Earlier, I linked to Sam Miller's article about this offseason's free agent market. Sam wonders why bad or mediocre teams, such as the Red Sox and Cubs, have spent so heavily lately compared to good teams. Via MLBTR's Free Agent Tracker, teams that were below .500 last season have issued the three biggest free agent contracts so far (Jon Lester, Pablo Sandoval and Hanley Ramirez), along with two more in the top ten. The No. 11 free agent contract went to David Robertson, who joined a 73-89 White Sox team that also made a number of other huge additions. This offseason hasn't been dominated by good teams trying to be great, but by bad teams trying to be good. So what's going on here?
At least this winter, the fact that historically high-spending teams like the Red Sox and Cubs had bad years in 2014 affects this trend, and you can also point to things like the Padres (who have taken on a lot of salary, though they've mostly done their spending in trades rather than on free agents) having new ownership and the Cubs having a bunch of young talent ready to contribute.
But Miller also points to broader trends. With the second Wild Card spot, more teams can credibly call themselves contenders. Meanwhile, some of the usual big spenders have spent less, giving teams like the Padres the opportunity to bid for top talent. (Five years ago, maybe it would have been the Yankees taking on Matt Kemp's contract.)
I'd add that other changes have played a role as well. Most teams are aware of the importance of defense and have increasingly sophisticated tools with which to evaluate it, and yet they're still able to cheaply assemble good defensive teams, partly because the free agent market and arbitration system still undervalue defense, and partly because younger players are generally much better defensively than older players. Also, the trend of pre-free-agency extensions has allowed teams in all markets to keep top players through their prime years. If the Pirates hadn't signed Andrew McCutchen to an extension, they probably would have traded him by now. Due to those factors and others, formerly hopeless franchises like the Pirates and Rays are now among the better ones, and as Sam mentions, teams like the Cubs and Astros, who have more capacity to spend, were rebuilding last year.
Sam also suggests another factor, though -- teams have realized there's a lot of value in just getting to the playoffs and letting the chips fall where they may. As you might have heard before, the playoffs are a lottery. A slightly weighted lottery, maybe, but a lottery nonetheless. Billy Beane famously said over a decade ago that his "**** doesn't work in the playoffs," and if we needed a reminder, there was Beane last summer acquiring Jon Lester and Jeff Samardzija down the stretch and getting bounced in the Wild Card game, or the Tigers acquiring David Price and getting eliminated a round later. So there's value in just trying to get to 90 wins and then hoping for the best. The Pirates got to the playoffs in each of the last two seasons. They didn't get far in either season, but they might have. They gave themselves chances.
We all know anything can happen in the playoffs, and yet the consequences of that knowledge are very hard to accept. It's hard when the team one roots for is rumored to be trading for Lester or David Price, only to fall short, and it still stings a little when the Pirates start Edinson Volquez in the Wild Card game and get steamrolled by another team's ace. Intellectually, we know that it would have taken a ridiculous pitching performance to keep the Pirates in that game, and that the teams to which Lester and Price were eventually traded fell apart anyway. But it's worth keeping in mind that there's value in the small-bet approach the Pirates appear to be pursuing. They're not spending heavily in the offseason in part because they don't want to or can't, and I hate that. But an expensive veteran is only likely to help so much in the playoff roulette game anyway.
Perhaps the main confounding factor here is that it's much better to win one's division than to win a Wild Card. Simply having to play a Wild Card game cuts one's chances of winning a World Series in half. (That's a simplification, but a fairly accurate one.) So if a team is going to go for it, it should do so in order to win its division, not necessarily to thrive in the playoffs. The Pirates haven't won their division in either of the last two seasons, and they paid for it last year.
It's consistent, I think, to lobby for the Pirates to spend more, but also to acknowledge that the strategy they appear to have in place right now (assembling consistently strong teams without ever really sticking all their chips in the middle) is a pretty good one, even if it's also annoyingly financially convenient. Now if only they could do that while also winning their division, they'd be set.