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BALTIMORE ORIOLES
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C-S Matt Wieters accepted the qualifying offer. [11/13]

When Colby Rasmus became the first player to take the qualifying offer, Matthew Trueblood wrote about how players were beginning to learn from Kendrys Morales and Stephen Drew's mistakes. How about agents? If Wieters' acceptance is any indication, the answer is yes. Wieters is represented by Scott Boras, the same Scott Boras who advised Morales and Drew to decline the QO in search of a greater payday. When those windfalls never came, Morales and Drew took one-year deals (worth less than the tender) and re-entered the market months later, following disappointing seasons.

In fairness to Boras, it makes more sense for Wieters to take the qualifying offer than it did for either Morales or Drew. He's been limited to 101 games the past two seasons due to Tommy John surgery, meaning he hasn't had a chance to prove he can still produce over a full season. This route affords him the opportunity to do so before hitting the open market next winter as the top catcher available (again). In other words, this is about maximizing the payout—not just in 2016, where he'll earn $15.8 million, but overall, because Wieters' price tag is likely to soar if he has a quality, durable season.

Staying in Baltimore might be the best way to accomplish that goal, too. The O's have a quality backup catcher and openings at first base and DH—or, in other words, the ability to give Wieters time at less-demanding defensive positions, which in turn could help keep him on the field and productive at the plate. In that sense, this might be the best-possible outcome for the team, player, and, yes, agent. —R.J. Anderson

TORONTO BLUE JAYS
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Signed RHP Marco Estrada to a two-year deal worth $26 million. [11/13]

We've covered the unlikelihood of the Blue Jays' rise before, and how their success required an inordinate number of low-probability outcomes. Estrada's 2015 evinces the same odds-defying tendencies. Among the things that had to go right (or wrong) for us to reach this point in time:

• The Blue Jays had to acquire Estrada last November from the Brewers;
• then had to opt against acquiring another starter throughout the winter;
Marcus Stroman had to injure his knee during spring training;
• then Daniel Norris had to get demoted after a tough April;
• the Blue Jays had to move Estrada from the bullpen to the rotation;
• then the Blue Jays had to stick with Estrada in spite of his own struggles in the rotation (he exited May having allowed 30 hits, 17 runs, and five homers in 28 innings);
• and so on . . . .

However improbable, those events occurred, guiding us here—where the Blue Jays are making a two-year commitment to a pitcher they deemed unworthy of a rotation spot seven months earlier. Ain't baseball odd? Based on the wide angle, you might call this contract odd, too.

There's a strong case to be made that Estrada won't pitch as well over the next two seasons as he did in 2015. He set new career-bests in innings, ERA, and hits allowed—the last feat stemming directly from holding opponents to a .216 average on balls in play. You can argue that Estrada is well positioned to post a low BABIP—he's a deceptive changeup artist pitching in front of an elite defense—but he did more than shatter his previous personal best (by more than 40 points): he finished with the lowest BABIP on the Toronto staff among pitchers with more than 50 innings . . . by 23 points.

Obviously Estrada is unlikely to suppress hits to that extent heading forward, meaning he's bound to allow more baserunners. That's problematic for any pitcher, but particularly Estrada, who has never—not even during the years he appeared in a handful of games—finished a season without allowing more than one home run per nine innings. One plus one equals two, just as more baserunners plus home-run issues equals some ugly outings.

Still, this deal looks fine. If you were okay with extending Estrada the qualifying offer in the first place, then you should like this. Provided his acceptance of the offer became a fait accompli—one that developed after the offer was made—the Blue Jays did well to secure another year of control for $10 million—or less than one season of his services goes for on the open market. Yeah, gaining a draft pick from Estrada signing elsewhere would have been cool, but don't forget that the Blue Jays need rotation help, too. If they weren't going to re-sign Estrada, they were going to need to sign an equivalent—most of whom also require draft-pick compensation, leaving the Jays playing a zero-sum game anyway.

Jays fans are probably more interested in who Tony LaCava and Mark Shapiro add to the rotation next, but this is a solid start to the winter. —R.J. Anderson

ARIZONA DIAMONDBACKS
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Acquired RHP Sam McWilliams from the Phillies in exchange for RHP Jeremy Hellickson. [11/14]

An eighth round pick in the 2014 draft, McWilliams remains more projection than pitcher. While he's still filling out his 6-foot-7, 190-pound frame, he shows the ability to touch the mid 90s on occasion (though he sits more comfortably in the 90-92 mph range). He also shows an average change and fringe-average curve, but those pitches lack consistency and often flash developmental. Unsurprisingly, his command is a work-in-progress as well. McWilliams is essentially a lottery ticket: one who is more likely to be an organizational arm than a mid-rotation starter—even if the latter is a somewhat realistic possibility. —Christopher Crawford

LOS ANGELES DODGERS
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LHP Brett Anderson accepted the qualifying offer. [11/13]

Depending on your perspective, Anderson was the free agent either most or least likely to take the qualifying offer.

At first blush, of course Anderson was going to take the tender. Sure he was coming off a career-high amount of starts and innings, but his medical past is more riddled than Lewis Carroll's canon; whatever multi-year offers he received were going to be loaded with incentives to protect the team from spending too much on an injury-prone arm who was regarded as a lottery ticket 12 months ago. If Anderson wanted to maximize his earning power, he would take the qualifying offer and try again next winter.

But it's not always that simple from the player's point of view. Yes, the time value of money suggests that taking the QO is almost always the smart bet for non-elites. Yet that there are other factors at play beyond the financial component. Players often value the certainty that comes with a three- or four-year deal because it means not having to worry about moving your spouse, kids, and dog across the country in 12 months' time. Besides, the differences in salaries can often be explained away using marginal utility—or the idea that the first $10 million carries more meaning than the subsequent $10 million.

From that perspective, Anderson seemed unlikely to take the qualifying offer. Why would he when he could gain some long-term security—a rarer commodity than money for an oft-injured starter. For Anderson to take the tender after all is an interesting decision. Not an illogical or bad one—there is no room for good or bad here—but an interesting one that reveals Anderson's thinking.

As for the Dodgers, expect them to add another starter before spring arrives. —R.J. Anderson

PHILADELPHIA PHILLIES
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Acquired RHP Jeremy Hellickson from the Diamondbacks in exchange for RHP Sam McWilliams. [11/14]

You might be shocked to find the Phillies trading a prospect for a walk-year veteran, but there's some logic to the move.

Namely, Hellickson—even in his present state—is a better, more intriguing pitcher than the Jerome Williamses, Chad Billingsleys, and Sean O'Sullivans of the world. None of the above is likely to provide much value, so why not roll with the one who you think has the highest ceiling—even if he's unlikely to reach it? Best-case: he pitches better than expected and earns attention at the deadline; worst-case: he's out of a job by the deadline or whenever the next young arm is ready to make the leap.

If there's something worth watching on a start-by-start basis with Hellickson, it's whether he tweaks his arsenal again. Historically a fastball-changeup pitcher, he leaned more on his curveball in 2015. Consider that an interesting decision, because Hellickson has never used his curve as more than a chase pitch—a statement that remained true last season. You can't help but to wonder how much effectiveness he would gain if he learned how to steal strikes early in the count with his breaking ball.

It's probably too late for Hellickson to learn that trick. But hey, it's mid-November and we're talking about a back-end starter joining a bad team. What can you do besides daydream? —R.J. Anderson