The Final Verdict
If we go from a strict on-field standpoint, the Astros got 1.6 WAR from Giles in the regular season. The Phillies have gotten 4.0 WAR from Velasquez and 0.1 WAR from Oberholtzer. None of the other players played for their new teams in the majors. So from that standpoint, the Phillies won the trade.
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On the other hand, the only player of any real value the Phillies got was Velasquez. While his WAR total is decent, his ERA+ of 91 indicates he’s been nine percent below league average with the Phillies. Giles had an ERA+ of 114 with the Astros, meaning 14 percent above league average.
There’s more to this story, of course. The Astros won the World Series in 2017 in spite of Giles, as his 0-2 record, 11.74 ERA and 2.217 WHIP in the postseason were downright gnarly. They gave up five players to get their closer of the future, and he really only had one regular season in which he pitched like they’d hoped. The other two seasons and his postseason weren’t good at all.
On the flip side, the Phillies only got meaningful contributions from one of the five players they got in this deal. That one player, Velasquez, has been a below average pitcher the past three seasons. So they gave up a potential All-Star closer and got very little in on-field contributions in return.
In truth, the Astros didn’t get a whole lot either. Giles looked like the best version of himself in 2019 with Toronto, of course, but had no shortage of difficulties in Houston. In the end, I would probably call this trade a wash, simply because neither team really got anything close to what they were looking for from this.