What if the Red Sox traded for Roy Halladay in 2009?

It is “What if?” week at SB Nation, so we’ll have a few posts throughout the week looking at some “What ifs” from Red Sox history. This is one of those posts!

During the summer of 2009, I peaked in terms of checking MLB Trade Rumors. I was a soon-to-be college junior and home for the summer. Meanwhile, the Red Sox were a team well within the playoff race and as the year moved through July, it was clear that they would be real players in the trade market. When I wasn’t working part-time at CVS or at my internship (shouts to the Times Union), I was checking up on what was happening in trade talks.

The first trickles came through with small moves toward the end of the month, but as the trade deadline drew near, the hype surrounding the potential of a much bigger deal intensified. That move came on July 31 when they acquired Victor Martinez from Cleveland.

However, there was another big-time player who was said to be a part of trade talks and one whom the Red Sox were at least rumored to be looking into. That player was Roy Halladay. Now, how involved the Red Sox really were and how much of it was my own optimism and shoddy memory more than 10 years later is up for debate, but Halladay was traded that year (albeit in December) and the Red Sox had been buyers just a few months earlier. That means there is a universe where the Red Sox trade for both Martinez and Halladay that July. So let’s jump into the quantum realm, head back to 2009 and see what that alternate universe would have looked like.

Halladay, who tragically passed away in 2017, was one of the best pitchers of his era and the Red Sox had a first-row seat for his dominance in the lead-up to the 2009 trade that sent him to Philadelphia. The right-hander spent 12 years with the Toronto Blue Jays and after struggling in his first few seasons, he made a habit of silencing bats and racking up Cy Young votes. He was the 2003 Cy Young winner with a 22-7 record, 3.25 ERA and 3.23 FIP, while posting the best bWAR among pitchers (8.1) and tying for the most complete games in baseball (nine). That last mark speaks to his durability, which was one of his greatest strengths. The guy just didn’t get tired, leading to massive inning totals through his career. Between 2002 and 2009, he surpassed 200 innings six times.

Of course, Halladay did more than eat up innings. He cruised through them. In his time in Toronto, even if you include his struggles early on, Halladay posted a 133 ERA+, 3.47 FIP and 48.4 bWAR across more than 2,000 innings. In addition to that 2003 Cy Young, he also made six All Star teams and finished top five in Cy Young voting five other times while a member of the Blue Jays.

So when the Toronto traded him to the Phillies in December of 2009, we all knew he was exceptionally good. Somehow, he was even better in his first two years with Philadelphia. He immediately won the NL Cy Young in 2010, going 21-10 with a 2.44 ERA while posting MLB-highs with nine complete games and four shutouts, including a perfect game. That also was the same season he tossed a no-hitter in the playoffs.

Ah the playoffs. That’s what every team is fighting for, or at least what they’re supposed to be fighting for each season. The Red Sox did make the playoffs in 2009 despite not trading for Halladay, but they were swept right out of the ALDS by the Angels. Halladay might not have been able to right that wrong by himself, but he certainly could have helped.

The Red Sox also were in contention the following year while Halladay was ingratiating himself in Philadelphia. Unfortunately, they fell short, going 89-73, which was only good for third place in the AL East. There were plenty of reasons that Red Sox team missed the playoffs, but uneven performances across the rotation didn’t help. Jon Lester and Clay Buchholz were both great, but every other pitcher to start in more than five games, including free agent addition John Lackey, was below average. If the Red Sox had dealt for Halladay, they might have gone further in the 2009 playoffs and they might have actually made them in 2010.

During his first season in Philly, Halladay was worth a then career-high 8.5 bWAR. (He’d pass that mark the following year). Let’s say the Red Sox traded for Halladay in 2009 and still had him for 2010. They likely wouldn’t have signed Lackey, who was worth 1.7 bWAR in 2010. Now let’s assume Halladay performs pretty much as well as he did in Philly and posted an even eight in bWAR since he would still be dealing with the DH. Even with that small (and probably generous) reduction, that’s an extra six or so wins for Boston. The Red Sox lost the AL East by seven games and the AL Wild Card by six that year. Now it is not entirely accurate to just plug those numbers in and say boom, the Red Sox make the playoffs if Halladay is on the team, but the 2010 playoff race certainly would have looked different if he was in Boston.

The same goes for the following year. As we all remember, the 2011 season ended in a nightmare and robbed Jacoby Ellsbury of his rightful place as AL MVP. Now imagine if that team had 2011 Roy Halladay. Once again, we’ll swap out Lackey, insert Halladay and round down his bWAR total to eight. (It was 8.8). Since Lackey was worth -1.9, that would have gained the Red Sox an extra 9.9 wins. Nine point nine! I know, right? The Red Sox lost out on the playoffs by one game in 2011. With Halladay on the roster, they likely would have coasted into the playoffs and who knows what would have happened from there.

Halladay’s run as a dominant starter ended after 2011. He was a below average starter in the next two years and maybe the Red Sox wouldn’t have won the World Series in 2013 if he was on the team and Lackey was not. The ripple effects go out further than that, of course, since we haven’t even delved into what the Red Sox would have had to give up to acquire Halladay. Even taking that into account, it seems that in this what if scenario, Halladay would have helped in the short-term but perhaps robbed the Red Sox of a title later on. However, he could have helped them win a title just as easily, albeit a few years earlier. We’ll never know.