Deep Dive: free agent left-handed relievers

Perfect timing: Will Smith saved 37 games for the Giants this year, and has the highest bWAR of any southpaw reliever in this year’s free agent class. (@White_Willy13)

“Deep Dive” focuses on the depth of each position in the Chicago White Sox organization. Each position is broken into a five-part series:

  1. Depth in the rookie levels (Dominican through Great Falls)
  2. Depth in A-ball (Kannapolis and Winston-Salem)
  3. Depth in the higher levels (Birmingham and Charlotte)
  4. Under the Radar-type detail on one of the White Sox players at that position
  5. Free agent options at that position

This article delves into the left-handed relief options available this offseason; as in most years, the pickings are slim.

Aaron Bummer clearly was the best left-handed reliever on the White Sox in 2019. However, the rest of the southpaw relievers struggled with control issues, injuries and/or overall ineffectiveness. What lefties are available who could supplant Jace Fry and/or Caleb Frare as the No. 2, or are any worthy of perhaps being the new closer? And is there anyone out there capable of being a fifth starter if injuries or ineffectiveness occur to someone like Reynaldo López? Below is an outline of left-handed free agents in this year’s class.

(age as of April 1, 2020)

Will Smith
San Francisco Giants
2019 bWAR 2.2
Stats 6-0, 34 SV, 2.76 ERA, 65.1 IP, 65.1 IP, 1.03 WHIP, 2.9 BB/9, 13.2 K/9
Age 30

Aroldis Chapman
New York Yankees
2019 bWAR 1.5
Stats 3-2, 37 SV, 2.21 ERA, 57 IP, 1.11 WHIP, 3.9 BB/9, 13.4 K/9
Age 32

Seems unlikely, but can opt out of two years, $30 million remaining on contract.

Sean Doolittle
Washington Nationals
2019 bWAR 0.9
Stats 6-5, 29 SV, 4.05 ERA, 60 IP, 1.30 WHIP, 2.3 BB/9, 9.9 K/9
Age 33

Doolittle has a $6.5 million club option with $500,000 buyout; it would seem that Washington would pick up that option.

Drew Pomeranz
Milwaukee Brewers
2019 bWAR 0.3
Stats 2-10, 2 SV, 4.85 ERA, 104 IP, 1.43 WHIP, 3.8 BB/9, 11.9 K/9
Age 31

Aaron Loup
San Diego Padres
2019 bWAR 0.2
Stats 0-0, 0 SV, 0.00 ERA, 3.1 IP, 0.90 WHIP, 2.7 BB/9, 13.5 K/9
Age 32

The Padres hold a $2 million club option on Loup.

Tony Watson
San Francisco Giants
2019 bWAR 0.2
Stats 2-2, 0 SV, 4.17 ERA, 54 IP, 1.26 WHIP, 2.0 BB/9, 6.8 K/9
Age 34

Watson has $2.5 million option that he can buy out of for $500,000.

Jake Diekman
Oakland Athletics
2019 bWAR 0.1
Stats 1-7, 0 SV, 4.65 ERA, 62 IP, 1.42 WHIP, 5.7 BB/9, 12.2 K/9
Age 33

Diekman has a $5.75 million mutual option, with a $500,000 buyout.

Tony Sipp
Washington Nationals
2019 bWAR 0.1
Stats 0-1, 0 SV, 4.71 ERA, 21 IP, 1.33 WHIP, 3.9 BB/9, 7.7 K/9
Age 36

Tony Cingrani
St. Louis Cardinals
Age 30

Missed entire season due to injury.

Zach Duke
Cincinnati Reds
2019 bWAR 0.0
Stats 3-1, 0 SV, 5.01 ERA, 23.1 IP, 1.67 WHIP, 6.9 BB/9, 6.9 K/9
Age 36

Brian Duensing
Chicago Cubs
Age 37

Didn’t pitch in 2019.

Mike Dunn
Colorado Rockies
2019 bWAR -0.2
Stats 1-0, 0 SV, 7.13 ERA, 17.2 IP, 1.30 WHIP, 3.1 BB/9, 7.6 K/9
Age 32

Hector Santiago
Chicago White Sox
2019 bWAR -0.4
Stats 1-1, 0 SV, 6.68 ERA, 33.2 IP, 1.90 WHIP, 5.9 BB/9, 10.7 K/9
Age 32

Jonny Venters
Washington Nationals
2019 bWAR -1.1
Stats 0-1, 1 SV, 12.38 ERA, 8 IP, 2.75 WHIP, 5.4 BB/9, 13.5 K/9
Age 35

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Despite my entire family being Cub fans, I grew up listening to Harry Caray and Jimmy Piersall on the radio as I listened to the entire season of the South Side Hit Men of '77. While it's true I have a myriad of other interests (American history, classic literature, classic rock, classic country, blues, jazz, gardening, family,etc.--not all in that order), few things aside from family surpass my interest in all things baseball--especially the White Sox.

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It would be nice to get Will Smith to go along with Will Harris. Tony Cingrani is a South Side boy, so maybe he’d like to join the Sox for next to nothing?

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Seems like he might be open to a MiLB deal to reestablish himself.


Cingrani is the only player I would want that will be available outside of Smith. Maybe Pomeranz as a swingman. Not bad low-cost options for us.