I’m not going to lie. It’s hard to make up ground in the standings this late in the season. Your fantasy baseball trading deadline has probably passed, so you’re left with playing hot hands off of waivers. You need to make sure you don’t hold until guys just for their names. In June or even July, I wouldn’t tell you to lose, say, Jermaine Dye for Matt LaPorta or Andy Marte, but it’s a whole new ballgame in September. There’s only so much your top players can even do in one month. For instance, Carlos Lee hasn’t had a month of more than 5 homers all year. If you really don’t need homers and you’re dying for steals, playing Carlos Lee over, say, Andrew McCutchen isn’t going to get you anywhere.
This goes even more so for Head-to-Head leagues. If you’re heading into the playoffs, or are in the last week of the regular season, it’s really time to put allegiances aside. H2H leagues are won in the last few weeks, so pitching match-ups and most recent starts need to be looked at for everyone. I wouldn’t ever tell you to play, say, Ryan Rowland-Smith over James Shields, but in an H2H league in September, it’s the kind of switch off that you may need to look at. Trust me, it’s a lot better to win with Ryan Rowland-Smith than it is to lose because your opponent grabbed him. As the season progresses, risk needs to be managed, not feared. In September, throw your business management cliches out the window and go for the win.
Lastly, there’s also the fantasy baseball strategy of screwing your opponent before they can screw you. If you know your opponent needs to start three pitchers to overtake you and there’s ten potential candidates for them to pick up, grab the top three options before they can. I.e., force their hand. Push them to pick up some schmohawks like Mitchell Boggs, Craig Stammen and Brian Moehler. As every hitting coach, who’s worth his money will tell you, make Craig Stammen beat you.