There isn't a baseball fan alive—myself included—that at one point or another hasn't been convinced that they could do a better job of running their favorite team than the general manager at the time.
Yet how many of us could honestly handle the pressure that comes along with the job?
How many of us, upon hearing that legendary bass line pounding in our heads, could stay the course and burst into the lyrics of the David Bowie/Queen classic "Under Pressure" instead of Vanilla Ice's "Ice Ice Baby," a classic in its own right?
I'd argue that number is far lower than anyone cares to admit.
With contingents from each of MLB's 30 teams, along with a throng of agents, players and media about to descend on San Diego for the 2014 winter meetings, which get underway Sunday, the chance to wheel-and-deal will never be greater.
For some teams, like the Philadelphia Phillies, that's going to be nearly impossible. As the Philadelphia Inquirer's Bob Brookover recently noted, nobody has a clue as to who is making decisions for the Phillies right now.
It's hard to strike a deal when you don't know who to talk to.
For the rest of baseball, however, the pressure is building for team executives to make something happen for their respective clubs. To emerge from the meetings with a better roster than they arrived with.
Which of those executives is under the most pressure?
Let's take a look.
Brian Cashman, New York Yankees
Pressure is nothing new for Brian Cashman—it comes with the territory when you're responsible for putting together the roster for the game's most storied franchise in the world's largest media market.
After appearing to confirm the report that the Yankees would not get involved with the highest-priced free agents in November, per the New York Daily News' Mark Feinsand and Bill Madden, cracks in Cashman's supposed resolve have begun to show in December.
Take, for example, how quickly the team's stance on free-agent reliever Andrew Miller seems to have changed in the span of seven hours.
With division rivals Boston and Toronto both making major additions, could the pressure to keep pace—and end his team's two-year absence from the playoffs—be getting to Cashman, forcing him to alter his offseason strategy?
As one executive tells the New York Daily News' John Harper, the reality of the situation may be setting in.
Look, I know Cash would love to build more from within. But if they want to have any chance at winning next year they need a front-line starter. Their offense isn't very good, but if they added a Scherzer they would have a chance to win with pitching.
Are you telling me they’re going to go into next year with (Masahiro) Tanaka as their No. 1, not knowing if his elbow will hold up? Signing Scherzer would give them another No. 1, and if they do get lucky with Tanaka and (Michael) Pineda, they could outpitch teams like Baltimore, Toronto and Boston.
With each additional transaction by baseball's other 29 teams, the Yankees find fewer and fewer legitimate, game-changing options to choose from to plug holes not only in the rotation, but at second and third base as well.
Coming back from the winter meetings with the same roster that he has now simply isn't an option for Cashman.
Dan Duquette, Baltimore Orioles
No team in baseball has seen its lineup take a bigger step in the wrong direction this winter than Baltimore, which lost its leadoff hitter (Nick Markakis) and cleanup hitter (Nelson Cruz) to free agency.
Combined, the pair accounted for 116 extra-base hits (54 home runs), 158 RBI, 168 runs scored and 570 total bases during the team's run to the AL East crown in 2014.
Replacing that kind of production isn't easy, though Duquette believes he has the internal options to plug one of those holes.
That's all well and good, but are the Orioles really prepared to rely heavily on that group?
Lest we forget: Steve Pearce was a .238 hitter with 17 career home runs over the first seven years of his career, Alejandro De Aza was a non-tender candidate before a late-season trade bought him to Baltimore and David Lough became an afterthought for the club in 2014.
Those facts don't exactly inspire confidence that any of them are up for the challenge of replacing consistent contributors like Cruz and Markakis. That's a big reason why we've seen the Orioles linked to Atlanta's Justin Upton in a potential trade by Fox Sports' Jon Morosi, and free agent Michael Morse, per USA Today's Bob Nightengale.
Whether it's Upton, Morse or someone else, leaving San Diego with at least one of those missing bats replaced is an absolute must for Duquette.
Andrew Friedman, Los Angeles Dodgers
As it stands now, nearly 30 percent of the Dodgers' 25-man roster heading into 2015 is comprised of outfielders: Carl Crawford, Andre Ethier, Chris Heisey, Matt Kemp, Joc Pederson, Yasiel Puig and Scott Van Slyke.
As Bleacher Report's Jason Catania wrote recently: "It's actually not healthy for the Dodgers to have this many outfielders on the roster."
He's right.
While Heisey and Van Slyke are used to serving as reserve outfielders, Crawford, Ethier, Kemp and Puig all fancy themselves everyday players. Throw in Pederson, the team's top prospect who has nothing left to prove (or gain) by spending more time in the minor leagues and, well, something's got to give.
The problem, of course, is finding a team that's willing to take on the bloated salaries of either Crawford, Ethier or Kemp. As Fox Sports' Ken Rosenthal recently noted, all three are overpaid when compared to the kind of deals that they'd command if they were currently free agents.
Matt Kemp is owed $107 million over five years, Carl Crawford $62.25 million over three and Andre Ethier $56 million over three, according to Cot’s Baseball Contracts.
Put those three on the open market, however, and their actual values would be less — significantly less in the cases of Crawford and Ethier.
At this point, I would guess that Kemp would go for five years, $95 million; Crawford for three years, $36 million; and Ethier for three years, $30 million.
In order to move any of them, Friedman is going to have to pick up a substantial chunk of that remaining salary—especially if he's expecting to receive useful talent in return.
There are enough teams still looking to add a big bat for a deal to come together. Kemp, arguably the most valuable of the veteran trio, has been linked to a number of teams, including Baltimore and Seattle, per The News Tribune's Bob Dutton, and San Diego, per Rosenthal.
Friedman arrived in Los Angeles with a reputation as something of a miracle worker, given his success with the financially strapped Tampa Bay Rays. It may take nothing less for him to alleviate the logjam in the team's outfield—but the pressure is on for him to do just that.
Note: Since this story was initially published, the Yankees have made their first move, acquiring SS Didi Gregorius from the Arizona Diamondbacks in a three-team deal according to Rosenthal. While it's a start, Cashman and company have quite a bit of work to do before the Yankees can seriously be considered contenders once again.
To talk winter meetings or anything baseball, find me on Twitter: @RickWeinerBR
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