 free-agent class this month, there are eight players who could have been free agents for the first time this year but instead chose to cash out early by signing extensions. Did they make the right decision?

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Though baseball’s Winter Meetings seem like the playground of the front office executive, there is one other baseball man who’s ubiquitous: the manager. Semi-required to attend media events and an annual luncheon, most of the sport’s managers descend on the meetings to make their mark.

For the most part, they field questions about next year’s lineup, and try to deflect queries about front-office moves. They’ll do a little reminiscing about last year, and a little looking forward to next year. It’s a bit of a dance, since most of the reporters are looking to find out how the roster is going to look on paper, and the person in front of them is mostly in charge of putting that roster on the field.

Still, it’s a great moment to get access to many managers at once. This past August, I asked a collection of players and writers how Bruce Bochy and Joe Maddon — managers with distinctly different approaches and pasts — could both find great success. I thought it would make sense to ask the managers gathered here about their craft, as well.

What has changed about managing? How are the demands on the modern manager different than they once were?

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Check out the MLB Trade Rumors page for Justin Upton, and you find something strange. Since a report on November 13 that the outfielder had been extended a qualifying offer, Upton has been invoked just three times there — in one case, with the Angels, merely to note that “nothing is happening” between Upton and the club. Los Angeles was merely engaged in “ongoing conversations” with Upton’s representatives. Whether those conversations are about a possible contract or fondue, no one knows. They’re having conversations.

Now check out the Ben Zobrist page. Even before signing last night with the Cubs, his name was ubiquitous across the site.

And that’s weird. One is 34 and was worth two wins last year. The other is 28 and was worth almost twice as much. You’d think the rumor count would be reversed.

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It’s an interesting thing in life when we can look at someone’s behavior and immediately identify its causes based on what we know of their past. Like when an actor tries to do a serious movie because they’ve only been seen as a comedian, or when a guy hits 40 and rushes out to by that ’86 Firebird he’d wanted since he was 11. These things are easy to diagnose, no degree required.

So, too, with Dave Dombrowski’s first offseason in Boston. He’s spent the balance of the last decade, it seems, losing in the playoffs because his bullpen failed him when he needed it most of all. So how do you counteract that? Easy! Get all the best relievers, or a good number of them, anyway. That was easy!

First, there was the Craig Kimbrel deal which did two things. It (a) caused the internet to freak out because Dombrowski dealt a seemingly silly amount of prospects to San Diego, and (b) added Kimbrel to the Red Sox bullpen. Then yesterday he traded Wade Miley for reliever Carson Smith (covered here by Jeff Sullivan). It’s easy to picture Dombrowski sitting down for the first time in his Fenway Park office, visions of David Ortiz’s grand slam flying just beyond the outstretched glove of Torii Hunter flickering in his brain like an old newsreel. He grabs a napkin out of his pocket and jots down the word “bullpen” over and over until he builds up then pops a blister on his finger. “The most dominant, unimpeachable, and impregnable bullpen yet seen on earth will be mine,” he thinks, “just as soon as I find a band-aid. OW! That smarts.”

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On July 7th, 2006, a 23-year-old righty made his major league debut against the Tigers. He entered the game in relief and immediately began putting up 99s on the radar gun. It wasn’t enough, however, to prevent Chris Shelton from singling to shortstop and beating out the throw. Brandon Inge also wasn’t afraid of the velocity, as he hit a ground-rule double to center. The young righty was now flustered. He hit Curtis Granderson to load the bases. He paced around the mound, gathered himself, and then rallied to strike out Placido Polanco, get a weak grounder from Ivan Rodriguez, and strike out Magglio Ordonez to end the threat.

On that day, Mark Lowe began a journey that started with the Mariners and continued on to the Rangers (in the Cliff Lee deal), and then the Dodgers, Angels, Nationals, Rays, Indians, Mariners (again), and Blue Jays. And now, almost ten years later, the Tigers have signed him with a two-year deal to be their setup man. It’s been quite a trip for him.

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On Monday, the Detroit Tigers held a press conference to introduce their newest acquisition, Jordan Zimmermann. As has become customary on these occasions, Tigers’ owner Mike Ilitch attended the media session and fielded questions from reporters. Most of the attention following the press conference centered on Ilitch’s comments that he doesn’t “care about the money,” and instead simply “want[s] the best players.”

