Photo Credit: AP Photo / Charles Krupa

In July of 2016, Dave Dombrowski made what was viewed by many as a questionable trade when he sent highly touted pitching prospect Anderson Espinoza to the Padres for left-handed pitcher Drew Pomeranz.

Many were left questioning why Dombrowski would be willing to part with what was a consensus Top 20 prospect in baseball for Pomeranz. The left hander was a bit of a journeyman before breaking out in San Diego.

The trade drew heavy criticism as Espinoza was promising and a mere 18 years old. Previously ranked in the top five of the Red Sox farm system, the young right hander flashed a fastball in the triple digits – garnering comparisons to Pedro Martinez.

In San Diego, Pomeranz had an 8-7 record, had logged 102 innings, posted a 2.47 ERA with a 10.1 K/9, and a 3.6 BB/9. At the time, the Red Sox were looking for controllable young arms and Pomeranz fit that mold.

Did Dave Dombrowski win that trade?

It’s hard to tell since Anderson Espinoza is years away from making the major league roster – especially after suffering a torn UCL last season.

For now, Dombrowski deserves credit for being aggressive.

Despite a shaky first stint in Boston, Pomeranz had a career year in the rotation behind Chris Sale. Drew posted a 17-6 record, striking out 174, walking 69, and finished with a 3.39 ERA.

The Red Sox avoided arbitration with their emerging left hander this offseason, but will be set to test free agency after the 2018 season. Dave Dombrowski must now decide whether, or not to extend “Big Smooth.”

Extending a player is crucial, but the Front Office must be smart to avoid breaking the bank for Pomeranz. Craig Kimbrel, Chris Sale, and Mookie Betts should all be priorities to extend to a longer deal.

After the Red Sox hired Alex Cora, it is likely that a solid relationship with his manager could convince Drew to hang around. In Oakland, Pomeranz and John Farrell got into a verbal disagreement in the dugout – likely causing turmoil in their relationship.

Details are not yet solidified, but Pomeranz’ performance in Boston is worthy of a modest, multi-year extension.