Phillies Nation

Raising Questions

What if … the Phillies traded Ryan Howard in 2008?


As we simulate seasons and look back at the past this week, we figured this would be a good time to ask ‘What if?’ So each Phillies Nation writer is posing a what-if question this week.

Today, it’s Tim Malcolm and the trade that changed fortunes …

It’s April 2008. The Phillies are 6-7. And I’m a dumb 23-year-old kid quick to shake up my favorite team because that Division Series loss to the Rockies stunk.

So I take to this here website and write: Why I Would Trade Ryan Howard

“It sounds almost ridiculous that a team in the top half of the payroll list contending for a World Series would want to trade its biggest power hitter, a man capable of hitting 60 home runs. But there are reasons to think heavily about dumping Howard.”

My reasons actually are prescient. Howard would become a designated hitter-type player, as I wrote. I actually also wrote this: “He doesn’t deserve the $25M or so he could gain in a couple years.” Words I actually wrote in 2008.

The Phillies didn’t trade Howard during the 2008 season. Instead, he helped push the Phils past the Mets for another division championship, then helped push the Phils to their second world championship. Without Howard, it’s arguable the 2008 Phillies do not win the World Series. Heck, they might not make the playoffs.

Well …

Imagine my piece turns into reality. Imagine that, around the 2008 trade deadline, with the Phillies floundering at 54-48 after losing two of three to the Mets, Pat Gillick pulls the trigger on a stunning deal. And imagine that deal is the one I recommended the Phillies make.

What if the Phillies traded Ryan Howard in 2008?


July 25, 2008. The Phillies trade Ryan Howard to the Yankees for RHP Ian Kennedy, OF Austin Jackson, RHP Ross Ohlendorf, RHP David Robertson, 3B Marcos Vechionacci.

My original trade included pitcher Chris Britton, but he was injured in July. Thus, I include Ohlendorf instead (who was, in real life, traded to Pittsburgh a day later). Also, just so we’re aware, I don’t think the Yankees even entertain this trade in 2008. But again, we’re suspending all disbelief for a few moments …

First thing’s first. Greg Dobbs becomes the temporary first baseman. Ohlendorf (6.53 ERA in 40 innings) heads to triple-A to be converted to a starter. Robertson and Kennedy also head to triple-A, both potentially getting to Philadelphia before the season ends. Jackson goes to double-A to continue developing. Vechionacci was coming off a decent 2007, but he stalled in 2008; for the purposes of this piece, we’ll forget him.

The Phils do need a roster spot filled, so Andy Tracy is called up to fill in some games at first. The 34-year-old has 17 HR and 73 RBI heading into August 2008, so maybe he helps a little. Either way, he or Dobbs are not long-term solutions at first.

Does the 2008 team make the playoffs? Hard to say. Howard was worth 1.8 WAR (and Dobbs 0.8 WAR), so maybe the Phils lose a game or two more. That said, Howard came alive in September (.352/.422/.852). For this exercise, let’s imagine the Phils lose two more games in September with Dobbs instead of Howard. That still gives them a playoff spot.

At that point who knows. Maybe the Phils have a tougher time against Los Angeles or Tampa Bay. But without Howard’s bat the Phils still look good in most of those games.


With Austin Jackson near the majors, Ruben Amaro Jr. might not waste a three-year deal on Raul Ibanez in the 2009 offseason. Instead, Amaro throws a one-year deal at Garret Anderson, who hits .268/.303/.401 with 13 HR and a -1.4 WAR in 2009. A temporary solution, and not the type of production the Phils get from Ibanez (2.9 WAR).

First base is a different situation; the Phils need a long-term solution there, so they sign top free agent Mark Teixeira to a five-year, $115 million contract through 2013. This gets tricky: The Yankees signed him to an eight-year pact in real life, but I’d imagine they’d be out of the running since they have Howard in this simulation. That said, the Angels, Orioles and Nationals were heavily interested in Tex. Maybe the Phils have to go seven or eight years. Maybe not. Let’s not dwell.

Teixeira is great in 2009 (.292/.383/.565, 39 HR, 5.3 WAR), and for that matter, good in 2010 (4.1 WAR) and ‘11 (3.4 WAR). Injuries in 2012 (still a 3.8 WAR) and ‘13 (-0.2 WAR) hurt his production, but his deal isn’t a major albatross, just a slight inconvenience. Howard, meanwhile, puts up a combined 5.6 WAR during those five years.

I’d imagine Teixeira and Anderson cancel out Howard and Ibanez for 2009, so the offense is in good shape. Meanwhile, Ian Kennedy joins the rotation in 2009 as the fifth starter (no Chan Ho Park) and pitches well, but an aneurysm unfortunately stops his season in May. That brings J.A. Happ into the rotation, and as we know, he pitches well.

