Regardless of whether you’re a fan of the outspoken Scott Boras, there is no denying he is one of the most successful and influential agents in the history of sports. Boras’ skill in landing mega-bucks for his clients has been on full display this offseason – a winter he entered representing seven players from MLBTR’s top 50 list of free agents. He has since secured a staggering $1,077,500,000 in guarantees for those clients. That figure trumps the predicted total of $842MM that we predicted for those players when free agency commenced.

Let’s check in on the work Boras did this winter for his biggest clients, including the three players who were the game’s highest-ranked free agents when the market opened…

Gerrit Cole, RHP, Yankees (MLBTR prediction: eight years, $256MM; actual contract: nine years, $324MM)

• One year after Boras secured the richest contract ever for a free agent – Phillies outfielder Bryce Harper’s 13-year, $330MM pact – he almost surpassed it. In many ways, he did. Cole’s deal breezes past Harper’s in average annual value ($36MM), ranking first in baseball history in that category. And the 29-year-old Cole also owns the longest and largest contract a pitcher has ever signed.

Anthony Rendon, 3B, Angels (MLBTR prediction: seven years, $235MM; actual contract: seven years $245MM)

• Nothing surprising about the value of this contract for Rendon, who was far and away the No. 1-ranked position player in this free-agent class. Among hitters, only new teammate Mike Trout ($35.5MM per year) earns more on an annual basis than Rendon’s $35MM.

Stephen Strasburg, RHP, Nationals (MLBTR prediction: six years, $180MM; actual contract: seven years, $245MM)

• It wasn’t long ago there were questions as to whether Strasburg would opt out of the remaining four years and $100MM on his previous contract, making this payday especially impressive. Strasburg will turn 32 in June, and he owns a somewhat checkered injury history, yet the World Series MVP was still able to score $35MM per season. As they tend to do, the Nationals included deferrals in the deal (approximately $80MM), but those come with interest in this case, so they don’t impact the present-day value of the contract.

Hyun-Jin Ryu, LHP, Blue Jays (MLBTR prediction: three years, $54MM; actual contract: four years, $80MM)

• On a per-inning basis, Ryu has been among the game’s premier pitchers last season, but he’s also a soon-to-be 33-year-old with a concerning injury history. But those factors didn’t stop Boras from crushing our Ryu projection and persuading a Toronto team that hasn’t finished .500 in a season since 2016 to splurge on the ex-Dodger.

Nick Castellanos, OF, Reds (MLBTR prediction: four years, $58MM; actual contract: four years, $64MM)

• There’s nothing eye-opening about the value of Castellanos’ pact, though it’s arguably a surprise relative to the way his market unfolded. The big-hitting, fielding-challenged 27-year-old went unsigned until late January, after all, and he netted his deal shortly after a similarly valuable outfielder (the Braves’ Marcell Ozuna) signed for three fewer years and $46MM less. Moreover, Boras convinced the Reds to throw in opt-out clauses after each of the next two seasons, which will give Castellanos the power to return to free agency in the near future if he’s so inclined.

Mike Moustakas, 3B, Reds (MLBTR prediction: two years, $20MM; actual contract: four years, $64MM)

• The other member of the Reds’ two-man $64MM club, Moustakas raked in more than triple what we forecast. That’s despite the fact that Moustakas entered this free-agency period coming off back-to-back offseasons in which he settled for relatively modest one-year guarantees. It’s also worth noting the 31-year-old wasn’t markedly more productive in 2019 than he was in either 2017 or ’18.

Dallas Keuchel, LHP, White Sox (MLBTR prediction: three years, $39MM; actual contract: three years, $55.5MM)

• Boras and Keuchel aimed too high in free agency last year, which is why the former AL Cy Young winner wound up without a job until the Braves added him for a $13MM commitment in June. Keuchel, 32, was more decent than great as a Brave, but he still managed to smash our predicted total this winter and get the multi-season guarantee he couldn’t find a year ago.

