Pitcher wins, as you may know, are now widely considered to be essentially meaningless outside of a fantasy context. For the same reason, they also make for a weird fantasy stat. For example, Rick Porcello only managed a 4.28 ERA in 2018, which ranked 45th out of 58 qualified pitchers. That ERA was also backed by just a 4.01 FIP, but Porcello was nonetheless one of just 11 pitchers to put up 17 wins last year. Zack Godley's 4.74 ERA was even worse, but he came away with 15 wins. (Porcello won't be particularly cheap in your draft at 163rd on average, but Godley is going 248th, although some of that is in hope that he can meet his potential, not expecting another 4.74 ERA.)
One implication of this is that some cheap pitchers can still get you some juice in that Wins category. Of course, it can be hard or even impossible to predict ahead of time who those will be. While the best option would be to switch your league's settings to Quality Starts (QS) instead, we don't all have that option. For that reason, we need to do our best to bolster that category.
Being on a good team helps, but run and defensive support can be unequal even on the same team. That said, it's about all you can go on if you want to play the win prediction game. With this in mind, here are some possibilities in the later rounds to help those in 5x5 leagues seeking a cheap source of wins.
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Ryan Yarbrough, Tampa Bay Rays
A Tampa Bay starter seems the least likely to join this list, given their popularization of the "opener." However, since relief pitchers don't have to go five innings to qualify for the victory, Yarbrough won 16 times last year while appearing in 38 games, starting six, and throwing 147.1 innings. He is being drafted 457th on average.
But if only wins is your goal, then going for Yarbrough, last year's most common "follower" in the Rays' opener strategy, might make sense. That said, it's not exactly a task that only a select few can fulfill, so anyone with this role doesn't have the most secure job in the world. Still, it's the first thing that comes to mind if you want to find cheap wins this fantasy season.
Anibal Sanchez, Washington Nationals
Outside of followers, wins can be found relatively cheaply with a job-secure but lesser-quality starter on a good team. A perfect example would be Anibal Sanchez, the clear fourth rotation arm in Washington.
The Nationals' top three starters--Max Scherzer, Patrick Corbin, and Stephen Strasburg--are being drafted fourth, 50th, and 59th on average, but Sanchez is going just 287th overall. There are reasons to be wary of Sanchez's 2.83 ERA from last season, given his terrible ratios the previous year, but even his 3.62 FIP made for a 90 FIP- (which is above average).
Sanchez's 10.5% swinging strike rate was just below the league's 10.7 average, which might indicate some regression from a 24.4 K% which was a couple points higher than the league's 22.3 average, but the difference is not massive. Even a league-average ERA from Sanchez on a club like Washington could be good for plenty of wins.
Jhoulys Chacin, Milwaukee Brewers
There is one other thing that can help with wins and that is pitching a lot of innings. Chacin led the Majors with 35 starts last year, which helped him throw 192.2 innings. He did win 15 games, and the Brewers should be a playoff contender again. Chacin is going 263rd overall.
Unfortunately, innings per start, which Chacin does not give you, are going to be highly correlated with being a good enough pitcher to not be available this late. (A starter who throws at least five innings more often will naturally get more win opportunities.)
CC Sabathia, New York Yankees
At this point, the players are already mostly relevant in deep leagues, or as streamers. Since wins are the focus, you still want good teams involved, but you are probably looking at someone without a guaranteed job. If healthy, Sabathia does not fall into that category. Still, he is old (by athlete standards, of course) and fighting heart and knee issues, so you can't put anything in the bank.
The hefty lefty may be entering his final season, but the conclusion of the future Hall of Famer's career comes at the potential beginning of a new Yankee dynasty. That should get him the run support to win a few extra games. Plus, even with four pitchers ahead of him on the NYY depth chart, Sabathia's job is fairly secure, since the Yankees don't have much starting pitching depth.
Sabathia also got swinging strikes 10.8% of the time last season, about the league average, and his highest mark since 2012. That said, he's only going 474th overall, which definitely qualifies as late but also means you won't be taking him in a standard league.
Conclusion
While there is a clear strategy to find wins on the cheap in exchange for limitations in other stats, and it is possible to achieve if you look in the right places, it is also very difficult. Another dangerous thing about trying for wins on the cheap during draft season is that they are usually best found in streamers.
Several pitchers become playable if they are facing the Marlins in Miami. The Orioles and Royals also figure to be juicy streaming opponents this season. It was not intentional that three of the four pitchers mentioned above come from the same division as Baltimore and Miami, but it could have been.
However, if you are late in a draft, and realize that your pitching staff has come mostly from middling teams, you might want to look to a strong contender for your next starting pitcher.