The Cardinals travel to Philadelphia to take on the Phillies for their next three-game set. After going 2-4 in a pair of disappointing series against the lowly Padres and some other ball team, the Cardinals find themselves 4 games behind the division leader Brewers and half a game back of the Cubs.

Probable matchups probably favor the Cardinals, in that we don’t have to face Aaron Nola. Mikolas/Pivetta tonight at 6:05, Weaver/Velasquez tomorrow at 6:05, and Wacha/Arrieta on Wednesday at 12:05. I like each matchup, but it won’t matter if the bats don’t build on last night’s outburst or the bullpen gives up 50 runs a game. On that last note: Greg Holland is traveling with the team, so be wary of shenanigans. Jose Martinez has been reactivated from paternity leave, and Marcell Ozuna just received NL Player of the Week honors for his thus-far torrid June.

The Phillies, like the Cardinals, are 4 games back in their division and half a game behind the NL East second-place team. The parallels between the divisions are manifold: each had a viable superteam projecting to run away with the division crown, a lock for last place, and three interesting teams set to squabble for second place and a shot at a wild card berth. In both divisions, an upstart has the division lead with a comfortable, but by no means dispositive, margin of banked wins (the Braves and the Brewers). In both divisions, the superteam is in second place, behind the leader by 3.5 games and still not quite firing on all cylinders (Nationals and Cubs). In both divisions, the lock for last place is mathematically eliminated from playoff contention through 2024 (Marlins and Reds). In both divisions, the fourth-place team is below .500 if for no other reason than that life isn’t fair (Mets and Pirates). And in both divisions, third place is held by a scrappy team with a 37-32 record, .5 games behind their respective superteam. That the Cardinals are in the mix and on pace to finish well over .500 but maybe just shy of the playoffs is not surprising; by contrast, the Phillies should not be this good this year.

When I wrote about the Padres’ recent history, we talked a little about the dangers of trading the farm to dramatically reshape a team. The Phillies present another sort of cautionary tale: what happens when you overpay big free agents.

Not terribly long ago, the Phillies were the NL East’s big red gorilla. The 2011 Phillies were a team without a weakness. You had to go to #8 in the Phillies lineup to find a below-average hitter; Ryan Howard, Shane Victorino, and 4th OF John Mayberry notched OPS+ marks around 30% better than league average, and 28-year-old Hunter Pence turned in 54 games of 60% above league average hitting. On the pitching side, reigning NL Cy Young winner Roy Halladay headlined one of the most fearsome front three in living memory. Halladay, Cliff Lee, and Cole Hamels combined for an incomprehensible 23.7 bWAR, while The Phillies’ #4 and #5 starters, Vance Worley and Roy Oswalt, notched perfectly respectable 3.3 and 2.1 win seasons.  Oh, and the bullpen was great, too. The 2011 Phillies finished 102-60, and actually underperformed their Pythagorean record by a game. As much as any team could be, they were prohibitive favorites to blow away the postseason field and take home their second ring in three WS appearances since 2008. (We all know how that worked out.) Even with their disappointing exit in the NLDS after flukey losses to an upstart Cardinals squad, the 2011 Phillies looked poised for a few more great seasons, if not a dynasty.

The 2012 Phillies finished 81-81, third in the NL East. Halladay finished the year with roughly 9% of his 2011 value after throwing 156 innings. He was 35, but the drop was still astounding. Cliff Lee only lost about half of his value, while Hamels put up more than 2/3 of his prior year’s output. (Hamels and Lee led the team in pitching value.) The offense employed mostly the same personnel, but only 3 regulars were better than average.

The 2013 Phillies finished 73-89. Roy Halladay struggled with injury and retired the following offseason. Cliff Lee and Cole Hamels paced the rotation again with 6.8 and 4.2 bWAR, but found themselves alone in a talent wasteland, a stars and scrubs construction where the scrubs were paid like stars and the stars were paid like stars and the rest of the team was probably just concessions workers wearing jerseys, because GM Ruben Amaro Jr.’s checks had started bouncing.

The 2014 Phillies finished last in the NL East. The 2015 Phillies, entering their first year of an overdue rebuild, lost nearly as many games as the 2011 Phillies had won. The 2015 Phillies played badly enough that the 2016 Phillies got the first overall draft pick. Amaro was canned in September ’15.

So what happened to the good times?

Amaro took over following the Phillies’ WS-winning 2008 campaign. His 2009 squad won the pennant but dropped the series to the Yankees in 6 games. The following offseason, Amaro traded Travis d’Arnaud, Michael Taylor, and Kyle Drabek to the Jays for Roy Halladay, simultaneously shipping Cliff Lee to the Mariners for a big pile of nothing. Halladay was owed $60M over the following three years. Amaro also inked Ryan Howard, 30 years old, to a 5 year/125M extension in April 2010. That extension wouldn’t start for another 2 years. The following offseason, Amaro brought Cliff Lee, now 32, back as a free agent on a 5 year/107.5M guaranteed contract with a 12.5M option for 2016.

Following the Cardinals’ upset of the Phillies in 2011, Amaro gave Jimmy Rollins 33M for 3 years of his veteran service, and another 50M to Jonathan Papelbon for 4 years of his relief pitching. Ryan Howard’s contract extension began. After the 2012 Phillies went .500, Amaro gave another $144M to secure Cole Hamels through 2015. After the 2013 Phillies were worse, Amaro gave an ancient AJ Burnett 2 years/22.5M, and an aging Chase Utley 2 years/27M.

The bottom line, I think, is that every time an Amaro contract didn’t pan out, he tried to spend his way out of it. The team ended up married to an incredible mass of immovable debt and lacked the resources to spend or trade its way out. To be sure, history will probably be kinder to Amaro’s tenure than his contemporaries were, as he also presided over the acquisitions of much of the Phillies’ young and exciting core (Odubel Herrera, Rhys Hoskins, and Aaron Nola, to name a few). The Phillies are well on their way to a recovery, and have settled a bit after a very strong April and May. But it’s telling that they’ve done that by rebuilding their farm, continuing to develop talent, and signing contracts that would’ve seemed like afterthoughts during the Amaro regime. With MLB’s present structure, it’s impossible to spend your way to championships, even for very large market teams. Amaro showed us that you’re likely to severely hamper your mid-to-long-term future if you try.

Amaro is a tragic figure–unlike AJ Preller, he’s not a bad guy, and baseball runs in his veins. He was a second-generation Phillies player before he came up through the FO, and he still roots for them from his new post as first base coach for the Mets. But the depth and duration of the dark half decade from 2012 through 2016 is also almost entirely the result of Amaro’s extreme spending spree from 2012 through 2013.

The Cardinals project as a better team than the Phillies in just about every way. This series is about as important as a series in June against a non-division rival can be for us; this team needs to be better, against better competition going forward, if we want to have a hope of seeing postseason baseball in St. Louis. But even if we miss the postseason, the FO would be wise to heed the lessons of Ruben Amaro Jr.’s fall from grace, and the horrible Phillies teams that preceded it.