Cubs signing Jon Lester

The best and worst signings of the offseason

Baseball’s long, dark winter is just about over, which means it’s time for writers to judge how each team did in the offseason with their signings, trades, and other transactions. It’s also time for everyone reading those articles to bookmark them and tell the writers how stupid they are when the season is over. It’s a cherished ritual of spring and fall.

But even with the threat of being called an idiot in October hovering over my head, there are a few deals from this winter that really stand out. Some are for good reasons, and some are for not-so-good reasons. And while some of the contracts handed out this winter seem like absolute steals, some don’t make any sense no matter how you look at them.

Let’s take a look at some of the best. And just for fun, some of the worst.

The Best

Jon Lester, Cubs.
Lester isn’t on the list because of talent, since everybody knows how good he is. He’s on the list because of what the move means for the Cubs, who won the battle for his services over Lester’s old Red Sox team and the defending World Series champion Giants. It signaled that the Cubs, after being mired in a complete tear down for years, were legitimate contenders again for the first time in a long time. Adding one of the best starters in baseball went a long way in establishing that they were back.

Michael Morse, Marlins.
Hitters with Morse’s power are rare these days, and the Marlins got a steal when they signed him to a two-year, $16 million deal. He’ll provide lineup protection for Giancarlo Stanton, and the Marlins are minimizing Morse’s defensive shortcomings by making him a first baseman. It’s the perfect spot for Morse, who’s always been a very dangerous hitter limited by his microscopic range in the outfield. But on a short, reasonable contract playing a position that is far less demanding, Morse is a great fit and should have a big year in Miami.

Padres signing James Shields

KANSAS CITY, MO – OCTOBER 15: James Shields #33 of the Kansas City Royals celebrates in the locker room after their 2 to 1 win over the Baltimore Orioles to sweep the series in Game Four of the American League Championship Series at Kauffman Stadium on October 15, 2014 in Kansas City, Missouri. (Photo by Jamie Squire/Getty Images)

James Shields, Padres.
Signing Shields put the capper on the Padres’ offseason, which was the most interesting offseason for a team in recent memory. Shields may not be an “ace” (whatever that means), but he’s a reliable, above average starter who’ll anchor their rotation and could put up big numbers at Petco Park. He gives the Padres’ rotation instant credibility too, something it lacked heading into the season, and he’ll likely serve as a mentor for some of the team’s young, talented starters. This was an all around great deal for San Diego: they signed a number one starter for a very reasonable price.

Chase Headley, Yankees.
$52 million over four years isn’t a bad price to pay for a third baseman of Headley’s caliber, especially considering Pablo Sandoval got almost double that from Boston and Headley’s numbers compare quite favorably to Sandoval’s. Headley seemed to rediscover his stroke in New York and playing a full season there would seem to only help him. He’s not far removed from MVP-caliber numbers, remember, and the hitter-friendly Yankee Stadium should play to his strengths. Plus his presence blocks A-Rod from playing third, an added bonus.

Adam LaRoche, White Sox.
You really could substitute any of the Sox’ signings this winter here, but LaRoche may be the best one from a pure value standpoint. $25 million over two years for a guy who’ll average close to 30 homers per year and hit somewhere around .260/.340/.470 is a great deal, and he gives the Sox another bat in the middle of the lineup to take some of the pressure off of Jose Abreu. Like Morse, it’s a reasonable, short deal that should benefit the Sox tremendously. Those are always the best deals.

Braves signing Nick Markakis

DETROIT, MI – OCTOBER 05: Nick Markakis #21 of the Baltimore Orioles looks on during batting practice prior to Game Three of the American League Division Series against the Detroit Tigers at Comerica Park on October 5, 2014 in Detroit, Michigan. (Photo by Leon Halip/Getty Images)

The Worst

Nick Markakis, Braves.
Here’s a sure sign you may have made a free agency mistake: when they player you just signed to a 4-year, $44 million deal has neck fusion surgery a few weeks after signing the contract. Maybe Markakis makes a full recovery, and maybe he keeps putting up the same kind of okay-ish numbers he did in Baltimore; problem is, that’s a lot of maybes for $44 million. Add in the fact that the Braves got rid of better outfielders in Justin Upton and Jason Heyward before signing Markakis, and the deal looks even worse. It was a weird offseason in Atlanta and this may have been the weirdest move of all. Are they rebuilding? If so, why spend that much on a broken down outfielder in his 30s?

Michael Cuddyer, Mets.
The Mets, in a perpetual rebuild, gave up their first round pick in order to sign the the soon-to-be 36 year old Cuddyer to a two-year, $21 million contract. That alone is puzzling, but when you consider that Cuddyer has only averaged 93 games played per year over the past three years, it’s downright baffling. Cuddyer is a good hitter who was very productive the past few years when healthy, but he definitely benefited from Coors Field and the switch to Citi Field probably won’t help him. It’s not like the Mets were one veteran hitter away from contention, either. Cuddyer seems like an odd fit.

Nelson Cruz, Mariners.
Yes, he’s arguably the most dangerous power hitter in the game right now. But he’s also a convicted steroid user who’s about to hit his late 30s and the Mariners are paying him $57 million over the next four years. This just feels like a deal that could go south in a hurry. He’ll likely provide an offensive upgrade to the Mariners, but there has to be some concern about whether or not he can keep putting up big power numbers in their ballpark. The move might not look so bad next year, but what about the three years after that?

Dodgers signing Brett Anderson

DENVER, CO – AUGUST 05: Starting pitcher Brett Anderson #30 of the Colorado Rockies reacts as he suffers an injury and leaves the game against the Chicago Cubs in the fourth inning at Coors Field on August 5, 2014 in Denver, Colorado. (Photo by Doug Pensinger/Getty Images)

Brett Anderson, Dodgers.
Proof that all parents should tie their kids’ right arms behind their backs and force them to do everything left-handed. In spite of only making 19 starts over the past three years, Anderson received $10 million for one year from the Dodgers with the hope that he’ll be able to recover from back surgery quickly enough to make an impact in 2015. If he’s healthy and productive, it’s a gamble worth taking. But it seems like everything said about Anderson over the past few years is predicated with “if he’s healthy and productive.” $10 million just seems like an awful lot for such a huge question mark. But if any team can absorb that kind of loss, it’s the Dodgers.

Edinson Volquez, Kendrys Morales, and Alex Rios, Royals.
The Royals, drunk off of an American League pennant, decided to throw a combined $48 million at this underwhelming trio rather than use that money to put together an offer for Shields. Volquez had a decent season for the Pirates, but he’s only two years removed from being one of the worst starters in baseball. Rios somehow hit only 4 home runs last year and will be 34 when the season starts. Morales looked finished last year, managing a .218/.274/.338 slash line. How do any of these guys make the Royals a better team?

About Dave Tobener

Dave Tobener has been writing about baseball for the better part of a decade. He's been to more Giants games than he can remember and was there when Ruben Rivera forgot how to run the bases. Follow him on Twitter: @gggiants