Earlier this evening, we checked in on how the five hitters who signed the richest contract extensions before last season began performed in 2019. Let’s do the same here with pitchers…

Chris Sale, LHP, Red Sox – five years, $145MM through 2024: It’s understandable why the Red Sox locked up Sale, who was then coming off an otherworldly season in which he helped the club to a World Series title. Sale battled shoulder problems late in that year, however, and dealt with further injury woes and a drop in performance last season. The 30-year-old wound up throwing 147 1/3 innings, his fewest since 2011, thanks in part to elbow issues. When he did take the mound, Sale put up a career-worst ERA (4.40) and saw his average fastball velocity drop exactly 2 mph (95.7 to 93.7) from 2018. Those are alarming facts, but the bottom line is that there’s still plenty to like with Sale in the here and now. He did, after all, post a 3.39 FIP/2.93 xFIP/3.00 SIERA with an eye-popping 13.32 K/9 against 2.26 BB/9 during his “down” 2019.

Jacob deGrom, RHP, Mets – four years, $120.5MM through 2023: This contract looks like a steal for the Mets, who retained arguably the best pitcher in the game for almost three times less than Gerrit Cole got in free agency this winter. After receiving his extension last March, the 31-year-old deGrom proceeded to put up his second straight NL Cy Young-winning season, during which he logged a 2.43 ERA/2.67 FIP with 11.25 K/9 and 1.94 BB/9 in 204 innings.

Miles Mikolas, RHP, Cardinals – four years, $68MM through 2023: Mikolas struggled in the majors early in his career, dominated in Japan for a couple years, and then thrived in his first season back in the bigs with the Cardinals in 2018. They were impressed enough to lock up Mikolas for the long haul before last season, but the 31-year-old declined somewhat. He still offered quality production, though, with his velocity and swinging-strike rates in the same vicinity as the previous season. Mikolas ended up tossing 184 frames of 4.16 ERA/4.27 FIP ball with 7.04 K/9 and 1.57 BB/9 (the fourth-lowest walk rate in MLB).

Justin Verlander, RHP, Astros – two years, $66MM through 2021: There’s not much to say here besides the obvious: This looks like a good decision. The ageless Verlander, soon to turn 37, just won the second AL Cy Young of his career. He’s in line to front the Astros’ staff, which lost Cole, for at least two more seasons.

Kyle Hendricks, RHP, Cubs – four years, $55.5MM through 2023: The soft-tossing Hendricks isn’t the flashiest, but the 30-year-old righty has typically kept runs off the board and limited walks. Last season was no different – Hendricks recorded a 3.46 ERA/3.61 FIP with 7.63 K/9 against 1.67 BB/9 over 177 innings. With a fastball that only clocks in around 87 mph, there’s little room for error, but Hendricks has made it work so far. Despite Hendricks’ unimposing velocity, his fastball was one of the most valuable in the game last year, per FanGraphs.

Photo courtesy of USA Today Sports Images.

We’re on the cusp of spring training, which is also a popular time for teams and players to work out long-term extensions. We saw several of those deals handed out before last season began. Let’s check in on how those pacts look now, beginning with the hitters who inked the five largest extensions of last offseason…

Mike Trout, CF, Angels – 10 years, $360MM: It’s anyone’s guess how this contract will look at the tail end of it (see: Pujols, Albert), but despite the amount, it has the makings of a wise decision at the moment. After all, the 28-year-old Trout, already one of the greatest players in the history of baseball, continued to steamroll the opposition in 2019 – a season in which he earned his eighth straight All-Star nod and the third AL MVP of his career. The Angels really had no choice but to lock up Trout, and had they not done so, he’d be entering a contract year right now. He would also be in prime position to land an even richer contract on the open market less than a year from now.

