September isn’t a terribly active month on the trade front as players acquired after August 31 are not eligible to join an acquiring club’s postseason roster. However, in recent years, we have seen some notable extensions hammered out in the final full month of the regular season. While most such agreements represent short-term arrangements with veterans, every now and again there’s a more significant pact to be found. Could we see one go down in the next week and change? Here’s a look back at some notable September extensions over the past five seasons…

2015

• None … but honorable mention to the Marlins’ early October agreement with Ichiro Suzuki on a one-year, $2MM extension with a club option. — The Fish pushed a 41-year-old Ichiro harder than had been expected in 2015, and he responded with a less-than-useful campaign. But he was still valued as a bench presence, and it didn’t hurt that 2016 promised a run at 3,000 hits. Ichiro not only passed that milestone, but has gone on to thrive in a more limited role this year, providing solid baserunning and glovework as well as a sturdy .292/.362/.363 batting line in 301 plate appearances to date.

2014

• Rockies sign Jorge De La Rosa to a two-year, $25MM extension. — De La Rosa saw a strong uptick in his fastball velocity in 2014, his second full season back from Tommy John surgery.  With an average of 92.3 mph on his heater versus 91.1 mph in 2013, De La Rosa pitched to a 4.26 ERA with 6.7 K/9, 3.2 BB/9 and a 51.9 percent ground-ball rate in 160 2/3 innings of work at the time of the signing.  This season, the hurler has pitched to a similar 4.17 ERA with 8.1 K/9 and 3.9 BB/9.

2013

• Padres sign Will Venable to a two-year, $8.5MM extension. — Venable had a breakout season in terms of his power production in 2013, so the Padres moved to lock in his remaining arbitration salaries, as further 20-homer/20-steal seasons would cause the price to soar. Unfortunately for the team, Venable’s decision to opt for security looks wise, in hindsight, as he batted just .224/.288/.325  in the first year of the deal and .248/.325/.356 in 2015.  This season Venable was moved to Texas in an August waiver trade as the Rangers looked to add outfield depth.
• Marlins sign Greg Dobbs to a one-year, $1.75MM extension. — This extension drew plenty of public scrutiny, as Dobbs’ on-field performance in 2013 (.228/.303/.300) didn’t warrant the deal. It was eventually reported that owner Jeffrey Loria negotiated the deal without consulting former president of baseball operations Larry Beinfest. The Dobbs extension would be one of many stories that were referenced when describing the rift between Loria and Beinfest at the time of Beinfest’s dismissal.
• Giants sign Hunter Pence to a five-year, $90MM extension. — The most notable of any extension in this post, Pence was positioned to be one of the top free agents in the 2013-14 class, but he took what looked to be market value at the time to remain in San Francisco. As it turns out, the market for outfield bats was more aggressive than many had thought, with Jacoby Ellsbury and Shin-Soo Choo landing seven-year deals worth $153MM and $131MM, respectively. Last season, Pence hit .277/.332/.445 with 20 homers.  This season, Pence has put up a similar .275/.327/.478 line, though he has seen only 52 games on the year due to injury.

2012

• Padres sign Chris Denorfia to a two-year, $4.25MM extension. — Denorfia’s strong season led former GM Josh Byrnes to lock in his final arb years with this modest extension, and Denorfia made the deal look like a good one in 2013 by hitting a solid .279/.337/.395 with a career-high 10 homers and excellent numbers against lefties. His production fell off in the contract’s second year, but the Padres’ triumvirate of interim GMs were still able to flip him to Seattle for outfielder Abraham Almonte and minor league righty Stephen Kohlscheen.
• Rangers sign Colby Lewis to a one-year, $2MM extension. — Lewis went down for the season in mid-July back in 2012, but he’d been enjoying a strong season and was expected to return for the 2013 campaign, making a $2MM salary a potential bargain for Texas. Unfortunately for the Rangers, Lewis had multiple setbacks and wasn’t able to take the hill the following season, but it’s not hard to see why they were interested in the low-risk deal; Lewis had turned in a 3.93 ERA over his previous 506 1/3 innings with the Rangers.