But it’s still likely the Phils trade for a starting pitcher, especially now that there’s depth in the farm system. And since there’s depth, maybe, just maybe, the Phils trade Domonic Brown, Kyle Drabek, J.A. Happ and Anthony Gose to Toronto for Roy Halladay.

The new rotation in August 2009 is Halladay, Cole Hamels, Joe Blanton, Jamie Moyer and Ross Ohlendorf. Halladay pitches to something like a 2.90 ERA down the stretch, while Ohlendorf adds a 2.75 ERA (which he did late in 2009). The Phils may still add Pedro Martinez (since Ohlendorf is basically Happ), which means the 2009 season ends in about the same way: a third division crown and a chance for another world championship.

And, by the way, David Robertson is called up and puts up a 3.30 ERA, helping a bullpen that suffers throughout much of 2009.


Jackson joins Jayson Werth and Shane Victorino in the Phils outfield, putting up a 5.1 WAR, a huge improvement from Ibanez’s 0.4 WAR in 2010. Kennedy also settles into the rotation, putting up a 3.80 ERA with 168 strikeouts at age 25. Halladay does what Halladay did (a Cy Young award). Hamels bounces back.

Ohlendorf (4.01 ERA, 1.8 WAR) offers the Phils a better option than Kyle Kendrick or Jamie Moyer. And with four solid starters, it’s likely the Phils don’t add Roy Oswalt for the stretch run, holding onto Jonathan Villar and bringing up top prospect Carlos Carrasco.

Robertson continues to help the bullpen (3.82 ERA, 0.7 WAR), joining a resurgent Lidge, Ryan Madson and J.C. Romero in the back of the group.

So the offense is better in 2010 (remember, Teixeira is at first base; plus, the Placido Polanco signing still happens since the team needs a third baseman), while the pitching staff likely improves on what really happened. Does that mean the Phillies get past the Giants in the Championship Series? Who knows …


This could be a lot different. Would the Phils sign Cliff Lee to a free-agent contract with Halladay, Hamels, Kennedy and Ohlendorf anchoring the rotation? And Carrasco waiting in the wings? It’s possible (they have the money), but even if they don’t, Kennedy throws up a 2.88 ERA with 198 strikeouts in 2011, finishing high in Cy Young voting.

Ohlendorf gets hurt in early 2011, and Carrasco suffers growing pains, so what I think happens is the Phils make a midseason trade, sending Jonathan Singleton and Jarred Cosart to Seattle for Doug Fister. The 27-year-old stabilizes the rotation with a 2.00 ERA down the stretch.

Then there’s the bullpen. Madson, Antonio Bastardo and David Herndon pitch well, but it’s Robertson (1.08 ERA, 100 K, 4.0 WAR) who stuns. He’s arguably the best reliever in baseball in 2011.

Meanwhile the offense remains good. The Phils could actually sign Jayson Werth to a long-term deal (since they have money to burn). Either way, Jackson contributes a 4.9 WAR (better than the -2.0 WAR Ibanez throws up). Teixeira is still hitting well. The Phils probably fare better in the postseason, though they may finish with a couple fewer wins in the regular season.

2012 and beyond

So this got exhaustive. But it’s really fun.

Jackson puts up another 9.0 WAR between 2012 and ‘13 (he was really good to start his career). Victorino doesn’t get moved at the trade deadline; instead, the Phils either still have Werth, or maybe they sign someone like Carlos Beltran.

Injuries catch up to Teixeira, so the Phillies scramble to find a replacement, but it’s likely that replacement (yes, maybe Darin Ruf gets his shot) fares better than an injured Howard.

The pitching staff starts to show cracks. We all know what happens to Halladay; meanwhile, Kennedy follows up 2011 with a few mediocre seasons. But Hamels stays good, and Fister, acquired in 2011, remains a steady No. 3 starter through his arbitration years.This could be where an in-season trade takes place.

Then there’s Carrasco. It’s hard to say whether the Phils would stay patient with him like Cleveland, but that result wouldn’t show until much later.

It is likely, however, that the Phillies don’t splurge on Jonathan Papelbon in 2012, since Robertson was so amazing in 2011. It really doesn’t matter, though, as the Phils bullpen in 2012 isn’t very good anyway.

I’d imagine that with a halfway healthy Teixeira, Jackson and an outfielder like Beltran or Werth, the Phils offense is good enough to keep them in the mix in 2012.

Things fall apart and get impossible to predict in 2013 and beyond, but if the Phillies pulled the trigger on the deal I proposed in 2008, they’d absolutely have more flexibility to remain contenders for longer than in reality. It’s also likely they would’ve been able to rebuild in a smarter, more progressive approach than the full-scale demolition we’ve witnessed over the last three years.

Of course, maybe we never get that championship.

We’ll never know.

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