Before the Brewers
Drafted by the Washington Nationals in the 6th round of the 2005 draft, Estrada made brief appearances in 2008 and 2009 with the team that drafted him. He made 11 relief appearances in his debut in August and September of 2008, surrendering 13 runs -- 11 earned -- in 12.2 innings. Sent back down to AAA-Syracuse for additional seasoning, Estrada resurfaced as a September call-up, making four appearances including his first MLB start, a 2.1 inning debacle in which he allowed five runs on three hits and three walks. Despite being ranked as the Nationals' 18th best prospect by Baseball America, Washington designated Estrada for assignment in early 2010, when he was claimed by Milwaukee.
With the Brewers
Estrada remained largely ineffective in his debut season with the Brewers, compiling a 9.53 ERA over seven relief appearances in 2010. He showed some promise in 2011, however, as he became an important swing-man for the 2011 NL Central champions. Over the next three years, Estrada would establish himself as an effective, if inconsistent, part of the Brewers pitching staff, recording a 3.97 ERA over 89 appearances and 62 starts. In 2014, after a sustained bout of gopher ball-itis, Estrada was removed from the starting rotation to make room for Jimmy Nelson. Estrada led the National League with 29 home runs allowed despite throwing just 150.2 innings, and looked like a potential non-tender candidate when Milwaukee dealt him to Toronto for first baseman Adam Lind, in one of the better mutually-beneficial trades in recent memory.
After the Brewers
Estrada enjoyed a career year with the AL East champions in 2015, finishing the season with a 3.13 ERA in 34 appearances (28 starts) while leading the league in H/9 (6.7). Perhaps the highlight of the 32-year-olds career came just a few short weeks ago: with the Blue Jays staring at elimination down 3-1 in the ALCS, Estrada twirling a Game 5 gem, pitching 7.2 innings of three hit, one run ball, striking out five in a 7-1 Toronto win. Alas, two days and one preposterously-sized Wade Davis strike zone later, the Blue Jays were eliminated, sending Estrada into free agency for the first time. In a mildly surprising move, Toronto extended a $15.8 million dollar qualifying offer to Estrada, ensuring them draft pick compensation in the event that he chooses to sign elsewhere.
Free Agency Outlook
There's a lot of different ways this can go. Estrada could become the first player to accept a qualifying offer -- if Brett Anderson and/or Ian Kennedy don't beat him to it. He'll have to consider it: the one year, $15.8 million offer is half-again what's he's made over his eight year career. However, ultimately I don't think it's likely he'll accept: while Estrada would certainly not command $15.8 million AAV on the open market -- even without the draft pick compensation hanging over his head -- he'll probably be seeking some long-term security in his first crack at free agency. For a player of Estrada's age, the more important figure is the total amount guaranteed, rather than the amount he'll make per year.
This leaves him with yet another decision. He can try to work out a deal with the Blue Jays -- something that may already be in the works -- who of course would not need to forfeit a draft pick in order to retain his services. This would avoid the issue of his value being artificially deflated by the consequences of a lost draft pick built into his negotiations with other teams. Of course, the Blue Jays know that, and will have leverage there as well. He's also of course free to work out a contract with any of the other 29 teams, albeit with that draft pick penalty hanging over him. If he goes that route, Estrada could find himself in the same limbo that players like Kyle Lohse and Kendrys Morales have wound up in -- refusing to take an insultingly-low offer, and having to wait until Spring Training begins, or in Morales' case until after the draft in June, to catch on with a team.
A couple of teams with top-10 protected picks in next year's draft will be looking to sign free agent pitchers and either of them might be a good fit for Estrada, since the cost to sign him won't be as high for those teams. The Tigers especially have made it known they plan to sign multiple starters this winter, while the White Sox will have an opening in their rotation assuming Jeff Samardzija finds greener pastures. It's also, as I mentioned, entirely possible that he'll remain with the Blue Jays, even if he rejects the qualifying offer. In a world where his value isn't artificially depressed by draft pick compensation, I would imagine he could fetch something around 3 years/$33 million on the open market at the high end. However, with the loss of a draft pick tied to signing him, I think he's more in line for something like the 2 year, $20 million contract with a $10 million third year club option that Edinson Volquez signed last off-season.