2011

• Cardinals sign Chris Carpenter to a two-year, $21MM extension. — Carpenter led the league in innings pitched in 2011 and had been generally excellent over the previous three seasons, prompting quite a bit of praise for this deal. He, in fact, restructured his contract and took what most expected to be less money in the long run, giving up a $15MM club option in favor of this two-year deal. Of course, Carpenter would sadly throw just 17 more innings in his career before injuries forced him to retire. While it looked good at the time, this deal didn’t pan out.
• Mets sign Tim Byrdak to a one-year, $1MM extension. — While the extension wasn’t particularly memorable and didn’t have a large impact on the 2012 Mets, Byrdak fired 30 2/3 innings of 4.40 ERA ball and was a strong weapon against lefties, making him worth his modest salary.
• Cardinals sign Lance Berkman to a one-year, $12MM extension. — After a huge rebound campaign in 2011, Big Puma was rewarded with this contract, but he totaled just 97 plate appearances the following season due to knee injuries. He wasn’t able to recover with the Rangers in 2013 and retired following that season, putting an end to an excellent career.
• Marlins sign Omar Infante to a two-year, $8MM extension. — This contract paid dividends in the sense that Infante was largely excellent for the Marlins over the next half-season before being dealt to the Tigers along with Anibal Sanchez. That trade netted former top prospect Jacob Turner, catcher Rob Brantly and lefty Brian Flynn — a respectable haul at the time but one that now looks lackluster. Miami dealt Turner to the Cubs for a pair of low-level relievers last season, and Brantly was passed over in favor of Jarrod Saltalamacchia.
• White Sox sign Sergio Santos to a three-year, $8.25MM extension. — Signed at the end of a breakout season as the White Sox closer, Santos found himself traded to the Blue Jays for pitching prospect Nestor Molina that offseason. Molina didn’t do much and was outrighted by the ChiSox in 2014, but they probably feel fortunate not to have had to pay Santos the money he was guaranteed, as shoulder injuries led to a 5.23 ERA and just 51 innings pitched over the life of his three guaranteed years with Toronto.

A previous installment of this post written by Steve Adams and Zach Links ran in September 2015.

A look back at the original reporting and analysis found on MLBTR the last seven days:

• In the early stages of the offseason, free agents David Price, Johnny Cueto, and Jason Heyward all inked lucrative deals which included opt-out clauses.  In January, Matt Swartz wrote an article for MLBTR to approximate the value of those clauses.  Days ago, he offered his analysis of the opt-outs given to Yoenis Cespedes, Justin Upton, Scott Kazmir, Ian Kennedy, and Wei-Yin Chen.  While many in baseball criticize teams for giving opt-out clauses, Swartz estimates that in these five deals, teams would have had to fork over about 10 to 15 percent more in a straight forward deal.
• In part one of his interview with Dave Stewart, Brett Ballantini spoke with the D’Backs GM about his eventful offseason.  In Part II of the interview, Ballantini spoke with Stewart about his unusual path from player to powerful agent to general manager.
• The MLBTR Podcast last Thursday included play-by-play man Len Kasper on the Cubs and Ben Nicholson-Smith of Sportsnet.ca on the Blue Jays and the extension market.
• Speaking of Chen, the Marlins laid out big bucks to land the left-hander.  MLBTR’s Jeff Todd looked back on Miami’s offseason moves, including the Chen deal and Dee Gordon’s extension.
• To kickstart MLBTR’s brand new College Series, Chuck Wasserstrom interviewed Reds Senior Vice President/General Manager Dick Williams about his days at the University of Virginia.
• Charlie Wilmoth reflected on the Cardinals’ offseason including the loss of Heyward and John Lackey to a division rival. Will additions to rotation and bullpen be enough?
• Mark Polishuk analyzed the Yankees’ unlikely offseason. The infamous big spenders committed $0 to major league free agents. They did make a number of notable trades, acquiring Aroldis Chapman, Aaron Hicks, and Starlin Castro in three separate moves.
• Mark also offered his take on the Blue Jays offseason which began with an unexpected need to replace former GM Alex Anthopoulos after their most successful season in over two decades.
• On Saturday, MLBTR was the first to report that Alex Presley would not make the Brewers and has a 48-hour window to be signed elsewhere.
• On Sunday, MLBTR was the first to report on the deal sending Chris Leroux from the Phillies to the Blue Jays.
• MLBTR was also the first to report the Dodgers signing of reliever Dale Thayer to a minor league contract. Earlier in the week Thayer had opted out of a minors deal with the Orioles.