Going All-In With a Keeper League Team

Live for today. That’s long been a mantra of mine in real life, and it applies to fantasy baseball too.

While some dynasty league owners start thinking of rebuilding come June or July, some of us choose to always go for it, no matter how bad the odds seems to be of getting back in contention.

First of all, we’ll let you behind the curtain for a minute to explain how RotoAce might have two opposite opinions on the topic of whether to rebuild. RotoAce is comprised of Phil Krugel and me, Rudy Ropp. We have been in the same keeper league together for so many years that we’ve lost track, but let’s just say it goes back to the ’90s. Phil has found himself near the bottom of the standings with a snakebit team as the All-Star break looms a handful of times and gone the rebuilding route. Meanwhile, I  don’t recall ever going through with a full rebuild despite find my team buried more than a few times.

Phil has had mixed results with his rebuilding efforts, coming back the following year to finish in the money one time and he’s in first this season on the heels of a retooling. He had seemed to do a better job of rebuilding two years ago only to be devastated by injuries last season that led to another reworking. Sometimes it works, sometimes it doesn’t.

Meanwhile, I’ve been mortgaging the future every year for over a decade and have still found a way to contend the next season. I came up just short of the money each of the past two years, finishing fourth when only the top three spots pay out, but took home cash five straight years before that. The year that I finished in first place, I was in 9th in late July and had taken a commanding lead by the end of August. It can turn that fast.

My case basically has three points:

1. Law of averages. Most of the time, it’s just a matter of a few too many of your key players underperforming that leaves you stuck near the bottom of the standings. This season, I was in 11th place out of 12 teams in mid-June, but I deemed that it was due mostly to slow starts from a handful of my top players – Hanley Ramirez, Aramis Ramirez, Alex Rios and to a lesser degree CC Sabathia, Cliff Lee and Mike Stanton. Once these guys started to heat up, my team would rocket up the standings. Sure enough, Aramis, Sabathia and Lee went completely nuts and Hanley and Stanton have picked things up too. Six weeks later, I’m in third place. And most of that happened in the first two weeks, when I moved up to fifth place. Meanwhile, teams that are benefitting from more than their fair share of hot-starters are bound to come back to earth as well.

2. Diminishing competition. The baseball season is a marathon, and some owners hit the wall near the midway point and start to let their rosters get stale. Then there are the owners that choose to rebuild, cutting out usually about a third of your competition. Our commissioner announced he was rebuilding in mid-June when I was still behind him in the standings, briefly making me question staying the course. But then I realized that was just one more team that I would inevitably leapfrog. If you just keep grinding, picking players off the waiver wire and making trades, you’d be surprised how often your team will make its way back up the standings.

3. Feed on the weak. Take advantage of the rebuilding teams, turning young players or injured stars into players that can help you more now. You have to know where to draw the line to protect your future – I have made Mike Trout untouchable despite the fact that every rebuilding owner has inquired about the elite prospect. The best trade I’ve made was to get Ryan Vogelsong for Jordan Lyles just as the Astros’ 20-year-old pitcher was getting called up. Accept that some deals will come back to haunt you, like when I dealt Eric Hosmer for veteran help last summer, but there’s a near-inexhaustible supply of prospects. Make sure you’re getting a reasonable return, otherwise it’s probably best just to sit on your asset. I shopped Shin-Soo Choo, but couldn’t find a match and chose to wait until he returns in mid-August to provide a late-season reinforcement. Sometimes you can get a rebuilding owner to overpay for young players, like when I traded Tim Lincecum and Yovani Gallardo in their rookie seasons for overpriced and unkeepable Bobby Abreu, Jose Valverde, Aubrey Huff and Kelvim Escobar. It was enough to push my team across the finish line in first place, but it stung when Lincecum and Gallardo turned into mainstays on the rebuilding team that then won two straight titles.

Turning our attention to my other keeper league – Diamond Life, a deep NL-only roto – where Phil and I share a team appropriately named the RotoAces, we have been toiling in last place most of the season. It has mostly been the byproduct of slumping stars, as we’ve been saddled by poor first halves from Hanley, Dan Uggla, Jayson Werth, Roy Oswalt, Ted Lilly and Juan Uribe. Rather than fold up tent and rebuild around Stephen Strasburg, we traded his cheap contract as the centerpiece of a blockbuster that netted us the expiring contract of Matt Kemp and the unaffordable contract of Troy Tulowitzki, among others.

We kept with the all-in approach by trading away a keepable Jayson Werth with a slightly overpriced and underperforming Lilly for an unkeepable Corey Hart and a dirt-cheap Vogelsong. We’re hoping Hart can match Werth while Vogelsong outperforms Lilly, although this is a bit of a crapshoot. We capped it off by shipping off a cheap Aaron Harang and the crappy Aaron Rowand for somewhat affordable Nyjer Morgan and Bronson Arroyo, hoping that Morgan can give us some of the steals we lost be trading away Werth and that Arroyo can repeat his career-long trend of huge second halves.

Now our season is pretty much in the hands of Tulo, Kemp, Hanley, Uggla, Lance Berkman, Hart, Chris Young and Matt Garza, but it’s a pretty impressive list of stars that matches up favorably with some of the teams we’ll be trying to catch.

In an 11-team league with four teams already rebuilding, we’re one of just seven teams competing for four money spots. We may still wind up out of the money or just taking the modest winnings from fourth place, but we’re confident that we can patch together a decent enough keeper list and have a good enough auction next year to contend again. With the trade deadline not until the end of August, we could always sell off some of our stars for future pieces if we don’t think we can make a push into the money in September.

I have so routinely used this approach to take lower-division teams to finishes in the money that I don’t mind if it slightly diminishes my chances for the following year. After all, the point of this is to win, and win now. And you should have some extra fun in the process.