Of potentially greater significance, however, was a related statement Ilitch made in response to a question about whether he’d be willing to allow the Tigers’ payroll to surpass the $189 million luxury tax threshold:

“I’m supposed to be a good boy and not go over it,” Ilitch said, “but if I think there are certain players that could help us a lot, I’ll go over it. Oops, I shouldn’t have said that.”

Admittedly, there is probably nothing to this statement. Ilitch was likely just speaking casually, acknowledging that while the team’s payroll would ideally stay below the $189 million level, he could be willing to eclipse that mark for the right player.

At the same time, however, Ilitch’s choice of words was rather odd. By stating that he’s “supposed to be a good boy” and not exceed the luxury tax threshold, Ilitch’s statement would seem to suggest that he is under some sort of external pressure not to allow the team’s payroll to cross the $189 million mark. Along these lines, Ilitch then appears to quickly realize that he may have spoken a bit too loosely, leading to his “Oops, I shouldn’t have said that” line.

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“I don’t care about the money,” (Mike Ilitch) said. “I want the best players.”

The Tigers owner made that comment at yesterday’s press conference introducing Jordan Zimmermann as the newest member of Detroit’s rotation. For sure, Ilitch has indeed backed up that comment with significant spending over the years, giving out big money deals to acquire guys like Prince Fielder and Anibal Sanchez while still retaining players like Miguel Cabrera, Justin Verlander, and Victor Martinez. The Tigers have consistently run some of the highest payrolls in baseball over the last decade, and Ilitch clearly isn’t looking to rebuild, given his own age and that of most of the team’s players.

But while adding Zimmermann should help stabilize the rotation, the Tigers should not yet be done spending. If Ilitch is serious about not caring about his budget — he stated he’d even be willing to go over the luxury tax if need be — he has a real chance to back up those words this winter, because the Tigers were not one Jordan Zimmermann away from being the best team in the AL Central. Even with Zimmermann, they don’t currently look like one of the five best teams in the American League.

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With Jordan Zimmermann, it’s so easy to focus on the downside. You’ve got a pitcher, coming up on 30, who’s already had Tommy John surgery once. He just posted a second-half ERA north of 4 despite playing in a woeful division, and he just lost a bunch of strikeouts, and he also just lost some fastball velocity. Every pitcher has red flags, and Zimmermann might have one or two more than usual. We’re all to some extent risk-averse, so it might not immediately seem like a great idea to guarantee Zimmermann $110 million over five years. In an ideal world, you’d like a bit more certainty.

Not that there’s ever such a thing as certainty. Someone as certain as, say, Carl Crawford dropped 8 WAR in between leaving the Rays for the Red Sox. Certainty is a lie, and beyond that, it’s not like Zimmermann wasn’t most recently good. By whatever measure, he had a three-win season. It was his fifth in a row. Zimmermann does actually seem fairly steady, even if you figure he peaked in 2014.

And underneath, Zimmermann has something going on. Most people are concerned with what’s physically going on. And, admittedly, what I’m going to highlight has an unclear link to ultimate performance. But Zimmermann has been changing himself, and in one way, he continued something he began two years ago.

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For four consecutive years, the Detroit Tigers sat comfortably atop the throne of the American League Central Division. Last year, they relinquished that reign and did so in dramatic fashion, fielding the franchise’s worst rotation since the 119-loss Tigers of 2003 while plummeting to last place in the division.

Clearly, the Tigers were going to add a pitcher or three in the offseason. The question was, would it be a series of band-aids to stop the bleeding, or something bigger to put them back on the attack? On Sunday, that question was answered, when the Tigers agreed to terms with Jordan Zimmermann.

Those terms, precisely, are five years and $110 million, which is less than the 6/120 that our crowdsourcing project predicted. In past years, the crowd has tended to err on the low side, especially with high-profile free agents, so any time a guy signs for less, it looks good for the team.

In fact, if you start with Zimmermann’s +3 WAR Steamer projection for 2016, assume he ages somewhat well and factor in inflation, Zimmermann’s contract comes out as a carbon-copy of what would be considered the fair, market price:

What the Tigers are paying for here is consistency. This is a team that gave 147 innings to Buck Farmer, Kyle Lobstein, Kyle Ryan, and Randy Wolf last year, and a team whose only qualified pitcher was Alfredo Simon. Even at the top of the rotation, there’s former workhorse Justin Verlander, who looked like his old self once returning from injury but still needs to prove he can throw 200 innings again; Anibal Sanchez, who has either been hurt or ineffective each of the last two years; and Daniel Norris, who’s never thrown more than 150 innings in professional ball and just had a cancerous growth removed from his thyroid.

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