Nolan Arenado, 3B, Rockies – seven years, $234MM: This deal already comes off as questionable for the Rockies, and it’s not because Arenado faded in 2019. On the contrary, the 28-year-old picked up his fifth straight All-Star honors and earned his seventh Gold Glove in a row. But Arenado is now known to be fed up with the Rockies because they haven’t done much to better their roster this winter after a horrid season, and he seems open to a trade as a result. However, his enormous new contract includes an opt-out clause after 2021, so teams probably aren’t champing at the bit to pay for seven years of Arenado in a trade when he could end up spending just two seasons in their uniform. And Rockies general manager Jeff Bridich isn’t just going to give away Arenado, Colorado’s franchise player, no matter how unhappy he may be with the organization. Needless to say, the two sides are in a spot neither expected to be in when they committed to each other for the long haul just months ago.

Paul Goldschmidt, 1B, Cardinals – five years, $130MM: Arizona’s version of Goldschmidt was an elite player for most of his tenure there from 2011-18, which led the Cardinals to trade significant talent for him more than a year ago. Unfortunately for the Cards, though, the 2019 edition of Goldschmidt was pedestrian compared to his D-backs self. Goldschmidt wasn’t bad by any stretch, evidenced in part by his 34 home runs and 2.9 fWAR, but the .260/.346/.476 line he posted in 682 plate appearances comes up way short next to his career slash of .292/.391/.524. The drop-off’s not a great sign for a 32-year-old at the beginning of the biggest contract in Cardinals history.

Alex Bregman, 3B, Astros – five years, $100MM: This has not been a banner winter for the Astros, and if you follow the game at all, you know why. They are coming off a pennant-winning season, though, and Bregman was a key part of it. The 25-year-old was in the inner circle of premier players for the second straight season, slashing .296/.423/.592 with 41 home runs and 8.5 fWAR in 690 plate appearances. The Astros still owe Bregman a lot of money, but he’s young enough that it seems safe to say they won’t regret ponying up for him.

Aaron Hicks, CF, Yankees – seven years, $70MM: Thanks to the injuries Hicks has suffered since signing it, this gamble hasn’t worked out to the Yankees’ liking so far. Hicks missed all but 59 games last year while battling back and elbow problems, and when he did play, he wasn’t nearly as effective as he was over the previous couple seasons. Worsening matters, Hicks underwent Tommy John surgery on his right elbow this past October, meaning the 30-year-old will sit out a sizable portion of the upcoming campaign.

Photo courtesy of USA Today Sports Images.

With just about every major free agent already off the board, it’s officially buy-low season across baseball. Plenty of teams are surely searching for diamonds in the rough at this point, and as we’ll explore below, there may be some left on the offensive side. Here are the still-unsigned hitters who had the most productive years at the plate in 2019…

Hunter Pence, OF/DH – .297/.358/.552 (128 wRC+) in 316 plate appearances

• The former star’s career looked to have flamed out a year ago at this time, but Pence took a minor league contract with the Rangers and enjoyed a resurgence at the plate. The right-handed Pence provided quality production against righty and lefty pitchers alike, clubbed 18 home runs and earned solid marks from Statcast (including for his speed, which is unexpected for a 36-year-old). Pence’s age, the injuries he dealt with last season and the fact that he didn’t play the field much in 2019 are all causes for concern, though, and have likely played a role in the fact that he hasn’t found a new deal so far this offseason. A reunion with the Giants – with whom he wouldn’t be able to DH – could be in the offing, however.

Cameron Maybin, OF – .285/.364/.494 (127 wRC+) in 269 plate appearances

• Another ex-Giant (among other teams), Maybin surprisingly emerged as one of the unsung heroes for the injury-ravaged Yankees, who acquired him from Cleveland in late April in what looked like a minor trade at the time. Maybin proceeded to turn in one of his finest seasons at the plate, swatting 11 home runs and swiping nine bases along the way. He also proved to still be a viable outfield option at the age of 32, combining for scratch defense (zero DRS, minus-0.2 UZR) in the grass, though the longtime center fielder didn’t see much action there. Maybin said back in October he wanted to re-sign with the Yankees, but there hasn’t been any indication that they’re going to bring him back. Pittsburgh’s a possibility, though.

