Losing is Hard to Break
When was your teams last winning season? When did they last compete in the playoffs? If it was more than 4 years ago, expect your team to overspend on free agents, and even that might not be enough. No one enjoys losing and athletes like it even less. Most of the top free agents will forgo a few million dollars to avoid playing on a team that doesn't have a chance of winning the World Series. Last season the Orioles couldn't lure a top free agent no matter how much they were willing to offer, when Mark Texieria was a free agent he opted for the Yankees and slightly less money than the Orioles offered. This season we have seen the Mariners get rebuffed by Josh Hamiltion (Angels), Nick Swisher (Indians), BJ Upton (Braves), and probably some others I have not yet heard about. New field dimensions be damned, these players do not want to waste their prime years merely playing the game, they want to play for October glory.
Those players who are willing to take money ask for, and receive, a king's ransom. Jayson Werth is easiest example, coaxing a then-losing Nationals team to give him more years (7) and money ($126 million) than any other team admitted to be willing to commit to him. This season two pitchers seemed to play the team against itself to get either more money (Jeremy Guthrie, Royals, 3/$25m) or years (Edwin Jackson, Cubs, 4/$52m). Nick Swisher with his 4/$52m deal with the Indians strikes me as another overpay. These players were able to convince a team to bid against itself in order to land their targets even when no other teams were willing to come near the terms agreed to. When it works the team starts to win and players are more willing to come over closer to market rate. The Nationals gamble on Werth paid off, they are now a top choice for players. The Orioles are now on the short list for players after their first winning season in 15 tries. They may have not signed any big names yet, but it is a start that other teams would pay for.
Pitching, Pitching and More Pitching
Pitchers get paid. True Kyle Lohse and Rafael Soriano highlight a list of free agent pitchers still available, but those who have signed are getting paid. Jonathon Broxton (Reds) and Brandon League (Dodgers) both landed 3/$21+million presumably to close. Neither are quite where Soriano goes and both have had issues in the recent past, but closers tend to get paid. Sean Burnett, Angels (2/$8m) and Mike Adams, Phillies (2/$12m) are getting paid handsomely to set up. There are still enough unemployed pitchers for bargain hunters, but for as much as GMs complain about the volatility of relief pitchers they spare no expense when addressing their own weaknesses.
Aside from the starters previously mentioned, Zack Grinke (Dodgers) has the offseasons top prize 6/$147m. It seems every year the top pitcher can name their price whether in years, average annual value, or total dollars and someone ponies up the dough. Other starters are not left searching for scraps either; Jeremy Gutherie and Ryan Dempster (2/$26.5m) from the Red Sox shows that if you have a track record teams will overlook a truly dismal performance for half a season when writing the checks. Francisco Loriano, Pirates (2/$12.75m), Tim Hudson, Braves (1/$9m), Dan Haren, Nationals (1/$13m) show that injuries and ineffectiveness are no barrier to an eight figure payday, and this is without mentioning Jorge de la Rossa, Rockies (1/$11m). If you can pitch long enough to show promise or longevity, someone will step up and extend your career and fatten your wallet in the process, not a bad gig if you can get it.
Never Underestimate an Owner
Finally, when a big free agent is available and the "mystery team" surfaces, look for the deep pockets of sole owners. George Steinbrenner made a habit of spending big on what he wanted, and usually getting it. Since his kids took over the operation the spending has been somewhat curtailed, but the pattern still rings true. Last year Albert Pujols was going back to the Cardinals, everyone knew it, all that was out there was some "mystery team" showing up late. Some players may use that specter as a marketing ploy, but Arte Moreno of the Angels was the wealthy old kook willing to outspend the Cardinals, by a large margin, to land the prized free agent. For these owners it is not about team needs as much as personal wants. These owners know they do not have a long time left and want to win a World Series before they go, so they will shell out whatever they feel necessary for that pursuit. Moreno was at it again this season, landing Josh Hamilton (5/$125m) with barely a whisper of his interest. Mike Ilitch of Detroit is another such owner. Last season he shocked everyone by signing first baseman Prince Fielder for a kings ransom (9/$214m), despite having perennial MVP candidate Miguel Cabrera at the position. They were four wins from that gamble working out and Cabrera certainly appreciated the protection. Ilitch is back at it this offseason, signing Anibal Sanchez (5/$80m) over the Cubs and I would not be shocked if he does not open the pocket book one more time to get Rafael Soriano sometime in January.
To recap: if your team has a history of losing expect longer or more expensive contracts for just about any player. If your team is targeting pitchers, going cheap will not help land their target players, at least one other team is likely to show interest and flash a bit more cash. And finally, if the team has an aging owner, do not be surprised on anyone they go after, and likely land. There are plenty of other factors that make up the actions of teams in the offseason, these three just stick out to me. Feel free to let me know if you notice something else.
*Contract information was from MLBTR 2013 Free Agent Tracker