Brad Miller, INF/ OF – .260/.329/.565 (126 wRC+) in 170 plate appearances

• Miller hasn’t turned into the standout many expected when he was a prospect, but he has typically been able to offer passable offense while playing several positions (albeit not that well, per the defensive metrics). Last season was pretty much the same story for the well-traveled 30-year-old, but he gave the Phillies much more than they could’ve realistically hoped for upon acquiring him from the Indians in the middle of June. That said, it’s worth noting the left-handed Miller wasn’t an option for the Phils against southpaws, nor has he performed well against them overall.

Wilmer Flores, INF – .317/.361/.467 (120 wRC+) in 285 plate appearances

• This has been a quiet winter for Flores since the Diamondbacks bought out his $6MM option after the season, but his market has reportedly begun to pick up. Still just 28, Flores has regularly mixed decent or better offense with defensive versatility, so could be a rather useful pickup for someone heading into 2020.

Domingo Santana, OF/DH – .253/.329/.441 (107 wRC+) in 507 plate appearances

• The youngest player on this list (27), Santana has flashed tantalizing potential at times – especially during a 3.3-fWAR season with the Brewers in 2017 – but hasn’t been able to put it together on a regular basis. He got off to a hot start as a Mariner last year before tanking in the second half, in part because of a nagging elbow injury. And Santana earned good defensive grades as recently as 2018, but he was among the game’s very worst fielders last season (minus-17 DRS, minus-16.1 UZR). Whether he’ll be limited to mostly DH duties in 2020 remains to be seen, and that’s if he even gets a major league opportunity. No one has been connected to Santana in the rumor mill since the Mariners non-tendered him almost two full months ago.

Brock Holt, INF/OF – .297/.369/.402 (103 wRC+) in 295 plate appearances

• The 31-year-old Holt has had an up-and-down career, but the longtime member of the Red Sox is like Flores in that he has usually given his team presentable offense and defensive flexibility. Last season was no different, although it was an injury-limited campaign. He’s now one of two MLBTR top 50 free agents still without a job, but the Blue Jays have shown recent interest in him.

Yasiel Puig, OF – .267/.327/.458 (101 wRC+) in 611 plate appearances

• The other remaining member of MLBTR’s top 50, Puig hasn’t had any luck this offseason in the wake of a disappointing year between both Ohio teams. Puig entered 2019 as someone with a rather productive track record, though, and still has another full season left in his 20s. The colorful Puig seems to be an acquired taste behind the scenes, but there’s a case for several teams to buy low on him and hope he returns to the form he regularly showed as a Dodger.

Brian Dozier, 2B – .238/.340/.430 (99 wRC+) in 482 plate appearances

• Dozier’s not the hugely powerful, bag-stealing second baseman he was during his halcyon days with the Twins. Still, he provided league-average offense last year as a National and, for the sixth straight season, amassed at least 20 HRs. In other words, a team could definitely do worse at the keystone than the soon-to-be 33-year-old. The Diamondbacks had interest in him as of last weekend, but they’ve since acquired center fielder Starling Marte, which means Ketel Marte will shift to second. Consequently, Dozier to the desert doesn’t appear as if it will happen.

Tim Beckham, INF – .237/.293/.461 (99 wRC+) in 328 plate appearances

• There are some obvious red flags regarding Beckham. For one, he’ll miss a sizable portion of the season after MLB hit him with an 80-game PED suspension last August. And while Beckham did manage a useful slash line before his year came to an abrupt end, the ex-Mariner struck out 31 percent of the time and didn’t get on base much. Defensively, he had a rough go at short (minus-8 DRS, minus-5.8 UZR) – a key reason the former No. 1 overall pick put up replacement-level production for the second consecutive year.